Do I Start a VC Job or Play Two More Years of College Tennis…The Not So Exact Science of Decision Making

Alex Yang
17 min readAug 16, 2023
Photo by Jens Lelie on Unsplash

Earlier this February of 2023 I was very content with life. I had just accepted a job offer in venture capital, the industry that I had wanted to work in for the past two years. All my networking, writing, and internships had paid off. Now I could enjoy my last three months of college and relax before getting started with my career.

This was the position I had wanted to be in. For all of my life I’ve tried to do the right thing and for me the right thing has always been the path that’s most traveled. I’ve never even considered a non conventional path.

But in late March I was on the bus back from tennis practice (I played D3 college tennis at NYU) and out of the blue my coach suggests that I should consider trying to play D1 college tennis and go to grad school instead of taking my job. I consider my coach to be an ambitious guy, and one of his strengths is his ability to look beyond the non traditional paths in life. I’m pretty much the opposite so I laugh when he proposes the idea. I do have two more years of eligibility to play college tennis, but the thought of forgoing my job to continue playing tennis seemed silly. I would just be delaying my career.

I dismissed my coach’s idea, but then he brought it up again after a few days. I had also met some former D1 players with the help of my coach, and they all strongly encouraged me to try and go D1 and do a masters at another school. The idea seemed slightly more plausible now — if multiple people believed that I could do this and enjoy it, then maybe I should consider it. The idea intrigued me enough and I knew that there were no downsides to just trying to reach out to schools and coaches.

I was so fortunate to have many amazing people helping me out in the recruiting process, including my coach at NYU and several former D1 players. They called up head coaches at D1 schools and went out of their way to help me. After some networking and calls with players/coaches, I had a call with a head coach and out of nowhere he wanted to fly up to NYC to watch me practice. At this point I was still not entirely sold on the idea of playing D1. But here I was in a position I never thought I’d be in…I had a potential option!

I told my coach and we were both pretty surprised about it. We talked and realize that things were getting serious. This coach was about to come watch me play, and if I had no intention of ever going to the school and playing tennis there I shouldn’t waste his time. I had to decide whether I actually wanted to do this.

The Underrated Difficulty of Decision Making

I don’t believe that we think about decision making as a skill as much as we should. The education system completely misses this — we’re taught to memorize things and gain skills that will helps us get jobs and maybe even succeed on the job. But when it comes to making difficult decisions, especially personal ones, I feel like there’s nothing in my high school or college education that I can reliably drawn upon to make the call. That’s why I feel so strongly about sharing this story of my decision making process — there needs to be more attention drawn to making difficult decisions, because quite frankly I felt ill equipped to handle the situation.

At this stage I was genuinely stuck between the two choices. I knew that I would really enjoy the D1 environment and getting to play competitive tennis at a higher level, but I was also afraid to lose a good job that I had worked hard for. I decided to try a bunch of different strategies that I thought would help me with the decision. I’ll analyze below how each one fared and how helpful it was to me.

Pro Con List

As someone who usually likes to think through things pretty deliberately, I started with a simple pro con chart. It didn’t end up working so well for me.

When you have a difficult decision to make and there’s no obvious choice in your mind, it probably means that the choices each have a ton of pros and cons. The problem with a pro con list was I wanted to be unbiased, so I ended up trying to make the lists equal lengths for each option. Moreover, each pro or con shouldn’t have been weighted the same, as some were way more important than others. This made me realize that in the grand scheme of things some of the pros and cons of my list probably weren’t important enough to even be on there, but deciding which ones should stay and go seemed too arbitrary of a process to me. The pro con list just became more and more complicated as I recognized its structural flaws.

Consulting Others

This was something I almost did too much of.

First, my coach and I communicated a lot about the decision. He was helping me throughout the process and helped me see that this decision was not just about playing tennis. He wanted me to see how team culture works at the D1 level, experience a new school and culture outside of the Northeast, and grow as a person under new coaches and mentors. These were things that I would’ve never even thought’ve factoring into my decision if not for him. The conversations I had with him were always constructive and he also knew how much I also valued my career. It was so important for this decision to have someone there to help talk things through, and I’m so grateful to my coach for that. Making a big decision can feel pretty lonely otherwise.

