Just Enough to Walk Away (how to find freedom faster)
Why you don’t need to wait until you have it all [The Other Side of Enough: Interview #8]
The Way of Work explores stories of where we fit in the world of work. This is part of the series, The Other Side of Enough, exploring what life is like when you have enough to never work again.
Getting all the way to “enough money” can be difficult. But what if you only needed to get part of the way there, enough to step out of a life that no longer fit?
Unlike the others in The Other Side of Enough series, Khe Hy didn’t have enough-to-never-work-again. What he had was enough-to-get-out — out from the life he no longer wanted.
Khe walked away from Wall Street in his mid-30s, leaving behind a high-paying career to bet on himself as an independent creator1. Eight years later, he’s still going.
Khe’s story is not just about stepping away, it’s about confronting the seductive pull of money and success. It’s about grappling with the trade-offs: the financial uncertainty and identity shifts. And it’s also about what you gain — the opportunity to explore and create a life that feels more your own.
He challenges us to rethink what “enough” really means. And consider: can we find freedom before we’re perfectly ready?
Origins of Ambition
For many, the drive to make a lot of money feels innate, like a universal aspiration. But often, our motivations have an origin story, forged by our childhood experiences. For Khe, those roots were planted growing up in New York City.
“When I was a kid, most of the time I was scared to walk home from school.
I remember leaving school, [thinking] ‘Oh, shoot! It's daylight savings. It's gonna get dark early, so what route am I gonna take home?’”
One day, walking home with his sister, they were attacked and robbed by a group of five kids. That moment of fear left a lasting imprint, becoming a driving force behind his desire for financial success.
“To make money was to never have to feel that way again. Success would be always living in nice neighborhoods.”
Scarcity played a role too. Khe grew up on a tight budget, receiving a $5 allowance that left little room for indulgences. He recalls the frustration of wanting more and craving the symbols of affluence that seemed just out of reach.
“I wanted stuff. Like a classic teenager in the 90s: Nintendo, starter jackets, Jordans, Ralph Lauren. I wanted that stuff.”
Money was more than a tool, it was an antidote to the things he didn’t like in life. So he makes the obvious conclusion:
“I'm gonna make the most money possible.”
The Purpose of Money
Like many, Khe didn’t have a clear vision of where he wanted to go when he entered finance. Instead of thinking about a career, his primary motivation was simple:
“I didn't know anything about Wall Street when I got to college. So I wasn't actually thinking about going to Wall Street. I was thinking about maximizing my income.”
But once he landed there, Khe quickly discovered it was a good fit, at least early on. While many of his colleagues struggled with burnout, he thrived:
“No, I loved it. I loved my twenties.
All of my friends from college became bankers. So it was like a 4 year extension of college. We were all single. We partied a lot. Just being in New York in your twenties was so fun.”
However, over time, the excitement wore off and he found himself increasingly disillusioned with the corporate culture:
“I got kind of bored.
I didn't like the politics. I walked around with my head on a swivel.”
And while the money continued to roll in, it didn’t hold the same allure as before. Let’s face it: people in finance make a lot of money, and for many, that breeds even more ambition. Money becomes a goal in itself. But for some people, like Khe, the rapid injection of money can have the opposite effect: it can make people realize they don’t really need that much.
“I was starting to see the diminishing utility of money.
Everyone wants to have that year when they have a million dollar bonus. Which I think was like [age] 32 for me. $1.3 million, I think.”
After taxes, that meant a $400,000 bonus. Sounds great, right?
“It feels really awesome. But, here's the thing... It's weird. It was actually way harder for me to spend money when I was making money, then it is for me to spend money now.
I would be like, ‘what's something nice that I want?’ I would go buy a $2,000 overcoat. I would have a nice dinner with [my future wife] Lisa – like $500 at most.
I have $397,500 left. And I'm like, ‘This is kind of silly. This doesn't seem that satisfying.’”
This prompted a deep reflection on what money really meant:
“What is the point of all this money? The point of all this money is freedom.”
Just Enough to Walk Away
“The goal was never to not work.”
While he still works to earn money, Khe’s life today doesn’t sound like a lot of work. Instead, he’s redefined what work means for him. Here’s a glimpse into Khe’s life today:
“I worked on my book.
I didn't surf because there were no waves.
I made music for an hour.
I wrote a blog post.
