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.