My coach also helped introduce me to former D1 players and D1 coaches. I also reached out to my best friend from home (who doesn’t play collegiate sports), and some of my former internship bosses in venture capital and startups. It was a solid mix of D1 tennis experts and also those who knew me well. And I was having a ton of calls. The problem was my mindset going into these calls. It’s like I wanted them to give me an answer, or to help strengthen one choice over another. At a certain point you talk to so many people and expect that a clear answer will come out of it, but it never comes. I kept on setting up more and more calls, hoping that someone would just hand me an answer on a silver platter, but deep down I knew that only I could decide what I wanted. That felt frightening. For most of the other decisions I’ve made so far in life I’ve been able to mostly rely on the advice of those close to me or the Internet to feel comfortable about making a decision. This time, I could consult people and they could provide various frameworks about how to decide, but they couldn’t make the decision comfortable for me.

What I did get out of consulting others though were some great frameworks that helped my decision. I was told by almost everyone (both those who played D1 tennis and those who did not play sports at all) that if I “loved tennis” I should pursue that. Hearing that from everyone gave me some form of confidence that I should use that heuristic in my decision.

Visualizing and Writing Thoughts Out

I once had a venture capital investor who I interned for one summer, and when thinking through an investment decision he would often write things out on pen and paper and to organize his thoughts. I tried it a few times myself that summer and found it very helpful.

At a certain point in making my decision, I felt like I had accumulated so much information from a variety of sources and it was becoming overwhelming. I wanted to write stuff out on paper just so I could make sense of it all.

I decided I should make a diagram to organize my thoughts. At the end of the day, it felt productive to put it together and write out my thoughts, but it ended up functioning very much like a pro con list since I was compiling evidence for both sides. I had made some progress in organizing my ideas and making sense of what evidence was important, but I didn’t feel any closer to my answer.

My attempt to “visualize my thoughts out.” It’s a complete mess.

Youtube and TED Talks

Youtube is my go-to source for learning anything. So when I was feeling very stuck about my decision, I wanted to learn more about decision-making and how to approach it. I wasn’t expecting to find a video that would give me my answer, but at least something that would help me feel less stressed out about the situation.

I found two TED Talks that proved to be very helpful. The first helped me see the decision making dilemma in a more positive way, and the second helped me to see why I was struggling with the decision.

The first talked about how in the world of difficult decisions we often believe that one decision is better than the other, and that we’re too stupid to see it. Instead, the speaker suggests that we see difficult decisions as multiple options that are on-par with each other and that neither is inherently better than the other. Watching the video helped me feel better about my decision — there wasn’t an obvious answer that I was too blind to see and it was ok that I was stuck.

The second TED talk spoke about fear. The speaker mentioned that when we give into fear, we disconnect from what we really want. When I heard this, I realized that part of why this decision was so difficult was because anytime I thought about going down one path, the fear of consequences from not taking the other path would immediately pop into my mind.

I was restricted by fear of the opportunity cost, rather than getting excited about the upside of either option. Removing yourself from fear is difficult, but once I became aware of my fears I realized that some of them were pretty unrealistic. For example, I realized that one of my biggest fears was that if I chose the D1 tennis route, I would ruin my career. I would never be able to go back into venture capital. Once I thought about that fear more deeply, I realized that that wasn’t true (presuming I continued to work hard and do all the right things). That was still totally within my control.

Using the Regret Minimization Framework

This framework was suggested by one of my mentors. He mentioned that the most helpful career advice he ever learned was from Jeff Bezos. When making a decision, Bezos suggests to think about when you’re 80 years old, which of the two options would you regret not taking more? It became clear to me that if I loved tennis and playing on a college team, I would regret not doing two more years of tennis way more than I would regret not pursuing this particular job in venture capital. This framework actually proved to be extremely useful to me.

Understanding What I Loved To Do

This may sound silly, but after all this I began to question how much I loved tennis. Everyone was saying that if I loved tennis I should play more. I actually became ultra paranoid and felt like I had to be 100% sure that I loved the sport.

I asked GPT — how do you know whether you actually love doing something or not? It gave me a great checklist of things to think through, like “How do I feel when doing this activity?” or “Am I looking for ways to improve my skills related to the activity?” or “Does time seem to fly by?” For all of these the answer was a resounding yes. I was overthinking it — of course I loved tennis. I dedicated 30 hours a week to it. Many weeks, I would take a 40 min subway ride to go practice up in the Bronx and I would do that 5 times a week and come back home at midnight after practice. No one in their right mind does that unless they enjoy the hard work and the sport.

