Will you get what you want, after reaching financial independence?
When you've focused on what others want [The Other Side of Enough: Interview #4]
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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.
Once all your material needs are met, wouldn’t it be so nice to finally do what you want?
But wait... what do you want? And are you sure it’s what you want and not what somebody else wants for you?
So many of us are driven by external rewards - money, status, achievements, and validation from others. We lean on the signals outside ourselves to dictate the path we take and the choices we make. In the process, we accumulate the equivalent of a graduate degree in listening to and pleasing others, but lack even an elementary skill in listening to ourselves.
Our lives have been built upon the scaffolding of extrinsic motivation. It’s so embedded within us, we barely realize it's there. We know no other way.
So what happens when that extrinsic motivation disappears? What reappears in its place?
Unfortunately, the answer, as my next interviewee in The Other Side of Enough realized, is not necessarily “intrinsic motivation,” where interest and satisfaction come from within.
Omar (not his real name) is a successful startup founder, having reached his version of 'enough' after exiting his last company.
The problem is that up until his exit, Omar’s life had been focused primarily on external rewards. Having the great fortune of meeting these milestones by the time he’s about 40 years old, he’s left wondering “what’s next?”
But he finds that the search for what he wants is much trickier than it seems.
Omar’s story shows the power and hold work has over our lives. How work can really suck, but still provide meaning. How we can get locked into status games without realizing it. And how when those games end, we can be left feeling stuck, without a guide for where to go next.
You may think his circumstances are unique, but his story is one that is all too familiar: being driven by what others want from us, rather than being driven from within.
Being a founder sucks
“I didn't really ever enjoy being a founder.”
Our conversation began unexpectedly. I had seen Omar from afar as a respected and accomplished founder. And to be honest, I’ve filled myself up with a lot of the mythology around being a founder. The joy of building something from nothing, the glory of hitting ambitious milestones, and the respect that comes with it. In America, founders are cultural icons.
But Omar had a different perspective on the founder experience.
“It was a cool identity - a strong signal that you're very unique. Raising capital, meeting people that have heard of you or used your product was cool. That feeling of uniqueness was intoxicating.
But at the same time, the job is terrible. It's one of the worst jobs.”
What was so bad about being a founder? Note the phrase “day-to-day,” as it’s going to come up again later.
“The job is pretty terrible day-to-day. All the shit rolls up to you. You have to tackle the hardest problems. There's the people-stuff, fundraising, and cash flow pressure. Nobody cares as much as you do. No one feels the urgency. But your brain is prewired to look for the worst case scenarios and try to navigate around that.
It's a pretty lonely job. But you're also trying to convince yourself that you're the exception to the rule.”
There’s an important phenomenon here: just because we’re good at something, doesn’t mean we like it. This happened to me, as well. Others see our competence and success from the outside, and assume that inside, we feel good about it.
This belief seems core to our cultural ethos; that acquiring skill and mastery over a valued profession equals satisfaction. But Omar shows how this isn’t always the case:
“I cared a lot about external validation. I had almost zero internal fulfillment.
It was very stressful. There would be weekends where I would come home from work, and then not leave my apartment until Monday morning, because I was burned out and depressed.”
In hindsight, Omar realized these external rewards, including money, were central to the drive that propelled him through a grueling day-to-day.
“I didn't realize how much I was motivated by money.
[I thought] ‘oh, I'm building this thing. I feel special and unique along the way. And I'm not doing it for the money. I'm doing it for the mission.’
And then I look back and go, ‘Yeah, I totally did that for the money.’”
Untethered escape
Omar’s relentless pursuit of external rewards—validation, mission, and money—had pushed him to the brink. When the chance to step back finally presented itself, he knew he had to take it. Burned out, Omar took a sabbatical. Not as a quest for self-discovery, but as a necessary escape from the work that had consumed him.
What he didn’t realize was that stepping away from work would leave him face-to-face with an unexpected void. At first, Omar set out to do nothing.
“I felt like I just needed a break.
I needed to catch up on my health and mental health. I felt like I was just so behind on that.”
But, as I’ve found for myself, it’s hard to just do nothing. Many of us have become conditioned to keep grinding away. Stopping yourself from working, it turns out, is really hard work.
“There was a ramp down period where I knew I was taking a break. But my brain was firing off with business ideas, listening to business podcasts, reading about AI, trying to figure out where to hustle.
I’m so used to my brain working a certain way.”
My own experience was similar. After leaving for a sabbatical, I plunged straight into business building for several months. My old working self was unable to stop itself.
He soon realized that his old ways of thinking wouldn’t vanish overnight. Omar decided he needed to “go cold turkey.” Cutting off work-related habits was the only way he could truly disconnect.
Slowly, a new version of Omar emerged. The old identity began to dissolve, replaced by new priorities.
“It's just trying a lot of things and not committing to anything and being comfortable with shutting something down. If I found something interesting I would try it. And then, if I didn't, I didn't feel guilty about stopping and moving on to the next thing.
So Omar fills his day with creative pursuits, health, hobbies he enjoyed when he was younger, and spending time with his family.
“All the work stuff started becoming smaller. And then I started adding all these other pillars, and they added up to this new identity that I don't think I could ever give up.”
Death of a clear identity
However, as the pillars of his new identity took shape, he had to contend with the death of his old identity as a founder.
“I knew that I didn't want to do it again, but it was much harder than I thought to change that label.
When it's gone, it's kind of weird, because it leaves a gap or hole, and you're trying to figure out how to fill it.
And if you're hardwired a certain way, it's hard not to fill it with starting another company, because the alternatives just seem so boring in comparison, even though you know that job sucks.”
We may hate our job, but sometimes we underestimate the direction it provides in our lives. That truth only reveals itself when the work is gone.
