“I know what I’m looking for,” he told me. “I just haven’t found it.”
“Tell me about the last woman you were seeing.”
“I liked her. We could talk for hours. She was attractive. But after a while, I started wondering whether we were compatible.”
“What made you wonder?”
“She wasn’t as interested in the frontier tech I’m into. I’d bring up a development I’d been following, but she wouldn’t have much to say. She didn’t follow any of it herself.”
“What happened then?”
“We’d talk about something else. It wasn’t awkward or anything. But I’d like to be with someone who gets excited about those subjects. Someone who’s been reading about them too.”
He went on to describe their differences around fitness.
“I’m interested in training, too. Getting stronger, improving my personal bests. I think I’d really enjoy preparing for a Hyrox event together, or doing CrossFit, or going for a cold plunge and sauna together. But she wasn’t doing any of it.”
He had a fairly specific picture of a good weekend. It included emerging technology and plenty of voluntary physical pain, preferably shared with a woman who enjoyed both.
He was in his forties and had been on the founding team of a company that went public. I’ll call him Daniel. Financially free, he had semi-retired. He could spend his days largely as he pleased, and he spent much of that freedom studying cutting edge tech and pursuing his fitness goals. Sharing those interests with a partner sounded appealing to him.
“Had she been interested in those things when you first met?”
“No.”
“What made you keep seeing her?”
“Well, I enjoyed being with her. I looked forward to it.”
“And later?”
“I still enjoyed it. But we were getting more serious. So I had to think about whether this could last.”
Apparently, enjoying her company had been sufficient reason to see her again until he began considering the possibility of building a relationship for the long term.
Eventually, he ended that relationship.
We discussed the other women he had seen over the previous couple of years. The same sequence kept appearing. Attraction, easy conversation, growing attachment.
But then he would begin considering their differences until he could explain, quite convincingly, why the relationship had no future.
None of these women had concealed a hatred of CrossFit until they had secured his affection. He had known their interests differed from his. But those differences became unacceptable as he became attached.
“What did you think you needed to do differently?” I asked.
“Find someone who was more interested in the same things I’m interested in.”
Fair enough. If you keep breaking up over the same differences, find someone without them. Preferably before another six months of dinners.
A better checklist
By the time we met, Daniel had hired a life coach to help.
“What did you and that coach come up with?”
“That I needed to be clearer about what mattered to me before getting involved. Otherwise, I’d get attached and then have to end it.”
The coach helped him turn his disappointments into definite requirements. He would establish earlier whether a woman ticked the boxes on his checklist, before affection complicated the assessment.
There was a satisfying logic to this. He knew how to set goals, assess information, and make decisions. He had helped take a company public. Surely he could get better at deciding whom to have dinner with.
“Did it help?” I asked.
“It helped me get clearer.”
“And when you met women who had those interests?”
“That wasn’t necessarily better.”
The few women he found who shared those interests were often drawn to men quite different from themselves: men who ran restaurants, or worked for nonprofits, or made their living in the arts.
These women could happily discuss technology and fitness with Daniel, but then go on a date with some other man whose life gave them something different to discover.
But Daniel saw their shared interests as a reason they should be attracted to him. Apparently, they hadn’t received the memo.
When the attraction was mutual, Daniel sometimes found much of what he had been looking for. They could discuss the subjects that absorbed him. He admired her discipline. Nobody needed persuading that a weekend could reasonably include a grueling workout that made stairs difficult on Monday.
“How did those relationships feel?”
“More like… friendship.”
But in the end, there was very little in the way of sexual chemistry. He just found that he wasn’t really into them.
The life coaching had accepted his requirements as a useful starting point. His experience suggested we needed to examine those very requirements.
He had begun our advisory engagement certain that he knew what he was looking for. I was becoming more interested in how he had become so certain.
An afternoon without a goal
When we discussed how he spent his own time, I asked what he enjoyed doing without trying to get better at it.
He described interests he pursued and goals he was working toward.
“And if you weren’t making progress?”
“I’d wonder why I was doing it.”
“Even if you enjoyed it?”
“I guess I’d feel I was wasting time.”
He had earned the freedom to spend an afternoon however he pleased. Enjoying it apparently still required a supporting argument.
I brought up what he had told me about his father: how he could become absorbed in a creative pursuit and forget the time.
“That sounds like the kind of afternoon you’re saying you couldn’t allow yourself.”
“My father wasn’t disciplined.”
