"It's actually to find the challenge," Dima said, his voice carrying a weight that surprised me. "That's the challenge now."
We were about twenty minutes into our conversation when he dropped this line. Dima is a successful solo entrepreneur - he's built a profitable software business, achieved financial independence, has a family he loves. By most measures, he's won the game. But here he was, describing his biggest problem as not knowing what problem to tackle next.
"It's a good problem to have," I acknowledged, "but it's still a problem."
"Yes, and I noticed, you know, it's like in support," Dima continued. "You try to close every possible ticket, but you will never close all tickets. There was a problem like, I need to have this money to cover my lifestyle. And then I reached this goal. And now I see, oh, okay. But it opens new problems like, what's the challenge?"
This hit me as profound - the endless nature of human problems, how solving one level reveals entirely new categories of challenges. Most entrepreneurs never reach this particular problem. They stay trapped in the survival game, always needing the next milestone to keep the lights on. But Dima had broken through to something else entirely.
...
"So the big question is, what's next?" I asked. "Or maybe, is there anything next? Is there a point where you can just literally relax, drink beer, watch football, and that's it? Or does life lose meaning if you don't have a big, audacious goal to chase?"
"I don't think that having a meaning in life is mandatory," Dima replied. "But I feel it really helps to answer why you wake up in the morning. I have some fears, you know, like if I don't do anything at all for a long period of time, I feel I might degrade, degenerate, and probably I won't be a nice person to hang out with."
We were dancing around something bigger here. Dima had inadvertently stumbled into a preview of humanity's future. As I listened to him, I realized he'd created his own post-scarcity environment - enough money, enough freedom, enough security that external pressures no longer drove his decisions. And with that freedom came a distinctly modern form of existential crisis.
"The reason I think your question is so important," I told him, "is that as humanity, it seems like we're edging closer to all of us having the same question. There's this theory that AI will solve all of our material problems, and then we will live in a society of infinite abundance. What I see is an explosion of depression, because the transition from 'I have to do things' to 'I actually don't have to do things' - well, that kind of situation produces this question: So what do I do?"
...
"We have annual inflation every year," Dima observed, "and even just this one factor forces me to not stay still and to make more money, and to make more money, I need to bring value to people. It's like baseline meaning for life that the system gives you."
"Like a built-in motivation," I agreed.
"Yes, and within a certain margin of error, you are in a state of abundance, sort of post-AGI abundance," I continued. "You created it for yourself. There's enough degrees of freedom in the world right now for certain individuals with certain skills to be able to create it for themselves. And you have."
This was the crux of it. Dima wasn't just dealing with a personal career transition - he was grappling with questions that our entire species will face as technology eliminates scarcity. The challenge isn't just finding the next challenge; it's learning to derive meaning and motivation from internal rather than external sources.
...
The conversation took an unexpected turn when Dima started talking about football. He told me about a recent game where a new, highly egotistical player joined who only wanted to score goals himself.
"I felt a little bit hurt, like my ego felt it's not good. I also want to score some goals," Dima admitted. "But then I thought, wait, wait, wait! Do I want to win, or do I want to score goals? What do I really want?"
"So I completely changed my game. I went to defense, and I was playing like 100 percent, just taking the ball from everybody and giving this guy passes. And he scored a lot of goals. We won every game that day, like no losses at all. And for me it was kind of a revelation."
This story revealed something crucial. The joy Dima found wasn't in individual achievement - he'd already mastered that in business. It was in the collaborative dynamic, the team adjustment, the shared victory. He was describing the exact opposite of the solo entrepreneurial path that had brought him success.
"It feels like too much time spent alone," he said. "Years, you know."
"Maybe what happened is that you've exhausted your capacity and need for selfishness and isolation," I suggested. "You've done for yourself, by yourself, and you want to collaborate with other people."
"Yes, I see it pretty clearly," Dima responded. "I love some kind of collaboration towards a shared goal. I feel it's actually - I probably understand it now when we were talking - like building something and achieving it with somebody."
...
That's when I said something I'd never said to anyone before: "Maybe what you're looking for is a job."
"Whoa!" Dima exclaimed.
I was as surprised as he was. Here I was, talking to a successful entrepreneur who'd built his own business and achieved financial independence, suggesting he consider employment. But the more we explored it, the more sense it made.
"Obviously you will never have a job in the same sense that you've had jobs before," I clarified. "It will always be more of an agreement between equals, because you have achieved equality status. But maybe this is terrifying because you're thinking you need to build a team of 10 people. Who said you needed to build a team? You just want to be on one."
"You're right. Precisely. I don't want to be managing people. I want to just play with a team," Dima agreed.
The shift was remarkable. We'd gone from his original framing - wanting to build a company of 10 people - to realizing he simply wanted to be part of something larger than himself. The courage required wasn't the courage to build or lead, but the courage to let go of existing identities and join something.
...
"But if you apply to a job without needing the income, and you apply because of the specific desire to work with interesting people on valuable problems, you're looking for a team you would like to play with," I explained. "This can never result in a suffocating agreement, because it's an agreement between two parties that voluntarily enter for the purpose of making something better together."
"How do you find something like that?" Dima wondered.
"It's a next step question," I replied, "because something happens when we're clear about what we're looking for. An hour ago, this was not part of what you thought you were interested in. Even if it crossed your path, you would not see it."
This is how breakthroughs work - not through force or analysis, but through conversation that reveals what was already there, waiting to be acknowledged.
...
"Thank you that you picked this one, caught this one," Dima said as we wrapped up. "When you're in your mind, you see it and you're like, oh no, I don't want to even go this direction, because it's so huge. But you forced me to talk about it, to clarify it a little bit, and to see it from this different perspective, which is crazy - to go back to 9 to 5."
We'd started with Dima saying his biggest challenge was not knowing which challenge was next. We ended with him having a specific, if surprising, direction to explore. Sometimes the answer isn't about finding something completely new - it's about rediscovering something familiar from an entirely different vantage point.
For the full conversation and to hear how this unfolds, search for "Finer Live" on Spotify or Apple Podcasts.
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