“You feel like you have this sense of direction and purpose. And then that just disappears.
You're just left with a void because you haven’t really thought about any other path.”
This also meant letting go of the external markers inherent within a career as a founder. Every career has them - some sort of status hierarchy, where there are always more levels higher up. Even if we hate our jobs, these milestones provide a sense of progress toward a purpose.
“There's founders. And then there's founders that have raised from the top VCs. And then there's founders that raised top from the top VCs that are in the top percentile of their portfolio. Then there's this even smaller subset of people that did that twice.”
Missing all forms of motivation
As Omar contemplates his next steps, he finds himself caught in a mental tug-of-war—torn between what he may truly want and the familiar allure of past motivations that might lead him astray. He struggles to connect with an authentic ‘why’ that doesn’t fall back into the same external validation-driven cycles.
Pay close attention to how he goes back-and-forth here:
“I would like to start working again. I still think work is important. But I'm not mentally committed. I haven't got hit with that motivation spark yet.
Right now, I know that to get motivated, I have to see something grow.”
But is the desire for growth another form of external validation?
“What I struggle with is… Oh, I shouldn't do this for that reason, because this reminds me of my last startup. It would be the wrong reason to do it.
But then I'm like, I know if I got addicted to that for a year I could grow this really big, and then shift gears or downshift it.
It's like a drug. The status game. It's intoxicating. But at the same time I thought I was way more mentally mature than this!”
But is that unhealthy motivation, while not ideal, better than having no motivation at all?
“Maybe I'm swapping one game for the other. But if that's my ‘why,’ right now, to just get my ass off the couch, maybe it's a good thing for 3-6 months or a year. Versus waiting for this intrinsic ‘why’ to pop up.
I'm just waiting for this special moment to happen where I'm enlightened, and that's my intrinsic motivation.
I don't know. I feel like unless I become mentally more mature, that might take a fucking decade for that to happen.”
But would he be sucked back into the burnout that drove his depression before?
“I feel a lot of guilt and shame that I don't really want to work hard.
One of my biggest fears is getting sucked back into working really hard again. Sucked back into grind mode and getting mentally obsessed with it.”
Free but stuck
“I just feel really stuck.”
Omar notices that the extrinsic motivation that fueled him before is now gone. But there’s no internal motivation to replace it:
“You go from this external to internal validation.
But I'm stuck in between. I'm not as motivated by the external stuff, but don't have an internal motivation that's pulling me.”
This is a core dilemma high-achievers face when they step back from a life driven by external rewards, without having discovered what will replace the void left behind.
“I’m not motivated to move forward…
So the work side just feels very stuck. Like I just don't know where to go. So I just stand still. I was always moving on the work side. I was always hustling. I always had a marker where to go next.
I’m supposed to be over it. But then there's this lagging ‘stuckness.’
I don't know. I wish I could fast forward a year and just figure it out. [The stuckness is] just always there. You know what I mean? It’s there! It won't go away.”
This isn’t a temporary hurdle—it’s the growing pains of an identity in flux. We often expect that change will be immediate (especially after a desirable outcome like hitting financial independence), but instead it’s messy, uncertain, and often takes way too damn long.
Day-in-and-day-out
While Omar’s story is filled with struggle and uncertainty, it’s also a story of quiet breakthroughs. He’s grappling with his former identity, motivations, and what he really wants from life going forward. Contrast that with many people, I’ve found, who just suppress these emotions and go back to their old self in order to avoid the pain of making a change. Omar is taking on his demons.
Toward the end of our conversation, he returned to an idea that has emerged in every single interview, the importance of finding joy in daily life (recall how bad he described his “day-to-day” as a founder).
“[I’m working on] just finding joy in my day-to-day life and gravitating towards that. The more I focus on finding joy, the less depressed I get.”
This newfound focus is subtle but important. It marks a transition away from chasing external outcomes to valuing the present. For someone like Omar, who spent years sprinting toward the next goal, this adjustment is a significant reorientation.
“I haven't found much joy in the grind-from-work standpoint. But I find joy in creativity or coming up with an idea, even if it's an idea that no one ever sees.”
In my own experience, embracing these moments of new meaning can be small, almost too small to notice. But they matter toward forging a new identity. Like a seedling breaking through the soil.
My last question to Omar: Was it all worth it? Enduring all that pain to get to the other side of enough?
“Yeah, 100% totally worth it.
I feel like I'm trending towards a complete reinvention.”
Thank you to Omar, who chose to be anonymous for this interview. This interview was transcribed, then summarized and edited for clarity.
Bonus Questions
What are resources that have helped you in your transition?
The Second Mountain, by David Brooks
What’s Next: The Entrepreneur’s Epilogue and the Paradox of Success
Before & After - on a scale of 1-10 (10 being best), how would you rate the following before and after enough:
Health: 2 → 8 (+60%)
Stress (10 is low stress): 0 → 8 (+80%)
Creativity: 2 → 6 (+40%)
Relationships: 4 → 7 (+30%)
Impact: 0 → 4 (+40%)
Meaning: 8 → 4 (-40%)
Work Hours/Week: 50 → 10 (-80%)
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:
I always hoped that achieving financial independence would be just a huge relief, but I guess we're not wired to do nothing.
It reminds me of an article I read years ago (don't remember where, sadly) about a woman who retired early and focused on enjoying life, like daily massages and living on a tropical island, but she got depressed because the high caused by the pleasures eventually reset to zero.
She ended up realising she needed struggles to enjoy the pleasurable parts of life by contrast, if I recall correctly
These keep getting better and more interesting, or maybe it's just the accumulative effect. I can't wait to hear what you do to assimilate all this into your own words at the end of the series.