Rich, Powerful, and Ready to Quit
A Wall Street power broker plans his escape – will he go through with it? [The Other Side of Enough: Interview #7]
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The Way of Work explores stories of where we fit in the world of work. This is part of the new series, The Other Side of Enough, exploring what life is like when you have enough to never work again. Check out the last one: After ‘Happily Ever After’
Imagine you're one year away from walking away from your job, financially free, with no need to work again. Only a few other people know about your secret escape plan.
What’s in your head? Is it relief, thinking “thank god!” Or is it creeping doubt, asking, “uh oh, what am I doing?”
Most stories from The Other Side of Enough series are from people who have already crossed the threshold to “enough” and left their old lives behind. But today’s story is different. It’s about someone who’s still in the middle of it.
Marlo (not his real name) is a senior executives at one of the largest finance firms in the world. He earns a high seven-figure salary, sitting comfortably among the financial elite. On paper, he has everything.
But Marlo’s story isn’t about triumph, it’s about hesitation. Despite having more than enough — money, status, and success — he’s wrestling with a deeper question: is he enough?
Marlo reached out to me as a reader, drawn to conversations about redefining life after “enough.” In between a packed day of meetings on a Thursday, he called me from his office overlooking Manhattan, opening up about his dreams, doubts, and plans for escape.
What’s next for Marlo? And what does it take to not only step away, but to face what lies beyond?
The Clarity of Competition
Most of us aren’t born with a calling. Instead, we often choose careers based on the signals and options around us. When we’re unsure of what to do, we gravitate toward what’s clear, even if it means forgoing a deeper search for something more.
For Marlo, his path to finance wasn’t intentional, it was circumstantial.
“I grew up in [an upper-class town near New York City]. There's a lot of investment bankers and financial services people there. So it was a path that was well articulated for me.
I had no idea what I wanted to do. It was not because I had a passion for high finance.
I was always jealous of those people who had a calling and wanted to be a doctor since they were 7 years old.”
If there’s one thing that shaped Marlo’s journey more than anything, it was his natural drive to compete. A high-achieving athlete and captain of every sports team he played on, Marlo found himself drawn to finance for its cutthroat nature and clear parallels to sports.
“[Finance is] super fast-paced. It’s pretty intense. There’s a lot of parallels to sports. Every day you win or lose.”
Finance became a natural substitute for the competitive drive that propelled him to the top in athletics.
“It was like, well, ‘what's the most competitive, hardest thing to get? I'll do that.’”
Like Marlo, I understand the seductive pull of competitive games.1 They offer clarity, a sense of progress, and the chance to move higher in the rankings. But while we compete to win, we often fail to ask ourselves: why are we trying to win in the first place?
Seduced by Success
While Marlo may have stumbled into finance, the benefits kept him tethered. The intensity, competition, and external markers of success offered an attractive allure.
“The trajectory was so stunning, like a hockey stick, that I was like, ‘What's next? What's next? What's next?’
Becoming this person of influence in the market. And of course, all the financial rewards. It was a level that I had never seen.”
These rewards, unsurprisingly, had the power to suppress deeper questions. Any underlying agitation or a sense that “this isn’t right for me,” was pushed back down below the surface.
“I think it probably muted that little voice in my brain that was kind of like: ‘Are you really passionate about financial markets?’
[Finance] wasn’t the answer. My career was much more about accolades and achievement, and just climbing the ladder.”
The cycle of work and reward can be self-perpetuating, keeping us hamsters on the wheel for quite some time. The lure of tangible wins and external validation can keep us running endlessly, without ever asking why.
“It was much more of a near-term tactical ‘win, win, kill, kill,’ as opposed to any sort of broader vision.
It had nothing to do with any concept of enough. Or what I want. The maturity wasn't there.”
Is this it?
After years of relentless grinding, Marlo starts to lift his head. He’s already achieved so much, but like so many of us, he starts asking himself: is this it?
Questions like this, hidden beneath for decades, inevitably bubble back up to the surface. We can only hold them down for so long.
Despite reaching a rare level of success, Marlo finds the next step increasingly unclear. He describes the shift in his mindset as his career progressed...
“[Later in my career], it was a little bit like, okay, I'm in rarer air, and started to [see] some of the political battles and the knife fights.”
This is when the realization hit: the next level might not be worth it after all. The people ahead of him are still grinding endlessly, despite their success.
“I've sort of felt like a square peg in a round hole, and don't feel like this world is like, really who I am.”
There’s a warning here for anyone chasing higher levels within an organization: Be careful what you wish for. The more you rise, the more you get mired in daily political battles and power plays. Life at the top isn’t always what it seems.
Meanwhile, after banking a good portion of his sizable salary over the past two decades, he suddenly realizes his situation: he already has financial freedom. Ironically, this fact brings with it more questions than answers.
“My financial advisor is telling me I've got all sorts of options. [I can do] whatever the fuck I want.
But wait a second, what do I want out of life?”
He’s faced with questions we often ask ourselves: who do I want to be if not this version of myself? What else is out there?
Turning Within
At this point, most people lean back on that same old strategy: shut the fuck up and get back to work! We simply don’t like to ask ourselves the big, uncomfortable questions, opting instead to forge ahead, further down our existing path. But unlike most of his colleagues, Marlo starts to take a different approach.
He turns inward, trying to understand what truly matters to him.
“There’s been a lot of deep work. And it’s more personal… what do I really want? What’s enough? And what do I really want out of life personally?”
Instead of chasing external validation or career milestones, Marlo begins to question the essence of his identity.
