This connects cleanly — Millerd's entire framework is about the restlessness as signal, the default path as performance, and contentment as the measure that replaces success. Your story is a more extreme version of the same arc.
The line that stopped me: "Until I quit my job, I felt the opposite of contentment: restlessness."
I want to offer a data point from someone who took a much more chaotic version of this path, because I think it validates something you're saying that the reader might not fully trust yet.
I graduated summa cum laude from the Technion in Computer Science. Started at Intel designing processors. Moved to Check Point. Then startups. Then freelance. Then tried a Master's in Quantum Computing. The pattern was identical every time — strong start, slow drain, eventual inability to make myself care about work that everyone around me said I should be grateful for.
But here's where my story diverges from the clean "I quit and found my path" narrative: I didn't quit strategically. I eroded. Each job lasted a little less. Each attempt at the default path produced a little less fuel. I kept diagnosing it as a discipline problem — laziness, ADHD, character flaw. I tried to fix myself instead of questioning the path.
I ended up making fundraising phone calls for my kids' school. From the president's list to cold calls. And what happened there is exactly what you describe — "not having a plan enabled me to see how much running away from the present I was doing." When the salary disappeared, the performance disappeared with it. And what was left — the writing, the building, the projects nobody asked for — turned out to be the thing I'd been doing in secret for twenty years while calling it procrastination.
Your framing of "leap capital" is useful, but I want to name something underneath it that the reader might need to hear. The 25-year-old on Wall Street isn't just asking "should I quit." She's asking "can I trust myself." Because the default path comes with external validation at every step — the title, the salary, the approval. And the pathless path requires you to generate your own signal about whether you're on track. That's the actual leap. Not financial. Epistemological. You're switching from a system that tells you how you're doing to a system where you have to feel it.
The restlessness she's describing isn't indecision. It's her internal compass disagreeing with her external scorecard. And in my experience, that compass doesn't get quieter with time. It gets louder — until you either listen to it or spend so much energy suppressing it that you have nothing left for the people you love by the time you walk through the door at night.
The question isn't "is it too early at 25." It's "how many more years of declining motivation are you willing to fund with your life before you trust what you already know."
I’m curious, Paul, why do you feel you may only be able to sustain your current creative path for 2-3 more years? What factors are causing you to feel that way?
We make a lot of tradeoffs that others would not be happy with. I only feel like I’m thriving because I am clear-sighted about the costs and benefits of the path for now and want to keep going.
Was it difficult to be ok with your trade-offs? I’ve noticed my biggest ongoing fear with being off the default path is that it won’t work out and I should have stuck with the default all along. But I’ve also noticed that the fear is not so much a question of finances but more a fear of a deeper threat that it not working out challenges my sense of belonging and acceptance like I’m doing something shameful and I should backtrack asap.
It definitely took a while. I think the pathless path was essentially self therapy giving myself permission to keep going. I think I continue to be excited about the present and future of my life so I want to keep going. Sometimes I do stress about not having options my well financed peers do but then I remember that I didn’t like those tradeoffs in that life
I find it ironic that being highly successful on the default path can actually make you feel more trapped. I assume this fellow might think, "Well, most people who quit their jobs were in a much worse position than me, so it was easier for them to leave." Unfortunately I haven't found a good way to frame this yet. But I wonder if the "survival rate" on the pathless path is actually higher for those who were already successful on the default path.
> She’s been with me from the early days, and we’ve been co-building this life together. I think my journey would have been a lot harder without her.
It sounds easier, at least to me, to walk an uncertain path if others around me are doing the same. Not just a partner, but friends and acquaintances too. Sometimes I think meeting more people on the "pathless path" is a great strategy to make the leap easier. But then I realize it is structurally improbable. I mean when you are trapped in a 9-to-5 you naturally end up in the same places and schedules as everyone else on the default path.
So as someone with the double nickel already in the rearview--a year past it last Thursday--I can tell you that this is what your mid-20s are like.
I'd ask what you would do instead?
What will you do when that fails? (Because the whole point is that it *will* at least once, and it's overwhelmingly likely that that will happen near the beginning.)
What would I change if I could go back in time? Only this: being aggressive about making and keeping up connections. A lot of smart, talented 20somethings are obsessed with long-term financial planning. Think of it like that, but with people. In fact, if I had to pick only one, I'd pick the people.
Man this one slapped. As an almost 25yo
Ah nice! Glad it resonated.
This connects cleanly — Millerd's entire framework is about the restlessness as signal, the default path as performance, and contentment as the measure that replaces success. Your story is a more extreme version of the same arc.
The line that stopped me: "Until I quit my job, I felt the opposite of contentment: restlessness."