“Was he enjoying himself?”
“Probably. That doesn’t mean it was a good thing.”
His parents had separated when he was young. His mother had harshly criticized his father’s carefree approach to life. He knew her account had influenced him; he had explored that history with the therapist he saw for a few years.
But when I suggested that some of the qualities she condemned might be worth recovering in himself, we were soon discussing the benefits of discipline.
“I like having goals,” he said. “I like making progress.”
I didn’t doubt it. Nor did I think another argument about the merits of leisure would help. He could acknowledge that people needed time off and then explain how he used his own time off to improve his health and fitness.
Even relaxation had a job.
Over several weeks, I kept returning to what happened before he dismissed an activity as wasteful. He would consider following an interest simply because it absorbed him. Then he would begin assessing whether it deserved the time.
“What bothers you about letting yourself continue?” I asked.
“There are other things I could be doing.”
“Things you need to do?”
“Things that would be a better use of the afternoon.”
When I connected that judgment with his mother’s criticism of his father, he could accept the historical resemblance.
“Yes, she would have said that. But I still agree with it.”
“What do you think would happen if you let yourself lose track of time?”
“I don’t want to get into that habit.”
“What would make it a habit you wouldn’t want to get into?”
“You stop pushing yourself. You get… comfortable.”
We were discussing an afternoon. He was considering what might become of him for the rest of his life.
In a later session, I returned to the distinction.
“Could you enjoy those qualities of your father without living exactly as he did?”
“I understand what you’re saying. But I like the way I live. Discipline has been good for me.”
“What do you feel is at risk here?”
“I didn’t get where I am by doing whatever I felt like.”
There was plenty I could have said about his freedom to relax. He could have agreed with all of it and still spent the next free afternoon measuring his progress toward some goal.
Instead, I asked about the objection itself.
“When I mention enjoying that quality in your father, what bothers you most?”
“I don’t see why I should encourage it in myself.”
“Even if you weren’t neglecting anything?”
“But that’s how it starts, you see.”
What he rejected in himself
When he described what he enjoyed about being with a woman, I noticed a resemblance to the qualities he struggled to accept in himself.
“You seem to enjoy her freedom to follow whatever interests her. That’s one of the qualities we’ve been discussing in your father.”
He thought about it.
“OK, intellectually, yes. I can see the connection.”
Over the following months, the connection came up again through the women he was seeing. He would describe the pleasure of being with the new woman, then his growing reservations about how she spent her time. I would point out when a quality he had enjoyed was becoming a reason to question the relationship.
Theory was considerably easier when it wasn’t deciding whom he would spend his life with.
When we returned to a particular relationship, we stayed with what had happened between them. What had he enjoyed? What had bothered him? Had she behaved differently, or had he begun to judge the same behavior differently?
Sometimes our conversation brought us back to his father. Sometimes we spent more time considering a difference that mattered to him. Recognizing a familiar reaction didn’t settle whether a relationship was right for him.
It took months of returning to those experiences for the connection to mean more to him than an explanation he found plausible.
Listening to the objection
During those months, we also spent time with the criticism as it happened.
When he began to dismiss an activity as wasteful, I asked him to pause.
“What are you noticing right now?”
“I should be doing something more useful.”
“Is there an interest in doing it anyway?”
“Yes. But I don’t think that’s a good enough reason.”
He could feel the interest. But he could also feel the objection. Usually, the objection won.
“Could we spend a little time with the objection?”
“What do you mean?”
“You don’t have to put the objection aside. I’m interested in what that part of you making the objection is actually worried about.”
He began explaining why he valued discipline.
“What is that part worried would happen if you just did what you were most interested in?” I asked.
“I’d get used to doing whatever I felt like.”
“And then?”
“I’d stop making any effort at all.”
This was part of our process. We used the word ‘part’ to refer to a response he could notice in himself. One part of him was interested in exploring. Another part objected. We could pay attention to each without needing either to disappear.
“How do you feel toward the part of you that keeps you pushing?”
“I think it’s been good for me.”
I agreed. Then I asked, “What do you appreciate about it?”
“It’s helped me get things done. I wouldn’t have achieved what I have without it.”
He had little trouble respecting it. But becoming interested in what it feared took more time.
When he described its concerns, he often began defending its conclusions.
“What does it think of the part that would like to try something just because it’s interesting?” I asked.
“That it doesn’t know when to stop.”
“And what’s your response to that?”
