Being 'over-productive'

Air Pods are peak productivity(?) (via  Unsplash )

Air Pods are peak productivity(?) (via Unsplash)

I’m not ashamed to say that I’m obsessed with life hacks and productivity. I swear by Google Calendar, use Notion for organizing my to-dos and thoughts, and feel pretty disappointed when I wake up past my goal of 8:30am.

I have conversations with friends about how to be ‘more productive’. Some things, i.e. meditation and hitting the gym consistently, work wonders for my productivity. Others, like intermittent fasting and blocking time, haven’t been as effective. Regardless, it fires me up to think there’s someone out there working harder than I am and achieving more, while I’m sitting idle.

In this post, I want to explain my approach to being productive, how it’s changed over the years, and why I strongly believe there is such a thing as being ‘over-productive’ — it can be toxic, and my generation is most susceptible to it.

It’s always a race

I went to a high school with regional programs (i.e. IB), so competition was ingrained early. It wasn’t a question of whether you got honours, but rather how well you did relative to the rest of the class. Classmates were heavily involved — leading clubs and extra-curriculars outside of school, playing on competitive sports teams, the list goes on.

I fell into that, and it stuck with me — all my friends were shooting for (and getting into) the top programs for their respective interests. Fast-forward 4 years and those same former classmates are in med school, working software engineering jobs in Silicon Valley, or grinding at top consulting or banking firms. Simply put, it’s not special to be an over-achiever, the question is to what extent you can take it.

College was a similar story, but instead of getting top executive positions in school clubs, it migrated to getting top internships at coveted companies. Friend groups began to shift apart, and I increasingly tried to associate myself with people who were always on the look-out for new opportunities, hustled hard when given the chance, and often sacrificed health (mental & physical) to get there.

Conversations were (and still are) very predictable. “What are you up to for the summer?”, “Did you sign full time?”, “How are grad school apps going?”, and countless other questions that solely related to your position as a student and success towards (supposedly) objective career goals.

The working world

Things changed when I started working full-time at Clearbit. The majority of the company was in their late 20s or early 30s; anyone who was caught in the rat race of being ‘furthest ahead’ burned out by 25 and had since found a proper balance, while those that were late bloomers found their footing and were well content with their life — both career related and not.

I was shocked to be in this environment, and to be honest, a little lost. There’s hustle porn galore in The Valley, but I increasingly started to realize that your job was only a fraction of your life. I.e. your friend group, the city you’re living in, and what you do / think about outside of work is what shaped you as a person.

The sheltered environment of college and highly concentrated interest groups make for a rough transition to the ‘real world’. Example? I work in tech, read tech, and talk about tech a lot. This is fine in college, and a large part of my friend group is very engaged in tech. Entering the work world, even people I looked up to a ton, with regards to their tech knowledge + career, never wanted to talk about it outside of work. My job is not what defines me as a person, no matter how much I threw myself at it.

Over-productivity

The idea of being ‘as productive as possible’ marks the transition of college/young professional life into what could arguably be regarded as ‘full adulting’. I’m guilty of all the cliches; I tried intermittent fasting, I still meditate fairly frequently, and I’ve used grayscale on my phone, Moment, and deleted apps like Instagram and Facebook to maximize productivity.

I can confidently say this isn’t living; life loses its zest when all your activities are reduced to a slot in Google Calendar or related to how it positively or adversely affects your productivity / career progression (trackable by a spreadsheet). So with that in mind, I’ve tried making a conscious effort to dive deeper into my hobbies and interests, making decisions that don’t optimize for productivity, but instead for experience.

Example — I could stay in on a Friday night, grab a coffee and my laptop, and meticulously work on building a company. I could also ditch the laptop, hit the bars to hear live music with my friends, many of whom I may never see (ever, or for a prolonged period of time) after a few weeks when we part ways.

Conclusion

There’s a beautiful simplicity to taking goals & objectives off your day-to-day, and instead being intentional about enjoying life. Not to say that being driven is a bad thing, or that goals should go out the window. But the minute that they drive every decision I make and result in me missing out on experiences I otherwise would not have had, is where I have to draw the line.

The crisis of choice

Now THESE guys knew how to make decisions. Or relentlessly colonize the world. Maybe both!

Now THESE guys knew how to make decisions. Or relentlessly colonize the world. Maybe both!

Merely a few decades ago, religion had a strong hold on society. While the Enlightenment had long since passed, and church and state were clearly separated in most developed nations, many would still have considered themselves ‘religious’. Around 81% of Americans identified as white and Christian in 1976; that number has since fallen to 43%.

Secularization, in the face of globalization and an increasing access to technology, has created problems that did not previously exist. In this post, I want to un-pack what I understand this shift to mean. Tl;dr is that secularization is not intrinsically a bad thing, but the lack of change in other aspects of society is. And for anyone about to close the tab, I’m not preaching that religion is/is not a good thing, nor that you should / should not convert — that choice is up to you! This is purely a thought exercise to flesh out my thoughts and why I view the world the way I do.

A solid foundation

Religion, across the board, is a great source of values and morals for the average person. Many religions, and as a Christian I’ll speak primarily to that, preach the importance of community, loving thy neighbour, and being honest and void of temptation (alcohol & other influences).

They also preach a specific way of life that adheres to their vision of a perfect world. This comes with gender roles, denouncing certain types of behaviour (read: social conservatism), and often altering the world order from its current state. Cue debates on whether abortion or homosexuality should be made legal or not.

In an era where religion was extremely salient, many individuals could lean on religion as reasoning for their beliefs and decisions. You didn’t need to justify why a certain viewpoint was valid, you could simply state that it says so in scripture. This alone may not sound like enough — however when the majority of the country is religious, mounting an opposition is challenging.

Over the years, this dominance eroded; not just in the population as a whole, but especially in youth. Exposure to The Internet meant you no longer had to rely on your parent(s) to develop a worldview, which included your view on religion. Why ask Mom why the welfare gap exists when you could ask Google?

The challenge to this is lack of guidance — someone between the ages of 8-15 doesn’t have a de facto system for browsing The Internet and discerning what is real/fake. More importantly, there is no system for discovering what path they need to pursue in order to live ‘The Good Life’.

This used to be provided by religion. When you were lost or unsure of how to act, leaning on religious values or even scripture itself was the solution. The rise of secularism frowns upon that — as an individual, you should pride yourself in being able to reason over everything else.

The education gap

This phenomenon doesn’t just affect youth, but adults as well; perhaps even more. While youth had little guidance on how to form their world view, adults had little guidance on how to alter their world view. As mentioned above, previous arguments that used religion as reason could no longer be accepted. An adult in 2019 needs to be able to justify their world views using reason.

I’ll be the first to admit that I’m not always the most reasonable person, agreeableness aside. Although I try to ‘logic’ my way out of most decisions and scenarios, emotions get in the way and my judgement can sometimes be clouded. Don’t believe me? I’ve written full posts on regret and decision-making to rationalize (to myself) why I operate the way I do.

While I do falter on occasion, I’d like to think I’m quite capable of thinking critically about decisions and coming to reasonable conclusions. I don’t know if this is true for the majority of people — especially those who may be less educated. A prime example can be found in fake news: how many people are guilty of reposting (and/or commenting on) something they didn’t verify as factual? Worse yet, how many people are guilty of doing this without verifying if it was factual?

Niche news outlets and pundits allow for your typical individual in 2019 to consume content that solely affirms their views and beliefs. If I was socially conservative (I’m not), then following Fox News and selectively listening to Jordan Peterson and Ben Shapiro could be enough to get by. I could find justification for anything I believed in, without needing to explain my reasoning.

I blame education more than anything for this phenomenon. For starters, the K-12 system is more interested in teaching history and biology than it is with teaching financial and digital literacy. As much heat as liberal arts degrees get today for producing ‘unemployable’ graduates, the benefit is that they teach you how to read, not what to read. Being able to identify the bias in an article, find comparable pieces, and come to a conclusion on your own is the essence of critical thinking.

For adults, this problem compounds. Most adults aren’t in an environment like K-12 or post-secondary education where they are forced to learn. 24% of Americans haven’t read a book (even in part) in the last year. For those that never developed the ability to reason and filter information — whether due to dependence on religion, lack of education, or other factors — are lost in an age that throws more information at them than ever before.

‘Societal norms’ aren’t helping this. The minute I identify as conservative (I do), a whole swath of people shut their eyes/ears like they are in a terrible combination of Bird Box and A Quiet Place. People are afraid of debate, whether due to micro aggressions and fear of conflict, or simply because they don’t want to rock the boat. The value of ‘reason’ that led us to the Enlightenment is being shunned in an age where we are more developed than we ever were.

Steps to reason

This is usually the point in an article where I have a solution that gets me high fives from a handful of friends (and my Mom), before stumbling into a conclusion. Unfortunately, I don’t have the answer to this ‘crisis of choice’, but I have a few ideas:

1) Re-evaluate

Set a timer for 5 minutes and write a list of statements that you believe to be true about the world, including about yourself. Look at those statements and find reason as to why they are right/wrong. Then, challenge yourself on your reasoning. For some points, you may have no qualms. For others, you may furrow your brow, urging you to dive into that topic.

2) Read & write

Find areas of interest and read a lot about them. Philosophy, finance, politics, gardening, whatever you fancy. Then write about it — leverage the monster we call The Internet to organize your thoughts in a way that is presentable to a general audience, and invites discussion around it. This post took me about an hour and had me researching statistics on religion and reading to either challenge or validate my points.

3) Debate

I have a number of strongly held opinions — corporate jobs suck, everyone can get experience + money while in college, and sales is an underrated career path. None of these opinions are universal, that much is obvious. However, it’s not until I put my thoughts out there (and have them challenged), that I either further validate or invalidate them. For example: corporate jobs don’t suck, they’re a great outlet for people in tough financial situations, specific paths (i.e. doctor), and/or technical routes (i.e. engineer).

Conclusion

The dominance of religion throughout the 1900s allowed many to lean on it as reasoning for their values, morals, and the basis of social order. Through challenging the status quo, society was able to progress to guaranteeing basic human rights and equality to a larger group of people (i.e. ending apartheid + segregation, allowing gay marriage, etc.).

Increasing secularization and The Internet brought an influx of information and variance of choice that requires the ability to reason and think critically in order to come up with valid opinions. Most people don’t do this, nor do they need to.

Aside from a shift in education, individuals need to re-evaluate their existing views, read to answer lingering questions, and write + debate to further improve their understanding of the world. Failure to do so will further embed a culture of toxicity and fear that has already polarized a number of nations (i.e. USA).

Thanks to Phillip and a few other friends for sparking this idea and giving their thoughts. As always, if you disagree or have a strong opinion, please message me!

Corporate jobs

Brad and Chad celebrate the launch of their new marketing campaign, which was ready 6 months ago but had to get approved ( via Unsplash ).

Brad and Chad celebrate the launch of their new marketing campaign, which was ready 6 months ago but had to get approved (via Unsplash).

I posted a tweet this past week that took a fair amount of heat around choosing startups / riskier roles with high upside compared to ‘stable’ corporate jobs. In hindsight, it was a generalization, although that’s hard to avoid in 140 characters. Hence, I decided to put together this post to dive into it in deeper detail.

The gist of this post is that, in general, as a new graduate pursuing a career in tech and/or with an interest in entrepreneurship, you are better off working at a startup than a large corporation. Is this a ‘hot take’? Of course — but it’s something I feel strongly about, and look forward to being debated on.

Disclaimer, exceptions, externalities…

I’ve watched a ton of debates and lectures on politics, philosophy, and other topics of interest that are fairly polarized. In the Q&A, there’s always someone that comes out with an ‘edge case’ on why the argument the presenter was making is wrong. I.e. if I make the argument that an area marked ‘danger, do not enter’ should stop people from entering. Someone may retort ‘what if the person is blind and/or can’t read’. That is valid, but it’s an exception to the rule, and a minority / ‘edge case’. So in light of that, let’s dive into groups / exceptions where my argument carries less (or no) merit.

Extreme Poverty / Vulnerable Peoples

The biggest retort to my tweet, and one that I agree with (to some extent), is if you are coming from a family with very low income, and your first job needs to have a solid, stable income to help support them. Startups are probably not your best route; they don’t pay as well, the hours are / can be more volatile, and benefits (i.e. health insurance to spouse + family) may not be sufficient.

Likewise if your parents / family is in an incredible amount of debt, and you have a responsibility to help with this. Other situations of vulnerability may include: you / someone in your family is gravely ill, you are an immigrant and need a corporate job to sponsor your visa, etc. I don’t want to sound like the guy at the end of a drug infomercial, but if you think you’re in this boat, then feel free to ignore my argument.

Technical roles

I’m not a fit for engineering, data science, or other ‘technical roles, so those paths aren’t ones that I can speak to. I’ve heard arguments from both sides — startups move faster and give you more responsibility, which are universal arguments I’ll make in this post. On the other side, corporate jobs give you exposure to larger infrastructure and problems you wouldn’t see at a startup. There isn’t a true Product Manager at a 10-person startup — you’re probably 80% engineer and 20% putting out fires. However, at a company like Facebook, Google, IBM, etc. this is a great role. You’ll learn how to work with different teams and see what it takes to push out a new feature / product. So if you’re technical and want to pursue those types of careers, this post may have value to you or it may not be applicable.

Other passions / paths

I added this part as an afterthought, so I apologize for the brevity. If you want to become a doctor but have an interest in entrepreneurship, then startups probably aren’t a good fit for you. Likewise, if you love finance and want to start your own fund, startups would be a poor choice. If you want to make a stable 9-5 salary, start a family, and retire in 40 years, then startups also aren’t the greatest path.

This post is for anyone who hasn’t decided on their path yet and is choosing a corporate job because of the benefits that supposedly prepare you for entrepreneurship + maximize learning.

Why choose startups

Great, so with that out of the way, let’s dive into why startups are an amazing path for those interested in tech + entrepreneurship. The main three points I’ll argue for are (1) Hands-on experience, (2) Versatility and challenges, and (3) Learning potential.

(1) Hands-on experience

I’m a marketing / sales guy. That means my background is primarily in email marketing, content creation, marketing analytics, paid acquisition, and partnerships. When I joined Clearbit, they were 22 employees, and I was the 2nd hire on the Growth (marketing) team. There was a lot to get done, and they really couldn’t afford to silo work and set barriers because I was an intern.

So over the course of the year, I setup multiple email drip campaigns that went out to 10,000+ users, set up a dashboard to monitor the revenue and marketing/sales stats for the company, and was the main point of contact for partnerships with Zapier. This is the reality at a lot of startups — you get hands-on experience since there is an infinite amount of work to be done.

This isn’t the case at a corporation. A company like Uber has very specific roles for each function of marketing — building community (3-5 years exp), coordinating influencers (3 years exp), analyzing marketing data (5 years exp), paid acquisition (5+ years exp), and the list goes on. It’s challenging to get an entry-level role where you get hands-on experience in any of these roles; it’s more likely they’re curating you to be a manager for these types of people.

Tl;dr — it’s hard to get hands-on experience and autonomy at corporations. Instead, you get to shadow and assist people who do.

(2) Versatility and challenges

During my first college internship at Shopify Plus, the organization was 60-people and in a unique spot — they had the resources of a public company (Shopify) but the autonomy to prove out their own model, similar to a startup. This meant there was a lot of work to get done and little precedent on who should tackle it and how.

Over the course of the summer, I had a variety of responsibilities. At one point, we had a ‘concierge’ service where I’d take incoming calls from the Shopify Plus website — very representative of an intern role. On the other end, I had the freedom to send multiple sequences of outbound email to potential Plus customers, conduct a discovery call, and, if it got to that point (which it didn’t), negotiate the contract and close a deal.