In hindsight the answer may have been obvious, but I’m glad I went through this exercise, because all throughout college I had undersold my passion for tennis. This was the thing I dedicated myself to. But when people asked me what I loved to do I would try to tell them other activities besides tennis because I felt like it wasn’t unique enough. Now I realized that I shouldn’t be ashamed because tennis was what I loved. I had given everything I had for this sport and obsessed over NYU tennis. My coach at NYU had seen this in me as well, which is why he really wanted me to pursue D1 tennis.

The Moment When I Actually Made My Decision

So I had spent about 5 days or so using these different frameworks / strategies, and although I had a sense for what was important to consider in making the decision, I was still stuck in decision paralysis.

But what got me out of that paralysis was actually remembering something that happened about four years ago. I was a senior in high school, and I decided I didn’t want to play college tennis anymore. I ceased talking to all coaches and decided that I wasn’t going to play seriously any longer. It could’ve ended up being the dumbest decision in my life had I not gotten lucky and had the chance to play at NYU. I could’ve thrown away something that I really cared about. And I almost threw it away because I thought that in college there’s no time for useless things like sports if you’re not going pro. My time in college proved that there was nothing further from the truth.

I realized that I was now in a similar position to the one from four years ago. I could either give up something like tennis since it was time for the “real world,” and just go down the conventional path. But knowing what I knew now about how much I love tennis and how much it meant to me these past few years, how could I possibly turn that down and make the same mistake again?

I thought about it further: what did I want my life to be about? I want my life to be something where I can do the things I love if I have the chance. Yes, it’s super cliche and extremely corny but that’s how I felt about this opportunity. For the first time in my life I was mature enough to see that something you dedicate so many hours and emotions into shouldn’t be reduced to something you throw away when it’s no longer convenient. You can embrace it as an important part of your life.

Suddenly, all the individuals frameworks I had thought through and all the conversations I’d had with others blended together seamlessly in a way where I knew what I wanted to do.

The Unsung Benefits of Making Tough Decisions

Part of what was so great about this decision making process that I appreciate now is that it allowed me to actually learn and relearn a ton about myself. In your pursuit to make a choice there’s an opportunity to look within yourself and determine who you are and what you care about, and also learn about how you tend to make decisions.

Moreover, thinking back on this decision I found that I was at points very frustrated and stressed about it. I couldn’t believe that I was stressing over something like this with only a month before graduation…I wanted to just be set on my post-grad plans already! I had willingly put myself in a position where I was yet again unsure of my post-grad plans. Yet, now looking back on it I’m glad I struggled. One, because it shows that I was thinking it through and not being impulsive. And two, because I learned a lot about decision making and that will help me to make other important decisions in the future.

Like I said at the beginning of this piece, no one is ever taught about decision making, so often our opportunities to learn come from getting reps and practice. Once I adopted the mindset that “hey, this is a big decision but consider it as practice for bigger and more important decisions later on in life,” it made me feel more relaxed. I also learned to be grateful that I had these options in the first place. It was a privilege to be stuck between two great choices, as one of my mentors reminded me. In a world of abundance it’s easy to feel trapped by the Paradox of Choice, and I had to keep reminding myself throughout the process that “hey, this is good! I have two really great choices and I can’t really go wrong.”

Why Was This Decision So Difficult For Me?

I found it so challenging to let go of making the decision with my brain and just embrace the decision with my gut. I believe part of this difficulty relates to my upbringing and personality. I was taught to be careful and logical and that applies to anything I do nowadays. It’s super helpful in a lot of situations, but I think for certain things it leads me to believe that I can reason my way out of anything. As I found, sometimes all the logic in the world can get you nowhere.

This suspicion to embrace emotions was corroborated when I came across this great piece by Jonny Miller about how emotions are actually essential to decision making, as proven by neuroscientists’ studies of patients with tumors in their frontal lobe who subsequently couldn’t make basic decisions due to limited emotional capacity. Emotions are not an impediment to our decision making — they help guide decision making and allow us to make sense of what’s going on in our lives.

What was also difficult about my decision was that this was my first big decision in my life. I didn’t have the luxury of knowing from experience whether it would work out or not. But I knew this and part of what helped me think through the decision was recognizing that I would likely have to make many decisions like this in the future. This would be the first of many. I thought to myself, if I chose the safer path this time, I wouldn’t overcome my fear of taking the riskier one. There’s actually a great quote from the Jonny Miller piece that I think describes this concept well.

If we’re resisting (consciously or unconsciously) a certain emotional experience, then we’ll make intentional choices to avoid feeling that way.

