On Turning 30

A decade of learning.

30 years old.

What a ride.

If my math is right, I started this decade on the heels of a terrible year.

As a newly minted frat star, I had been convinced (by myself, the internet, the boys), that steroids were a good idea, so my hormones were upside down from a cycle of some of the good stuff (you lose all your gains when you stop, not worth).

My life was very much just a series of moral transgressions against myself trying to maintain an image that I was tough, and cool, and rich, and successful, after spending the preceding decade mostly feeling weak, and left out, and poor, and unrealized.

I wanted nothing more than to find a nice girl who would love me for me and get a good job that would prove I wasn’t the failure-to-launch I always felt like. I went about that by drinking 40+ beers a week, dedicating my mental cycles to maximizing my bench press instead of maximizing my career prospects (it worked, but damn we never trained calves back then), and eeking out hungover 3.5s toward an engineering degree that never interested me.

I had opportunities to be with that girl and achieve that success and realize that potential, but instead I self-sabotaged by playing with my hormones, my image, and my liver function. I was solidly depressed for 4 years, but at least I was a celebrity on campus. No one’s ever made that deal before.

When I started my masters, I had finally arrived. I was at one of the best schools in the country, I was sober, and I was handsome. But god damn was I lost.

I felt guilty and ashamed for all the wasted years, I had no conception of how to actually be an adult, and I was impatient.

After finishing at the top of the class, I was confused: where was my 6 figure job offer, my beautiful girlfriend, my admirers? They must have gotten lost in the mail, or maybe…I was the problem? No, that couldn’t be it.

When I finally got my first job after what I can only describe as a HORRIBLE, very dark 6 months, I was making meh money, in a meh place, with meh career outlook.

I was still measuring myself against the yardstick of my high school peers, and *meh* wasn’t even on the yardstick. I needed a better job and until I got one, I would need to worry about it 100% of the time, because that’s really productive and healthy.

I tried dating for a few years, hoping to find someone to give me a hug every once in a while, and all I really got out of that was heartbroken in a bunch of ways I didn’t understand.

I eventually gave up on myself. I felt helpless. I started blaming outside things for inside problems. I hardened my heart. A deterministic way to unlock the bad thoughts.

All that led me to startups—where insecure men test their mettle. That’s not…entirely true, but it was for me at the time. I was bitter, angry, and depressed (again).

I’d outwork everyone, and I did! But a lesson for anyone who is seeking validation from their work: you won’t find it there. And a lesson for anyone who thinks you can work around the clock: no matter how motivated, you will burn out.

When you’re in the gym, the goal is not to simply be moving weight as often as possible, it’s to make progress. Progress requires rest and restraint so you can get better and have time to heal and learn. I’m not wired this way, especially when it comes to my goals (I still struggle with this), so while I did outwork everyone, I ended up building the wrong things (lack of learning and reflection), pathologically lonely, and so deep in a hole that my body had to start flashing alarm bells.

The first alarm bell was a general feeling that something was wrong: I felt awful all the time, my brain literally stung, I couldn’t think, etc.. But that wasn’t enough for me to slow down. My body had to break glass in case of emergency.

It had to…make me less hot. Damn body, what the heck man.

I hadn’t even realized I was attractive—I always felt fat and 2 feet tall, even at my height, with abs, and a 300 lb bench—but I had started to realize that the scant amount of attention I got from pretty girls wasn’t a given, and what little self-esteem I had was almost solely derived from that attention. Life was good back then, but I never realized it.

My hair fell out in clumps in like 2 months. Lame.

I decided I couldn’t find happiness the old fashioned way, but if I started a successful company I could… buy my way to happiness? (that’s definitely not how that works, for the record). I had to double down.

Nice try body.

I got another job, this time a really cool one. I was so shocked. This one as a product manager at a data science startup in Palo Alto that exclusively hired Ivy-leaguers or equivalent. A literal dream job and a cognitively dissonant one for my self-esteem. Why would they hire me? I was…me. Whatever, I’d show up and do my best, and maybe that’d be enough.

After a few months people were shocked (in a good way). I wasn’t just doing fine, I was doing really well. I was accountable, dependable, quick to pick things up, organized, invested, easy to work with—I was great. I was absolutely an HR liability (during my first All Hands, I introduced myself with the requisite embarrassing story by recounting my serenading of a lesbian, mentioning that she looked lesbian-y, and me asking her if she was a lesbian. She was.), but that was fine, and even endearing to most after the cringe wore off. Everyone liked my work and they even liked me (HR included!). I had some good years there.

I look like a ghoul here lol

But it wasn’t enough.

Never mind the promotions, the support, the praise—I knew people making more money with flashier titles, so this wouldn’t do.

Was this what happiness demanded—constant dissatisfaction?

