31 - The Metric That Matters For Ambition And Slowing Down
31
This is the first year I’ve really wanted time to slow down.
It’s always been about what’s next.
In middle school I had 1 close friend outside of the guild I ran in my MMORPG. I wanted to find some people who I could jive with in high school.
In high school I was mostly a chubby late bloomer. I needed to get the hell out of there for…a lot of reasons. College would be a fresh start.
In college, I was under-stimulated at a school that gave me alcohol and bodybuilding as the only options for occupying an idle mind. I was meant for more, so I’d go to a good grad school.
In grad school, I was surrounded by the cream of the crop, but I wanted to go make something of myself in my 20s, so I counted the days until it was over.
In my mid 20s, I wanted to build a financial base, fill out my resume, figure out women so I spent the whole time self-improving.
And now at 31, I’ve got it all figured out.
I am just kidding.
I can say, however, that I don’t have much more to do.
I’m running a company, I have people who like me, a house, some money, experience, a rock band, competence.
I spent 20 years building and growing toward who I am today, and yeah I got a lot done and that’s something to celebrate, but I was depressed for like half of it, I hated who I was a lot of the time (not because I did anything bad, but because I believed I wasn’t good enough to like myself), and I delayed gratification so much so that I’ve yet to taste it.
There’s nothing to “look forward to” anymore. I’m here. I’ve arrived. And I can’t help but look back and kick myself for not appreciating literally any of that, at least not as much as I should have.
The car got to where it was going and got better along the way, but we put a lot of wear and tear on the engine because the only fuel I knew was dissatisfaction.
When I went from chubby to muscular, I did so through self-derogation. You’re fat, you’re small, you’re weak, you’re worthless.
When I sucked with girls, I beat myself up about it. No one wants a p**sy. Be a man, Be better.
When I wasn’t an A player at work, I called myself a loser every day until I was.
When I too afraid to start my rock band, I reminded myself daily that I was gonna die full of regret because I was a coward.
All of these worked. All that discontent kept me moving. I can’t speak for everyone, but I suspect many face these same challenges, and many walk this same path.
For the first time, I tried the same playbook and it didn’t work. It didn’t work because I didn’t need to grow in the same way.
You can never be happy when you spend every day self-flagellating, all you’re doing is adding pain to an already hard thing.
To put this only slightly more clearly, until recently I thought beating myself up was the best path because it had always gotten me somewhere. Drive fast at all costs.
But this year it became clear that driving really fast is not a deterministic way to make progress toward anything but engine failure.
It’s not the movement that matters, but the direction.
When you have a lot of room to grow, everything equals progress. You’re becoming a better driver, you’re learning the roads, you’re getting seat time.
But when you’re trying to eek out that last 5% to become exceptional, almost nothing equals progress.
I didn’t need to lose the last 10 years to disappointment. I needed to slow down and actually think about what was working and what wasn’t.
I say this is the first time I’ve wanted time to slow down because I’ve exhausted all the easy gains. Every day now is up to me to make something of.
I can’t put the same caustic fuel in the tank and do a bunch of donuts in the parking lot and call it a day.
There’s plenty of actual evidence, like hours of video’s worth, that I like doing donuts in cars, on motorcycles, etc. But I don’t want to do donuts with my life. I want to go places.
Which leads me to believe that directed action is the thing that matters—it’s to know where you’re going rather than to know you have a cool car and drive it as fast as possible expecting to end up somewhere worthwhile.
My directive today is to act intentionally.
I’ve gathered a bit of wisdom over the years and some of that did come from donuts, but my donut wisdom era is over.
You have 2 choices.
Plan, react, adapt. You follow other cars or obsess over changing traffic patterns or just pick a spot on the map that looks cool. This can be good when you’re starting out to learn how life works, but you aren’t always going to know what’s going on or where you’re going.
You decide where you’re going before you start driving and you figure out the best way there.
Building your own convictions is scary, because what if you’re wrong? The wisdom of the crowd is convincing!
But especially these days, I’m less convinced the crowd has all that much wisdom, and the few people that are doing well started by walking their own paths and picking up crowds along the way.
Picking your own path not only lets you work on something you care about, but it lets you understand what’s going on while you’re getting there.
That was the missing piece.
How I feel about driving—what I use to fuel the engine—may change. I can break down or get some upgrades so the car may change too. But the direction should not.
Yes, things come up, you may gain new information, but Sam and Frodo knew they were going to Mordor, so it became about the route, not the destination.
I used to think it was all about the car. Keep driving. Keep suffering. You’re probably getting somewhere, I mean look at all that evidence.
But when you look in the mirror at a car that has all the things you’ve been working for, you realize you still have go somewhere in it. Gauging success by how many miles are on the odometer isn’t going to help you get there, picking a good route will.
I am an agent of change. I am cause, and I am made to have effect. I am not potential, I am action. I am not made to be capable of awesome, but to do awesome.
