How do you know when it’s time to go?

I'm leading a group, and it's Lisa's turn.

She comes across as composed, professional, open and focused. Lisa is part of a small peer coaching cohort — five colleagues at the same company in a six-month program. I invite her to share her intention and how the group can support her.

Lisa tells us she left a government job, just shy of getting her student loans forgiven, to join this company. She was recruited as a senior leader, but when she arrived, was told she needed one technical certification before she could be fully onboarded at that level.

She got the certification. She requested the role she'd been promised. And the goalposts moved.

Make it make sense

Each time she met with her manager, there was a new bar. Lisa kept notes of her 1:1s. She tracked every time she'd met and exceeded her quantitative metrics. She did this for two years, before finally transferring to another team. A month later, a "re-org" meant her former team all got promotions. Lisa was still at the level below.

I could tell she was wavering between recounting the timeline with control and letting her emotions show. The body language. The eyes occasionally moving away from the camera. The deep breaths getting slightly more ragged.

She was hurt. And the question underneath it all was: why should she take the risk of being vulnerable again? Hadn't she put herself out there enough?

We're Not Supposed to Get Our Feelings Hurt by "Work"

We’re supposed to work hard but not take it too personally. We're supposed to work overtime when the project is due, but stagger our time off so it doesn't upend the team. We're not supposed to cry about work. It's just work, right? It's not life or death.

What made Lisa's story so extraordinary was how ordinary it sounded.

While other group members — employees at different levels and divisions of the same company — asked totally valid questions about skip-level managers and performance reviews, I was sitting with this weird mix of angry-indignant-outraged-resigned-proud-hopeful.

She'd named it now. Angry.

Angry at what her managers — up to four of them — kept doing and not doing, saying and not saying. Angry at herself for leaving a job with such a huge payoff coming, to take a promise that was never kept.

Lisa is not alone. Lisa was professionally gaslit. Lisa may have been hit by a whole constellation of isms — race, gender, age, identity as a parent, ableism. She couldn't know for sure. All she knew was that the metrics she'd been told to meet and exceed had been met and exceeded long ago. Her performance reviews were glowing. Her peers on the call spoke of her reputation as someone who gets things done.

How Do You Know When It's Time to Go?

Lisa had started with a practical request: how do I navigate an upcoming meeting with my new skip-level manager?

But as she kept talking — as we witnessed the moments when her eyes watered and her voice broke — the practical question dissolved. She reframed it herself:

"How do you know when it's time to go?"

This question matters so much to me, because what I keep witnessing is women feeling difficulty, stuckness, burnout — and then personalizing it. Telling themselves they need to change, or that they can't cope with what is "required."

And then I hear from people who've come through that tunnel, and they say they don't aspire to leadership positions anymore. That's a rational choice in the face of real pain, real sacrifice, real barriers. But when that happens, nothing changes. We all end up perpetuating the idea that only those who survive an inherently soul-sucking process are fit to lead.

It's also worth saying clearly: if you have had a bad boss — or even just a boss who doesn't know how to manage — you don't have to make it mean something about your capacity to handle leadership. We will all have bad boss experiences. Some will feel obvious and overt. Others will just be someone who doesn't know what they're doing, whose lack of direction, feedback, or compassion quietly causes real damage.

Why I Still Have Hope

Lisa saw what was happening. She put a name to the feeling, and that name was Anger.

She decided it was time to go. And one of her peers offered her this: don't just run from something bad. Try to run toward something good — something wanted, something inspiring.

When that happens — when we name where we are and decide to move toward what we want — that's when we make it happen. That's when I have hope.

Because it means that person is ready to take a pause and figure out what comes next.

If you're in your own version of Lisa's moment — doing everything right and still feeling like something's off — I'd love to talk. Reach out and let's figure out what comes next, together.