I was confused: I was happy-ish, but I was butting up against an asymptote that I just couldn’t seem to break through.

Then we got hit with Covid. I was riding bikes more, my hair was growing back, I met a girl that somehow liked me—things were actually okay.

Then I tore my pec, I blew it with the girl, and my hair fell out again.

6 months in a sling for a guy who started every day with a workout was torture, until it wasn’t.

Having no fitness escape hatch gave me no choice but to slow down. I found big old books full of wisdom, I found authenticity, and I found the one ingredient I seemed to be missing all along: Gratitude.

My parents were (and still are) together and legitimately care(d) about me. I was/am smart, likable, tall, funny, generous, humble (lol). I was an uncle to the greatest, most outrageous little girl (I have 2 nieces now, but second came after this part of the story). I had a handful of great friends and cool hobbies and strong morals and a big heart and a good, now mostly hairless, head on my shoulder.

But my lens was always focused on the deltas instead of all that stuff, and when you focus on the deltas, you will always feel insufficient. You will always feel small.

You might make less than your friends. You might be deep into a 10 year bet on startups that violates everything you know about expected value and compound interest. You might still not have hair after taking literal poison for 4 years that was supposed to grow it back but only made you sick, tired, doubtful, and dumb. You might be lonely.

But I’m sure there’s something you could be grateful for, and maybe you can spend more time thinking of that and less time thinking of the things that make you feel like you’re meh.

I started this decade bitter. I had had horrible OCD that made high school impossible, I had been a late bloomer, I wasn’t rich, or good looking, or anything, in a town that was dominated by sports, money, vanity, and success. When I was 10, I was always the kid that asked the new kid if they wanted to eat lunch with me so they didn’t have to eat alone. At 20, I was spiteful. At 30, I’m finding my way back to 10—that was a good kid.

Despite the tough years, I’m grateful for all that stuff and grateful for struggle, and identity reconstruction, and failure. I’m grateful for my stupid alopecia, and tearing my pec, and feeling inadequate, and being alone, because I really do believe that I’m on a path to living the life I always wanted, as the person I always wanted to be, and that pain was the price.

(I think 10 year old me would probably be most stoked on the muscles, bikes, and rock n roll, but he’d probably at least think it’s cool that I’m a man he’d look up to)

And the people in my life, wow. I don’t deserve you. I’ve got incredible friends, mentors, and family members. I can attribute like 70% of my somewhat-newly-found mental health to simply reconnecting with my family, and spending time with great friends from varied backgrounds. Who knew family and friends were important? The last 30% from a healthy combination of lifestyle choices, bikes, and rock n’ roll (everyone knew those were important).

Happiness is simple, and it’s easy if you prioritize the right things. Yes, social media has a way of bubbling up the friend doing better than you or the party you’re not at, but those things become background noise when you’re living a life that brings you real joy.

I started this decade meticulous, and anxious, and misanthropic, and then I realized that few books are worth reading that have a cautious, inhibited, lonely protagonist. Things needed to change, and I’m happy to say I’ve started writing a book worth reading.

This last few years felt strange, because I felt like I was right back where I started this decade. Life has a way of throwing the same test at you over and over until you finally pass it, and that’s what happened this time.

I finally started that rock n roll band after being too scared and distracted to do that the other 10 times I wanted to.

I finally put my head down and stuck to one path and built that company that actually made some money.

I finally stopped seeking approval from women and peers and financially successful people and started seeking approval from myself.

I finally did me.

I still felt (read: feel) lonely at times. I still felt ugly, and stupid, and anxious, and 2 feet tall, usually when my work-life balance was favoring work. I still felt that familiar insecurity and depression creeping in. I still wanted to prove that I’m as good as I’ve always believed myself to be. I still made impulsive emotional decisions and overshared. And I definitely still pondered if me deviating from the well-trodden path will end up being my biggest regret or the thing that makes my life worth living. But all that stuff is normal, at least for me, and can be mitigated by gratitude, love, self-reflection, play, and hard work toward meaningful goals.

Ok, wrapping this thing up.

I’ve been a bit of a ghost the last 6 months, so not a lot has changed. I don’t want to be 35 still working too-many-hour weeks for less than I made when I was 25, so I went full gas on creating things with all this wisdom I’ve been accruing, and that’s been cool.

I don’t have a ton of plans for the next year/decade.

I cracked some of the code on the money machine, so I want to keep pulling that lever while also taking time to appreciate it and be more methodical. I want to stop deferring putting myself out there (believe it or not, this isn’t that). I want to find a partner who complements me as I/we build toward the starting line of life (having a family). I want to get my music in front of a million people and play for 1000. I want ten million people to benefit from my products.

Other than that, I’ll probably work a little too much, spread myself a little too thin, and worry about stuff that doesn’t matter.

Thanks for riding with me y’all. Let’s do even more in the next 10.