A Visit from Lyle
Editor’s Note: I’ve been exploring an idea I’ve named Duality of Self. It’s the friction we feel when two parts of ourselves want two different things. How should we decide which way to go?
My friend Lyle McKeany shared how he’s answered that question throughout his career, which has ranged from touring musician to assistant golf pro, and even full-time poker player. Incredible, I know. His piece below — one of his advice-column-style posts — felt perfectly on point for me, and I hope it will hit home for you too.
Hey Lyle Letter #005
I hate being young.
I think part of the peer pressure to be young is that there's an implication that while you have the energy and metabolism, you can still achieve Great Things™. There is an idea that this is the time for experimentation, but also that if you don't "find a stable footing in something" (whether that's your life, your career, or whatever it is), then it will get exponentially harder in your thirties. But I also think a lot of this pressure to Make Something of Yourself in Your Twenties™ or the deluge of content around Things I Wish I Told My Younger Self™ is making me feel incredibly stressed out with the few remaining years of my twenties.
I'm torn between using up every waking minute of my day towards some grander goal of productivity. I won't deny that I have extreme FOMO for what appears to be anyone who has ever had a holiday. But I also worry that specializing in something will cause me to lose out on opportunities that I am not exploring.
At what point do you decide to go really deep into something and at what point do you decide that there's time to look up? How does one conceptualize time in the sense of it ruthlessly moving forward, and yet thinking about "Will my future self need this thing I am doing today?"
Thanks in advance,
Unqualified Member of the Twenty Seven Club
Hey Unqualified Member,
When I was twenty-seven, it was 2004 and my music career had already come and gone. I was living in Santa Barbara and working at a golf course. I had just started playing poker on the side and was getting good at it.
Fast forward a year and I was making more money playing poker than I was as an assistant golf pro. I’d spend long hours in front of my computer playing online or drive over the hill to the local indian casino. There were many times when I’d pull an all-nighter at the casino, drive back to open the golf course at 7:00 am and try not to nod off in between helping customers.
A few months before I got married on New Year’s Eve 2005, my wife-to-be (now ex-wife) surprised me when she suggested I focus on poker full-time. I calculated my hourly rate and it was over double what I was making at the golf course. It was exciting but also frightening because any safety net I had was suddenly gone. If I had a bad run at the poker tables, I could go broke.
I never went broke, although I did have some awful runs. One time, during a visit to my parent’s house, I was playing online after they went to bed. I was on four tables at once where the maximum buy-in was $1,000 each and I lost over $4,000 in the course of about fifteen minutes. I was visibly shaken from it. I had to call my brother so he could help calm me down.
Playing online was all well and good, but what I really wanted to do was play in the big tournaments I obsessively watched on TV at the time. After a few tries, I finally qualified for the 2006 World Series of Poker $10,000 buy-in Main Event. Anyone can buy in by ponying up $10,000, but I won my seat in an online tournament that cost nothing.
In late July 2006, I made the drive from Santa Barbara to Vegas with my friend Aaron who had also qualified. We walked into the hall at the Rio Hotel and Casino and were immediately hit with a cacophony of poker chips riffling, cards shuffling, and people talking. The sound was intoxicating and gave me chills. I might’ve been intimidated had I not been playing so well leading up to the event. Instead, I was anxious to get the tournament started the next day.
The Main Event is one of the slowest poker tournaments in existence. That might sound bad to most people, but to skilled poker players, it’s ideal. It gives them plenty of time to navigate the competition and not have to take huge risks to gain chips. This Main Event was also the largest field ever for a live poker tournament with 8,773 players and a first-place prize of $12,000,000.
After twelve hours of play, I made it through Day 1 with an average-sized stack of chips.
Day 2 didn’t go quite as well. At one point, I was involved in a big pot and an ESPN camera crew started filming me. I remember I had two kings in my hand and I was worried about an ace on the table. If my opponent had any old ace in his hand, I would lose the pot. He bet big and I took so long to make a decision that the camera crew gave up and left. I folded my hand and the other guy later told me he was bluffing.
But I still made it through another twelve hours of play on Day 2.
About four hours into Day 3, my chip stack was dwindling. Not much had been going my way and I was mostly biding my time since we were getting close to the money. Typically, poker tournaments pay around ten percent of the field. If I made it to 873rd place, I would walk away with $14,597.
I was finally dealt a decent hand, a pair of tens. I faced a raise from the guy with the largest stack of chips at the table and I thought, Welp, this is it. I pushed all my chips in, everyone folded around to him, and he called. He flipped over a pair of jacks. The dealer dealt the rest of the cards and none of them helped me. I was sent packing without making a dime. I later learned the guy who knocked me out was Michael Binger who went on to finish in 3rd place and win over $4,000,000.
After getting oh so close to achieving my Great Thing™, I went back home. Back to playing the smaller games online and at the local casino. I felt deflated and uninspired.
It was also starting to feel strange making my living by winning money off of other people. When I went to the casino, I’d always see the same players losing over and over. It was depressing to watch and I didn’t feel like I was contributing much to society.
My thirtieth birthday was looming that October. I was feeling the same pressure to Make Something of Myself in My Twenties™ you’re experiencing right now, Unqualified Member. Trust me, for someone in your late twenties, you’re not alone in these feelings. It’s perfectly normal to feel something akin to lost youth when the first digit in your age is about to tick over to the next number.
