What I’ve Learned About Holding on Too Long

A soft guide to knowing when you’re done

Leaving — Rendered by the author in DALL-E

As much as it pains me to admit it, I’m the undisputed champion when it comes to holding on too long.

Jobs that drained me. Spaces that didn’t feel like mine anymore (if they ever did). Relationships that shriveled into raisins before they were even off the vine, all kept alive by duty, memory, or sheer inertia. I’ve held on to old roles, outdated ideas of who I am, and stories that never truly belonged to me — anything and everything.

And I didn’t stay because I somehow loved boredom, pain, or dissatisfaction. I stayed because I somehow wasn’t sure who I’d be without those things.

Letting go sounds like the easy choice when it’s not your choice. But when it’s something you’re facing in real time and real life, it can feel like walking off a cliff and hoping there’s a bridge or a net down there somewhere, miraculously keeping your next step from being your last.

Why We Stay

There’s always a reason. Usually, several.

We stay because we were taught that leaving means failure or that quitting is shameful. We grow up hearing that endurance, loyalty, and the willingness to “be the bigger person” are virtues, especially if you’re also a woman or…