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 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 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’. Despite social pressures, I think I’ll enjoy life 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 will not be working in an execution / individual contributor role. 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 in the short-term is to run my own business full-time.

Conclusion

It felt like yesterday I was in high school (I wish!) — over the past years, everything from my interests, friend groups, and even my hair has changed. 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.