In my 2nd summer at Shopify Plus, the organization had grown to ~ 300 people. I was on the revenue operations team, had great direction & mentorship, and learned a ton. However, there was the added bureaucracy and red tape of a bigger company. Certain projects were high-priority and out of my scope, others I had the freedom to tackle but had to jump through hoops to get approval for moving it forward.

Large corporations can’t afford to (and honestly don’t need to) take chances on new grads to get work done. Instead, they have training programs like these — two years of rotating between different departments so you can learn how the organization functions and how to navigate it. This is an incredibly powerful role, but keep in mind that they have this program for a specific purpose.

More specifically, there are things they’re expecting you to do, and things they aren’t. They know how to challenge you, and what you’re capable of doing. You’re most likely the 95th+ person to go through this program, so there shouldn’t be any surprises. I have friends in some of these roles where it’s frowned upon to work beyond a certain amount.

Startups don’t have this — in (most) of the roles I’ve taken, I was doing things I’ve never done before or didn’t know how to. I was challenged beyond my means (which helped me to learn faster), and my role was never silo’d into one thing or another. Early on in your career, I think that’s exactly what you need to grow.

Tl;dr — corporate roles are well-defined, in terms of responsibilities and challenges. Startup roles aren’t, and that helps you grow faster.

(3) Learning potential

I’ll never forget an interview I had with a sales manager at Shopify Plus in late 2016. I was ecstatic about sales, and made my entire ‘pitch’ about my passion for it, what I wanted to learn, and what I could do. His response made me think I didn’t get the job:

You can learn sales anywhere. The most you’ll take from this internship is seeing what happens when a company is growing this quickly. It’s a rare opportunity.

He was right — the sales team was ~ 10 people, and we were very much still figuring out what worked and what didn’t. Witnessing those conversations, how people sold a new product, and what experiments worked (or didn’t) was infinitely valuable.

That’s the benefit of a startup. Things move so quickly, that your role (and the company) 3 months ago is very different from what it is today. These learnings helped me understand what it took to build a business. What it meant to hire for sales, find new channels for leads, retain customers once you’ve signed them. Essential learnings, in my opinion, to being a good entrepreneur.

Corporations don’t give you this opportunity. The business has been around for decades (if not more), meaning that while it has changed, it does so slowly and not in ways a new grad can observe. I.e. the conversations on what direction Facebook is taking certain products will not be visible to someone who is in charge of shadowing the person that grows the use of Facebook Marketplace in Canada.

Tl;dr — corporations move slowly and are siloed, so learning how the business grows is stifled. Startups change quickly, so learning what it takes to go from $1M to $5M, or $5M to $10M is drastically different.

Conclusion

I’d assume (and hope) I ruffled some feathers with this post. So to clarify, I see a ton of merit to corporate jobs, and I don’t think anyone is making an objectively ‘bad’ decision by pursuing one. You get a good salary, clear opportunities for progression, and far more resources for mentorship. I have friends in these roles — whether it’s consulting, banking, product or product marketing — and I think those are phenomenal opportunities.

You learn how to be a manager, how to work with different stakeholders, and how to solve problems. These are universally applicable skills, but I don’t believe they are (as) useful as an entrepreneurship. You need to know how to sell to start a business. To generate leads and grow your presence as a marketer. To retain the first customers (and revenue) your business has ever seen. This all happens with limited resources and no direction. Working in startups prepares you for this a lot more than working at a corporation ever will.

I omitted a few points for startups that didn’t fit neatly into the categories above. Throughout your time, you’ll develop a huge network of people (marketers, salespeople, developers, etc.) that you may eventually want to start something with, or hire them. You’ll also meet mentors who have done it before and venture capitalists who can fund your idea. There is overlap here, as I’m sure you’ll meet this types of people while working at a corporation like Facebook or Google. Unlikely you’ll meet them at a CPG company or a big bank.

Lastly, I want to stress the absolute nonsense of prioritizing salary / prestige if you’re not in the ‘exception’ boats I mentioned above. I’m 22, what am I really going to do differently if I’m making $100k instead of $70k? Factoring in taxes and other factors, not much. I’d also be very hesitant to start a company with anyone who doesn’t have execution experience, regardless of whatever brand name they have on their resume. Management skills, in my opinion, are far less important when you don’t have product-market fit or consistent revenue.

The next Facebook

Imagine if the ‘rating girls’ app in  The Social Network  blew up INSTEAD of what we know now as Facebook? Actually, don’t imagine that…

Imagine if the ‘rating girls’ app in The Social Network blew up INSTEAD of what we know now as Facebook? Actually, don’t imagine that…

There’s no question that companies like Facebook, Apple, Amazon, Netflix, and Google (FAANG) have disrupted their respective industries, in many cases creating new ones that are worth billions of dollars. When I mention tech to the average person, these are the names that come to mind. Be the next ‘Zuckerberg’, 'Jobs’, etc. But what does it take to build the next Facebook?

In this post, I’ll go over my thoughts around the characteristics of massive tech companies, what it might take to build the next one, and emerging players that could be exactly that. A lot of this stems from a convo I had with a friend at Penn (thanks Will!), so giving credit before we jump into anything.

‘It’s a platform play’

Within the tech / VC community, this phrase is seen more as a meme or joke than a serious consideration. Any startup looking to raise capital will have at least thought of mentioning this in their pitch. To build a massive tech company, it’s not enough to have product-market fit and a profitable model — there’s a need to build something that has the ability to foster additional businesses.

A company like Salesforce isn’t just CRM software; they have an ecosystem that provides an environment for other integrations (i.e. email marketing, data enrichment, etc.) to thrive. Their market capitalization is $115B, but their ecosystem is valued at around $859B. The same goes for companies like Facebook, Apple, and Shopify (each with their own app stores).

I’ve mentioned in past posts that it’s an incredible success to build a business that has product-market fit and is profitable as a company. However, I don’t believe that alone is enough to be the next Facebook. In fact, there are businesses that make 8-figure revenue whose sole clientele are Salesforce customers. This goes the same for platforms like Shopify — agencies like BOLD and BVAccel generate tons of revenue for Shopify, and in turn, Shopify Plus customers make up a big portion of their revenue.

Industry & market size

I personally hate the mentality of ‘shoot for the moon’ when you’re building a business, especially for the first time. Sure, it’s more exciting to be tackling an industry or problem that is massive and ready for disruption, but this makes execution especially important — and for entrepreneurs with no track record or background, probability of failing (which is already very high) skyrockets.

There is a difference, however, between ‘moonshot’ businesses and ones that try to tackle a unique industry, with a lot of potential for expansion into a large target market. Amazon didn’t start as the de facto option for ordering online, it started as an online bookstore. If you looked at the company 1-2 years after starting, no one would have predicted the rise of Amazon Web Services — which has since risen to become one of the incumbents in the web hosting space.

An easy example to look at to better understand the difference is Square. They started with a Point of Sale (POS) reader that allowed merchants to take electronic payments. There was no dashboard, fulfillment integrations, or services for discounting and customer management. You’d be a fool to think they would ever venture into being a financial institution — offering loans, debit cards, or P2P money transfers. And that’s exactly what they did.

They didn’t do it from day one, with a slide deck and a 5-year plan. Square did it by starting with something they knew they could tackle (POS), and grew to involve other aspects of the business. Eventually, when a huge portion (if not all) of a business’ revenue was being processed by Square, they could predict future revenue and costs, allowing them to offer loans with a high probability of repayment. Square is now emerging as a financial institution, and is on its way to taking over the industry.

Tackling the right niche / problem, with potential to expand into a larger market, is another characteristic of businesses that will become the ‘next Facebook’. I have personal conviction behind the idea that finance will be the next industry where this happens — hence my bullish attitude towards Square, Shopify, and other companies that are tackling this (directly or indirectly).

Good timing

With an incredible team, product, and level of validation, a company can achieve success. Without the right timing, it will always fall short of its true potential. When I think of timing, the last two elements (industry and problem it solves) comes to mind. A great example comes in the form of Virtual Reality.

The possibilities of Virtual Reality are endless; it would reduce the need for many visual displays (i.e. TV, monitors, etc.) that we currently require for other devices (i.e. computers, gaming consoles) to function. The idea that you could have what is basically a brick-and-mortar experience from the comforts of your living room is mind-blowing. At some point, it could make remote working experiences the near equivalent to the physical office environment.

But not yet. Although it has some consumer appeal, Virtual Reality is more of a luxury than a practical piece of technology. Startups tackling this space may see some success, especially if they can find a niche and execute well, but really blowing up is challenging when consumers just aren’t ready. Facebook hit the timing well, when consumers were being used to having computers + the Internet in their everyday lives, but lacked an (effective) method to stay connected with each other.

In order for a company to become the ‘next Facebook’, timing will have to be near perfect. Anyone who comes too early will either fail or see limited success, while those who come late will see strong returns but fail to be the incumbent.

Conclusion

Technology companies have been changing our lives for 20+ years. It started with IBM and Xerox, then Apple and Google, and finally with Amazon and Facebook. Each one of these companies found a problem with a larger target market they could grow into, and had great timing. Others may have tried, but couldn’t get the formula right, and are eventually forgotten. Try it yourself — I can easily name ~ 5 companies that have recently failed; I’d be hard pressed to do the same for the 1980s.

The caveat in all of this, as I mention with many of my blog posts, is that I know nothing and am constantly learning. The elements I mentioned above could be essential to the ‘next Facebook’, or they could be entirely irrelevant. Send me a message if you disagree, and your thoughts on the ‘next Facebook’.

2019 — Checking in

Need to be on course for 2019! Avoid rocky waters! More sailing puns! (above: Mexico — 2018)

Need to be on course for 2019! Avoid rocky waters! More sailing puns! (above: Mexico — 2018)

I’ve mentioned in past posts that 2018 was easily the most eventful year of my life, thus far. There were a lot of ups — solid career experience, met amazing new mentors, and found a strong support system — and also lots of downs — injuries, loneliness, and heartbreak. Overall, it sets the bar pretty high for 2019, which makes it all the harder to plan for.

In this post, I want to dive into my plans for 2019, revisit my 2018 goals, and share my thought process. This is more of a personal exercise for me than anything, but I hope anyone reading takes something from it as well.

The past year

I’ll start by outlining a few of the goals that I had from 2018 and the progress I made on them. I think this will help set the stage for 2019, see what went wrong, and how I can improve.

(1) Reading

I’ve heard countless times that reading is the #1 thing that successful people do, and I back it. There’s the actual information you take in from a book, but more importantly there’s the reflection you do while reading. I.e. if you’re reading Steve Jobs’ biography, how do his experiences make you think about your approach to life, and the things you’ve done?

Unfortunately, I didn’t make a lot of progress on this goal. I read 3/10 books that I planned to, and am only just starting the 4th (River Out of Eden). My friend Kanwar gave some advice on this that I’ll share here:

“Life is too short to drag your feet through a book. Get the main ideas from it, and don’t be afraid to move onto a new one”

That’s paraphrased from my memory, which may have been impaired by a few beverages, but the idea sticks. I spent 3-4 months trying to read Meditations by Marcus Aurelius, and only got ~ 1/4 of the way through. I have a similar goal in 2019, to read a ton, but I won’t hold myself to a list of books or week-by-week goal. Instead, I’ll block off time to read every week (i.e. 30 minutes every 2 days), and not be afraid to start a new book if I’m not making progress. The following categories are especially interesting to me:

  • History — what happened between the 10th and 15th century? Before that? What can I learn from this? I believe that any book that survives the test of time has something to offer.

  • Philosophy — I fundamentally believe that any successful person operates from a sound value system. Similar to Principles, they know why they make the decisions they do, and don’t have weak beliefs. I believe different approaches to philosophy (i.e. stoicism) can help me get there.

  • Autobiographies — Successful people did something right, there’s no question there. So learning from how they think and specifically what they wish they hadn’t done can help me achieve my definition of success.

  • Business / Self-Help — I’m not sure what category 4-Hour Week Work or Principles falls into, but they were both great reads and I hope to continue to find books similar to them. Also nice to switch things up, since they’re typically a lot lighter reading than history / philosophy.

  • Fiction — I should force myself to read more fiction, since the only book (in recent memory) that I’ve read is When Breath Becomes Air, and it was phenomenal (though not entirely fiction). I hope to enjoy reading a lot more by switching it up with fiction books.

(2) Personal health

I tried becoming an early riser this past year with little success. I found the biggest issue was having a reason to get up — if I didn’t have class, someone to meet, or another commitment, there wasn’t much incentive to get out of bed. A part of this was probably my poor quality of sleep, which is a consequence of sleeping late, drinking coffee / other stimulants (i.e. alcohol), and not having a good routine.

I’ve heard before that everyone has their own biological clock and some people function better as night owls. I don’t believe this is true (for me), but I think a smooth transition is in order. So I’ve decided on the following goals:

  • Wake up at 8:30am (latest) everyday — I’d assume with work / school I might have to get up earlier, but I think committing to this regiment will help maintain a somewhat predictable sleep schedule

  • Meditate for 15 minutes per day — I’m a huge fan of Headspace, and used it frequently from July through October. While I will strive for 15 minutes in the morning and before bed, I think setting the bar of once / day is a good start.

In terms of my other personal health goals (food + fitness), I felt like I made some solid progress. Although I ate out a lot while working in SF, from Sept — Dec I had home-cooked meals usually 5/7 days of the week. I also made progress on my weight training goals, and have considerably better cardio thanks to intramural soccer and squash (Victor & Chris, I’ll beat you one day!).

(3) Mentors & skill development

This is by the far the goal I am most proud of making progress on in the past year. While in SF, I met a number of early-stage founders who have been incredibly supportive and helpful in my entrepreneurship journey. — people at companies like Slab, Kettle and Fire, Mattermost, and Zypsy. The biggest thing I learned was that no one really knows what they’re doing. Sure, some founders are better equipped than others, but everyone faces challenges that they’ve never seen before, and they’re not afraid to ask for help.

I’ve received some questions recently around how I approach reaching out to people, coffee chats, etc. Personally, I don’t feel the urge to reach out to new people anymore. I’m always open to meetings, but I think the generic “tell me about your life / career” didn’t yield many positive encounters in 2018. Hence, I want to use 2019 to only reach out to new people if I have a specific ask / value-add, OR if someone introduces us and thinks there is something there.

Instead, I’m going to direct this energy towards improving relationships with people I already know. I’m not ashamed to say that I have a Google Sheet with ~ 150 people, which tracks their name, position / company, the time we last chatted, and any relevant notes (i.e. had a child, left their job, taking karate). I want to further refine (reduce) this list in 2019 and be very intentional in how I improve those relationships.

For example, I’ll make a note 1-2 times a month to reach out to a set of mentors and see how they’re doing + share my progress. I’ve already scheduled recurring calendar events every ~ 2 weeks for close friends that I want to keep in better touch with. I recognize this is weird / unconventional, but I urge anyone who likes to be organized to give it a shot!

New goals

My goals this past year were great, and I’ll still going to pursue some of them, with varying levels of vigour. However, looking to 2019 I have two main goals that I want to be public about so I can be kept accountable. Here they are below:

(1) Social independence

This may sound like a(n intentionally) confusing term, but allow me to explain. I’m a natural extrovert, and I thrive off being around people. However, there are some people I enjoy being around more than others. To make up for the deficit, I’ll often have to use some sort of crutch — typically via going out / drinking alcohol. This is a convoluted (and unnecessarily more serious) way of saying “drinking + dancing at a function where you don’t know anyone so it’s less awkward”.

