Chaos into Order — 2020

Before I tell you how my year has changed, let me tell you what my life used to look like.

I’m a football player at Princeton. The demands of D1 athletics and University academics undoubtedly keeps me pretty busy around the clock. If I’m not at a practice, lift or football meeting then I’m studying or completing homework, while finding time for food and a social life somewhere in between. My life is defined by responsibility. I have a responsibility to my teammates to improve myself athletically and a responsibility to my family and myself to improve academically and professionally. Balancing school and football and a social life is incredibly hard and extremely time consuming, I never really thought of much else. Fast forward to 2020.

COVID-19 sends all University students home for the rest of the semester. I am immediately thrusted into online learning and team zoom meetings. School ends and I begin working for a micro-VC based in Austin, TX (TXV Partners). Eventually, August rolls around, my summer internship ends, and the school notifies us that football season is cancelled and that classes will continue to be online during the fall. In what was a serious blow to morale, I became disillusioned. Eventually, I do what’s best for me and make the decision to take a gap-year.

Being back at home and living with my parents, especially after experiencing the freedom of University for two years — was weird. As I began searching for new employment, I suddenly found out that had way more time on my hands than I knew what to do with. At first, I didn’t know how to spend it. I was sleeping in, spending way too much time on social media, and traveling to fill the time. The most productive aspect of my day was my afternoon workout. I was lulled into a repetitive cycle, each day blurring with the next. Aimless. Disappointed that I wasn’t working, but continuing to search and network as best I could.

One day I realized this — the time I have been gifted was an opportunity to grow and further develop myself on my own terms.

I have hobbies. I have a desire to learn new things and to develop an understanding of ____. Finally, I could use my days to refine those ambitions. So what have I been doing? Among many other things I have:

  • Learned how to invest in the market and manage a personal portfolio. ETF and value investing most and swing trading a little just for fun. CNBC is always on.
  • Deleted Twitter and TikTok and put time constraints on my other social media accounts. I’ve supplemented this time by:

Reading (personal finance, self-improvement, philosophy, classics — reading list to follow).

Diving deep into the world of VC and startups. This included listening to podcasts (list to follow) and reading the likes of TechCrunch, VentureBeat, and various VC blogs.

  • Improved my golf game (I finally can swing an iron).
  • Learning how to cook.

This past semester has been one of a kind. No football, no school, minimal employment. But what has been priceless is the time afforded to me and the desire to make the most of it. What will always fuel me is an unrelenting inclination to be better today than I was the day before. This Medium page and the way I have spent this semester is a testament to that.

Student-Athlete @Princeton, class of ’23. VC/Startup News and Analysis, book reviews, thoughts on markets, sports and more.

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Matthew Jester

Matthew Jester

Student-Athlete @Princeton, class of ’23. VC/Startup News and Analysis, book reviews, thoughts on markets, sports and more.

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