"Should I quit?" is almost always the wrong question.

Last week, we discussed drift and how years in “fine” can turn into a great career becoming a quiet one.

A few of you asked:

“So... should I quit?”

Leaders come to coaching stuck.

They spend months weighing pros and cons, building spreadsheets, talking with their partners, taking quiet interviews, and building an exit case.

But they remain in the same seat.

When we look more closely, the question underneath is almost never about the company.

It is usually something more personal:

“What part of myself have I abandoned to keep succeeding in this seat?”

“What boundary am I avoiding setting right here, in this role, with these people?”

The wrong question keeps you in the same loop.

You change the building, the manager, or the logo, but the same frustration follows you under a different roof.

When you treat your role like a home, you expect it to provide security, validation, and identity.

You remodel it.

You repaint it.

You invest more and more of yourself into making it feel right.

Then, when the role stops feeling like home, you feel betrayed and start searching for the next place.

But what if you treated your role like an Airbnb?

You show up.

You do what you came to do.

You use the amenities.

You appreciate the view.

And you remember that you are passing through.

Your role is not your identity.

It is not responsible for validating you.

And you do not have to stay past what it was meant to provide.

Stop remodeling a place you do not own.

Most leaders already know the conversation they need to have.

They know the boundary they need to set.

They know the role they need to leave or renegotiate.

But they keep collecting information because it allows them to delay the discomfort of acting.

They wait for permission from their manager, partner, coach, mentor, or some stranger on a podcast.

Nobody is coming to give it to you.

Clarity does not always come from more analysis.

Sometimes it comes from having the courage to act on what you already know.

Whatever you name is probably hiding something underneath.

Write down the version of the decision you are afraid to make.

Even if you decide to leave, that boundary will come with you.

If you cannot name it here, you may not name it in the next role either.

Usually, it is not simply to leave.

It may be a smaller, more honest action:

The move is often not the exit.

It is the thing you have been performing around.

Before quitting, change how you hold the role.

Set the boundary.

Have the conversation.

Stop needing the role to serve as your identity.

Show up as someone who is passing through and fully here at the same time.

For some of you, this will confirm that it is time to leave.

That is valid.

But you will leave cleanly, not reactively. You will also be less likely to repeat the same pattern in the next role.

For others, you may realize that the role was not the problem.

The way you were holding it was.

Either way, you move.

That is the difference between quitting and activating.

Working Identity by Herminia Ibarra.

The core argument is simple: you cannot think your way into a new career chapter. You have to act your way into knowing.

If you have been analyzing the same decision for six months, you already know where that can lead.

The BBC’s “Why are fewer people quitting their jobs? The Global Story on the Great Resignation, five years on.”

Anthony Klotz and FT columnist Sarah O’Connor discuss quitting rates, AI, enjoying your current job, and the best ways to quit.

Answer question number two in writing for ten minutes.

Do not edit.

Reply with one word describing the question underneath your own “Should I quit?”

Not the answer.

The real question.

With Clarity,

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