I was listening to a podcast interview with Annie Duke the other day—if you don't know her, she's a former professional poker player turned decision science expert. She said something that made me stop and rewind:

We have so many words for perseverance—grit, resilience, hustle, stick-to-it-ness...

But for quitting? Pretty much just... quit. Maybe "giving up." Maybe "flaking out."

That really hit me.

Because doesn't that say everything about how we've been taught to think? We glorify persistence but stigmatize stepping away—as if continuing down a misaligned path somehow demonstrates character while choosing a different direction shows weakness.

What if that's completely backwards?

What if knowing when to quit is actually one of the most powerful skills you can develop?

Here's what I've come to believe after years of quitting things (some by choice, some by force): Staying in something that's no longer right for you isn't strength. It's fear wearing a costume.

And not once—not a single time—have I looked back and thought, "I wish I'd stayed longer."

Learn to tell the difference between grit and stubbornness

Let's talk about mountain climbing.

We're constantly fed this narrative about scaling peaks: pick your mountain, plan your route, power through the pain, eyes always on the summit. Never look down, never look back, never even think about turning around.

But here's the thing no one tells you about mountains: grit will get you to the top, sure. But if it's the wrong mountain entirely? Every step upward takes you further from where you actually need to be.

Maybe you're like me, nodding along because you've been there. Early in my career, I found myself slogging up a mountain that wasn't mine to climb. I was working in ad sales, and I was spectacularly, catastrophically bad at it.

Not just having-a-rough-patch bad. Fundamentally, irredeemably terrible.

Each month, my sales reports looked like a case study in what not to do. When our sales director would walk by my desk with that "let's talk about your numbers" look, my heart would race. I'd put on my best confident smile and say something like "Yeah, I'm about to close this one, I have a good feeling about this week!"

But we both knew there was no way I'd meet quota. Again.

This wasn't just a career struggle—it was an identity crisis. I'd always been that person who mastered anything I tried: straight-A student, perfect test scores, achievements that came easily. Having something just not click, even after my hardest efforts, felt like a fundamental betrayal of who I thought I was.

So I did the unthinkable: I stepped off that path entirely.

I became an office manager to the very sales team I was failing to be part of.

From the outside, it looked like climbing down rather than up—an Ivy League graduate choosing to make copies and process paperwork? Everyone thought I was throwing away my potential.

It wasn't some noble choice about alignment or authenticity—it was pure survival instinct. I saw the writing on the wall and knew I was about to get fired. But that strategic retreat saved my job and gave me something unexpected: room to breathe. It gave me predictable hours and mental space to build my blog, Racialicious. It eventually led to TV appearances, speaking engagements, and consulting fees I couldn't have imagined while trying to force myself into a role that clearly wasn't right.

Grit isn't a personality trait to worship. It's just a tool, useful only when applied to mountains worth climbing. What looks like resilience from the outside is sometimes just expensive stubbornness.

So here's your permission slip: You don't have to keep climbing just because you started. You don't need to prove anything by pushing through a path that no longer fits. You're allowed to look around, see that you're on the wrong mountain, and choose a different one entirely.

That's not weakness. That's wisdom.

Get honest about what not quitting is costing you

Picture yourself halfway up that mountain.

The air's getting thinner. Your pack feels heavier with each step. Your knees ache. Your lungs burn. But you keep going.

Because quitting still feels like the scarier option.

But here's what we rarely talk about honestly: the mounting cost of staying on the wrong path.

Yes, quitting might cost you something. But staying could be bleeding you dry in ways you've stopped noticing.

I learned this the hard way. At one point in my life, I was trying to do everything at once. I had a job at a hedge fund. I was editing Racialicious late into the night. I was helping run our martial arts school.

And I was nine months pregnant.

From the outside? It looked impressive. Look at her go! So accomplished! Such a hustler!

But on the inside? I was crumbling.

I wasn't sleeping. I wasn't taking care of myself. Every individual element was something I cared about—but together, they were crushing me.

It wasn't just about time. It was about energy. Identity. What I was sacrificing just to keep everything going.

We're experts at calculating what we'll lose if we quit—status, income, identity, relationships—but we rarely tally what it's already costing us to stay.

In real mountaineering, there's something called the "point of no return." It's the moment where if you don't turn back soon—while the weather's still stable, while there's still daylight, while you still have energy reserves—you might not make it down safely.

Once you pass that point? Even if you want to turn back, it's too late. You're committed to the summit bid, for better or worse.

That's exactly what staying in the wrong situation feels like. At first, you promise yourself you'll just keep going a little longer. Push through this next part. Wait for things to improve.

But if you keep ignoring the warning signs—burnout, dread, misalignment—you can lose your window for a graceful exit. You get too deep in. Too depleted. Too trapped.

And now, the cost of leaving is even higher than it was before.

So here's your challenge: Get ruthlessly honest about the toll. Make the invisible costs visible. Your energy, your peace, your health, your joy—those aren't renewable resources you can infinitely deplete.

If staying is costing you all of that? It's okay to let go before you reach that point of no return.

You don't have to earn your way out with exhaustion.

Know the difference between a full quit and a pivot

You're still climbing that mountain, muscles burning, when suddenly—you see it. A fork in the trail.

One path continues straight up. It's the route you've been following: familiar, predictable, requiring no new decisions. Just keep doing what you've been doing.

The other path veers sideways. It's unclear exactly where it leads. It might take longer, might be messier. But it also might get you somewhere better aligned with where you actually want to go.

This is the moment where many of us freeze. Because taking that turn doesn't mean giving up entirely. But it does mean letting go of the path you planned for. And sometimes that feels just as scary as quitting.