I’m a strong supporter of, especially career-wise, committing to things and doing them regardless of social norms. There’s no reason this shouldn’t extend to my social interactions. So, the first soft goal here is to stop being a ‘yes man’. I know it’s my last semester and I’m supposed to ‘send it’, but I think I’ll enjoy it considerably more if I say ‘no’ to more things and spend that same time with people I truly enjoy being around, ideally doing more wholesome things. Think karaoke, board games, or sports instead of hitting the bars.

The stronger goal here involves the ‘social crutch’ that I mentioned earlier. For 2019, I’m planning the hard goal of not drinking once I’m back in school. I’m incredibly impressed with friends who do this and don’t abstain from social environments (i.e. bars / clubs), so I don’t plan on cutting those out entirely. However, I think that cutting back on alcohol intake will help me understand myself better, and allow me to turn my ‘social self on/off without the need of a drink’, as a good friend once said.

(2) Starting a business

I’ve been committed to tech for the past few years, but only this past year did I realize that building something (entrepreneurship) was what most excited me. I’ve been grateful for a few opportunities this past year that have primed me for that path, such as getting into the Next 36 and joining Dorm Room Fund as a marketing partner.

The fact is, I’ve never started a business that has been revenue-generating. In fact, from failed attempts I don’t even think I’ve had a single user. Regardless of how much I might think I know about tech and startups, this is a hurdle I really want to climb to see what it’s really like to be an entrepreneur, from day one.

Hence, the soft goal for the 2019 is to start a business that is revenue-generating. Not contracting, or a strictly-services business (i.e. moving lawn), although that is already more than I’ve done. Since early October, I’ve done user research + launched a pilot for a venture that is coming to a close. I want to focus the majority of my energy on scaling it in the New Year and making it a profitable business.

The hard goal? Truth be told, and in an ideal world, I would not be working in an execution role after graduation. That includes sales, marketing, customer success, etc. for a company as small as 10-people to as large as Shopify (3k+ employees, public company). I’ve done it with Clearbit, and it was an incredible experience that I am forever thankful for. But entrepreneurship, as of now and going into 2019, is the goal. So my hard goal is to graduate and be running my own business full-time.

Conclusion

For any other students / new grads out there, you’ll relate when I say that every year seems drastically different from the last. It felt like yesterday I was in high school, let alone starting university and now into what is essentially my last semester. Everything from my interests, friend groups, and even my hair has changed over the last few years. It can be overwhelming and hard to keep up.

I find solace knowing that my goals will always change. That’s understandable, I’m human. What needs to stay the same is my ability to constantly question my goals, set milestones to achieving them, and be intentional with what I’m learning and why I’m doing what I’m doing. As long as that’s my mindset, I can’t to see what 2019 brings.

Contract work

My first contract role with the Turnstyle Solutions crew (now  Yelp WiFi )

My first contract role with the Turnstyle Solutions crew (now Yelp WiFi)

College can be a stressful time for a number of reasons. For starters, the endless flow of information is a plus, but the similar flow of assignments is a drawback. Beyond the classroom, there’s the responsibility of extra-curricular activities, sustaining a social life, and finding a job.

Jobs can be tricky, and in college, usually fall into the realm of ‘I don’t like it, but hey, it makes money’. Read: cashiers, waiters, etc. Don’t get me wrong, I have a lot of respect for those jobs and for the people who take them. However, I think there’s another category for jobs, which goes more like ‘I like the work and it makes me money’.

Contract work is a great way for students to dive into what they’re interested in, learn new skills, and most importantly, make some extra cash. In this post, I’ll walk through my experience with contract work, and tips I’d have for getting into it.

Marketing… Yeah that sounds cool!

Wrapping up my first internship, I realized that as cool as sales was, I was more excited by marketing. The only issue was that I knew nothing about it. This introduces the paradox of job hunting — they’re looking for people with experience, I don’t have any experience, but I need experience to get a job.

The first step I took to become prepared for a marketing role was to start reading up on it. Like with other skills (programming, design, etc), a lot of the content is available online (usually for free) that can help you break into that career path. Although I’d recommend anyone interested in marketing start here, I personally read a ton of posts on HubSpot and listened to Neil Patel (SEO) podcasts.

The plot twist? A lot of that information (and to be frank, some of my earlier posts on this blog) wasn’t very effective. It wouldn’t help me kill it in a marketing role, or even have a thorough understanding of that skill, whether it be email marketing, SEO, etc. What it did give me was a foundation — a basic understanding of that field, and a list of questions I could ask that would show that I was (a) genuinely interested in it and (b) eager to learn.

As I mentioned, this parallels a lot of different paths. If I was really interested in learning how to code, FreeCodeCamp and Codeacademy are both incredible resources. Odds are I won’t become a good developer through either, but it’ll give me a head start on knowing what to learn. The same goes for other jobs that build off a skill set, like Design.

Hit me with your best shot!

With a basic skill marketing skill set, I set out to find my first job. As many new grads will notice, there aren’t many roles out there that require “0 years experience and a smile”, even if you have a genuine interest in the job. The difference-maker is proving to the hiring manager that, despite your lack of experience, you’ll pick things up quickly. This is perfect for most ‘junior’ roles where the work doesn’t really require you have done it before.

My first contract gig in marketing came through Turnstyle Solutions (now Yelp WiFi). It was a fluke really — I was at a hackathon in Toronto (didn’t know how to code), and I reached out on their website for a demo account so I could help my team use their product in our hack. The ‘demo request’ went to someone on their Customer Success team, who was actually a Western University grad.

Where to go from there? Well, I had to be a little ambitious and flaunt my (limited) marketing knowledge. I mentioned in the reply to him that I had some background in email marketing and user acquisition, and I’d love to chat with someone on their team to show what value I could bring.

Note: The “I have background in X and want to chat with someone to see how if I can add value” is a fool-proof approach. Even if you definitely can’t, they’ll be willing to take a call with you in most cases.

I ended up getting an intro to their VP Marketing (now a great mentor of mine), and took a call to learn about their marketing efforts. Looking back, he could probably guess I had no clue what I was doing, but he could see that I wanted to learn. So he took me on as a contractor, where I’d get paid $20/hr for a few hours a week to help with their marketing.

Note: Experience is rarely a requirement if you’re looking for roles as a student. They know you have no full-time experience, and are typically open to helping you out if you’re driven.

Not your typical retail job

At this point, it’s worth noting that I wasn’t making an incredible amount of cash. I was, however, getting tangible experience in something I was interested in, AND I could do it from the comfort of my room (on my own schedule), since the work was remote and based on what I delivered (outcomes). That’s another beauty of contract work; in many cases, you’re not tied to a schedule, so if you want to wake up at 2pm and work until 10pm, as long as the work is done for the next morning, you’re golden.

Throughout this time, I also want to stress that I was still learning. There were a lot of tasks I got that I didn’t know how to do, so I spent a lot of time digging on the web and reaching out to people I thought might be able to help. The latter is amazing for finding mentors in your space, or even new jobs. Look at the two questions below:

“Hey I’m interested in marketing and want to learn more about it, can we chat?”

“Hey I’m doing email marketing for XYZ Company, can I see how your company tackles it?”

This works especially well for marketers, but imagine the same question for a designer or developer? I.e. “I’m putting together a branding guideline for XYZ Company, would love to see how you did yours” or “I’m developing a mobile app for XYZ Company, curious how you guys tackled it”.

With a bit of experience and a growing skill set, I stumbled upon my next contract job a few months later, and have kept up with part-time gigs since. Contract work initially helped me splurge on a meal out once a week, but after gaining experience and a portfolio, now helps me pay for trips and school fees.

Where do I start?

If you’re interested in doing contract work for a specific skill, try the same approach of (1) learning about the role (2) reaching out to people to see how they do it (3) offering your services. Even if you don’t have a specific skill, you can try sites like Upwork to get some solid paid work — whether it’s testing an app or conducting Google searches. For obvious reasons I’d recommend the former approach of targeting a skill, but whatever floats your boat.

A couple of things I’ve learned over my time doing contract work:

Communicate frequently. In most roles, you’ll be taken on as a remote employee, which means you won’t be in the office and your work is project-based. The former means you’ll miss a lot of context on projects that happen in casual conversation, and the latter means that you can’t ask questions or give updates on-the-fly. It helps to set check-ins with your manager at a certain time every week, and don’t be afraid to ask questions if you’re unclear on a task.

Give specific value. In the initial outreach, and throughout the contract, it may be tempting to ask for ‘general’ work related to your skill set. I.e. “Can I help with marketing”. For a lot of companies, being a generalist is fine if you’re a full-time employee, but they hire contract workers for specific purposes. So even in the initial outreach, saying “Can I help with your email marketing strategy” or “Can I help with the design of your homepage” is a lot better than “Can I help with marketing or design”.

Learn constantly. As a student, contract work is (should) not be seen solely as a source of income. It’s an opportunity to sharpen your skills in a specific field, work your way up to bigger (and higher paying) roles, and eventually launch your full-time career in that area. If you’re doing work that is repetitive, that might be a red flag where you should ask for new tasks, or better yet, think of new skills you want to learn and tasks at the company that involve that. For some of my earlier roles, that meant doing solid work in their CRM (more repetitive) and asking to help improve their SEO strategy (new waters). That helped me broaden my skill set to include SEO, and have tangible projects to practice on.

Conclusion

Clearly there are professions that don’t allow for contract work; if you want to go to med school, any ‘contract doctor’ role is probably sketchy and might get you arrested. But for work in tech (and a number of other fields), contract work is a great way to make money, gain new skills, and prepare yourself for full-time work, all while being in school and in the comfort of your home!

Finding your dream job

Action shot of the Clearbit sales team and I at Base CRM’s annual conference.

Action shot of the Clearbit sales team and I at Base CRM’s annual conference.

Needless to say, the college environment and the work environment are drastically different. They both have their pros and cons — for the former, I have a lot of free time, a predictable schedule, and I’m surrounded by people at a similar stage of life as me. The latter has its perks too — the work is more engaging, I have a consistent source of income, and there are a ton of people to learn from.

Chatting with friends who are also wrapping up their final year, the conversation varies. Most people fall into one of the following buckets:

  • Signed a full-time offer / committed to grad school, enjoying the year

  • Know what they want to do, but still looking for full-time work / applying to schools

  • Not sure what they want to do, aren’t sure where to start

I’ve written a fair amount about finding internships and succeeding in the workplace, but the tl;dr is that it all comes down to finding what you’re both interested in and good at (usually correlated). In this post, I want to dive into how I found my passion for technology and marketing, what questions I needed to answer along the way, and what role I think is the best for new grads.

Dazed and confused

First year was a bit of a mess. Trying to adjust to school work and a new social environment is hard enough, without everyone stressing about finding jobs and being the best at whatever you’re interested in. My older brother had just graduated from Western, and the friends he introduced me to, who had done the business program (Ivey), were committed to paths in finance. You get to wear a suit, make lots of money, and work in ‘capital markets’, so that had to be pretty sick, right?

The first piece of advice I received and still stick to today, is that you need to dive deep into whatever you’re interested in. It’s not enough for me to say “yeah I think finance is cool”, without having ever spoken to anyone working in the industry, learned any of the material, or discovered whether I’m good at it. The sad reality is that a lot of people never make it past the ‘interest’ stage; I could have gone through all 4 years of college being ‘interested’ in a variety of roles, but when it comes to getting a job, I would have been unqualified for them, and more importantly, would be unsure which path I wanted to commit to.

So following this logic, I started to dive into finance. I read Mergers & Inquisitions to learn about the work and lifestyle, talked to older friends who had worked in finance, and started the (in)famous Breaking Into Wall Street prep course for future financiers. After months of digging and figuring out…

Well actually, scratch that. It didn’t take long at all. In about 3 weeks, I realized some key points:

  • Finance was cool, but I wasn’t really interested in how the markets worked

  • The work (at an early stage of your career) was dry and repetitive

  • The lifestyle involved gruelling hours and being constantly on-the-clock

Keep in mind, this is my personal view of finance careers. I have a ton of friends going down that path, many of whom are genuinely interested in finance, and I commend them for it. It’s an amazing career for many people. Just not for me.

Tech? But I can’t code…

Back to square one, I had to do some deep thinking to figure out what I was really interested in. A lot of my friends told me about management consulting; a job where you get to solve problems, work in different industries, and travel! It sounded glamorous, and a pretty great fit for me. Most importantly, it would ‘help me figure out what I wanted to do’.

There were two small issues with this: first, if I was in first year, I had at least 3-4 years to figure out what I wanted to do, by trying different roles and diving into my interests. It didn’t make sense to commit (that early) to a job path that would eventually help me answer those questions. Second, they typically only hired 3rd year business students for summer internships, so I had to do something in the meantime, right?

Hitting the career fair at Western, I met a recruiter from a large telecommunications company. I was bright-eyed and eager to learn, so I asked them about their internship program. Their response:

“Love your enthusiasm, but we only hire 3rd Year students in the Ivey HBA program”

Great, well that wasn’t helpful. I had plans for Ivey but still had a ways to go. After talking to a variety of firms at the fair, I didn’t have too many leads to run with. Returning back to residence, I realized I signed up for London Tech Fest — a night of free food and informational booths from tech companies. I couldn’t find anyone to go with, so I hopped on the bus solo to get to the venue.

At the fair, there was a green booth with a familiar name: Shopify Plus. I had heard about Shopify before, and though it was a pretty cool place to work. Unfortunately, I wasn’t in engineering (or even business), and didn’t think I had much of a shot. So I walked up to the recruiter, and tried to think of a way to impress him. The conversation went something like this:

Me: “Hey I’d love to work for Shopify, but I’m only in first year and I’m not in business”

Him: “Why would that be an issue?”

Me: “Well I went to a career fair today, and (telecommunications company) said they would only hire 3rd year business students”

Him: “Screw (telecommunications company), we do things differently here”

In a matter of minutes, I was already a big fan of Shopify — they didn’t abide by the status quo. During our short chat, I kept telling him how I wanted a role where I could hustle hard and do work that mattered. He gave me his card, and said to reach out about a sales internship.

Naturally, I was still a little shocked that my limited education wasn’t a barrier. So I asked if I should learn how to code. He told me that ‘tech’ companies don’t just hire engineers — they need salespeople, marketers, customer success experts, and a ton of other non-technical roles to grow and succeed. These people should know about the product, but they don’t need to know how to code. So I ran with it.

Sales: the ultimate launchpad

Fast forward a few weeks of interviewing, I got the offer to join the Shopify Plus team for Summer 2016 as a sales intern. Keep in mind, during this process I was never asked for my transcripts or GPA. I learned later on that those things are a filter for ability, but don’t predict how you will perform in the workplace. Most small to mid-sized tech companies don’t care about your major or grades, they just want to know if you can do the job well.

The interview process was challenging, in that I didn’t really know what to expect. I read up a ton about Shopify as a company and their various products, along with reading up on sales and what it entailed. I reached out to people working there to see what they had to say about a career in sales — here are some of the key points:

You’re a consultant, not a salesperson.

Wow, that got me excited. I was planning on doing consulting anyways, so imagine what this could do for me! In all seriousness, every rep I talked to stressed how important it was to understand the needs of the person you’re selling to (a lead), what their hesitations are, and how your solution might be a fit for them. Shoving products down someone’s throat doesn’t get you anywhere — in fact, it actually costs the company more if they leave (churn) soon after becoming a customer. The best salespeople help leads figure out what they want, and the leads sell themselves.

It takes perseverance, hustle, and creativity.