“What am I all about if all I’ve been is this turbo executive for 20+ years?”
If I really think I am of a different ilk. And I have a lot of these other things going for me. And I'm an introspective guy. And I want to really reimagine what is an engaged existence. What if I had to put my proverbial money where my mouth is?
If you can’t live a wonderful, amazing life with the amount of resources I’ve amassed, you’re a fucking asshole, in my opinion.”
You can hear Marlo challenging himself, in a sort of what-am-I-made-of sort of way. Maybe he’s competing again, only this time, between his old vs. new self. But the familiar comforts of his old self keep creeping back in.
“What happens if I step off the treadmill?
There's no question that [losing] the status of being a super senior person at one of the biggest companies in the world… that's definitely a fear, and I'm sure I underestimate what [losing] that will even entail.
My definition of scarcity is not having a high 7-figure comp every year. It’s kind of insane to me intellectually, and I'm embarrassed to even say it. But there's a weird fear…”
Plans of Escape
Marlo is planning to quit next year. Only a few people know his secret. He’s talked to lawyers, forecasted the financial implications, and even planned out his exit conversation.
“A guy like me doesn't just fuck off and downshift without a plan.”
He's considered all the potential reactions from the company, including their inevitable attempts to retain him. He’s also wondered how his decision will be received by those around him:
“I often think about when that news hits. Who goes, huh, that makes sense? And who goes, that guy's fucking crazy? He's a ‘made guy’ here. What the fuck is he thinking about? He's out of his mind!
Maybe deep down in some recess of their brain [they want to quit too]. They haven't done the deep work to figure out: what is enough?”
This desire to defy expectations seems rooted in Marlo's competitive spirit, constantly pushing against the grain.
“So part of me feels tremendously engaged and fired up about [having an] un-fuck-with-able energy that I can carry, just zigging when everyone else is zagging, and that is a tremendous source of [motivation] right now.”
In his planning, Marlo also envisions life after the exit—thinking through the practical aspects like how he’ll spend his time: getting back into health and sports, traveling, diving into intellectual pursuits, and spending more time with loved ones. But he also has a longer-term vision:
“I also feel a responsibility, like I've been really fucking lucky. Like I hit the jackpot in many ways. I need to use my skills and my talents for something else.”
Marlo knows that what lies ahead won’t be without challenges. He anticipates a period of identity crisis (which, to his credit, he recognizes in advance). So, what does he imagine life on the other side to be like?
“Besides the inevitable 3 to 6 months of like, ‘Oh, my god! What have I done?’
I think a lot about: what's my average Tuesday going forward?”
Marlo recognizes that the structured existence he's built will be completely upended. The stability he's relied on will give way to openness and an uncertainty about what comes next.
“I'm a rigorous, disciplined, structured guy. That has been an anchor and a balance. So the other side of that open-endedness definitely feels really scary.
I have some idea of where I'm gonna be and what kind of things I'm doing day to day, but not a lot.”
To Be Continued
Beyond the practical day-to-day activities, Marlo knows he’s in for a personal reinvention. He doesn’t know what he wants, only that this is not what he wants.
“It goes to the core of, who do I want to be?
Do I want to be this turbo executive, stressed out, pressed for time, but achieving and accomplishing in a business sense? Or do I want to be a more thoughtful, engaged person?
Because whatever I choose to do next, it's more for me. It's much more about who and what kind of person I want to be.”
As he envisions his future, Marlo is filled with a mix of emotions:
“But honestly, even as I describe what a year from now looks like…
I really have no idea which sounds fucking, frightening, and also kind of awesome.”
Unfortunately, I can’t wrap this up neatly—Marlo’s story isn’t over. We, like him, are left with questions.
Will he go through with his plan to quit next year? When his company inevitably comes back with even more attractive rewards, will he still be able to pull the trigger on his escape?
What is he letting go of that he might later regret? What will Marlo do when the anchor of competitiveness is removed and the direction becomes less clear? Will he simply latch onto another game?
Or will he uncover something more inside himself? Another side he doesn’t even know exists yet.
Thank you to Marlo, who chose to be anonymous for this interview. This interview was transcribed, then summarized and edited for clarity. Any emphasis is mine.
Bonus Questions
What are resources that have helped you in your transition?
The Untethered Soul, by Michael Singer
The Wisdom of Insecurity, by Alan Watts
Die With Zero, by Bill Perkins
On a scale of 1-10 (10 being best), how would you rate the following:
Since Marlo has not transitioned out of his current life, I just asked for a current snapshot:
Health: 7
Stress (10 is low stress): 3
Creativity: 6
Relationships: 6
Impact: 5
Meaning: 4
Work Hours/Week: 65
This is part of the series, The Other Side of Enough, exploring what life is like when you have enough to never work again. Check out the next part:
If you want to learn more about the seductive pull of games (and how they exist everywhere in life), check out the philosopher C. Thi Nguyen’s great book, Games: Agency as Art (one of the best books I read in the last year).
One thing that I was surprised by after I quit : no one cared 😂. I think there is so much anticipation. Yes they tried to retain me. Yes I was prepared. I did my best until the end and that was it. Of course I wasn’t an executive but other than my peers being jealous I had the time money and circumstances to quit no one cared!
Wow, I actually found that little profile rather harrowing. Marlo seems to be standing on the edge of a precipice ready to jump … but absolutely unsure what he’s jumping into. My guess, and it’s only a guess, is that it will take much longer to figure out how to live differently than he suspects.