I want to offer a data point from someone who took a much more chaotic version of this path, because I think it validates something you're saying that the reader might not fully trust yet.
I graduated summa cum laude from the Technion in Computer Science. Started at Intel designing processors. Moved to Check Point. Then startups. Then freelance. Then tried a Master's in Quantum Computing. The pattern was identical every time — strong start, slow drain, eventual inability to make myself care about work that everyone around me said I should be grateful for.
But here's where my story diverges from the clean "I quit and found my path" narrative: I didn't quit strategically. I eroded. Each job lasted a little less. Each attempt at the default path produced a little less fuel. I kept diagnosing it as a discipline problem — laziness, ADHD, character flaw. I tried to fix myself instead of questioning the path.
I ended up making fundraising phone calls for my kids' school. From the president's list to cold calls. And what happened there is exactly what you describe — "not having a plan enabled me to see how much running away from the present I was doing." When the salary disappeared, the performance disappeared with it. And what was left — the writing, the building, the projects nobody asked for — turned out to be the thing I'd been doing in secret for twenty years while calling it procrastination.
Your framing of "leap capital" is useful, but I want to name something underneath it that the reader might need to hear. The 25-year-old on Wall Street isn't just asking "should I quit." She's asking "can I trust myself." Because the default path comes with external validation at every step — the title, the salary, the approval. And the pathless path requires you to generate your own signal about whether you're on track. That's the actual leap. Not financial. Epistemological. You're switching from a system that tells you how you're doing to a system where you have to feel it.
The restlessness she's describing isn't indecision. It's her internal compass disagreeing with her external scorecard. And in my experience, that compass doesn't get quieter with time. It gets louder — until you either listen to it or spend so much energy suppressing it that you have nothing left for the people you love by the time you walk through the door at night.
The question isn't "is it too early at 25." It's "how many more years of declining motivation are you willing to fund with your life before you trust what you already know."
I’m curious, Paul, why do you feel you may only be able to sustain your current creative path for 2-3 more years? What factors are causing you to feel that way?
Incomes declining on most things im doing
And there is no path to reversing that? Or, not one you would enjoy?
yeah exactly
- the obvious easy money bad soul paths
- the clear wins that might cost me energy
- then the potential ambiguous exciting paths that seem totally impossible or unclear (i usually aim here)
My fave part:
We make a lot of tradeoffs that others would not be happy with. I only feel like I’m thriving because I am clear-sighted about the costs and benefits of the path for now and want to keep going.
Is that success? Who knows.
That’s for you to decide :-)
Was it difficult to be ok with your trade-offs? I’ve noticed my biggest ongoing fear with being off the default path is that it won’t work out and I should have stuck with the default all along. But I’ve also noticed that the fear is not so much a question of finances but more a fear of a deeper threat that it not working out challenges my sense of belonging and acceptance like I’m doing something shameful and I should backtrack asap.
It definitely took a while. I think the pathless path was essentially self therapy giving myself permission to keep going. I think I continue to be excited about the present and future of my life so I want to keep going. Sometimes I do stress about not having options my well financed peers do but then I remember that I didn’t like those tradeoffs in that life
I find it ironic that being highly successful on the default path can actually make you feel more trapped. I assume this fellow might think, "Well, most people who quit their jobs were in a much worse position than me, so it was easier for them to leave." Unfortunately I haven't found a good way to frame this yet. But I wonder if the "survival rate" on the pathless path is actually higher for those who were already successful on the default path.
> She’s been with me from the early days, and we’ve been co-building this life together. I think my journey would have been a lot harder without her.
It sounds easier, at least to me, to walk an uncertain path if others around me are doing the same. Not just a partner, but friends and acquaintances too. Sometimes I think meeting more people on the "pathless path" is a great strategy to make the leap easier. But then I realize it is structurally improbable. I mean when you are trapped in a 9-to-5 you naturally end up in the same places and schedules as everyone else on the default path.
Loved the honesty and in particular your reflection on the allure of “success” with no real definition.
So as someone with the double nickel already in the rearview--a year past it last Thursday--I can tell you that this is what your mid-20s are like.
I'd ask what you would do instead?
What will you do when that fails? (Because the whole point is that it *will* at least once, and it's overwhelmingly likely that that will happen near the beginning.)
What would I change if I could go back in time? Only this: being aggressive about making and keeping up connections. A lot of smart, talented 20somethings are obsessed with long-term financial planning. Think of it like that, but with people. In fact, if I had to pick only one, I'd pick the people.
Agree. It is sad and probably still inevitable that your friends from your 20s do drift away a bit