Most high achievers I know struggle with the same thing: we're terrible at quitting.
We're wired to finish what we start. We've been conditioned our entire lives to see quitting as failure, to push through pain, to never give up. That mindset serves us well most of the time, but it can also trap us into pursuing things long past the point where they make sense.
I've withdrawn from races. I've exited business partnerships. I've discontinued services that no longer align with our direction.
Some of my best decisions have been knowing when to stop—but it took me years to develop a framework for making those calls without ego getting in the way.
Seeing the Sunk Cost Trap
Picture this: you're 60% through a project that isn't working. You've invested time, money, and reputation. And no matter what, you’re banging your head against the wall, desperately trying to make it work. And it’s just not coming together.
The logical part of your brain knows you should cut your losses, but you keep going because stopping feels like admitting all that investment was wasted.
Continuing something that isn't working doesn't honor your past investment. It just compounds the loss. Ultimately, what matters isn’t how much you invested–it’s whether or not continuing that investment makes sense from where you are right now.
But how can you know quitting is the right call?
4 Questions to Ask Before Quitting Anything
Whether it's a race, a business initiative, or a commitment I've made, I run through the same mental checklist:
Am I quitting because it's hard, or because it's wrong?
There's a vast difference between temporary discomfort and fundamental misalignment. Every ultramarathon is hard. Every business has difficult quarters. The challenge isn't whether something is difficult—it's whether that difficulty is moving you toward something beneficial or just creating suffering for its own sake.
What am I protecting by continuing?
Sometimes we keep going because we're protecting our ego, our reputation, or other people's expectations. I’ll tell you right now, this is the most dangerous question to skip. Are you continuing because this still serves your goals, or because you don't want to be the person who quit?
What becomes possible if I stop?
Oftentimes, we focus so much on what we're giving up that we don't consider what we're gaining.
Sunsetting a product line might free up resources for something with real potential. Stepping away from a commitment might open up bandwidth for opportunities you can't even see yet. Reallocating that mental energy you’re spending to maintain something that doesn't work can pave the way for new innovation.
Is my judgment reliable right now?
I learned early in endurance training not to make big decisions when I’m physically depleted. The same is true with business decisions made under stress, sleep deprivation, or burnout. Sometimes the right answer is: I'm not in a position to decide this clearly yet. Give yourself permission to table the decision until you're thinking straight.
Build Your Exit Criteria Early
You want to know how to make this work? Make your decision-making criteria before you're in a pressure moment.
Before I commit to something significant, I define what success looks like and my exit criteria. What warning signs would tell me it's time to reassess? What circumstances would make continuing more costly than stopping?
In business, this means setting clear milestones and decision points for projects. Not vague "let's see how it goes" checkpoints, but specific markers that trigger honest evaluation: If we haven't achieved X by this date, here's the conversation we're having.
You’re not planning to fail when you do this. You’re removing ego from the equation when you're most vulnerable to its pitfalls.
What Quitting Really Looks Like
The leaders I respect most aren't the ones who never quit anything—they're the ones who know how to cut their losses and redirect their energy toward better opportunities. I’d bet the same is true of you, too.
Quitting is about being honest enough with yourself to recognize when continuing would be the actual mistake.
Your energy, time, and resources are finite. The question isn't whether you can push through and finish everything you start. The question is whether you should.
What are you continuing right now that you should probably quit?