You weren’t put here to be “trying to get better” the whole time. Having a nice car isn’t the point. Conversely, you also weren’t put here to go out and party or drink mimosas or go shopping every weekend. Getting car washes, street racing, paint jobs—fun matters, but hedonism is also not the point. These are not meanings.
If you’re unhappy with how little you’re getting out of life, maybe you do need to spend 5 years in pain to find your way back to something meaningful, but don’t mistake that for a meaning in and of itself.
You are here to make an impact—on your family, your community, the world (probably in that order)—and that’s a blessing worth celebrating, not castigating or shirking.
This year I gathered more evidence that I am who I say I am. More level ups in areas that matter. More perseverance. More adversity. Those are all good, but they’re just evidence that the car is improving. I’ve already got enough evidence. I can self-improve in perpetuity.
While I don’t plan on getting out of the car, I am shifting my focus to navigating.
Movement is no longer the metric.
This next year is going to be pretty make or break. I am under a lot of pressure, and I believe that taking my own steps at a pace that makes sense—rather than reacting to the steps of others—will buy me clarity, conviction, execution, and a bit more happiness.
I haven’t slowed down in a decade, and this year I think I averaged a disgusting amount of hours/week. I don’t feel good about that. I don’t think well. I don’t really smile anymore. That’s stupid and I don’t like it.
I hope to find a some solace and clarity in catching my breath. In thinking before jumping. In knowing where I’m going before shifting into a higher gear,
I’m grateful for that, and grateful I still have time to course correct before I wake up one day curious where it all went.
If you’re done reading here, fantastic. I appreciate you. I hope you got something out of this.
Love,
Jack
Below is a version of this I did that is more narrative driven and less abstract. It’s funnier, it’s more tangible, so if you want to keep reading, go for it. It’s mostly there for me but you will get something out of it.
This last 6 months has been a lot of hard lessons. Showing up on time was the biggest one. If you know me, you know I’m 5 min early to everything, which makes this ironic. We were late, and being late means pushing a boulder up an ever-steepening hill. Sisyphus was actually working on a start up. The Greeks were so ahead of their time.
We had a lead investor pull out the day they were supposed to wire money (we had just hired an engineer who had left his job to work with us), we got dozens of nos, we soft pivoted 3 times, we bet the farm on ourselves twice. Each of these would have been among the hardest things I’d ever dealt with just a year ago.
But we showed up every time. Every time. There were problematically few days off. You don’t get a million chances to get off the bench, so you make the playtime count.
There were many bad days. Mostly bad days if I’m being honest. We had to deal with awful people who disoriented us and treated us poorly just because they had power over us. We had serious bad luck at a monthly cadence. We had to come to terms with losing (not an easy thing to do for people who like winning), so that we could dissect why we had lost.
But we had a few people who believed in us. Self-belief is important, but it can only take you so far. If you’re full of conviction with 0 external validation, you’re probably delusional. But when you have believers, they couldn’t possibly be delusional too, right?
Well we did have believers, and those people are important and I will remember all of them forever no matter if they are also crazy.
But believers come in different forms.
Some people pretend to care about you to curry favor and will turn on you at the first sign of trouble. Avoid these people for they will have you questioning yourself. They are not believers. They are the opposite.
But the people who are honest with you and who give you a hand when you fall and even the ones who reject you but stick around to tell you why, these are the people who believe that you have the capacity to change and that you can do the thing. That’s beautiful.
My mental health was something I kept an eye on. I was juggling a dwindling company bank account, a dwindling personal bank account, a product that was not working, market signals that told me the exact opposite of what I wanted them to, and I felt alone throughout much of this. As the leader, I put it on myself to take as much of the burden as I could, and I don’t think that was good for me.
My mental health was usually bad. But enough time unhappy has helped me understand how brains work.
Depression is expecting a bad tomorrow. Trauma is having (sometimes reasonable) sensitivities to things that have burned you in the past. Anxiety is trying to hold two conflicting beliefs in your head at once, usually one thing you want to be true and another that actually is. I have done my best to remain hopeful and to internalize missteps without being afraid to continue walking. But I have worried. A lot.
I can confidently say I’ve spent 90% of my waking hours either working on the business or thinking about working on the business. But thinking can be a crutch. It’s common to want to solve all your problems. But some things are out of your control. And some things take time to transpire.
I’ve had many (many) sleepless nights. This was written during one of them. Many days where I come home after a long day and end up staring at the wall or scribbling in my notes app for hours as my apartment grows dark. Some of this is helpful - it helps organize thoughts. Good ideas do occasionally come from it, but if I’m being honest, if I had never done any of that we’d probably be in the same spot.
The best antidote to worrying isn’t worrying. You can’t “worry it all out”. Worry feeds itself, not the other way around. The best antidote to worrying is action. Ideally directed action. Gather data, ask questions, gather more data, and make an objective decision.