Sales is not a cushy job. You don’t have vague deliverables or layers of promotions before you actually get to do the job. From day 1, you’re learning to sell and getting direct contact with leads, soon after getting a quota that you need to hit. If you don’t hit the quota, you’ll be placed on an improvement plan and eventually fired. It’s the only job where there is no cap on the amount of effort you can put in — the more you sell, the more money you make and the better for the company. It’ll teach you how to hustle, get creative with your outreach, and hit your goals (your quota).

You’ll become an expert at controlling conversation.

My initial reaction to sales, like many people, was that it’s a sleazy profession that doesn’t involve many ‘hard’ skills — you basically just need to be good at persuading people. The reality is that it’s not that simple, especially when you have to convince the 50 year-old executive of a multi-million dollar enterprise that your product is worth their time of day. Most of my sales colleagues at Shopify Plus were under the age of 25, many of them fresh new grads. They sold to Drake, Tesla, Big Baller Brand, and Kylie Jenner. I can’t think of anywhere else where you’re the main point of contact to such incredible companies, let alone where you’re solely responsible for bringing them on as a customer. Knowing how to drive conservation, set deliverables, and get someone from “I don’t care” to “Take my money” is a magical process — and it’s called sales.

You’re working up from ground zero.

The best part about careers in sales is that there is really no ‘ideal path’ into it. Some of the best salespeople were psychology majors and never sold a day in their life. All entry-level sales positions, whether it’s at Google or a 10-person startup, will teach you how to sell and eventually turn you into a confident salesperson. There is NO pre-requisite, except an ability to think quickly and a willingness to learn fast and hustle hard.

The world is your oyster.

After learning how to sell, you can stay in sales and move up the chain to be a killer account executive, or move to management and run a full sales team. You can also make other transitions — people I know who started in sales have gone on to become successful entrepreneurs, marketers, product managers, and much more. Sales is the ultimate toolkit / skillset that will enable you to succeed in a number of career paths.

Okay — Where do I start?

There are hundreds of tech companies that are hiring new grads as salespeople. All it takes is preparation to learn the sales basics and an open ear from the hiring manager. I saw this gap over my time in tech, both in Toronto and in San Francisco.

That’s why I’m starting a program to get more new grads into tech sales. It involves a 3-week bootcamp on learning how to sell, written by current sales professionals, and then we refer you to a variety of companies — everything from 10-person startups to UberEats — to interview and get a sales job.

If you’re graduating in April 2019 and are still looking for full-time work / aren’t sure where to start, or know someone who is, shoot me a message so I can get you involved in the next cohort.

Regret

I can’t regret a burger right? Especially In-N-Out?!

I can’t regret a burger right? Especially In-N-Out?!

I wrapped up my last post mentioning how I’ve made a lot of bad decisions. The typical feeling associated with these decisions is regret. The question I’ve been thinking a lot about lately is how to discern between the different types of regret I can feel, and what is the best way to handle it.

Revisiting a decision

A key part about decision-making is that I have a certain amount of information available to me at the time of the decision. For example, I could bet on a specific stock if I’m impressed with what the vision and current progress of the respective company is.

After making this decision, a number of things could happen:

  • The stock skyrockets, in line with my assumptions

  • The stock skyrockets, in ways I could not have foreseen

  • The stock plummets, contrary to my hypothesis

  • The stock plummets, in ways I could not have foreseen

Whether the stock goes up or down, if it was unpredictable given the knowledge I had at the time, then I (should) feel confident that I made the right decision. In contrast, if the stock performs outside of my expectations, whether up or down, I can start to question whether the decision was a right one.

Revisiting that decision involves a frank discussion with myself about what I should / shouldn’t have known at the time of making the decision. As I mentioned in this post, if I put a good amount of thought and effort into picking a stock, that in itself should make me comfortable regardless of the outcome.

The challenge here is forcing myself to revisit decisions I make, regardless of the outcome. If the stock went up in ways I didn’t predict, the outcome is in line with what I want, so I won’t question whether the decision was a good one. Though realistically, that lack of questioning might lead me to make an even riskier decision down the road, using the same (probably flawed) line of thinking, that ends up hurting me a lot more.

Forceful re-evaluation

With those scenarios in mind, it’s clear that decisions can be bad ones if they are not revisited. However what makes me want to revisit a decision in the first place? Regret.

Regret is an emotion that is often sparked by the outcome of the decision, but can be associated with the decision itself and/or the outcome. I wouldn’t regret going to the gym unless I hurt myself, nor would I regret playing video games unless I had something pressing to do.

So I can accept that there will be decisions that I make in error; specifically where I don’t consider all the possible factors and end up choosing the wrong option. That’s life, and I’ll learn from those decisions.

What frustrates me the most, is feeling regret from decisions that I am / was very confident in making. Ones that I put an incredible amount of thought into, got insight from people I trusted, and gave it time to ensure I wasn’t making any impulse decisions.

This is what I would call ‘regret from outcome’. Leaving San Francisco is a primary example of this for me. I miss the work, the people, and (sometimes) the city, and that can make me wonder whether it was a regrettable decision. However, I’m still confident in the logic behind the decision and the process I went through to get there.

Handling regret

So what exactly should I do with ‘regret from outcome’? It’s purely emotional, and I can’t exactly logic myself out of it (trust me, I’ve tried). I’ve had it plague me in influential areas like my career and relationships, as well as everyday areas like eating and sleeping. This past weekend, I regretted the feeling of not eating a 2nd Big Mac, but it was the right decision (right? Right?!!).

There are a few strategies I’ve found that are especially influential here. The first is to really dive deep into why I’m feeling regret, what it stems from, and eliminate (if possible) any notion that the decision was the wrong one. This includes both journalling and talking to people I trust about a decision and all the feelings that accompany it.

The second is to think of the opposite emotion, and when I’ll be able to experience it again. For the Big Mac, there will be a day in the coming weeks (or less) where I exercise a significant amount and feel good about eating it. For careers, there will be another role that I’ll feel as passionately about, especially if it’s my own project.

The last strategy on my list to dealing with regret is to, well, feel it. Some days it’ll drain me to the point of not being able to function, constantly thinking about those emotions. There’s no point fighting this, or suppressing it via other mediums. In fact, distracting myself only makes it worst, as it just delays the (eventual) feeling that I’ll have. So the solution is to feel regret of outcome; watch TV, listen to sad Drake, eat some Cheetos and go to bed.

Conclusion

I read a significant amount about ‘hacking’ life — daily habits, stoicism, frameworks to implement, etc. At the end of the day, I’m still human, and there’s something reassuring in that. I’ll feel regret, just as everyone else does.

The key is to discern between ‘regret of decision’ and ‘regret of outcome’, have a concept of the future, while still being present when those emotions hit me. Is it harder than it sounds? Of course! But knowing it’s the logical way to deal with things is enough for me.

Principles & decision-making

Not exactly a ‘fork in the road’, but hopefully the fact that it’s original counts!

Not exactly a ‘fork in the road’, but hopefully the fact that it’s original counts!

Being back in a school environment has been phenomenal — it’s a space for learning, making strong relationships, and figuring life out. In catching up with friends, the conversation quickly shifts to jobs, career planning, and what seem like existential decisions.

I faced similar challenges when deciding to take a year off and work at Clearbit. I had concerns around being behind and missing my friends / family, both of which were valid at the time. Even currently, I struggle with decision-making (both career-related and not), but found strategies and frameworks to make it easier, which I’ll break down in this post.

Personal goals

In his book Principles, Ray Dalio explains how the decisions he made at his hedge fund (Bridgewater) were largely based on a series of statements that the company agreed to be aligned upon (principles). Everything from investment strategies to hiring policies needed to match the principles, and anything that didn’t match should be scrutinized.

For individuals, I see principles being tightly coupled with personal goals. They can involve career aspirations, but for me they include non-career pieces too. Here’s a rough idea of my principles:

1. Be constantly learning

This one is straightforward, but easy to overlook. Every job I’ve taken since coming to college has involved something that I didn’t know, and wanted to learn. In my earlier days with sales internships, it was strictly learning how to sell. Later, it evolved into understanding the full funnel (paid ads, email marketing, etc) and being data-driven (SQL, reporting).

This principle isn’t unique to jobs — while I’m guilty of taking some ‘bird’ courses or module (required) ones, a lot of my classes are ones that I have an intrinsic interest in. Outside of class, a huge component of this is reading. I love discussing my thoughts with friends and being willing to shift my viewpoint. It’s more of a mindset than anything, where I try to come into a conversation with the intention of truly understanding what someone is saying, and challenging them if I don’t agree.

2. Build a strong support system

This is more recently embraced principle, that I adopted mainly after returning from my year in SF. While college gave me a false impression that things were always looking up (internships, grades, etc), I soon realized that life is a combination of good and bad times. It can almost be seen like a portfolio; my work could be going well, while my relationships suffer. Or maybe they’re both in good places, but my physical / mental health is poor.

I believe the ultimate defence against these fluctuations is a strong support system. Friends, mentors, family that I can depend on when certain parts of life are getting me down. While they are all awesome, I rely on different people at different times. My mentors and friends that have similar mindsets career-wise are incredibly helpful when I’m lost in that regard, both for giving advice and being a soundboard for my thoughts. The same goes for school planning, physical / mental health, and handling relationships.

3. Surround myself with people smarter than me

Being wrong or making a mistake is one of the best things that can happen to me — it forces me to re-evaluate, understand what happened, and learn from it. This is especially powerful when I’m with people who are smarter than me, in a work environment but also in life. The former helps me understand how others react to failed projects, slow days, meeting expectations, and being overwhelmed. It’s incredibly helpful to get feedback on poor work when I have an immense amount of respect and admiration for the person I’m working for / with.

The latter is crucial to goal #1 (learning), but is more of an indirect catalyst. I have great friends that don’t challenge me, and sometimes that’s a good thing. But I also have others who will scrutinize my decisions (even when I don’t ask), which is a very powerful quality. Surrounding myself with these people keeps me on my toes, ensuring I have some level of reasoning behind what I’m doing.

4. Be financially independent

I’ll keep this one short, but it ties well into my goal of building something. I’ve heard great arguments around why a 9-5 job is like slavery, where you’re tied to the income given to you and the schedule set for you. I strive to go beyond this, by finding roles where I’m either financially independent or working towards it (i.e. learning skillsets to get there).

A much smaller component around this is budgeting and being fiscally responsible. This ties to decisions that maybe aren’t career-related, and are more dependent on my stage of life and my aspirations. I.e. getting a car (and what kind), taking trips, going out, etc.

5. Discover and refine my value system

The college environment is a double-edged sword when it comes to this one; on one hand, it gives me tons of free time to discover and refine my interests, but on another hand, it often gives me a viewpoint (i.e. through classes / professors) that I don’t need to challenge.

I find this to be one of the advantages of a liberal arts degree, as the classes I’m taking (philosophy, political science) dive into a more epistemological approach to course content. I.e. it’s not just memorization and regurgitation, but rather understanding what different perspectives yield, why they think that way, and developing a critical opinion on what I believe. Beyond the classroom, there are various areas I want to gain a deeper understanding of, like religion / faith and philanthropy.

Application to life

These goals / principles shape a large part of my decision-making, whether at a small or large scale. For the former, it’s everything from cooking more in the week (goal #4) to taking classes that are more challenging / interesting (goals #1 and #5). For the latter, it meant deferring a full year of school so I could learn a ton, be around smart people, and build a skillset (how companies work) to get me closer to financial independence.

Opportunity cost

With an understanding of principles / personal goals, I find existential crises with choosing job paths & internships confusing. Calculating opportunity cost at face value is simple — the difference in salary, prestige, alignment with interests, etc. However, when I factor in my principles, my analysis reaches a new level.

For an imaginary example, choosing a full-time marketing role at Uber in San Francisco over being the first business hire at a promising startup in Toronto might seem like a no-brainer. For the former, the salary is higher, it’s more prestigious, etc. When factoring in my principles, the following thoughts might arise:

  • The majority of my support system (including family) is based in the Toronto area; keeping in contact will be challenging — Goal #2

  • I want to be learning as much as possible; a large company like Uber will provide a safe environment where I can’t (as easily) make mistakes, but it also means I won’t be able to learn from those mistakes, or try areas outside my role — Goal #1

  • Uber is a company that is already thousands of employees; while the salary is higher, it can be argued that learning how to build a company (Toronto) will lead to eventual financial independence faster than simply executing in a role — Goal #4

  • There are a ton of smart people in the Bay Area, and that environment will challenge me more than Toronto would — Goal #3, Goal #5

Is there a clear-cut answer here? Not with the information given, but it did make me think a lot more critically about why I’m choosing one role over the other, which I think is the real value to depending on a set of principles.

Conclusion

I’ve made plenty of bad decisions, and while I try my best to learn from them, it doesn’t change the fact that I made them. Sometimes the “what ifs” can be overwhelming — and if it was a poorly reasoned decision, it makes it all the worse. However, in a lot of cases, using this type of logic helps me either justify good decisions, or question bad ones. Principles, for me, are constantly evolving, and that’s a sign of growth and self-reflection more than anything.

All in all, I’m still 21 and most decisions won’t have much weight in the grand scheme of things. Career choices are far from being set in stone — even a commitment to tech can shift to finance after an MBA, or to being a developer after a bootcamp. Life decisions follow a similar mentality — friend groups will change, value systems will shift, but as long as I’m staying in the present and being accepting + forward-looking for life, the world is my oyster.

A year of life

Company trip to Mexico — a great highlight of the year, and a solid cover photo! 

Company trip to Mexico — a great highlight of the year, and a solid cover photo! 

A large part of me really wanted to name this post "A year in the valley", but I don't think it would do it justice. This year has in many ways been the best and worst of my life, and little of that is connected directly to the idea of being in The Valley, or at least what I imagined it would be like when I wrote this post. 

This will be a lengthy one, and is you're mainly curious about the outcomes, then skip to "An Inflection Point". Otherwise come along for the ride, it's a bumpy one! 

A quick timeline 

I moved to San Francisco in September 2017, right after completing a 4-month internship at Shopify Plus. I was 20 years old doing Growth at a Silicon Valley startup, making an amazing salary and having absolute freedom in what I could do. There was no one here to judge my decisions, there was no precedence on what I should be doing or how I should approach the year. The world was my oyster. 

I also didn't have a strong support system. My family and all my friends were thousands of miles away in a different country, 3 hours ahead. I'd get home from work and realize everyone was already asleep. I'd see the college fun I was missing out on via Instagram (which I no longer use), and the events I couldn't make. While everyone was figuring out life, I had exactly what I wanted (and supposedly, had it figured out), but I wasn't happy. 

The first 3-4 months in San Francisco were rough. I tried hard to make friends here, and find something that gave me value beyond the workplace. I hopped on all the dating apps — Tinder Plus, Bumble, Coffee Meets Bagel (you'd be surprised how many there are) — with hopes of finding someone that would make San Francisco feel a little more like home. I also developed a lot of poor habits and an unsustainable lifestyle, trying to drown myself in work and partying excessively when given the opportunity. 

Things I used to love — gaming, working out, even tech — started to lose value. I wasn't performing to the level I wanted to at work, and not being 21 meant it was hard to participate in the events and social activities that my older friends enjoyed. To sum things up, it's a gut-wrenching feeling to have everything you always wanted and not be happy. 

An inflection point

Eventually, thanks to some very generous introductions and a few chance encounters, I started to get used to San Francisco. Around the start of the new year, I felt like I had a better understanding of my position at work, found a solid friend group of people my age, a girlfriend, and started to warm up to the city. 

