Going Big or Staying Home
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Today’s piece is the final part of a series from , , , , , and me. You may remember our past series on fatherhood and recovery. This week, we explored the topic of work. It has been a pleasure meeting monthly and collaborating quarterly with these exceptional writers and men. Check out their pieces for the series linked at the bottom.
One of my wife’s favorite stories to tell about our first date is how boring she felt after hearing about my life. From touring in a major label signed band to playing professional poker, and a plethora of odd jobs in sales, insurance underwriting, and the golf industry in between, mine has not been a straight, nor typical, path.
While most people listen to my unique background with awe, I can’t help but think about how many things haven’t worked out for me over the years. I’ve lost track of how often I’ve started over. Of how many times I’ve gotten excited about the next big thing, only to have it fall short again.
This pattern of yearning for outsized success developed early on.
My band Pressure 4-5 signed a deal with DreamWorks Records in late 2000. This was the first time I tasted what outsized success might look like.
We decided to sign with a major record label rather than an indie label because we felt it gave us the best chance to make it big. The major labels and publishing companies had the money, connections, and marketing firepower to turn average Joes like us into household names. We saw our friends in the band Papa Roach do it when their single Last Resort took off. Why not us? So we signed a contract with DreamWorks, the same label they were on, and a publishing contract with EMI, giving up more rights to our music than we probably should have and ceding our future as recording artists to our record label's whims.
Everything was humming along as it was supposed to—we were on tour, our single was released to radio, we were doing magazine interviews, and we saw our video on MTV2 late one night at a motel on the road. And then, 9/11 happened. The world stopped and nobody gave a crap about a new upstart band.
We toured on and off for over a year. We filmed a show in Denver for an MTV special with our friends in Alien Ant Farm. We released another single for our song Melt Me Down, albeit with far fewer marketing dollars behind it.
But nothing worked.
We drove from what we didn’t know would be our last tour stop in Lousiville to our home in Santa Barbara, and went back to the drawing board to write some new songs. We recorded them in our practice studio and sent them to our A&R guy at DreamWorks. He encouraged us to keep writing more music, which meant he didn’t hear what he deemed a single-worthy, radio-friendly song, which meant we weren’t going to get our next advance for our second album anytime soon.
I was running out of my allotment from the first advance, so I got a job at a local golf course. My band kept writing more songs, but eventually, I left to join my brother’s band, and later on, they called it a day and never recorded another album. I tried to get my new band hooked up with a manager and other industry contacts, but the music business was changing rapidly. Napster and other file-sharing tools were freaking out the record labels. Heavier music was fading from the mainstream.
I felt burned out and left my dream of making it big as a musician behind.
But my pattern of searching for outsized success continued.
A friend taught my brother and me how to play poker. We’d play home games with friends, I dabbled in online poker, and I worked up the courage to play in the poker room at a nearby casino. Then a guy named Chris Moneymaker won the Main Event at the World Series of Poker (WSOP) in 2003 for $2 million. Later that same year, another friend hooked me up with an invite to be a proposition (prop) player on a new poker website called JetSet Poker where they would pay me an hourly rate to keep cash games going so they could collect their cut of each pot.
I’d pull all-nighters at the casino, show up for my opening shift at the golf course, and try to keep myself awake until my shift ended and I could go home to sleep. One time I even played an online tournament on the same computer we used as the golf course cash register and I ended up winning a trip for two to a series of poker tournaments in Curaçao. I ended up making thousands of dollars on that vacation.
It became clear that I was making more money playing poker on the side than I was at my day job, so I quit and spent more time playing cards. I made most of my money playing cash games and steadily grinding out a decent hourly rate as a prop player. But I dreamed of going deep in a big tournament for a big score.
In 2006 I qualified for what was then the largest WSOP Main Event field in history, a $10,000 buy-in tournament with 8,773 players and a $12 million first-place prize, until last year’s Main Event field eclipsed it with 10,043 players and $12.1 million up top. It felt like it was my time. I was confident and my game felt solid. But on day 3, after roughly 27 hours of play, I was busted out of the tournament a couple of hours short of the initial money payouts by Michael Binger, the guy who would go on to place 3rd and win over $4 million.
I kept playing and was profitable, yet I never cracked through to a sizable tournament win. The long hours sitting at the table began to wear me out. This thing that was once a fun hobby was now something I was spending nearly all my time doing. If I wasn’t clocking in online, I was headed to the local casino or driving to play in Vegas. My mood was dictated by how well I was doing at the tables. My relationship with the value of a dollar became unhealthy.
Yet again, I felt burned out and left the dream of making it big as a pro poker player behind.