The truth is, humans created a base ten counting system because we just so happen to have ten fingers and now we get worked up about each new decade of our lives as a result—except when we’re ten and we get worked up in a good way about our one and only double-digit birthday.
So in September 2006, I cashed out the majority of my online poker bankroll. I was about to go on a two-week European trip for my honeymoon anyway and wanted some extra spending cash.
I didn’t hop right back into playing poker when I got home from the trip. Instead, I contemplated what the next chapter of my life should be.
Thirty felt like such an adult age to me. Up until that point, my career—outside of hourly wage jobs—was anything but traditional. I had even dropped out of college to pursue my music career. Turning thirty felt like an opportune time to grow up, get a “real job”, and perhaps even finish school.
My ex-wife and I had been discussing moving. Job prospects in Santa Barbara weren’t the best and our nearest family were my parents in San Jose, a four-and-a-half-hour drive away. Within a month, she lined up a new job about an hour north of San Francisco in Santa Rosa where one of her aunts lived. It felt like the fresh start we needed and her aunt offered up a free room for us to stay in until we could save up some money and find a place of our own.
Not too long after we moved, I landed a job as an insurance underwriting assistant at State Farm. They offered tuition reimbursement, so I enrolled at Sonoma State University as a business major. I was ready to work hard and Climb the Corporate Ladder™.
And I’m telling you, Unqualified Member, I was damn good at that job. I was almost always near the top of my department in work output and I was doing all sorts of extra things like running committees. I even wore a tie to work sometimes.
I was grinding it out working full-time and going to school either early in the morning or after work during the evenings. A couple of years in, I put my hat in the ring for a promotion to a full-fledged underwriter, which came with a $12,000 per year pay increase—a huge amount for me at the time. But it required a bachelor’s degree and I still had one semester left. My boss encouraged me to apply anyway. I felt confident about my chances. I interviewed in front of a panel filled with managers who knew me and my track record. It seemed like a foregone conclusion. Until it wasn’t.
Instead, they hired someone fresh out of college who had zero insurance experience whatsoever. I was crushed. She was a super nice person and she became a great underwriter, but it still didn’t sit right with me. The momentum and excitement I had about the company and my career suddenly dissipated. All of my hard work felt like a waste of time—but hey, at least I got a college degree out of it.
So, Unqualified Member, what do you think I did next? You guessed it. I started thinking about my next chapter.
This is how it has gone for me in my professional life for as long as I can remember. I wish I could say it has all been part of some master plan, but it hasn’t. My career has felt mostly haphazard and random. I follow my interests at any given time. I dabble for a while. I get good at something. And then I go deeper. If things don’t work out, I repeat the process.
When my plans go awry, I can choose to look back at them as valuable life experiences that build character and provide fodder for stories, or as scars and reminders of what could have been. Enough of them have accumulated over the years that it can feel disheartening. My mind riddled with the scars of failure. But most of the time, I chalk them up to incredible life experiences, some of which very few people get to have.
You should follow your interests too, Unqualified Member. If you become obsessed with something, then go deeper. But go deep with your eyes wide open. It’s common to have Big Dreams™ but it’s way more common to not realize them. And it’s common to feel like it’s our fault if they don’t come true.
Going deep doesn’t mean neglecting all other aspects of your life either. The garbage bins need to go out to the curb every week, you should do some sort of physical activity regularly, you should call your parents from time to time, and if you have a partner or kids, you should spend quality time with them often.
If you want to achieve Great Things™, then you must go deep. But achieving Great Things™ isn’t a requirement in life. Ask yourself what achieving your Great Thing™ means to you.
It doesn’t have to be career-related. Maybe it’s raising a family and being the best parent you can be. Maybe it’s volunteering for a non-profit and helping your community. It could be any number of things.
Perhaps you haven’t yet found what you’re ready to dive deep into. That’s okay too. Nobody is sitting around waiting for you to figure out what you want to spend your time on. Most people are too wrapped up in their own lives to give a crap about what’s going on in yours.
I’m forty-three now, so I’m statistically on the back nine of my life and feeling the You Better Do Something Of Substance With Your Life™ type of pressure. In my case, the pressure doesn’t come from external sources as much. No, society generally doesn’t have many expectations of people my age. We’re supposed to have everything more or less figured out and now we’re getting promoted, building wealth, and raising our kids. The pressure I’m feeling is more internal.
It’s not the fear of missing out (FOMO), it’s the Fear Of Already Having Missed Out™ (FOAHMO).
This is where I believe the pervasive narrative and subsequent content you mentioned comes from, Unqualified Member. It comes from a place of fear from those who feel like they haven’t achieved enough. Call it Shoulda Woulda Coulda Syndrome™.
There’s pain in those stories. There’s regret. There’s loss. And, if we’re not careful, regret and loss can haunt us for decades. We humans are fantastically good at finding the faults and errors in our ways.
The best way to combat this tendency is to give it your best. Pour your whole self into it. If you attempt to achieve Great Things™ and you fall short, knowing you gave it everything you’ve got will help you sleep at night.
You’re right that time is ruthlessly moving forward, Unqualified Member, whether we like it or not.
But there’s still plenty of time to find your thing.
When you find it, you’ll know it.
And you’ll be more than ready to dive into the deep end.
Until Next Time,
Shiv + Lyle
Stories by Shiv and Just Enough to Get Me in Trouble are part of Wayfinder, a writer collective exploring questions that matter.