When I stepped away from Racialicious, it was a complete exit. I didn't just change routes—I left the mountain entirely. And at the time, it made perfect sense. I had just had a baby. I was running a business. I was completely burned out.

But looking back, I realize that wasn't the only option. I could have pivoted instead of fully quitting. Maybe cut back on the media commentary. Brought on different contributors. Changed how often we published. There were ways I might have kept the mission alive without carrying the same weight.

But I didn't have the capacity then to see those options. The decision felt binary: do everything or do nothing. And so, I walked away completely.

I don't regret the choice—it was right for me at that moment—but I do recognize now that it wasn't as black and white as it seemed.

Sometimes quitting doesn't mean abandoning the mountain. Sometimes it just means finding a smarter path to the summit.

So if you're standing at that fork in the trail—don't assume your only options are "keep climbing exactly as planned" or "give up completely." You might just need to pivot. Change your pace, adjust your route, take that intimidating turn.

You're not abandoning the climb. You're just choosing a path that actually gets you where you want to go.

Expect regret (even when you're making the right move)

Let's say you make the decision. You stop. You pivot. You turn around completely.

You're back on solid ground. You know leaving that mountain was the right move for you.

But even then—there's this little voice that visits sometimes. Not screaming. Just whispering.

"What if you'd kept going?"

Because here's the truth nobody prepares you for: Regret doesn't only appear when you make the wrong choice. Sometimes it visits after the right one, too.

I'd be lying if I said I never wonder what if. When I see my peers from the Racialicious days hosting their own cable news shows, leading major media brands, publishing multiple books, teaching at prestigious universities—yes, occasionally a twinge of regret surfaces.

Where would I be if I'd stayed that course? Would I be a professor? A public intellectual? A more "official" kind of success?

But here's what I've learned: Regret doesn't mean you made the wrong choice. It just means you're human enough to recognize the roads not traveled.

Every "yes" costs something. Every decision closes doors as it opens others. And that doesn't invalidate the wisdom of the path you chose.

Because when I reflect on what leaving Racialicious and my hedge fund job gave me—the chance to help build our karate school, to be present with my family during those early years, to develop skills that would serve me in completely unexpected ways later—I know I made the right call. The skills I developed running a neighborhood business taught me things about community, marketing, and leadership that I couldn't have learned anywhere else.

So imagine you've made it back down from that mountain that wasn't yours to climb. You're safe. You're warm. You're home.

But occasionally, you catch yourself glancing up at the summit. You wonder what the view might have looked like from up there.

That's okay. You don't need to pretend you never wanted to reach the top.

You just need to remember why you chose the path that brought you peace.

Redirect your energy into what's next—not what you left

You've turned back. You've made peace with not reaching the summit everyone expected you to conquer. You've shed the weight of what wasn't working.

And now? You're back at basecamp.

You've got your breath back. You're clearer. Lighter. And you're finally asking yourself the question so many of us never give ourselves permission to explore:

What mountain do I actually want to climb?

Because that's the thing about quitting well—it doesn't leave you empty. It frees you up to start something new.

A few years into running our martial arts school full-time, I hit a wall. We were dealing with nonstop staffing issues. There was a neighboring business owner who ran a daycare and, for some inexplicable reason, had decided that our karate school was somehow competing with his childcare business. His business was failing, and he blamed us for it, doing everything possible to sabotage us.

The pressure was relentless. And then, my father suddenly died that year. We had been estranged for years, and that loss hit me in ways I wasn't prepared for.

I experienced what I can only describe as a complete breakdown.

For the first time in a long time, I stepped back entirely. I took a real break from the school. In that pause—that deliberate step away from the mountain I'd been climbing—something shifted. It gave me distance to see the truth: This chapter was ending. I couldn't keep doing this, not in the same way.

The school had been my husband's dream. I had helped build it, gotten it running, and I was proud of that. But I'd put my own ambitions on pause to do it. And now? It was time to think about what I wanted.

I didn't leave that day. I didn't even know what would come next. But taking that break gave me the clarity to admit the truth—this path wasn't sustainable. And that opened the door to something new.

Eventually, that led me to create Top Flight Family, a luxury family travel platform that would grow to over a million followers across social media. It didn't happen overnight. But that pause—that willingness to stop climbing and reassess—was the beginning.

Sometimes the most crucial part of quitting isn't the leaving itself. It's the pause that gives you clarity about what's next.

That's not quitting out of failure. That's quitting with intention.

So if you've let something go—or you're thinking about it—remember: this isn't the end of your story. It's the beginning of something more aligned. More intentional. More you.

You don't need to summit the mountain everyone else is climbing.

You get to choose your own peak. And this time, the climb gets to feel good.

The courage to choose again

So what have we learned about quitting?

Grit is powerful—but only when applied to the right mountain. The longer you keep climbing a peak that isn't yours, the more it costs you. You don't always have to abandon the mountain entirely—sometimes you just need to find a different route. Even the right decision can come with moments of regret. And the most powerful thing you can do after turning back isn't to dwell on the summit you didn't reach—it's to choose a new mountain that actually calls to you.

What are you currently climbing that no longer feels aligned—but you're afraid to step away from? What would it look like to pivot instead of push through? And if you did let go... what might you finally have the space to pursue?

You don't need to be applauded for your endurance on a peak you've outgrown. You don't owe anyone a summit photo from a mountain you never wanted to climb. You are allowed to change direction. To choose again.

And when you do it with clarity and purpose?

Quitting isn't failure. It's freedom.

What's something you've quit that everyone told you to stick with? Have you ever walked away from a path others thought you should stay on? Share your "quitting victory" stories in the comments 👇

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