On the cusp of turning 30, I decided it was time to find a “real” job. I became an entry-level underwriter at State Farm, and, when they decided to close that regional office, I moved to a sales position at a company specializing in niche scientific equipment, where I was working when I first met my wife nearly 11 years ago.
But the starting over was just beginning.
I still remember the impetus for getting into tech startups. I was listening to a podcast interview with the founder of Uber and he said they were growing 25% month-over-month. A week or so later, I ran the sales numbers for the team I managed at the scientific equipment company and we had only grown 2% over the entire year. Sure, there were many valid reasons for the paltry number, most out of my team’s control, but the difference in the two numbers was stark. I wanted to build something that could grow more quickly and hitch a ride on that rocket ship.
There’s this concept in the startup world called failing fast. You try something out, and the sooner you figure out it’s not working, the better. Because then you can adjust and pivot to something else, or scrap the idea entirely. For many years, I’ve been drawn to that way of working. It fits nicely with my tendency to be interested in many different things, and how I rarely feel strong enough conviction to fully commit to only one thing for an extended period.
During my time in early-stage startups, I thought I’d eventually hit on something that worked and could help scale it up into a life-changing outcome for all involved. And yet, I’m left with a resumé full of company names hardly anybody but my close friends, family, and former coworkers recognize.
My story with work was scripted by this point—find my next passion, immerse myself in it, and when it invariably failed or when I felt the inertia of my passion subside, rinse and repeat.
A monthly golf subscription box idea. The next health food bar. Cracking into the crypto space.
Most recently, I had dreams of becoming a well-known author. It was part of the catalyst for starting this very publication. For over three years, I felt a sense of urgency to keep writing and publishing and building my audience, all in service of some seemingly distant goal of writing a bestselling book.
But the constant hustling also burned me out, so I stopped publishing weekly.
My work has historically been deeply tied to my identity. Like many American men, I saw success in my work as a measure of my self-worth, and the fact that I kept falling short left me feeling insecure and unsure.
I’ve grown tired of chasing the big win. Sure, it would be nice to see another digit tacked onto the total in my bank account. But I know on an intellectual level that it wouldn’t solve all my problems or necessarily make me any happier.
My wife and I have been smart with saving our money, and we’re lucky enough to receive some help from the state for our nearly six-year-old daughter due to her cerebral palsy (although we’d forgo that money in a heartbeat if there were a cure for it), which affords us some options with our work. We own a house with a reasonable mortgage in the suburban city of Sonoma, a town that people travel from all over the world to visit, and we don’t plan on moving anytime soon.
So what am I chasing a big win for? Who am I chasing it for?
Maybe my desire for outsized success has diminished because I’m getting older. Or maybe it was inevitable after the perspective-changing, traumatic birth of my daughter.
Recently, I’ve settled into a more steady way of being, where my work at Foster (check out our new website!) is just one of many things I do. I value having a flexible schedule and not needing to commute two-plus hours each day so I can be there for my family. My passions and hobbies don’t have to bring in any income at all. Ever. I can write because it’s fun to push myself creatively. I can play golf because it’s a challenge to improve my game and it’s nice to hang with friends outside in the sun. I can dedicate time to work on myself and learn how to enjoy the life I already have.
Those daydreams of the big win still show up sometimes. But they don’t feel as urgent anymore. Maybe it’s because I’ve won big in life already.
Check out the rest of the work series:
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Loved these two paragraphs: "My work has historically been deeply tied to my identity. Like many American men, I saw success in my work as a measure of my self-worth, and the fact that I kept falling short left me feeling insecure and unsure.
I’ve grown tired of chasing the big win. Sure, it would be nice to see another digit tacked onto the total in my bank account. But I know on an intellectual level that it wouldn’t solve all my problems or necessarily make me any happier."
Chasing the big win as a writer is an increasingly cruel fantasy. I keep reminding myself of Bill McKibben's idea of durability (for the planet, but also for ourselves). The racehorse economy that cycles through explosive highs and sudden crashes is a poor model for our lives -- but there are no big wins without riding that horse. The workhorse who plods along through the mud and doesn't accelerate much down the home stretch, but who doesn't break a leg either, is a better prototype to live by.
Professional baseball was my first dream. I've been chasing the book dream for a while, but publishing my memoir was a reality check. Substack dangles the same idea in front of its writers, and I think it has to be resisted in favor of McKibben's idea. Sustain yourself, sustain your family and local community, and you'll have what you need (without risking catastrophe).
That’s the wisdom of age kicking in. I think contentment is a better path to happiness than “success.” If you enjoy what you have more than wish for what you don’t have, you will probably have a good life. Life is making memories. And it sounds like you have plenty. That is a successful life.
Ask any old person and they will tell you, relationships are more valuable than things. Or careers.