She took the day off, told her assistant she’d be unavailable, and stayed home. Not to rest — she had work to do. It was something she did every year — a hard look at every part of her life, no exceptions.
She had a system. Each area got the same scrutiny: career, finances, health, relationships, personal growth.
She started with the easy ones. Revenue was up. She’d restructured her team and it worked. Her doctor was pleased with her bloodwork, and she’d finally booked the hiking trip she’d been putting off for two years. She made notes. Adjusted goals. It felt good to see progress.
Then she got to “relationships.”
She looked at what she’d written the year before:
Try a different dating app. Stop wasting time on text threads that go nowhere. Say yes to setups. Don’t get pulled in by charm if there’s no follow-through.
It was still true. Every word of it. A year had passed, and the problems hadn’t changed.
She opened a new note and wrote down everything she could remember:
Eight first dates.
Three second dates.
A tech founder she saw for six weeks who talked about the future, then ghosted after she mentioned introducing him to friends.
A cardiologist who said he wasn’t ready for anything serious — after three months of acting like he was.
She sat back and stared at the list. Then she wrote:
Still stuck. No real progress.
Another year. Same outcome. She’d been patient, been open, been willing to try. And here she was, right back where she started.
Then she said it out loud:
“I’m so tired of this.”
She wasn’t sure anymore if it was bad luck or bad judgment or something she couldn’t see about herself.
For the first time, she asked a different question:
What if this isn’t about finding better men—it’s about approaching this differently?
That question doesn’t give you an answer. It just points toward the only part of this you can change: what you do next.
But it’s the right place to begin.
It’s not easy to see what’s off when you’re close to it. Even if part of you suspects there’s something in your approach that isn’t working, it’s hard to name what that is — or what to do instead.
Asking “What if I need to do this differently?” puts your focus on something you have some control over – how you’re approaching dating. Not whether it’s easy or hard to meet men, not whether you’ve had bad luck, but whether your own way of doing this is working for you.
When you’re inside your own situation, you can’t always see what’s actually happening. The things that feel natural might be working against you. The choices that seem obvious might be steering you in the wrong direction.
Interrupting the Automatic
When you’ve been dating for years, some things become habit. You don’t decide how to respond – you just respond the way you always have.
A partner at a law firm texts to make plans. You check your schedule, suggest a time, confirm the details. It seems straightforward.
He cancels Thursday night. “Client emergency.” You say it’s fine, you’re busy too.
He cancels again two weeks later. Same reason. You say it’s fine again.
Now he knows your schedule gives way to his.
You let it go because you don’t want to seem difficult. You’ve done this a hundred times – smoothed things over, given him the benefit of the doubt, kept things light.
But maybe there’s something else you could do. Maybe you could pay attention to how his invitation makes you feel, not just whether it fits your calendar.
What if you said something? Not to start a conflict — just to see what he does with it.
These are small moments. The kind that happen on every date. But how you handle them matters more than you might think.
Changing doesn’t mean transforming your entire approach to dating. It means trying something different in one of these moments. Just once. Just to see what happens.
Change starts when you stop doing what usually makes sense — because it isn’t working.
What Happens When You Don’t Do What You Always Do
When something hasn’t been working — but it’s familiar — it takes more than insight to change it. You can know what the problem is and still reach for the same answer out of habit.
You try something different. Ask a different question. Don’t fill in the silence. And it feels wrong. Like you’ve made things worse.
That feeling isn’t proof it’s wrong. It’s just unfamiliar.
It’s natural to interpret awkwardness as “this isn’t working” and go back to what feels normal.
That awkwardness is information. It shows you how automatic your usual response was — so automatic you didn’t realize you were doing it.
But that discomfort is revealing something you couldn’t see before: how ingrained the pattern is, and that you actually have a choice. That awareness is the foundation for everything that comes next.
Start Where You Are
The question she asked herself that afternoon – “What if this isn’t about finding better men, it’s about doing this differently?” – is one you can ask too.
She didn’t need to try harder. She needed better information — about her default responses and the choices she thought were smart but weren’t working.
Dating powerful men can involve complications no one prepares you for.
There’s less margin for error when the man across from you knows exactly what he’s doing.
Even highly accomplished women aren’t immune to blind spots about what’s driving their attraction and what actually works in these situations.
That’s the work of a good consultation: to make the invisible parts visible.
After thirty years as a psychiatrist, I’ve developed specialized expertise working with accomplished women on exactly this.
Some women reach a point where even their best instincts need rethinking. That’s where I come in.
If you’re ready, let’s talk. Contact me here.