I say make an objective decision as if that’s easy. Being objective is the hard part. If you have all the data points and you still refuse to draw a line through them, you will remain unhappy. Changing directions is not natural. We spend years trying to justify our current direction, no matter how bad, no matter how much data we collect, no matter how wrong it feels. Pride is the worst sin because it blinds us to truth. Get rid of your pride. Have some humility. We know the answers to our problems immediately and spend years coming to terms with them. Skip the years.
And give yourself space.
You don’t think well in noise, but in silence.
Good ideas don’t materialize in the wind tunnel that is anxiety, nor from going to social media for a dopamine hit that confirms, or at least distracts from, destructive, comfortable beliefs. Good ideas come from peace.
One thing that I knew quickly but accepted slowly is that we were late. Being late meant every day felt like grasping for fewer and fewer straws. Yes, we dug very deep to remain relevant in a race we knew we should not have been in, and yes that’s bad ass, but we’re not here to lose. If you find yourself in that position, find a new race.
I’m not saying quit. Doing hard things can feel like climbing a mountain. Quitting is letting go. There is gravity to letting go. It will get you down the mountain. You can lick your wounds and find something else to do and join the millions of people partying at basecamp. But anything worth doing involves a summit, so the decision becomes about the route, not the climb.
If you’ve chosen a bad route, find another route. You might have wasted months on the current route, but that isn’t justification for continuing. That is hubris. Homer already did an entire Odyssey on that. You don’t need to do another.
And that brings us to today.
29 was a year of finding stable ground. 30 was a year of sprinting on that new footing. 31 will be a year of breathing.
I came into 2025 confused. I had been running for so long I forgot that running isn’t the point. Getting somewhere is.
I was out of breath. You can’t think when you’re out of breath. You can’t write when you’re out of breath. You can’t do anything when you’re out of breath. It’s reactive. It’s anxious. It’s by definition not homeostasis.
That is no way to live.
Today everything is convenient. It’s very easy to have a very easy life. But ask anyone with an easy life where they’re going and the answer is going to be as vague as their direction. And then ask them if they’re happy.
With comfort so accessible, so encouraged, suffering becomes a barometer for progress.
It’s why ambition doesn’t concern itself with the molasses of criticism from the stationary.
That’s where I would have stopped before, but things have changed.
Bouts of anger, sadness, loneliness, disappointment, anguish. A couple moments of joy. That’s how I’d describe this year.
As I’ve said before, you only learn outside your comfort zone. Winning is uncomfortable. But I don’t believe life needs to be hard all the time, and hard != good.
Everyone has some magic within themselves, and to access it they must scrape away layers of debris. That process is painful, making pain a good initial gauge for progress.
But the opportunity cost matters too. I feel like I’ve been asked to pay an admittance fee of the best years of my life for a ride I’m not even sure I’ll be able to get on, and the older I get, the more I realize that’s part of the game.
That’s not to say hard games shouldn’t be played, but that is to say playing isn’t the reason we play. Being in the game isn’t the point. You don’t want to lose 10 years “in the game” for the sake of being in the game.
A vector has magnitude and direction.
I spent a lot of time maximizing magnitude this last year. We went FAST. You know how I feel about that. I love that shit.
But my job as a CEO is first and foremost to know where we’re going. You can’t read a map when you have 100mph of ocean breeze in your face (we’re now on a speedboat in this analogy).
I need to slow down.
If I do this right, the speedometer reading will go down. But the miles traveled toward the destination should go up.
I started pursuing music by sprinting. I went to 3 open mics a week, I talked to everyone, I practiced relentlessly, I went to everyone’s shows. Then I learned the game, I figured out the direction, and I could slow down. 2 years later, I played a show for 200 people (that was February and it was insane) and I feel confident I can continue growing the band without the motion blur.
Business looks a little different, but the song remains the same. Sprint toward knowledge even if most of it’s garbage. Use that knowledge to establish a direction, then set cruise control to something you can maintain.
I’m grateful that I get to play this game. In some ways it was forced on me. But in others it was the only path I could have taken. I get better every day, I learn lessons I already knew but had too much pride to accept. I’m learning and getting better, and most importantly, I’m making stuff.
All victories become Pyrrhic because they will destroy you, and that’s a good thing.
Parts of me die along the way, other parts get watered. I’m not sure if I’m becoming who I am supposed to be or who I need to be, but I’m definitely becoming something.
I have a company with employees. I have a great rock band that makes music I am obsessed with. I am pretty unflappably confident in my ability to do hard things (even if my self esteem and self consciousness don’t always make me feel it).
This is sort of a ramble, but that’s because this last 6 months was sort of a ramble.
30 was a year I’ll never forget even though I probably would be better served doing so. I mostly struggled, but I was recruited for a podcast with a great friend that’s starting to grow, I randomly became an actor (a lifelong dream), I played my biggest show to an amazing crowd that loved my music, I bought and renovated a house (thank you mom and dad for the help), and I started a company that despite innumerable setbacks, is on its way up.
That all happened this year, and that’s amazing.
Love,
Jack