28% Loaded.

Another trip around the sun. Some thoughts on saying goodbye to my mid-20s, going monk mode for a few months, etc.

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I turned 28 last Tuesday. 28 isn’t a particularly notable age, besides the fact that I cannot, in good faith, continue to say that I’m in my “mid-20s.” However, 30 now feels less like a distant milestone and more like a tangible reality, as noted by the following observations from my first week of 28:

1. I was sore for several days after playing basketball for the first time in months. And not, like, “I haven’t used these muscles in a while, therefore I’m pretty stiff” sore, but, “Wow, I’m in physical pain trying to lift my left arm above shoulder level. Do I need an MRI for this?” sore. I guess this is a telltale sign to prioritize warming up and stretching. Tragic.

2. My recovery time after boozing over the weekend has slowed tremendously. On one hand, this is a bit annoying, but on the other hand, it’s a good reminder that I’m not in business school anymore and testing my body’s limits should be increasingly reserved for specific occasions (like, say, turning 28 and booking an all you can eat, all you can drink dinner at an Israeli spot where the hostess supplies all guests with tambourines and cranks up the music to 11 after dark).

Anyway, now that my mid 20s have come and gone, and I’m another revolution around the sun closer to death, I would like to share some more detailed musings on this “mid-20s” stage.

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Every young person should blow up their life at least once.

The first time I blew up my life was the summer of 2021, when I was 24 years old, and the second time was a few months ago, on the tail end of 27. At first glance, these two blow ups couldn’t look more different.

In the first, I was dissatisfied my job, so I quit to spend the year living out of a backpack in various hostels and Airbnbs across Europe and Argentina with three goals in mind: I wanted to have as much fun (here, defined as time spent drinking/wandering around various foreign cities with the other 20-somethings who inhabited my lodging choice of the week) as possible, I wanted to see as many cool places as possible, and I wanted to live out as many novel experiences as possible in a 12-month period. I did have some loosely defined professional goals (writing newsletters, for example), but my primary motivation was optimizing for adventure over anything with little to no concern for stacking cash or advancing my career. 1 year, maximum fun, back to the real world after.

The second blow up was the opposite. After realizing I wasn’t satisfied with my post-business school career choice, I spent months chatting with, and applying to, different venture capital funds with one goal in mind: land a role at a solid fund where I could 1) learn a ton and 2) redirect my career. I did have some loosely defined personal goals (see friends on weekends, etc), but my primary motivation was optimizing for professional progress over anything with little to no concern for “fun-maxxing” or whatever. This motivation made it much, much easier to say “Sure, I’ll move to SF,” instead of balking at the possibility of moving across the country for work at a moment’s notice. So now I live in San Francisco.

Two entirely different motivations, one professional in nature, the other entirely unprofessional, but they shared a couple of commonalities:

1. Both decisions were, at a foundational level, driven by a fear of failing to take advantage of a finite window of opportunity.

2. Once I’d made my mind up, I attacked both decisions with intentionality.

Mid-20s are a weird transition period: on one hand, it’s one of the last times that you can have pure, low-cost, unadulterated fun for an extended period of time without it posing serious risk to your personal or professional life. On the other hand, it’s a critical period for building the foundation for the rest of your life, both professionally and personally. It’s the best time to be exploration-maxxing and stacking memories, but it’s also the best time to prepare to lock in.

24-year-old me knew that he had a small window to accumulate as many weird, crazy, and, above all else, fun, memories of his youth without negatively impacting the trajectory of his life, and 27-year-old me knew that he had a small window to readjust his career trajectory or he risked getting “stuck” on a path he wouldn’t have wanted. It’s very, very difficult to get everything you want in this short period of time, especially when the two things you desire most are so diametrically opposed. Like, yes, of course I want to make millions of dollars as an investor, but also, have you ever been hiking in the Patagonia? What if I want to drive a Fiat 500 around Spain for a few weeks, eating paella and drinking Rioja? The duality of man. It’s tough.

The tricky part about all of this was figuring out when and how to make the switch, because there are tradeoffs to both of these things:

1. Time spent in pursuit of pleasure and fun translated to less money in my bank account, and I might be a year “behind” in my career compared to someone on a similar path who locked in a few years ago.

2. Time spent focused on work cuts into hypothetical memories, adventures, and other shenanigans that I could otherwise be doing.

The only solution (at least for me) was to go all-in on the current thing, attack it aggressively, and then when I needed to flip the switch… flip the switch.

Some people prefer balance in their lives. A certain amount of time working, a certain amount of time socializing with friends, a certain amount of time with family, a certain amount of time on hobbies and side projects, etc. I’ve realized, after 28 years, that that’s just never going to be me. I’m much more effective prioritizing a thing and attacking it obsessively before moving on to the “next thing.”

Last week, a buddy of mine was visiting New York, and we ended up having a pretty deep heart to heart over beers where we discussed what was going on in our personal and professional lives, our fears/hopes for the future, and all of the other things you talk about over beers with friends that appear in your city unexpectedly. Between beers two and three, this friend mentioned that his biggest fear was failing to actively “live life,” falling victim to the same passive autopilot loop that captures so many people.

I think the key to actively “living life” is to continually optimize for what’s fun, while accepting that your definition of “fun” changes as you age. Having a good feel for what excites you at different stages of life is how to decide where to go all-in. Misunderstanding what actually excites you now and instead optimizing for what “should be” or what “used to be” fun is how we screw up.

I spent most of my mid-20s focusing on stacking memories (as you could see from reading some of my early blog posts), but over the last year, those priorities have shifted to setting the foundation for my career. It’s not that I’m no longer worried about “fun” as much as it is my definition of “fun” is now more correlated with progress than it is with geographic explorations.

And staying on theme with my propensity for going “all in,” I kicked off 28 with… a lot over the last few months. I need to finish a book. I need to learn a ton on a new job. I moved to a new city. And, as we discussed earlier, I’m terrible at the whole “balance” thing. So, as a result, I’ve decided to begin my late 20s in the exact opposite fashion of how I kicked off my mid-20s: by going “monk mode” for a few months, as my fellow Zoomers like to say, to get on top of all of these things.

This is 28, happy to be here.

- Jack

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