“I’m inclined to agree.”
We didn’t need to force a different answer. He was telling me how that part of him felt. There was more to understand before he could give those impulses much more leeway or freedom.
Letting himself follow an interest just for the sake of it
Over several weeks, he became more familiar with this response. He could notice the concern about losing discipline without immediately having to decide whether it was correct. He could spend time with it and hear how much it expected to go wrong.
Sometimes we could then return to the interest it had interrupted.
“What appealed to you before you began wondering whether it was worthwhile?”
“I was curious. I thought it might be fun to try.”
“Can you still feel any of that?”
“A little.”
“What happens as you focus more attention on it?”
“I start thinking about what I could do.”
We gave him time to follow that interest. If the criticism returned, we could hear from that part too.
Nobody needed to win the argument.
The impulses he had learned to distrust were often small. He felt like losing himself in the creative play of it. He wondered what would happen if he tried an idea just for fun. He was enjoying himself experimenting in this way and felt like continuing.
That took patience. He knew how to set a goal and pursue it. It would have been easy to make ‘play’ another area in which he had to perform for some far off goal.
Room to enjoy himself
As the months passed, he began telling me about time he had spent tinkering with designing a game for fun or or painting or playing songs he liked on the electric piano he bought recently.
“What were you trying to do?” I asked.
“I wasn’t trying to finish anything. I was just seeing what happened.”
“And how was it?”
“I enjoyed it.”
“Did you feel you should be doing something else?”
“Sometimes. But I was interested in what I was doing right then and there.”
He could remain with that interest more often. He could leave an activity unfinished and return to it later.
The result no longer had to justify every hour.
He also described becoming curious about areas outside technology and fitness. In our sessions, he had more to tell me about subjects he would once have ignored. He could appreciate them without deciding he had to become good at them.
The same change began appearing in his accounts of the woman he was seeing.
“What have you been enjoying about being with her?” I’d ask.
He’d tell me about their time together: They just wandered aimlessly around the old part of the city, café hopping, popping into random shops. He enjoyed her company and respected her character.
He could also describe her interests without immediately comparing them with his own.
“Are those interests you share?”
“Not really. But I’m interested in what she enjoys about them.”
We could discuss her ambitions without turning to what he thought they ought to be. He was more able to appreciate the effort she put into an area she had chosen, even though it was very different from his own interests.
He already had demanding goals for his own development, professionally and personally. But she no longer needed a matching set.
He could look forward to seeing her without also planning who she ought to become.
Back to building
His semi-retirement had also become less retired. He had invested in young businesses and become involved in building two of them. Apparently, helping take one company public had not exhausted his interest. After all, he was still in his forties.
As he gave more time to other interests and to his relationship, he began noticing a difference when he returned to those businesses.
“How has your work been going?” I asked.
“Better. I’m more interested in getting back to things.”
“What do you notice?”
“I feel refreshed. I have more ideas. I appreciate what we’re doing more.”
He would tell me about a weekend spent tinkering or being with her. He had followed interests unrelated to his businesses. He had enjoyed hearing about hers. By Monday, he felt more able to return to the companies with enthusiasm.
Earlier, even relaxation had needed a job. Now he could enjoy an afternoon without needing it to contribute to any future goal.
Often, he returned to his businesses feeling more rejuvenated and inspired. That was a welcome result. He didn’t need to make it the purpose of the weekend.
Remembering his father
Our conversations about his father changed too.
He began remembering more of the time they had spent tinkering together when he was a young boy. They had played and built things. As those memories returned, he had more to tell me about what he had enjoyed with his dad.
“What do you appreciate about those times now?” I asked.
“That he enjoyed it too. We could get absorbed in it together.”
We spent time with those memories. His father had died, and he began to visit his grave every few weeks to lay a fresh flower. There would be no new afternoons together with his dad, but he could appreciate more of the ones they had shared.
The qualities he had spent years trying to avoid now belonged to memories he valued. His father could follow an interest and forget the time, even though his mother criticized his dad back then for doing so. He recalled that as a boy, he had sometimes been there with his father, enjoying it.
He could remember his father’s failings and also feel grateful for those afternoons back then. One no longer had to erase the other.
Being a little more like his dad had once seemed dangerous.
But now, there were ways in which he was glad to be like him. And that made all the difference.
Note: This account is based on a former client. Dialogue has been reconstructed, and identifying details have been altered to protect confidentiality.