It was around this time that I started to give more thought to long-term goals; realizing that at 21, it's highly unlikely that I was (A) at the top of my game and (B) in a role that's perfect for me. So I started to focus a lot more on the goal I knew (starting a company) and the goals I didn't know (what else do I want out of life). 

For the former, that meant reaching out to early-stage founders and others who had scaled successfully, to understand the validation process and what exactly went into building a good business. There are a few things I learned from these individuals, which definitely don't apply to anyone, but are points I'm sticking to in the coming months to building a product:

(1) Validation

If I have a hunch that X product will solve Y problem, I should be validating it. Emailing / calling people you think have that problem, talking to them about their business and how it operates, and learn whether this is something that will actually make a difference in their lives. There is a caveat to this, in that I should validate until I am confident & comfortable committing to this project. For me, that could mean having a large enough sample size of interested users, commitment to pay (or already paying), and a good understanding of what the MVP will look like.  

(2) Scaling 

I should be able to do the majority of the work at a very early stage. I shouldn't be hiring marketers, engineers, designers, or even finding a co-founder until I'm past the validation stage. A similar story for raising capital — yes it's sexy, and lets me have a salary + office, but those factors aren't necessary to success. I don't need a TechCrunch article before having a paying customer. I should be scaling slowly, with confidence, and building a good business. 

(3) Customer Development 

If I am able to secure a few people who are interested in trying my solution to their problems, it is crucial to be very committed to their success. That means expressing constant gratitude and being diligent about timelines and features. They should know that it's going to be a rocky experience this early on, but they should also know that I will deliver on the $$ they pay me. I don't agree with "selling the idea" — I should be able to give them value where it's due, and be accountable to these early users. 

(4) Technical Acumen

I've read the Ryan Hoover post that you don't need to be technical to start a business. I'm also following the various products that allow you build a no-code MVP, or outsource your development while still having full control. They are all valid, and in many cases I'm a huge fan of what they've built, but they're not something I personally subscribe to. At the moment, I'm largely non-technical, but plan to dive deeper into coding this coming year. I believe I need to be somewhat technical to successfully run a business — whether it's building 10% of the MVP, clearly outlining what needs to be built to early hires, or explaining to my first customer what's going wrong when the MVP (inevitably) crashes. I don't want to handle the business side, I want to build a business. 

Cali or bust? 

There are a lot of benefits to being in San Francisco, that I had an idea of when I wrote this post, but couldn't fully grasp. The concentration of tech talent, and the communities between them, is a game-changer. This happens both at an earlier stage, where new grads and young professionals are enticed by an environment with a high concentration of companies, job opportunities, and mentors, as well as at a later stage, where finding a CTO that has scaled an engineering team from 5-25+ in a specific industry doesn't involve a worldwide search. 

This latter point is especially fascinating to me, and a huge win to San Francisco. There's no doubt that you can start a company almost anywhere, and while growing it may be easier in The Valley, it's not a necessity. However, at a later stage, I find it hard to argue with the logic that being located in The Valley is a significant advantage. Finding people to scale your org is one thing, but it's another altogether to find someone who has done it before, and even more so if you're particular about the industry / space you play within. 

The weather is also a huge benefit. I'm not ashamed to say that I laughed when I saw it snowing in April in Canada, while it's 15C - 20C year-round in San Francisco. It rarely rains, making the climate quite desirable. At the same time, you also miss out on the passing of seasons, which is highly associated with the passing of time, the various activities that are native to a specific season, and the different fashions that come with them, respectively. I don't miss -30C weather and multiple feet of snow, but there's something unifying about growing up in that environment. 

The salary conversation is a difficult one. Yes, it's way more expensive to live in San Francisco than other cities. I paid for a single bedroom (3 people, 1 bath) in San Francisco what would get me a comfortable one bedroom condo in Toronto. With that being said, salaries are also inflated to give you a reasonable standard of living, so in my opinion it balances out. 

All-in-all, I'm not a fan of the "Cali or bust" mentality, unless it's well thought out. Do I need to be in San Francisco as an early-stage founder? Not really, but it might help. If I wanted to be an Associate Product Manager at a mid-sized tech company, should I be here? Probably a good idea. 

Becoming a better marketer 

I've mentioned in past posts as well that I had an irrationally high level of confidence going into my role at Clearbit. For some reason I thought that a string of internships and contract work made me suitable to be solely responsible for driving the growth of a product. After many failures, and a lot of team support, I'm proud to say that I've learned a ton about being a competent marketer. 

First, my ability to write copy has improved significantly. In school, I was used to essay-format, where structured introductions, content, and a specific type of prose was looked upon favourably. That's not the case in marketing — get your point across quickly, use a tone that matches your company's brand (took a while to learn, very key), and ensures your call-to-actions are clear. When I first launched campaigns at Clearbit, the copy required multiple rounds of review and performed poorly. Upon leaving, some campaigns I launched had 2x to 3x higher click-rates and higher conversion rates. Long story short (pun intended) — copy matters! 

The other area I improved significantly in was analytics. Last summer, I worked on the Rev Ops team at Shopify Plus, having to learn SQL, how to attribute marketing spend, and calculate sales performance. I was thrown into the deep end at Clearbit when I was tasked with developing a dashboard that reflected all these stats — except it hadn't really been done before. More than SQL (although those skills have improved), I learned the importance of diving into the logic behind analysis and dashboarding. Yes, I can explain the tables that I pulled from to calculate churn. But what is generating those numbers? Are tags firing correctly when someone signs up? Or should we revisit how we set up the tracking? Questions that are extremely important at a startup, and a general approach that is useful at all levels. 

Lastly, I learned the importance of setting expectations and working with teams. This is universal to anyone in the work force, but not something I grasped when completing internships. With a short-time internship, the timeline is short — the first month is spent ramping up, 1-2 additional months of gauging expectations and trying things out, then (maybe) a month of executing. With a full year, I hit that last stage by December, and had an additional (8) months to make an impact. 

What this did was force me to have candid conversations with my boss and team about what I was able to do, what I was interested in doing, and what I wanted to learn. Balancing these factors was a huge focus for me, as it would allow me to get the most out of my internship — learning a ton, but also having something to show for it. I also learned how to work with partnerships, a beast that requires a lot of attention, cooperation, and accountability. My work with Zapier started as a simple conversation on how to promote our app, and a year later, evolved into a guest post on their blog (1M+ readership) featuring Clearbit and a happy customer. 

Managing life

While my professional development was great, the biggest win from this past year was my personal development. I took the college environment for granted — you're surrounded by people your age who are trying to figure themselves out, and by consequence (either artificial or not), you're in an environment where doing so is encouraged. 

The workplace is a very different environment. While my colleagues were very fun to be around, they were largely in their late 20s or early 30s, meaning discussions I was just beginning to have (i.e. perspectives on life, hobbies, etc) were ones they've been having for the last decade. While this stalled me for a while, I eventually decided to take this problem of self-actualization by the horns. 

I quickly realized that career aspirations, which had an incredible focus in college, were only a part of life. Over the next 10 years, my career will progress (at varying paces), and that happens almost automatically. What doesn't happen automatically is personal development; understanding my value system, and what intrinsically motivates me and satisfies me.

Beyond that, there's the question of lifestyle and routine. How I handle stress and the ebs & flows of my relationships (both related to work and not) can make or break my entire day. Understanding when I'm most productive, how to plan out my day, and know when to call it a night is crucial to my mental & physical health.  

Another big part of self-actualization is building a strong support system, something I didn't have when I first moved to San Francisco. I started to really contemplate who I enjoyed spending time with, how I make time for those people, and how I support them in their lives — both career related and not. There's only so much time in the day, and I'd rather have 10 good friends I can depend on than 30 acquaintances I occasionally spend time with. 

I don't have all the answers to these questions, and that's something I'm content with. After all, I'm only 21, and it's more important to ensure I keep thinking about these questions instead of worrying about whether I have the answers to them. Needless to say, I'm far more concerned about how I manage my life over career progression. 

Conclusion 

This year has been an unforgettable one, and I hope this lengthy post conveys some of my thoughts & emotions. On one hand, it was enriching, eye-opening, and helped me mature a lot. On another, it was isolating, depressing, and made me question a lot of my motivations. Regardless, a number of people made this year what it was, and I want to end this post by highlighting them. 

First, it's obvious that none of this would have been possible without the Clearbit crew, led by the ever-inspiring Alex MacCaw (CEO). It's one thing to take a chance on someone. It's another to hire someone in a different country, off a Tweet, with limited experience and no guaranteed payout. Alex, I can't thank you enough for hiring me and making this year possible.

I also want to give a huge shout-out to my boss, Matt, who was not only an amazing manager, but also a phenomenal mentor and friend. I came in as an overly-eager intern, with high expectations of what I would do, and you took that in stride — helping me ramp up, become a part of the team, learn what I wanted, and make an impact on this incredible organization. 

My parents, and the amount they support me regardless of the decisions I make, are the foundation to my life and I can't thank them enough for that. For any 1st gen or 2nd gen readers, you'll relate to the fact that my parents grinded insanely hard to allow me to access these opportunities, hold myself to a higher standard, and strive for a life that is 10x what I currently have. Money and achievement are not the only goals, but I feel it's not doing them justice to settle for mediocrity, when they overcame all the odds to give me a middle-class upbringing in a first world country. 

To my friends, both new and old, I want to thank you for supporting me throughout the year. There are obvious examples of this, like hanging with me in a city I wasn't familiar with and making me feel welcome, and less obvious examples, like sporadic check-ins that helped me get through some tough times and challenging decisions. I can't wait to see how we grow together and the things we'll accomplish, all while having people to spend it with. 

Lastly, I want to thank myself. I'm a meticulous planner, and there were times this past year where every week seemed drastically different and unexpected. Times where I thought my productivity at work was dismal, I was treating people poorly, and lacked any concept of a horizon. But perseverance is key — it's what makes us stronger, happier, and seek meaning beyond the present. 

I look forward to the coming year at school (Huron College) and what it brings. I can't wait to dive deeper into my interests, learn to be a better coder, and launch my own company. To all the surprises, disappointments, and unexpected outcomes — I'm ready for you. 

City life

View of San Francisco from the LinkedIn office (thanks Jay) 

View of San Francisco from the LinkedIn office (thanks Jay) 

Traveling is often seen as an opportunity to see a new city — visit tourist attractions, try new foods, and overall just to relax. After all, traveling is often associated with vacations, and the last thing you should be doing is working. 

Over the past year, I've had the privilege of visiting a number of cities for the first time, across North America. Some were in the Pacific Northwest, like Vancouver and Portland, others on the West Coast, like San Francisco and Los Angeles, and a handful on the East Coast, like Boston and New York (where I'm currently writing this post). 

In a lot of ways, I succumbed to the typical approach of visiting a city. I had a list of places to go and restaurants to try, making it a priority to check them off my list. At the same time, I had an urge to not just see the city, but experience the city — to understand the people that live there, their attitude towards life, and how the city affects that. 

In this post, I'll be diving into the differences I noticed in the cities I visited, how I think it affects one's lifestyle, and what that means for me moving forward. 

Physical factors 

There are some stark differences between North American cities that even Captain Obvious would laugh at. It snows on the East Coast, rains heavily in the Pacific Northwest, and has a temperament climate on the West Coast. 

This affects you depending on what you're looking for in a city. If you hate the snow, then maybe the East Coast isn't the best fit. If you don't really care for nature, the Pacific Northwest won't have the same allure. These are observations that are easy to make. 

I found physical factors to have a reasonable impact on where I want to live, but less so than other people. Growing up in Canada, I'm used to the snow, extreme weather (hot/cold), and a bit of nature to enjoy. Moving to San Francisco and having the same weather year-round was odd and also wasn't necessarily a good / bad thing. With that being said, I'm sure someone who lived in LA and moved to Toronto would be shocked by the snow, and will probably either love it or hate it. 

The reason being, that physical factors dictate a lot beyond what the city looks like. In Toronto, there's winter style, summer style, etc. In San Francisco, that's really not the case. From another angle, there's a changing of seasons in Toronto, and that helps you identify with the passing of time, whereas in San Francisco, it looks the same year-round, so it can be hard to tell. 

Transportation 

There are also observations that will take some more thought, like analyzing how the city is built. I rented a car when I visited Los Angeles a month ago, and it was a decision I'm glad I made. It can be 45-60 minutes from Venice Beach to Koreatown, and similar distances to the downtown, Santa Monica, and other areas of the Greater LA area. 

The lifestyles of people who live in LA are impacted by this factor. Compared to New York, where the entire city is accessible by 20-30 minutes on the subway, people I met in LA had to think more deeply about their plans and friend groups. If you live on the Upper West side in NYC, grabbing drinks with a friend in Manhattan doesn't take a lot of effort. For someone in LA, there are a ton of factors — is there parking where I'm going? How is traffic? Will I drink too much to drive? How badly do I really want to see this friend? 

Chatting with a friend in NYC who moved from LA, these were all valid considerations. It led to a smaller friend group, largely based by where in LA you lived. In New York, that isn't as much of a concern, so your friends are spread out across the city — and you typically have a lot more of them. 

Now contrast that to San Francisco, where the subway (BART) only runs through one part of the city, and Uber is necessary to get anywhere else. I never go and visit my friends in South Bay (San Jose, Mountain View, etc), and rarely go to the West side of the city (Outer Richmond, Sunset, etc). There are distinct communities based on where you live, and a divide between SF proper and the surrounding Bay Area. This changes based on the city you live in, and affects how large your friend group is and what you do with them. 

Attitude

The biggest difference I've found between cities is the attitude that people have — towards work, friends, and really just their general outlook on life. In LA, the vibe was pretty laid back, with people working hard but taking time to enjoy the weather, restaurants, and shopping. Conversations with friends here showed me that there was rarely one hard focus (i.e. work, specific interest, etc), and things definitely moved a little slower. 

There's nothing inherently wrong with this, but it made me wonder what type of person I'd be (or need to be) to live in LA. Draw a contrast to New York, where most people I met were laser-focused on a specific goal or interest. A friend working in education technology wasn't distracted by what else the city had to offer, instead spending 90% of his time on work or other endeavours surrounding that interest. The same went for people in finance, advertising, etc. It's a city that moves fast, and you either know yourself before going in, or the city dictates it for you. People I met weren't necessarily happy with their current lifestyles, but they knew their goals and why they were doing what they were doing. 

Now a final contrast to San Francisco; I found that despite all the stigma around brutal work culture, the city itself upholds a good work-life balance. People are larger companies (Google, Facebook, etc) commute from SF to South Bay (~ 1hr), putting in reasonable hours from Monday to Thursday, and working remotely (from the city) on Fridays. Weekends are an open window — trips to Tahoe, day drinking at Dolores Park, and lining up for brunch on Sundays. Everyone works hard, and stays accountable to their projects, but I found SF sits in the middle of the spectrum between LA and NYC — there isn't a laser-focused mentality, but there also is a fair amount of direction around what you're doing. 

Conclusion 

So what's the verdict — what is the best city to live in? I think the answer is: it depends, largely on your value system and what your goals are. If you're young, very interested in a specific area, and want to commit to that, maybe NYC is the place for you. If you're more interested in personal development and a more chill culture, then LA could be a better fit. And if you're... Well, if you're in tech and want to maximize that, then SF is a solid choice. 

Unfortunately I didn't spend enough time in Portland or Boston to have a solid opinion on them, but I know they both have their unique allure and culture that you'd have to experience to understand. Boston is flushed with post-secondary institutions, has distinct areas like New York (Cambridge, South Boston, downtown), but to a smaller scale. I didn't feel it being very fast-paced, but the industries (healthcare, tech) that thrived there fed into the vibe. Portland is known for craft breweries, nature, and a hipster culture, but I couldn't really place the work culture or general vibe. 