I'm talking to you.
I have a coffee with a friend, slash potential client.
I'm gonna go lift.
I'm gonna have dinner with a friend.
And then I'll meditate.
Go to bed.Seems like a retired life to me.”
Khe has embraced a variation of the financial independence movement known as CoastFIRE2 — that doesn’t require waiting decades to reach the traditional ‘enough number’ to retire. Instead, it focuses on achieving just enough to downshift into a life with more autonomy, less stress, and more fulfillment.
The challenge of full financial independence often feels daunting and can seem unrealistic, demanding trade-offs and requiring a whole lot of luck. Khe realized that aiming for perfection wasn't worth the sacrifice. Instead, he chose a path that offered more flexibility, by instead only needing to get part of the way there.
So he created a financial cushion using his career earnings, in order to explore new opportunities that felt more aligned. Now outside of Wall Street, his goal was simple:
“The name of the game was, can I cover my living expenses?”
Sometimes, having “enough” doesn’t require a massive monetary milestone—it’s about having just enough to reclaim your life.
Betting on the Possible
“[It] was a bet I was willing to take on myself.
I don't know what I'll do. I definitely didn't think that I would be doing what I'm doing.
I was betting on the possibility of myself.”
Leaving Wall Street wasn’t just a career change, it was a gamble and an identity shift. It meant trading prestige and a clear trajectory for ambiguity and self-doubt.
“I think that finance and these traditional career tracks attract people who are scared of that bet. They like certainty.”
But Khe wanted the freedom to carve his own path.
“I didn't even have a track. I was forced to figure it out with resourcefulness.”
The drop in status was stark. Leaving behind his prestigious role at one of the best financial firms in the world, only to become a “newsletter guy”? Well, it wasn’t exactly a lateral move. In fact, it sounds like a significant step down. To outsiders, his decision seemed baffling.
“Has he fucking lost his mind? What the fuck is wrong with him?”
As he started to build his new life, money or success didn’t come quickly. But his fear was less about making money than about having to go back. It was about admitting failure, publicly undoing his boldest decision, and facing the judgment of others who never understood why he left in the first place.
“The whole fear is I'm gonna have to go back. That was the biggest deal. I'm gonna be embarrassed.”
Instead, he focused on the small wins that served as votes of confidence for his new direction. Getting featured in Bloomberg and CNN helped. Being able to make some money from inbound coaching requests was a breakthrough.
Betting on himself was a long, slow process. But over time, the small wins compounded, and so did his belief in the life he was building. It wasn’t about replicating his former success, it was about redefining success entirely.
Opportunity Cost
Every decision has a price, and Khe’s choice to leave Wall Street came with a staggering one. By his calculations, staying in finance for the last decade could have netted him an additional $18 million to $30 million3. He admits:
“It stings a bit.”
When we walk away from a high earning opportunity, it's easy to imagine what we’re giving up — the bigger house, nicer car, paying off debt faster, or more financial security for our family. These are tangible visions that make walking away feel like an enormous loss.
And it also isn’t just about losing money. It also means you’re starting over with your status, power, and relevance. For most, the potential of losing all that they've built is too risky.
“There's a significant risk that you won't recoup the opportunity cost, and most people don't want that.”
But Khe argues that focusing solely on financial opportunity costs is shortsighted. What about the unseen costs of staying? The trade-offs we rarely calculate?
“There's the financial golden handcuffs. But that’s the easy part. The real handcuffs are the complete lack of possibility in your own life.”
Khe may not have those extra millions, but what he has gained is something far more valuable: the freedom to live life on his own terms. In his eyes, the opportunity to build this life far outweighs the money he left on the table.
True Independence
Khe may not have total financial independence, but he does have something that even the financially free often lack: psychological independence.
Something that took me a while to understand is that there are two types of financial independence: material and psychological.
Material independence is what most people chase. It’s "hitting your number" – having enough to never work again. Many believe that reaching this milestone will bring peace, but as we've seen, they often find themselves grappling with new anxieties and insecurities.
Psychological independence is different and rarely talked about. It's when you are no longer a slave to money in your head. You stop obsessing over financial worries or chasing more wealth as a proxy for self-worth. You don’t let money dictate your every decision. While financial concerns never disappear entirely, you develop a healthy, balanced relationship with them.
