“I thought I’d feel better than this.”
He’d recently left the company he co-founded. The exit had been in the nine figures. He was in his early forties and, financially, he never had to work again.
“For the last few years, I kept thinking, just get through the exit,” he said. “Then I’ll be set, and I can have a life again.”
“And now?” I asked.
He laughed. “Now I have no idea what to do with myself.”
For years, he had worked around eighty hours a week. His calendar had been full before the week began. There was always a meeting, a decision, a problem, someone waiting for an answer.
Now there was almost nothing he had to do.
So he had started travelling more. He’d also started looking for another relationship.
His previous relationship had ended during the final stretch leading up to the exit. By then, he and his girlfriend were barely seeing each other. When he periodically came up for air, he’d notice that she’d become more distant. Eventually she left him. By the time the exit was finished, she was with someone else and seemed happier.
He didn’t sound angry about it.
“I get it,” he said. “I wasn’t there.”
“So now you’re looking for a new relationship?” I asked.
He nodded. “I mean, I’ve got time now. I can actually have one.”
We talked for a while about the women he had been meeting and what he hoped to find.
Then I asked him what the rest of his life was like.
“What do you mean?” he asked.
“Well, for example, who do you hang out with?”
He mentioned several people. All of them were in the same industry. Most were on the org chart in the company he co-founded.
“And outside that?” I asked.
He thought for a while. “Not that many.”
“Who do you call when nothing’s wrong or needs fixing?”
“Let me put it this way. Who do you call when nothing’s wrong or needs fixing?” I asked.
That stopped him.
“Not when you need advice,” I continued. “Not when you want an introduction. Not when there’s a deal to discuss or a problem to solve… Just because you want to talk to someone.”
He looked away for a moment.
“Honestly? I don’t really know.”
That was the first point in the conversation when I became less interested in his search for a girlfriend.
The Problem He Thought He Had
His theory of the problem was straightforward.
He wanted a serious relationship, and now he finally had time for one. So he approached finding a partner much as he had approached other important problems in his life: review the checklist, meet enough people, pay attention to what worked, and keep going until he found the right person.
There was nothing foolish about that.
He wanted someone to share his life with. Someone he loved and who loved him. Someone to travel with, come home to, talk to at the end of the day, eventually build a family with.
Those were good things to want.
But as he talked about the women he was meeting, I began to notice how much depended on finding one for a relationship.
To him, a girlfriend would not merely be a girlfriend. She would be the person with whom his personal life finally began.
Some of the people he felt closest to had been there almost from the beginning of the company.
Back then, there had been little distinction between colleagues and friends. They stayed up late solving problems nobody knew how to solve. They ate whatever was still open at midnight. They argued, made stupid jokes, worried about running out of money, then showed up the next morning and did it again.
“You were friends?”
“Yeah. Definitely.”
“What happened?”
He thought about that.
“The company got big.”
One of their founding hires used to work beside him but now had a manager. That manager had a director. The director reported to someone who eventually reported to him.
“So suppose he thinks his manager is terrible,” I said. “Can he tell you?”
He laughed.
“Not really.”
“Why not?”
“Because then I know his manager is terrible.”
“And you can do something about it.”
“Right.”
Which meant the conversation was no longer simply between two friends.
The same problem appeared everywhere. A friend could complain about his marriage. He could complain about traffic. But complaining about the company, his compensation, his boss, the strategy, or another executive became complicated when the person listening could alter any of them.
Even disagreement changed.
When two young founders or early employees argued over dinner, it was an argument. When one of them later controlled budgets, promotions, hiring, and careers, the same argument could carry consequences neither man intended.
Nothing bad had to happen for this to matter.
Power changed what people were willing to say out loud to each other.
And friendship depended, among other things, on being able to say something inconvenient but true without first calculating what it might cost your career.
Success had changed the conditions under which some of those friendships had begun.
As we kept talking, I started to see why the missing girlfriend had seemed like such an obvious answer.
For years, the company had given him people to talk to every day. It gave him a place where his decisions mattered. People noticed whether he showed up. They relied on him. He belonged somewhere, even if that belonging came with enormous pressure.
His girlfriend had given him something different. There had been affection, companionship, private conversation, physical closeness, and another person who knew him outside the company.
Then, within a relatively short period, both were gone.
Too Much Riding on One Person
“What do you think you’re hoping a relationship gives you?” I asked.
He began with the obvious things.
Someone to spend time with. Someone who cared about him. Someone he could talk to. Someone who would be there. Someone with whom he could build a family.
As he spoke, I wrote four words down:
connection, intimacy, passion, play.
I showed them to him.
“These seem to be coming up a lot.”
He looked at the words.
“Yeah.”
“What else?”
He thought for a moment.
“Fun. Obviously.”
“What kind?”
“Travel. Trying new things. Going somewhere on a whim. Having someone to share experiences with.”
He kept going.
Affection. Sex. Companionship. Someone who knew what had happened that week without needing the backstory. Someone beside him at dinner, on a plane, on a Sunday morning. Eventually, perhaps, children and a family of his own.
