39: How to Decide: Should I stay or should I go?

SisterSmart Leadership · Feb 12, 2026 · 23m

Should I stay or should I go?

This is a question many of my clients come to me with. You've invested years at your company, built strong relationships, and know how to do your job well. But something feels off. Maybe you've gotten too comfortable in your groove. Maybe the company culture has shifted. Or maybe you know deep down that you're ready for more.

Our client, Dorothy, a negotiations coach herself, found herself at this exact crossroads. She was working at a large Fortune 500 healthcare organization and knew it was time to move up—but couldn't see clearly whether that meant staying or…