There are a bunch of externalities to this that I didn't mention, like if you value being close to home, have a significant other, etc. Personally, I'm not sure where I'll end up after graduation. But I'm glad I visited a bunch of different cities to see what they're really like, and chatted with people living there, as it really gives you a better sense of what that city is like (and if it's a good fit for you).

Leaving mobile

phone.jpg

One of the distinct things I remember about first moving to San Francisco is the isolation. New city, new job, and your closest friends are thousands of miles away. After a few weeks, I finally started to get into a groove — work became more routine, it didn't ruin my day when a homeless person yelled at me, and I even stopped converting USD to CAD! Social apps, however, still made me feel like I was missing out on something. 

There were some evenings at the office where I'd get a Snap from someone at school, raving about how amazing a house party was. I'd stroll through Instagram, see smiling familiar faces, and wonder why I wasn't having as much fun as they were. Even Facebook gave me a bit of FOMO, the number of times I'd be invited to an event just to realize it was in a different country. 

I've since moved past that, but a big part of that shift in mindset was understanding what matters most to me. People, activities, things that I genuinely enjoy and don't just do for the sake of doing them. For once in my life, there was no real 'norm' of what I should be doing, no obligations to social events, or similar lifestyles that I could relate to. 

The role of mobile

So how does this involve mobile? I started to notice and question some trends in my behaviour. For example, I'm guilty of taking Insta stories of food, cool events I'm at, and even the periodic post with a relatively witty caption. The question I couldn't answer to that, is why do I do it? 

It's a known fact that humans enjoy social validation. A lot of the things we do, and talk about, make us feel better about ourselves when someone notices and comments. Social media makes it even easier to get this, since it takes little effort to pull out your phone, grab a photo, and throw together a caption to share with your XXX followers/friends. 

I'm a little ashamed to say it, but it's hard for me to do something I genuinely enjoy — whether that's eating good food, working out, etc — without feeling the need to share it online. This is a little frightening, because it really made me question why I did those things in the first place; was it for the activity itself, or the validation I got from sharing it? 

The other aspect to social media that has recently unnerved me is the idea of connectivity. I used to find it absurd when people would "quit" social media for a defined period of time, leaving their phone number if you really needed to get in touch. Now I do see the allure: who really wants to talk to you? 

Sure, it's easy to be swiping through hundreds of Insta stories and send a message to someone about something they're doing, or comment on a post while you're aimlessly scrolling through Facebook, but what level of connectivity does that really show? 

For me, I thought more about who I really enjoy spending time with. Who would I message out of the blue, feel like something's missing if I haven't chatted with them in a while, or reach out to for advice and consolation for things happening in my life? Out of 3,500 friends on Facebook, is it optimistic to say 50 people fit that bill? 

It's a goal for me this year to start making meaningful relationships with people I care about. Talking on a regular basis, reaching out when I'm feeling off, and spending time with them when I can. I think that only happens when I limit other interactions, only doing things that I know I'll find satisfaction, happiness, and energy from. This led me to try an experiment that I hypothesize will help me get closer to that goal. 

Trying something new

Like any habit, it's hard to kick right off the bat. So my initial challenge was to delete the majority of social apps off my phone — Instagram, Facebook, Snapchat, etc. I left Messenger on there as a communication tool, but after a few days, the results are already noticeable. 

I don't feel like I'm missing out on as much as I was before. Sure, it does make bathroom breaks a little boring, but if I'm having eventful bathroom breaks, there's probably a bigger issue there... 

I also have less of an urge to check my phone. It's helping me be more focused when I'm at work, and actually be engaged in tasks or activities I'm doing, i.e. school work, watching a video, or even writing this post! 

As a closing note, I don't think social media is a bad thing. I don't plan on deleting Facebook or other mediums anytime soon, but I hope that this break from mobile apps will help me focus more on myself, personal development, and doing things I'm passionate about. I also imagine I'll feel less of the FOMO I used to, and that will help me be more present in the things I'm doing.

Have any of you tried leaving social media, or some variation of it? I'd love to hear what works for you, and what else I can try. 

Staying motivated

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I feel quite privileged to be able to write a post like this. Billions of people, many even within Western societies, hold responsibilities beyond what I could ever imagine having to deal with. I've seen countless posts for Father's Day that praise dads for persevering, having a deep rooted motivation to provide a better life for their children. I know my father reflects that, and I'm thankful for him everyday — that, to paraphrase Aziz Ansari, "My parents grinded so I didn't have to". 

Now with that being said, I'm far from being without responsibility. It's those circumstances that were overcome that heavily influence the goals I have today. Aspirations to not only attend college but do well in it, get a solid job in a respectable field, and take every advantage of the opportunity that my parents afforded me. 

I hope to outline my thought process around goals and motivations in this post, share some of the experiences I've had, and raise some questions to anyone reading. 

Finding goals 

I've written in past posts about the 'sprint VS marathon' mentality, and how a lot of my goals in previous years were very short-term and built around the herd mentality. You're judged by your academic success, so it should be a goal to achieve a good grade, whatever that takes. You're judged by your career readiness, especially for those who are inclined towards careers in business, so you're judged by the internships you get. This is a very reactionary approach to goal-setting, and one I fell into (and continue to fall into) too many times. 

Attached to this idea is what I would call 'expected goals'. If you are in a certain position, with certain opportunities, there is a bare minimum that you should be able to accomplish. If you're in business school, it isn't enough to get a job in business — that much is expected of you. After all, if your parents paid thousands of dollars in tuition for you to receive a business education, shouldn't you at least get a job in business? This mentality extends, in my opinion, to a lot of disciplines. If you enter college as pre-med or pre-law, it's an expectation to get into med school or law school, respectively. Studying software engineering or computer science means you should be getting a job as a developer. It's not so much a goal, as an expectation

For me, this meant that a lot of these 'expected goals' were motivated by fear — that if they weren't accomplished, I would be a failure. Hence, I tried to navigate life in a way that would raise the probability of those goals being achieved. Even though the college experience should educate you, challenge you, and leave you an enriched member of society, concepts like 'bird courses' and 'easy professors' are tossed around. There are even groups where these concerns are the main ones raised when choosing courses. 

I started to give 'expected goals' more consideration throughout college, but not in the ways I should have. For example, I learned that it was easier to do well in classes I was interested in. Pursuing jobs that leveraged my skill sets, and what I enjoyed, were easier to obtain than otherwise. This has led me down a rather unique path — namely, a Political Science major with a background in growth marketing for tech companies. 

I've given goal-setting an increasing amount of thought in my year off. In a lot of ways, working in growth at a startup in San Francisco was my goal throughout college. Hence, when I actually got here, I was a little lost as to what my next steps should be.

That led me to really wanting to challenge the idea of 'expected goals', and start defining pathways for myself that reflect what I'm really interested in. If I want to start a company, I should be building a skillset that better equips me to do that, not choosing opportunities that will give me the most external gratification from friends & family. My current role gives me that opportunity, but that should be the reason I'm motivated to do it, not the end goal of being in a specific role.

So how do you choose these 'real goals'? Unfortunately, I don't really know... But there are a few things that have helped: 

  1. Read. Read different subjects, areas of interest, and take notes on what you learn, are confused by, and outright dislike. Recently, that hasn't taken the form of business / entrepreneurial books, but ones around philosophy — buddhism, historical thinkers, and modern philosophers. It's NOT relevant to my career, but it does help me reflect on my goals, approach to life, and why I do what I do. 
  2. Talk to people. Can you remember the last really good conversation you had with someone? Why was it great? Are there others that come to mind? Surround yourself with people that challenge you, stimulate you, and support you through life. I've been making a conscious effort to invest more in those relationships, and I'm grateful I did. 
  3. Do. If you have an interest in web development, hop onto Code Academy and start learning. Set your mind on a project and try to make it happen. If it's medicine, fix your mind on an area or problem and dive deep into it, with a goal of what you want to learn. I'm trying this with entrepreneurship — validating ideas, talking to founders, and seeing what really makes me tick. 

Motivation and over-achieving 

There is a stark difference between over-achievers who have 'expected goals' and those who have 'real goals'. The former are constrained by the expectations (as the name says) placed on them from external sources. If the expectation from school is to get a job in your field, then an over-achiever will strive to get the best job in that field. Anything less is a failure, right? 

In my experience, staying motivated in that boat is very challenging. There are many forces that are out of your control, and no matter how you try to de-risk it, eventually you can lose motivation. Contrast the two goals below as an example: 

  1. "I want to get a job in Silicon Valley for a tech company" 
  2. "I want to build a product" 

Goal #1 is binary — you either get it or you don't. There are other forces at play (i.e. visas) and restrictions that could make it more or less challenging to achieve. You can be motivated, but if that motivation is tied to a binary goal, you basically have to be putting in 110% effort until you achieve it. And when you get it — then what? 

Now consider Goal #2, which is not binary. There are a variety of roles you could work in — marketing, sales, engineering, etc. You're not restricted by location, salary, or any other (arguably) binary variables. Instead, it's a goal that is driven solely by you, and is rooted deeper than Goal #1. It also, in my opinion, never really ends. You can build a product, but are you happy with it? What can you do to make it better? Did you build it the way you wanted?  

I can think of a handful of explanations for why someone wants Goal #1, but I cannot even begin to imagine the motivations for Goal #2. When you set goal(s) that are 'real' and reflect who you are, then the motivation becomes rooted in something deeper than the outcome. It involves what you learn, and that shapes how you think about the goal. 

So how does this relate to over-achieving? Simply put, Goal #2 is a lot harder for an over-achiever. Since it's not binary, and has an arguably wider scope, you're left wondering how to over-achieve. If it's a goal that's strictly built by you and meant for you, then is it even possible to over-achieve? I haven't exactly come to terms with this, nor do I have a good answer, but the implied answer is "no". As long as you're moving towards that goal, you're achieving it. 

Conclusion 

Goal-setting and identifying what motivates you is a very scary experience. It challenges what you believe in, what gets you up in the morning, and what shapes your outlook on life. A lot of people that I think have this down are not 'crushing it' from an external point of view. If you held them to the 'expected goals' we discussed earlier, they probably wouldn't do too well.

That's because it's hard to rank someone that isn't playing your game. And if you're not playing, then it's no longer about winning or losing, since you're enjoying yourself either way. As a final note, I am terrible at internalizing this perspective, but it's a goal of mine to do so. I think that doing so makes 'staying motivated' a lot easier, and will give me more purpose and fulfillment than I currently have. 

How good are political party emails?

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Although I'm physically far removed, being in another country while my provincial elections take place, I'm far from isolated. Like with any industry, politics is no stranger to marketing and technology. While some campaigns still painfully hit the phone lines, major political parties vie for voter attention via social media, email marketing, and other channels. 

I subscribe to a number of these updates, and want to use this post to explain what can be improved. It shocks me that while companies around the world are striving to improve customer experience, email communication is so behind. I'll review emails from all provincial parties (PCs, Liberals, NDPs, and Greens), giving my thoughts on what is good and what can be improved.  

Unapologetically cynical (PCs) 

I get it. You want my attention and the best way to do that is to anger me — make me frustrated with what our current government is doing, why opposing parties are getting it wrong, and why your party has the answer. I respect that, and if it's well-reasoned and informative, then by all means, keep it coming. Here's an example from the PCs: 

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I get that you're angry from the results of a pollster, and I'm sure some Ontarians will be discouraged to see that the NDP is that far ahead. It may even discourage them from voting. However there are ways to point out that the poll is bogus without resorting to what is essentially complaining. 

"They're lying again" — what image does that give me in my head of the potential, future leader of our province? You've got my attention, but not for the right reasons. A good marketing email should capture the attention of the reader, have coherent content, and leave them better off than before. On that second note, let's move onto the copy. 

"They’re calling it a poll, but it’s junk science. They did the survey online, and it was 802 people."

Again, this tone is the last thing that I'd want from any politician, political party, or government. I get the craze around making emails feel like conversations, that I'm on a 1:1 with Doug Ford and he's explaining his frustration over the recent poll, but this type of content just annoys me.  

Naturally, the ending of this email (like all of them) is to donate. Somehow, donations are going to fund campaigns that get them the win. That is the only thing that a reader can do to help. I don't see any call-to-actions that encourage me to share the truth (which is the goal), volunteer my time, or other solutions. All the parties want is your money. How is that supposed to motivate me to vote for the party?! 

To avoid this turning into a hypocritical complaining session, I'll suggest a better email below: 

Subject: The NDP have 43% of the vote? 

Hey Trevor,

There was a misleading poll by a company called Pollara that stated the NDP have 43% of the vote, compared to the Progressive Conservatives at 32%. This is false, and you need to know why. 

The survey only included 802 people and was conducted online. This is far from scientific; it is not nearly big enough to represent Ontario, {{your city}}, {{your riding}}, and most importantly — you. 

Your voice deserves to be heard, and together we can make that happen. CBC's Poll Tracker reports that the PCs are leading the province, but we need your help to guarantee the win. 

There a number of ways you can help — just click below and give even a few minutes to give this province the leadership it needs, a Progressive Conservative one. 

{{donate now}} .  {{volunteer your time}} . {{share this message}}

This is far from a perfect email, but it's easy to follow, has a tone that is relatable to voters, makes them more informed of the issue, and gives them something they can do about it. 

Confusing and Lengthy (Liberals)

Let's take a look at a Liberal Party email. The subject line already is confusing — does the regular Ontarian know what GOTV even means (Get Out The Vote)? I can only imagine that open rates are extremely low amongst political parties, and I don't see how this would help. 

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Secondly, the text blob is giving me a headache. I'm going to assume that if you have my email, you probably know what riding I'm in. If that's the case, why not just use Liquid to only send the candidate that matters to me? Do I care who is running in Windsor if I live in Mississauga? 

This might feed into the issue of lack of data in politics, and the danger of public opinion if you collect it, but I don't see how someone will take the effort to find their candidate in this list, and THEN take action on it. 

Lastly, let's take a look at the call-to-action: 

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There's a weird switch in the call-to-action that focuses on volunteers. A basic rule in email marketing is that the focus should be narrow, and the call-to-action follows that. To drop a bunch of names and then ask me to support volunteers doesn't directly connect — is the goal of the email to get me to vote, or to donate?

If it's the latter, which by the subject line it looks to be, then why mention the candidates at all? Wouldn't it make more sense to solely focus on the volunteers, maybe highlight a success story of a senior citizen or new immigrant that's been helping out, and then focus on donating to thank them? 

On the right track (NDPs) 

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I've taken a look at a few NDP emails, and I have to applaud them overall. It's hard to pick at any distinct pieces that make their emails objectionable. The subject makes sense — I'm either going to choose their government, or the PC government: 

The body connects well to the subject line. They start by outlining what their future could look like — less student debt, lower hydro bills — and then show what the other future could look like — budget cuts and terrible hospital visits. Although the call-to-action is hard to read, given that it's (3) lines of hyperlinked text, it follows a strong narrative and I am enticed to click it.

A little tweaking (Greens) 

In the spirit of being completely non-partisan, I knew I had to include at least one email from the Green Party. There are some improvements that can be made, but overall it's a solid effort: 

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While the subject is vague, the content of the email has the right approach. The goal of this email is finally NOT to have me donate, but instead to have me vote. There's a link with details on what type of ID is needed to vote and information on when voting occurs. Sure it would be nicer with an infographic or something sharable, but relatively speaking this is a good email. 

Frequency 

It's common knowledge among companies that spamming your users, even with useful information, is most likely going to result in an unsubscribe, being reported as spam, or a direct reply complaining how annoying the emails are. 