Many achieve material independence, but remain psychologically dependent. They’ve acquired enough but still don’t feel like they are enough. Interestingly, some people like Khe, are able to reach psychological independence, without material independence.
“There's nothing that I can achieve that can fundamentally shift my baseline happiness.
So, for example, if you say, ‘Okay, tomorrow you can have James Clear’s success (the bestselling author).’
I'm like, ‘cool.’ I mean I wouldn't say ‘no.’ But my interior world wouldn't change. And [realizing] that was really liberating.”
Instead of defining success by external metrics, Khe reframes it entirely:
“[This is] gonna sound very woo-woo… but I use the word, and I say it often to myself, ‘peace.’
So, for example, if I run the calculation that I left $18M on the table, and I start chewing myself out in my head. I'm not at peace.
If something comes up between my wife and we go to bed angry, I'm not at peace.
If I run my hand through my head and watch the hair fall into the drain, and I'm like ‘fuck, my hair loss is accelerating,’ I'm not at peace.”
His focus has evolved away from an ambiguous pursuit of success to something more simple and real:
“What do I need to do to be more at peace?”
Dream Different
“There's a lack of creativity in how people think about their lives.
That does not mean, do what I do. In fact, most people shouldn’t. It's a little bit crazy.”
He notes that people often look for answers in the wrong places, chasing traditional markers of success.
“I see people that did go down that track, and they're just not happy... Not only do I know that that's not the path to happiness, I'm more and more convinced that that's the path to unhappiness.”
Instead, Khe advocates for a shift in perspective.
“I think if people sat down and [realized they are] artists of their own lives… they would actually record so many simple wins.
By dreaming smaller, people could actually start hitting their dream."
The ultimate irony is that Khe now coaches successful people who “have it all,” but would rather have an independent life (even Wall Street types that Khe used to work with).
Khe's story shows us that you don’t always have to achieve the perfect financial independence to redesign your life. Perhaps you don’t need to have it all. Perhaps, all you need is just enough. And perhaps you can decide what “enough” means to you.
Special thank you to Khe Hy for sharing his story. To learn more about Khe’s work:
Check out his podcast: YouTube | Spotify | Apple Podcasts
This one is a good place to start 😉
Khe’s program for “Post-Achievement Professionals”: Coaching
Learn more about financial independence:
What Is Coast FIRE And Is It The Right Retirement Path For You? Financial Samurai
Your Money or Your Life, by Vicki Robin
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?
What has been your best purchase, since hitting enough?
Paying a premium rent to be in walking distance from both the beach and school
Meditation bench that I use 2x a day
What has been your worst purchase, since hitting enough?
A second digital camera (somehow thinking it would level me up as a YouTuber)
Before & After - on a scale of 1-10 (10 being best), how would you rate the following before and after enough:
Health: 4 → 9 (+50%)
Stress (10 is low stress): 6 → 9 (+30%)
Creativity: 2 → 10 (+80%)
Relationships: 7 → 9 (+20%)
Impact: 2 → 6 (+40%)
Meaning: 4 → 10 (+60%)
Work Hours/Week: 65 → 30 (-54%)
This is part of the series, The Other Side of Enough, exploring what life is like when you have enough to never work again. Some other articles from the series you might like:
Everywhere But Home: The search for belonging after reaching financial freedom at 32
If Khe sounds familiar, it’s because he interviewed me a few months back for his podcast.
FIRE = Financial Independence Retire Early
While we're more about the mind than the money here, the basic principle of FIRE is to save a high percent of your income (by both raising earnings and lowering spending). The most common goal is to save ~25x your annual spend. At a 4% withdrawal rate (returns from your portfolio), you can live off your savings forever. For example…
$50K annual spend
X 25
= $1.25M savings
X 4%
= $50K income for spending
P.S. I used a lot of the FIRE principles to create the freedom I have today.
The high end, e.g. $30M, assumes he would have continued to grow his income along the same trajectory.
The top 3 realizations since leaving my corporate job 30 months ago:
The hardest loss was not the paycheck but identity.
"Enough" is not defined by numbers but state of mind.
I still can't (and shouldn't) do everything I want.
Great article and a big fan of Khe myself. If I recall correctly he walked away with $5m+ and for most people that’s full FIRE status. Still the point stands. To walk away from a career that is so lucrative is not easy to do in your 30s.