None of this struck me as excessive. A good romantic relationship should contain many of those things.
But taken together, the list revealed something.
I drew a circle around all of it.
“You know what this looks like to me?”
He waited.
“Too much riding on one person.”
That made him smile.
“You’ve basically created a key-person problem in your personal life.”
He laughed.
He had spent years thinking carefully about what happened when too much depended on one person, one company, one market, or one source of capital.
Yet in his personal life, he had begun imagining one future woman as the main source of connection, intimacy, affection, sex, play, adventure, companionship, belonging, and family.
“She can be incredibly important,” I said. “But if she has to be your entire personal life, that’s a lot of weight to put on one person.”
He looked at the page, then grinned.
“Right… So I need to diversify the asset portfolio of my personal life.”
Now we were both laughing.
There was nothing pathological about wanting any of these things.
A person needed food, but that did not mean somebody else had to feed him. In the same way, human beings needed connection, but another person did not become responsible for curing their loneliness.
Still, you could not have a friendship by yourself.
Some of the things he wanted could only exist between people. He remained responsible for building a life in which they could come from more than one relationship.
Rebuilding the Rest of His Life
So we looked backward.
Before the company took over most of his life, I asked him, where had these things come from?
There had been old friends he travelled with. Friends who made him laugh at two in the morning. People who had known him before the company mattered, before the exit, before anyone cared what he thought about markets or leadership.
Some shared his appetite for adventure. Others were people with whom he could talk for hours about ideas, relationships, family, politics, whatever happened to matter that night.
They knew entire chapters of his life without needing them explained.
“What happened to those friends?” I asked.
Once the company really started scaling, he stopped calling them as often. Then he stopped showing up as often. The gaps became months, then years.
Nobody had fallen out.
Life had simply continued while he doubled down on scaling the company.
So he started rekindling these.
He began with the people he missed.
Some of the messages were easy.
“Been way too long. I’m finally out of the company. Want to catch up?”
A few friendships restarted almost immediately. Within months they were travelling together again, having long dinners, picking up old jokes as if less time had passed than either of them expected.
Others did not.
One old friend was always busy. Another replied warmly but rarely initiated. My client made several attempts, then stopped.
“That one bothers me,” he told me.
“Why’s that?”
“We used to be really close.”
He was quiet for a moment.
There was something painful about discovering that a friendship could remain important to you after it had stopped being important in the same way to the other person.
He had not meant to abandon those friendships. At the time, the company had always seemed to require one more quarter, one more crisis, one more push.
Years had passed that way.
Now he had the time again.
Some of the people he missed were glad to have him back in their lives.
Others had moved on.
“That’s tough,” I said.
“Yeah.”
“And I imagine part of it is realizing you can’t just pick up every friendship where you left it.”
He nodded.
There was grief in that.
He could reach out. He could apologize where an apology was due. He could make time now. He could show that the friendship mattered to him.
But he couldn’t make the other person feel the same way.
Part of rebuilding his personal life was mourning friendships that now belonged mostly to the past.
He also began making new friends.
This was where his life became a more sophisticated version of I Love You, Man. He wasn’t searching for a best man before a wedding. He was simply becoming more deliberate about noticing people he genuinely liked and making room for them after years in which the company had taken nearly all the room.
Some became the people he called when he was thinking through something serious.
Some were the people he travelled with.
Some mostly made him laugh.
Some shared a particular interest.
He began inviting people to his home for dinner without turning the evening into a disguised networking event. Nobody had to meet anybody useful. There was no agenda. They stayed at the table and talked.
They didn’t all have to become intimate confidants.
Different friends mattered in different ways.
What Changed in His Love Life
And his dates began to feel different too.
If a woman he liked was busy on Saturday, Saturday did not suddenly become empty. If she had no interest in something he loved, he had friends who shared it. If she did not like travelling the way he did, he already travelled with people who did.
A woman he liked no longer had to carry his whole personal life.
“Before, I think I was asking, ‘Could this become the relationship?'” he told me.
“And now?”
He thought for a moment.
“Now I’m more interested in how well suited she is for me and the life I’m creating for myself.”
That gave him a simpler set of questions.
Did he enjoy talking to her? Did he respect her? Did they laugh together? How did they handle disagreement? Did they want enough of the same things from the next ten or twenty years?
He could also let a relationship end without feeling that the rest of his life had disappeared with it.
He still wanted a partner. He still hoped for marriage and a family.
But he no longer saved travel for a future girlfriend. Instead, he booked trips with friends or went ahead solo.
He organized long dinners with several friends at his favorite restaurants.
He kept old friendships alive when the other person wanted that too, and he made room for new ones.
He made weekend plans whether or not he had a date.
And he kept meeting new women.
The woman he hoped to meet could still become one of the most important people in his life. She just didn’t have to become his entire personal life.
Note: This account is based on a former client. Dialogue has been reconstructed, and identifying details have been altered to protect confidentiality.