I counted — 5 emails from May 24 to June 1 from one political party. That's almost an email everyday! I understand advance polls were approaching, and you needed to get your message out, but is a flurry of emails the best solution? Imagine if your parents emailed you 5x per week, each time berating you with details, issues, and complains about an event that's coming up. You'd probably be annoyed, but you'd still hear them out, help where you can, and most likely show up to the event, since they're your parents and you care. 

Now imagine that's a political party. The event (voting) is coming up, and they're trying every which way to get your attention. You have the option of ignoring it (unread) or telling them to stop (unsubscribing). Neither of those will result in a positive benefit to the political party, especially not a donation. 

Conclusion 

I hope if anyone involved in politics is reading this, they can take this advice to heart and give some serious thought to how they're communicating with potential voters. From what I've heard, some of these email lists contain tens of thousands of people, and I'd be genuinely curious to see what the engagement rates are like. 

If there's two pieces of advice I can give it's to stop focusing on donations and give the voter something to care about, a track to becoming a bigger part of the party, and empower them to want to donate eventually. The second would be to pay a lot more attention to the approach of an email, thinking more about subject lines and how the content should flow. 

Misconceptions about startup success

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Startup culture can be very nuanced, especially to someone who isn't engaged in it day-to-day. Having contracting for various startups and interning for larger tech companies, I made some assumptions about what classifies a 'successful startup', and how to dismiss others. 

Approaching my one-year mark in the Valley, I've had the privilege of diving into startup culture first-hand. This starts with my current company — dealing with customers + learning about how they see the landscape, and especially chatting with my colleagues who have worked at various tech companies both in and out of the Valley for years. 

In this post, I'll explain which misconceptions I use to have around successful startups, and some ideas I have around how to sift through the noise. 

"What's your funding look like?"

This is a common question I get, and while it's understandable, it makes me laugh every time. Back home, I use to evaluate startups solely based on this metric. A startup who hasn't secured funding was weak, and the more funding you amassed, the better you were. This was also (unfortunately) a consequence of the Canadian tech ecosystem. Venture capital is more sparse and focused there than in the United States, so it was an anomaly to come across a company at Series A with $10M funding, and hence the first reaction was to glorify it. 

So let's squash that assumption right off the bat — your funding level doesn't indicate very much about the level of success your startup has seen. If you're not convinced, take a look at Startup Graveyard, which has overviews of a handful of startups that 'died' in past years. Notably there's Homejoy (~ $40M), Optier (~ $103M), and Calxeda (~ $100M). 

Funding, in a lot of cases, simply means runway. It's money given to you by a venture capitalist to pursue certain goals, that will run out in X number of months. For startups that don't yet have revenue/a product, the funding might go towards developing it + taking it to market. For startups that are past that stage, the funding might help them take on market leaders + expand their sales/marketing efforts. 

The challenge to this, is that taking this funding keeps you accountable to certain goals defined by the venture capitalist. A startup with $1M in ARR might take a $10M Series A, with the promise of hitting $3M in the coming year. If they fail, they might shut down, and if they succeed, they might secure even more funding to hit new goals. 

This also spills into the idea of employee count — it's possible for a 30-person startup to have the same ARR as a 100-person startup, it's just that the latter raised more capital + hired more aggressively. A company like BuiltWith has less than 10 employees, but has numerous customers including Fortune 500 companies — don't count them out. 

Tl;dr: Funding doesn't indicate success or lack thereof, it's simply one way of growing your startup. 

"Tilt got acquired by Airbnb! They're killing it." 

Being acquired was another assumption I made that indicated a successful startup. The first example is Tilt.com, the famous money transfer product popular amongst college students. They were acquired for ~ $12M cash by Airbnb, which at first glance is incredible. The reality? They raised ~ $67M in funding and had a valuation (the previous year) of ~ $375M.

This is a better alternative to shutting down, but it means that no one emerged victorious from this acquisition; investors took a heavy loss, employees were laid off, not to mention losing their stock options (now worthless). 

There are other examples, even for startups that get acquired for more than their amount of funding. Venture capitalists expect a multiple on what they invest — if it's $10M Series A at a $40M valuation, then an acquisition for $20M is generally regarded as a failure. 

It's also important to note why acquisitions happen. In some cases, it's an acqui-hire: a larger company wants the talent working for a smaller (possibly struggling) company, so they offer them a discounted offer to acquire those workers. In other cases, it's a result of intense competition: a startup taking on Google might gain some speed, but will need an incredible amount of resources to make a considerable dent in their market share. This happens (via funding), like Airtable taking a $52M round to battle Microsoft Excel. But in a number of cases, the company realizes it won't be able to compete, and takes the offer. 

Tl;dr: Acquisitions don't indicate success of lack thereof; they're very circumstantial and can either be good or bad.

"So what defines startup success?"

For an outsider looking in, it can be fairly challenging to (at a glance) determine the level of success for a startup. The main challenge is figuring out what you think is 'successful' — is it a 2-person company that manages to make $1M in ARR with basically no costs? Or is it a 500-person company that has secured $100M in funding and is on the cusp of taking on industry leaders? 

If you're simply looking at a startup from afar, there are some things you can consider to determine whether it's successful in your eyes. For starters, what is the product? Is it something you think is objectively interesting + game-changing?

Maybe you value the user interface (GUI), and how accessible it is. Or maybe you value the actual content of the product; is it extremely powerful, even if you can only use it via an API? For example, I rarely pass judgements on medical tech startups because I don't know enough about the industry + don't find them interesting. But if you show me something in the sales/marketing space, i.e. a CRM for nail salons, you best believe I'll have an opinion. 

Conclusion

There are tens of millions of startups around the world, all with varying degrees of success. The word itself is subjective, and really depends what you're looking for. Don't assume a startup with lots of funding and employees is successful, and don't praise a startup for getting acquired without digging deeper. Startups without funding can be extremely successful too! 

Start by determining what you value in a company, and what you would regard as successful. Don't be afraid to have an opinion about a company that goes beyond emotional reactions, but also don't be afraid to admit when you're wrong. 

I'll handle the business side

Being "technical" and starting a venture

This is a stock image and I have no idea what it means. 

This is a stock image and I have no idea what it means. 

I use to think that it was a common misconception that you had to be “technical” to have a job in tech. Every software company, whether a giant like Google or a smaller startup like Clearbit, is built with a balance of technical and non-technical people. 

Roles like marketing, customer success, and sales are crucial to the growth and viability of a startup. So to answer that question outright, no — you don’t have to be technical to have a job / be successful in tech. With that out of the way, I’ll tackle the more controversial question of “do I need to be technical to start a tech company”. 

In the first months of a startup, where the idea is still far from validation and the product is laughable, there is a definite need for technical people. In this post, I’ll dive into why I believe it’s incredibly difficult to build a tech company if you’re non-technical, why this is the case, and how I think it can be fixed. 

No vision in building 

It’s quite possible for non-technical founders to build products that can scale, in terms of purpose and product-market fit. When I refer to this, I’m speaking primarily to the business as a whole, not the product specifically. 

From chats I’ve had, and personal experience, non-technical founders don’t have full visibility or understanding in how the product is being built, with relation to its purpose and feature set. For example, if you’re building a product like Slack, there are intentional directional changes you need to make at an early stage to ensure it scales properly. 

I heard this via a fireside chat at the Startup Grind conference with the Head of Infrastructure Engineering at Slack. Had a strong technical backend not been taken into account, with regards to how Slack manages load, handles downtime, stores messages, etc, then Slack successfully scaling at the rate that it did would be near impossible. 

It’s definitely possible to change products at the later stage, but it becomes increasingly difficult the larger you get. And if your core team is largely non-technical, this is something that won’t be seriously considered. 

Building an MVP 

This is a thorn that bugs me to this day, and pushes me (step by step) to learn how to code. In my opinion, getting a product validated and determining whether it’s feasible is not incredibly difficult. It requires lots of conversations, cold emails, and going back to the drawing board when things don’t make sense, but it’s definitely doable. 

The rising popularity of venture capital, and subsequent willingness of investors (especially in the Bay Area) to take risks on largely undeveloped and untested ideas, means that raising capital (as a whole) is easier than ever. The explosion of Initial Coin Offers (ICOs) and angel investors makes that even easier — products, mainly involving cryptocurrency, can raise millions of dollars in capital with nothing more than a white paper (read: collection of thoughts with no product). 

The challenge I consistently face, and have yet to hear an alternative to, is building that “Minimum Viable Product” (MVP). It’s possible to validate VERY simple ideas without being technical — a combination of fancy advertising and Google Forms can give you a sense of whether people are interested and wiling to pay for your product. For anything else (even if it might be simple), it’s hard to create an MVP. Without an MVP, you can’t fully commit to an idea of truly test it out with a cohort of customers / interested users. 

In these cases, it’s possible to hire a developer / outsource the work, but I’ve outlined in a past post the challenges of this — namely that it can be incredibly costly, as the MVP will inevitably change drastically in the early days.

Gaining trust 

Let’s run with the last example — you’ve spoken to numerous people and validated that your business problem exists (read: Step 1) and you’ve vetted an idea that MIGHT address that problem. Now the final step is to build an MVP and see how users react. 

I outlined in the last section the challenges of building the MVP itself, but let’s evaluate the solution of finding a technical co-founder. 

I’ll preface by saying there are a ton of jokes in the engineering community around finding a technical co-founder. There’s even a large Facebook group where people post threads and calls-for-submissions they’ve seen where the “business guy” will give equity to the engineer, assuming they are highly qualified (in their eyes). The extreme majority of these cases are based around foolish ideas, where the “business guy” did no validation around the problem OR idea, let alone would know how to find demand / sell the product if it ever materializes. So, for the sake of this scenario, let’s assume the business problem is already validated, there are potential pilot users, and all you need to do is build the product. 

For someone that is largely non-technical, finding someone to join you on this arduous, early-stage journey is very difficult. The main reason is the aspect of trust; both in terms of your idea and how you plan to execute it. 

What do I mean by this? Imagine you’re in this position, and you find an engineer willing to join you. The engineer builds an MVP, investing many hours into the project. Here is my understanding of their fears, in no particular order: 

(1) You are unqualified

The business guy, despite having validated the business problem, is not able to handle pilot users, find demand, and effectively sell the product. Despite the idea having merit, the engineer now sees his co-founder as dead weight, unable to contribute to the project and leaving the engineer wondering “Damn, couldn’t I have just done this myself?” 

(2) You are uncommitted:

It’s challenging to validate a business problem. I’ve sent about 400 cold emails and 6-7 strong chats with pilot users for a product I’ve been trying to build. This may have taken 2-3 months of on / off commitment, but to an engineer, often this isn’t considered as “real work”. Quite honestly, I don’t blame them — managing relationships can seem a lot less taxing than building a product that actually does something. The caveat is that this balance (and mutual respect) is needed for a business to function. It’s the exact reason why engineers at large tech companies have disdain for “sleazy salespeople” who make the same amount they do, through what they might see as simply emailing + calling various people. If a prospective engineer falls into this boat, they will be very hesitant to jump on board, expecting you to give up the second things don’t work out. 

I’ll go out on a limb and say that the reason most successful software companies are started by two technical co-founders is not because that’s the only model that works, it’s because both people had a mutual respect for each other and were willing to figure out the “business side” together. I strongly believe that this would be a lot more effective if both parties were on the same page. 

Conclusion 

At the end of the day, I can rant and argue as much as I want, but this is the tech reality that we live in. So to the original question, of being “technical”, with the goal of starting a company, I find it harder and harder to refute this point. 

The challenge, and what the note I’ll leave on, is that this is easier said than done. Being a developer requires an intrinsically different skillset than sales / marketing, the latter of which I fall into. Often developers are known as people that think logically or systemically, and have a strong math background. Salespeople, in contrast, are known as people that are relationship-focused — they understand how people function, can read reactions, and can frame problems and solutions in ways that many people understand. 

So for the time being, I will be diving deeper into coding / development. I regret that this is the most effective option at the time — it’s definitely not the most efficient. But I believe it will benefit me the most in the long-term. 

1 Year of Blogging

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Yearly subscriptions are a blessing and a curse. On the bright side, it’s an upfront payment that you suffer through and never have to think about again, but renewing is always a challenge. Given that the sum is reasonably large, you’re left wondering whether you made the most of that annual subscription, and if you should indeed commit to another year. 

While I’m still on the fence about subscriptions like Netflix or Amazon Prime, I can confidently say that my annual subscription to Squarespace, which hosts this blog, is one I’m happy to renew. Blogging has given me a lot of perspective on life and opened new doors. I hope to share some of the things I’ve learned after a full year of blogging in this post. 

The Beginning 

I started this blog after returning from a reading week (Americans: spring break) trip to San Francisco, with hopes on summarizing what I’d learned. It was actually during a dinner with a mentor in SF that I was prompted to start a blog. He’ll remain anonymous, for fear of misquoting, but the gist was:

Blogging is a forgotten but invaluable tool. It’s an investment — a reflection of your work + what you’ve learned, and an opportunity to experiment with new subject matter. For a marketer, it’s indispensable.

My first posts were strictly to reflect on my trip to San Francisco, and were more matter-of-fact than an engaging narrative. Silicon Valley 101 and Canucks in the Bay weren’t exactly captivating reads, but they helped me distill my thoughts in a public fashion. 

Unfortunately, few people in my network were interested in reading about a trip to SF, or hearing the stories of people I met (as captivating as they were to me). After 1-2 months of blogging, I had racked up only a few hundred views, leading me to question whether starting a blog was worthwhile. The game-changer was when I started to write for my audience. 

Two of my most popular posts, “How to Get a Summer Internship” and “How to Rock your Summer Internship”, struck well within my audience. Reflecting back, they did so well (~ 700 views in a day) because they (1) came from personal experience and (2) were applicable to my network. 

The hurdle I had to overcome in writing these posts is that they were no longer matter-of-fact; they had opinion, tangibility, and were open to scrutiny. What I realized, was these elements are what makes a great post. 

Documenting your work 

The best bloggers are far from actual experts in their field. The top marketers are too busy running a business to blog. The top engineers are too busy creating products to write about it. And the top financiers know that sharing their edge would defeat the purpose of doing so. 

With this in mind, I came to the conclusion that I didn’t HAVE to be an expert to write about something. So that’s exactly what I started to do — I blogged about SEO, content creation, drip sequences, and more things “marketing” to summarize what I was learning in those areas. Looking back (and take note if you plan on reading them), a lot of what I said in those posts was inaccurate and/or inapplicable beyond my specific use case. Did this mean the posts themselves were useless? 

Not at all. The value here was that I was showcasing what I knew, and this was entirely public. A blog for a marketer is like Github to an engineer; nothing speaks better to a line on a resume than somewhere a prospective employer can see it themselves. 

This was exactly the case when I started to interview at Clearbit for my current role. Despite numerous errors and lack of cohesiveness, it was easy to show them what I knew and what I still had to learn. I regret to say that while the blog landed well, my terrible puns still do not (sorry team). 

Dabbling in the rough 

More recently, I’ve begun playing around with different topics that interest me, and blogging about them. Specifically, I’ve started to blog about finance, building companies, and more things I, quite honestly, have very little hard knowledge about. 

The reason being, I want to be challenged and learn more from my peers. I would love to blog around my opinions on the medical field, or political scene, just to have someone shoot me an angry Facebook message denouncing my work. Controversy creates virality, sparks conversation, and (in my opinion) is the backbone of a strong blog. 

Unfortunately, as I’ve only recently begun experimenting with new topics, I haven’t had a lot of this. But if you’re reading this and want to give me a piece of your mind about something I’ve read, please do! 

