I have been thinking about something for a few days now, and I keep coming back to it.
It started when I was rereading Brene Brown’s The Gifts of Imperfection, the part where she draws a line between two things most people use as if they mean the same thing. Fitting in and belonging. Brown writes that fitting in is about assessing a situation and becoming who you need to be in order to be accepted. Belonging, she says, is something else entirely. It does not require you to change who you are. It requires you to BE who you are.
She also says something that gave me a chill: “Fitting in is the greatest barrier to belonging.”
So freakin’ true it hurts. I have been rehashing that ever since, because I think it explains something I see all the time in senior leaders who are in the middle of a career transition.
They are working incredibly hard to fit in somewhere. And in doing so, they are making it nearly impossible to find where they actually belong.
What fitting in looks like in a job search
When you are in transition, especially after a long tenure or after a role that defined a big chapter of your life, there is a pull toward conformity that is almost gravitational. You start reading job descriptions and quietly reshaping your story to match them. You notice what the market seems to want and you sand down the edges of your experience to fit that shape. You walk into interviews presenting a version of yourself that is optimized for acceptance rather than for truth.
It feels like a good plan. It feels like it’s gotta work because it always has before.
But what it actually is, if you are honest about it, is a performance. And the exhausting thing about performance is that even when it works, you end up somewhere that only wants the version of you that you performed. Not the whole kahuna.
What belonging actually requires
Brown’s research points to something that is rather itchy for high-achieving people: belonging requires vulnerability. Not weakness. Vulnerability. The willingness to show up as you actually are and let that be the thing that either lands or doesn’t.
In a career context, that means getting honest about what you are genuinely great at. Not what you have done across every job. What you are, at your core, built to do. The kind of problems that energize you rather than drain you. The culture where you do your best thinking. The type of leadership that brings out your real capability rather than just your compliance.
Most people in transition have not done this work. Not really. They have updated their resume. They have practiced their answers. They have optimized their LinkedIn profile. But they have not sat down and asked the harder question: where do I actually belong, and what does that place look like?
That is not a question you can answer by reading job descriptions. It requires something slower and more honest than that.
The clarity question nobody is asking
Here is what I find myself saying to leaders at this stage more than anything else: before you figure out where to go, you need to figure out who you are going as.
Not who you have been. Not who the market says it wants. Who you actually are, right now, with the full weight of everything you have learned and built and survived. What that person is genuinely for. What that person makes possible that is hard to find.
When you know that, something changes in the search. You stop trying to fit. You start looking for resonance. You walk into rooms differently. You ask different questions. You stop auditioning and start evaluating.
And the offers that come are different. Not always more, not always faster, but different in a way that matters. They come from places that want the real thing.
That is belonging. And it is available to you. But it does not happen by accident, and it does not happen from the outside in.
This is the work ReflectionPoint Advisors does first
Before we touch positioning or narrative or outreach, we work on clarity. The kind that comes from actually sitting with what you are great at, what the market needs right now, and where those two things meet in a way that is specific enough to be unmistakable.
Not because clarity makes the search easier, though it does. But because without it, you are not really searching. You are fitting. And fitting, as Brene Brown spent years of research demonstrating, is the thing that keeps you from finding the place where you actually belong.
You have worked too hard and built too much to settle for a room that only wants the version of you that sounds like everyone else.
The work is finding the room that wants you.
That room exists. Let’s find it together.
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