Why “Never Give Up” Should Carry a Caveat

I’ve been sitting with an idea for a few months now. It started when I read something by Susan David (the Harvard psychologist and emotional agility expert) about the hidden benefit of quitting. She challenges one of the most deeply embedded mantras in our cultural operating system: never give up.

I’ve been noodling on it ever since. Mostly because I hear the opposite message relentlessly in my work with leaders.

“I can’t quit now. What will people think?” 

“I’ve invested too much to walk away.” 

“Leaders don’t give up.”

That last one. That one’s the killer.

We’ve romanticized perseverance to the point where it’s become almost indistinguishable from stubbornness. We hand out trophies for grit. We tell our teams (and ourselves) that the difference between success and failure is just one more push. Even Winston Churchill, the patron saint of perseverance, added a caveat to his famous “never give in” speech: “except to convictions of honour and good sense.” We conveniently forget that part. 

Sitting across from leaders in coaching conversations, I’ve noticed that the ones who are most trapped aren’t the ones lacking effort. In fact, they’re drowning in effort; grinding away at something that has stopped making sense: a strategy, a role, a relationship, a version of themselves … because somewhere along the way, “not quitting” became a measure of their character.

Susan David’s insight cuts right through that. She makes the point that there’s a meaningful difference between giving up because something got hard, and letting go because something is genuinely not working, or worse, is actively costing you. The former might be avoidance. The latter is wisdom.

Try this on: Sometimes quitting is the most courageous thing a leader can do.

How does it feel? Care to challenge me?

I work with leaders from all sectors – business, non-profit, public service, and I’ve had many share their fierce desire to make a difference, to show up fully, to not let people down. That’s beautiful and I applaud it, but it’s also, occasionally, what keeps them stuck.

I’ve had clients (seasoned executives, brilliant humans) who’ve stayed in toxic organizational cultures for years past the point when every signal was telling them to leave. I can remember one leader who told herself she was being resilient, that real leaders don’t abandon their people, that it would turn eventually around if she just stuck around long enough. When she finally left, she said something I haven’t forgotten: “I thought quitting would feel like failure. It actually felt like coming back to myself.”

Hers isn’t a story about weakness; it’s a story about delayed courage, and triumph.

We’ve all heard of the sunk cost fallacy (we keep investing in something because of what we’ve already put in, rather than what it’s realistically going to give back). Well, leaders are not immune. If anything, leaders are more vulnerable to it, because their identity gets tangled up in outcomes. Quitting can feel like a verdict on who they are, not just what they’re doing.

Are You Staying Because it’s Right, or Because Leaving Feels Wrong?

I tell my clients that courage isn’t one-dimensional. Yes, courage is sometimes the white-knuckled decision to stay in the ring. But it’s also the willingness to look clearly at reality, including when it’s uncomfortable, and act on what you see. Courage is saying: this chapter is over, and I’m going to close it with intention.

The question I’ve started asking is this: Are you staying because it’s right, or because leaving feels wrong?

Those aren’t the same thing.

There’s a version of leadership development that’s all about building resilience, grit, and tenacity. I believe in all of those things, but I also believe in something I take from David’s work in emotional agility, which is the capacity to hold your values and your situation clearly, without letting fear or ego make the call for you.

Sometimes the bravest move on the board is the one nobody celebrates in the moment.

Quit the thing that’s diminishing you. Walk away from what’s run its course. Give yourself permission to redirect.

That’s not giving up. That’s growing up.