Learning from failure 

The posts I’ve written that I’ve learned the most from are the ones that expose some level of vulnerability, combined with a strong narrative. Posts like “21 & Up” and “My Failed Startup” forced me to revisit previous assumptions I had, confront them, and evaluate if they’re still true. For the former, it meant leveling with the idea of “good jobs” and focusing more on finding purpose and value. For the latter, it meant diving deeper into something I wrote off long ago — why did my idea fail, and how I can ensure it doesn’t happen again? 

I hope to continue this trend throughout 2018, as it has helped me immensely in understanding where I’m at in my life, what I should be learning, and where I need to be. Just like keeping a diary, I found blogging to be mildly therapeutic, helping to keep me level-headed, rational, and most importantly, observant of what was happening in my life. 

Consistency is key 

I’m often hesitant to put out a new blog post. Even if it’s been weeks since my last one, I often wonder whether it has enough value, a strong enough narrative, or (quite honestly) something captivating that people will want to read. The conclusion I’ve come to, is that to someone reading, it will. 

I’m sure my self-reflection posts strike better with people my age who might be in a similar walk of life. Posts on marketing get a lot more traction on LinkedIn, getting views from people I’ve never met, and helping them to understand the space better. I know that as I continue to expand my scope of blogging, this will grow as the case. 

The one thing that has hurt my blog traffic and engagement the most is a lack of consistency. No matter how good / bad the post is, I get a lot more engagement if the time between posts is low, compared to if it isn’t. It’s something I’ve given more thought to in recent weeks, and plan to change my blogging frequency to match once per week (if not more). 

Conclusion 

It makes my day when I get a message about a post I’ve written. Since starting, I’ve received a handful from people I haven’t chatted with in years, sparking conversations about their life and what they’re up to. 

If you’re considering starting a blog, regardless of the niche or focus, I’d highly recommend doing so. If you’re consistent with it, the value you will get out of it looking back in a year will be immense — both from self-reflection and external opportunities. 

I look forward to blogging more in 2018, and as always (if not more now), reach out to me if you have any thoughts or comments on what I’m writing. 

Investing for Non-Investors

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The first job I ever had was a paper route. I had about 33 houses on my route, and made about $25/mth. Say what you may, but in elementary school, this was an enormous amount of cash. I could buy pizza in class for $1.50/slice and occasionally splurge on Yu-Gi-Oh cards. 

Unfortunately, my dad caught on to my spending habits, and gave the most sound investing advice you can give to an 11-year-old: put it in the bank. Safe to say, had I put those meager dollars into Bitcoin back in 2008... Well, we'll get into that later. 

In my personal opinion, a savings account is a bit of a hoax for students. It gives you the allure that you're saving money, since it isn't easily accessible like a chequing account or cash, and makes you think you're "investing" since the interest rate is slightly higher — approximately 0.1% depending on your bank. 

Although I've stressed in past articles that I'm far from a math major, the economics classes I did take in high school taught me that inflation was around 1% to 2% annually. So in reality, by keeping my money in a savings account, I was losing money. 

Coming of age 

I was left powerless at this realization throughout high school, as you needed to be 18 to open an investing account. Eventually, entering university I forgot about it — I come from a fairly frugal household, so saving money came quite naturally and there was never a need to invest. 

Regardless, I was fortunate enough to have a good friend who worked part-time as a bank teller and told me the advantages of building credit early. Even something as small as only paying your phone bill (on-time) via a credit card for a year can make a huge difference to your credit score if you're starting at ground zero. 

It was more of a coincidence that I opened an investing account around the same time, although it wasn't until a few months later that I actually started to use it. As a non-investor and someone that wasn't innately interested in finance, taking money out of a savings account and throwing it into "the markets" was daunting. 

For starters (and if I'm being honest), I knew absolutely nothing about financial markets. Despite appearing business-savvy, I couldn't tell you what exactly a mutual fund did, or an ETF — hell, even bonds were reasonably confusing (am I investing in the government?). So where do you start? 

Understand your tolerance 

The biggest step I made in my approach to investing was understanding my risk tolerance. Basically, if you're in your mid-30s with a spouse and two kids, along with consistent credit card debt and no savings, then your risk tolerance would be quite low. This meaning, if you invested money and lost it, it would probably have a significant impact on your life. For me, I was a student and saved fairly well, so I wasn't too concerned about losing the money I was planning to invest. 

The second part of risk tolerance that I considered was liquidity. Even if your current economic status is not fragile, you still need to consider your short-term goals and what you will need money for. In the last scenario, locking up even a small sum of money for a few months in the markets could be chaotic. Again, in my scenario I didn't need an incredible amount of liquidity in the near-future (2-3 years) since both my parents and I had saved reasonably well. 

What I avoided 

Before I dive into my approach to investing as a non-investor, I thought I'd shed some light on what I avoided, as a non-investor: 

Automated investing

If you have no interest in investing whatsoever, but still want to reap some level of reward from it, automated investing platforms like Wealthsimple can be a great option. You can select your risk tolerance (among other things), and they'll choose portfolios to invest your money into.

For me personally, I wanted to see what I was investing in. If I put money into a company and lost it, I at least wanted the ability to look at that company with disdain for the foreseeable future. The challenge with platforms like Wealthsimple, is that you really can't do this because you don't really know what they're investing in. 

Mutual Funds 

A mutual fund is a portfolio that is actively managed by investment professionals, and aims to beat the market. There are two challenges with mutual funds that turned me off from them. The first challenge with mutual funds was that aiming to beat the market can often go the other way (underperforming). So similar to automated investing, I had little autonomy / responsibility for the money that was being invested. The second challenge with mutual funds was that the fees on mutual funds are significantly higher than trading by yourself, or even an index fund. 

Picking stocks 

My approach to investing was to pick companies that I both (A) understood and (B) believed in. I'll be honest in saying I didn't scrutinize their 10k reports, balance sheet, and other financials because my understanding of them wouldn't have had a significant impact on my investing decision anyways. The other reason for this is that I lean towards long-term investing (2-3 years), so how the company is currently doing isn't as important to me as their vision and track record for success. 

The easiest example of this (and my first investment) was Shopify. I interned there in Summer 2016 and was instantly impressed by everything they were doing — the industry (e-commerce), their various product offerings, and their plans for the future. There was skepticism (and still is) around the business model, leadership, and potential to grow. But that was when the stock was at $45 — it's now at $170. 

The second example of this is Amazon. Similar to Shopify, I was impressed by their track record of growth, and sheer dominance in a number of industries (e-commerce, AWS, etc). I believed (and still do) in them long-term, and was confident that Amazon in 4-5 years would be an even bigger force to be reckoned with than it was a year ago. 

Of course, there are exceptions to this rule. Investing in either Twitter or Groupon 2-3 years ago would have been a terrible idea, as you would have lost 35% or 32% respectively. And if I was in that boat, and had evaluated the model of Twitter / Groupon in 2015 and truly believed in what both their businesses were doing, I would be jaded but ultimately okay with that investing decision. 

Hedging your risk 

Of course, I know that there's a reasonable chance that both Shopify and Amazon could go under, or lose a significant portion of their value, at any time. The probability, however, of the market as a whole losing a ton of value is lower. Obviously not impossible — I'd be surprised if there were 2008 Recession deniers just as there are Flat Earthers — but less likely by a fair margin. 

So my response to this was investing in index funds. These are essentially portfolios with (reasonably) low fees that aim to match the returns of the market. With the exception of the dotcom bubble (2000-2003) and the housing crisis (2008-2009), the S&P 500 has been up consistently each year. Reverting to my initial story about inflation, the S&P 500 is up about 12.5% in the last year, which beats inflation by a huge margin, not to mention any rate a savings account would offer. Therefore, my mentality was that by adding index funds to my portfolio, I'd be hedging against some of the potential risk that comes with investing in individual stocks / corporations. 

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Volatile investments 

I have to admit that not all of my investment decisions have been as sound as they should've been. The most recent example of that is the hype surrounding cryptocurrency. I bought into Bitcoin and Ethereum, two of the most popular types of cryptocurrency with the highest market cap, back in November and saw incredible returns. I also invested in a number of "alt-coins"; significantly smaller types of cryptocurrency focused around different problems, many being payment transactions but others involving online gambling (FunFair), Internet of Things (IOTA), and even processing power (Golem). 

I made a crucial mistake with cryptocurrency, mainly because I was investing in something I really didn't understand. Sure the vision sounded intriguing, but the vast majority of cryptocurrency projects are in their very early stages, many without even a working prototype of an idea that is backed by millions of dollars. The only thing I did right with cryptocurrency, and the advice I'd pass to anyone interested, is only invest what you're willing to lose. I've been both up and down by ~ 50% in the last few months, but either way, I'm not going to lose my house if crypto goes under. 

Conclusion 

My investment journey has been an exciting one, and I'm glad I embarked on it. If you take anything from this post, it's that savings accounts are not a sufficient investment, and everyone who doesn't have a very low risk tolerance or need immediate liquidity should consider entering the markets. 

As a final disclaimer (if it wasn't clear already), I really know nothing about the financial markets and am speaking purely from personal experience. So if you decide to invest and lose... ¯\_(ツ)_/¯.

21 & Up

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I never imagined I'd wake up to 15 degrees (Celsius, I'm not converting) on my 21st birthday. If you asked me at the beginning of university, I would predict that I'd be stressed with my first year of business school and recruiting. A few years earlier, I could have expected this occasion to be a lot bigger, as I had my eyes set on a few US schools, where being 21 brings new-found legality. 

I've written a lot about career advice, choosing pathways, and learning about tech, but I've rarely touched upon the idea of personal development. Not for the sake of scoring a top internship, or making a lot of money, but for truly becoming a better person. Figuring out what makes you tick. Understanding what you did, why you did it, and how that changes what you plan to do. 

It's always a sprint 

As humans, we're very used to 'sprinting' in life. You 'sprint' in high school to get the best grades. Then you 'sprint' in university to get the best internships. Typically, if you 'sprint' for 4 months during an internship, you'll get a full-time offer. Then it's the next sprint — moving up the corporate ladder, exiting from a job you hate into a job you hate less, or rinsing and repeating if you still have no clue

My first few months here followed a similar mentality. I was determined to be the highest performer on my team, put in the most hours, and produce the most results. And for the first few months, it appeared to be working. I launched some unique campaigns, met interesting people, and... I started getting a little bored. 

I expected San Francisco to be this new challenge in my life that would be impossible to surmount, and I'd extract something incredible from it. In reality, I was still working at a company (as awesome as it is), doing fairly typical work, with better weather. It was around this time (November) that I hit a wall and started contemplating why this time was different from the rest of my life / more recent experiences. 

With a typical internship, you're typically put on projects that are short-term in nature, or you play a small part in a larger project. One of my old bosses told me 

At the end of the day, you’re here to learn. I might send you down a rabbit hole with no results, but if you learned something from it, that’s a win

In contrast, being here for a year, a lot of my responsibilities were larger in focus. I was responsible for content projects that went through several rounds of review. I launched email campaigns that took a few months to complete. And I realized that I suck. 

The results from my campaigns were fairly dismal and the content pieces weren't revolutionary. This 'sprint' mentality, for the first time, had failed. Despite numerous blog posts and cool internships, I was, (at best) a mediocre marketer. Why was that the case? 

Still Only 21 

I started reflecting on a lot of goals I had leading up to this point in my life, and how they played out. You compete for the best universities in high school, then the best jobs in university, and finally the best 'exit opportunities' from those same highly coveted jobs. Life is a constant circle of 'sprints', until you realize the majority of those sprints (in context) were meaningless. At the end of the day, I'm still a 21 y/o undergrad that has never held a real job, just as I was at 18, and 14, etc. 

My friend group here has given me a lot of perspective this issue. Two of my roommates are from Wharton, arguably the best business school in the world. A few of my older friends left investment banks and are onto new careers. They've all achieved those conventional levels of success, but spending time with them has given me a new look on the 'sprint' mentality. 

For instance, they think a lot more than I do. Conversations are rarely dominated by recruiting or gossip, as I often led them to be in university, but instead about what books we're reading, challenges we're facing, and projects / ideas that intrigue us. From these conversations, I realize how limited I am in various aspects of life (i.e. handling relationships, mental health, political views). This hasn't led to any enlightenment by any means — but being in such a different environment has led me to the following conclusions on my 21st birthday. 

Goals 

Having already failed a rather superficial New Year's Resolution, I'll take my early birthday as an opportunity to set some public goals that build on what I've mentioned above for this year, and (hopefully) reject the 'sprint' mentality I've often fell into, and start striving for real personal development. 

(1) Reading 

In university, I've often had to read 70-100 pages per week of dense material on everything from early political philosophers to the economic development of African nations. They were interesting, but I regretfully read them with one purpose — regurgitation and application to their respective course. I rarely applied any of my learning to my own life, or used it to challenge or develop my personal perspectives. 

Hence, a goal of mine is to dive a lot deeper into various genres of books this year that will make me a better person. I want to be able to comment on politics and economics beyond what I read in the news — and have sound reasoning behind why I believe what I do. I want to be deliberate with the time I spend outside of work — the hobbies I have, and why I'm interested in them. 

The following books / authors are a start to what I'm hoping to read: 

  • Epictetus
  • Principles by Ray Dalio (100pg note) 
  • The Upside of Inequality (Edward Conard) 
  • The Lessons of History (Will & Ariel Durant)
  • River out of Eden (Richard Dawkins) 
  • Hero with a Thousand Faces (Joseph Campbell) 
  • The Sovereign Individual (James Dale Davidson)
  • Status Anxiety (Alain de Botton)
  • A History of Western Philosophy (Bertrand Russell)
  • Reasons and Persons (Derek Parfit)  

(2) Personal Health 

I've neglected my health over the past few years in a number of ways — for starters, being a university student, both my sleep schedule (sleeping 5am to 12pm) and diet were atrocious.

Hence, I'm making the commitment to become an early riser, ideally waking up at 6am and sleeping by 11pm. I've tried this with a fairly low success rate over the past few weeks, but I plan to be more religious with it in the coming year. 

I'm also committing to home-cooked meals by buying a Costco membership and using apps like MyFitnessPal to track my progress. I know both sound pretty lame, but I think it's a solid start. I've also have some aspirations for gym / weight goals that I'll deliberately leave out for fear of public shaming. 

(3) Mentors & Skill Development 

I have some incredible people in my life that help to guide my decisions and career path, but I rarely put any deliberate work into finding + nurturing those relationships. First Round put out a great post on how to find a mentor which I've been following, narrowing down my approach to both early-stage founders and growth marketers. Expect a post in the new month or two on this!

I also want to give back in whatever way I can, so if you're reading this and need help / advice with anything, don't be afraid to reach out. I've been scolded in the past for doing this, but I promise you I won't give you the response I once got below. Unless you use a drip sequence like I did... Then I'll commend you on the hustle. 

Shoutout to drip sequences and marketing! 

Regarding skill development, I'm learning an incredible amount about marketing and growth through my current role, so I have no direct plans around that. However, I am going to make an effort this year to learn how to code. There's an incredible amount of literature out there on the value of coding, even at least knowing what's possible / how to read it, so I'm committing to that for the year. 

Conclusion 

Despite all my ramblings about enlightenment, learning, and perspectives regarding life, I want to make it clear that (being 21) this year will still be filled with debauchery, terrible mistakes, and new realizations. I'm not even halfway through my time in California, and I can't wait for how the rest of it plays out. Thank you to everyone's that made this a blast thus far, I wouldn't be writing this without you.