For myself, there was some obvious discomfort to choosing to go play tennis for two more years, especially when all my peers from NYU were soon going to start their first jobs. If I interpreted that discomfort as something to avoid, then I’d probably be in Boston right now onboarding onto my new job in VC. But if I embraced that discomfort and chose the path less traveled, then I could break that seal of emotional resistance for the first time. I would realize that it wasn’t as scary of an experience as I thought it would be.

An analogy (not backed by science at all) to illustrate this is imagining someone jumping off a 10 meter diving platform into a pool. When they get up to the top they’re feeling nervous. It’s a long way down. There’s discomfort with jumping down immediately…the brain is sending out warning signals and the heart is pumping. But the longer the person resists jumping off, the harder it is for them to do it. Maybe they resist it so much that they actually decide they’re not going to do it at all and they take the ladder back down. Now imagine that person going back up the 10 meter platform a second time, thinking they have the courage to jump off this time. But when they get up there, the feeling of nerves is even worse than the first time. Because they didn’t jump off the first time, they avoided the emotional experience and in doing so increased the fear associated with the experience.

If I metaphorically jumped off the platform the first time and was ok, I felt like I could set a precedent for future decisions that I would have to make. Who knows what sort of crossroads I could be at later on in life? Taking the path less traveled this first time could free myself up mentally to maybe choose the less conventional path again at some point. But if I resisted this first time, I was afraid that the next time I was at a crossroads I’d be even more likely to resist the non-conventional path.

Final Thoughts

I wanted to share this as an update on where I am in life, but also because I find decision making so interesting. It seems like my friends and I are at the age where decisions seem increasingly consequential. What med school to go to, what city to work in, what job to take. I’ve even started to learn about the science behind decision making (see Appendix) and ask my friends about important decisions they’ve made and tried to understand their process. I’m sure for others the same strategies I used have different levels of success for them: maybe visualizing their thoughts works way better or they’ve found a way to make pro con lists work for them. Decision making is a unique experience for everyone. If you have any thoughts on decision making I’d love to hear from you! What works best for you when making tough decisions? What hasn’t worked as well? You can email me at alexyyang15@gmail.com or DM me on Twitter.

Also, there are so many people I have to thank for helping me make this decision and making a crazy idea a reality. I’m writing this now and just thinking back to 4 months ago when I absolutely had zero faith that this would work. Now I’m actually on a D1 team and doing my Masters in Finance! To Coach Chanmeet Narang, Spencer Bozsik, my parents, Nevin Walia, Ryan Frisbie, Amanda Joseph, Jin Chow, Tony Wan, Dan Porter, Aashay Mody, Josh Shapiro, Armando Santana, Billy Rowe, Mariano Argote, Ida Krause, and all my teammates on NYU tennis who supported me…thank you. Now the real work begins.

Appendix: Metareasoning and Cognitive Costs

Recently I’ve found that there’s research being done on decision-making, specifically by Professor Tom Griffiths at Princeton. He uses the term “metareasoning” to describe the process of making decisions about how to make decisions. In this talk, Griffiths suggests that humans often use metareasoning to select decision making strategies that minimize cognitive costs, the mental effort required to make a decision, even when it may not be the most optimal outcome. I’ve found these statements to be quite true when I attempted different decision making strategies.

For example, when consulting others I found that I wanted others to hand the answer to me, reducing the amount of cognitive effort that I had to put in to make the decision. In the end I was able to recognize that this approach to consulting others wasn’t working out and could lead me to a suboptimal outcome (or lead me to use the wrong reasons to justify the optimal outcome).

Griffiths also discusses the idea of whether increasing cognitive costs or time spent on a decision improves decision making quality — the idea of whether you’re using your brain power wisely. Griffiths proposes that this relationship between brain power used and the value of the decision follows a curve of diminishing returns. After spending a certain amount of time thinking through the decision, additional time spent is no longer as useful.

When thinking about my own decision, I can definitely see that there were diminishing returns to spending more time on the decision. It was an important decision that I don’t think should’ve been made in a couple minutes since there was a lot of information to consider, but I wonder whether I spent too much time contemplating the decision to the point where it stressed me out, leading to a upside down U-shaped curve rather than just one with diminishing returns. At a certain point too it also becomes too emotionally taxing to contemplate a decision for that long.

--

--

Alex Yang

How I Decided | Grad Student at SMU | NYU Stern alum