Winners Do Quit—And That’s Why They Win
We’ve all heard, or even said, "Winners never quit, and quitters never win." It’s an inspiring mantra, one that fuels determination, grit, and perseverance. But let’s be honest—this quote, while motivating, is often misapplied. It assumes that quitting is inherently bad, that persistence is always noble, and that walking away from something means failure.
Yet, the reality is that the most successful people—true winners—quit all the time. They just quit the right things. They understand that not all battles are worth fighting, not all investments are worth saving, and not all paths lead to progress. They quit strategically, knowing that clinging to something out of pride, fear, or misplaced loyalty can be more damaging than letting go.
The Time I Quit A Safe Job
I know this to be true because I’ve lived it. At one point in my career, I had what many would consider the ultimate professional achievement: a tenured full professor position at a respected university. Tenure—the coveted safety net that provides job security and academic freedom—was something most in my field aspired to and worked their entire careers to achieve. It was the pinnacle. The safe bet. The thing you never quit.
But me, not being normal, did.
I walked away from a full professor tenured position to take a huge, uncertain risk—to develop a Doctor of Athletic Training (DAT) program with a focus in an area many consider only to be secondarily important to the profession. There was no guarantee of success, no guarantee of tenure, and no roadmap for what we were attempting to build. All we had was an idea of what might work and could possibly provide more value than many assumed it could. We had a belief that athletic training education needed to evolve, and that a DAT program, with a focus on entrepreneurial thinking, could revolutionize how athletic trainers saw themselves.
Was it scary? Absolutely. Did fear of making a stupid decision keep me awake at night? Yes. Was it exhilarating? For sure.
Leaving a senior faculty position that took me 14 years to earn wasn’t quitting in the sense most people think about it. It was quitting the safety of the known in order to pursue something greater in the unknown. And because I took that leap, I was able to have a far greater impact—on my students, on my profession, and on the profession of athletic training as a whole. If I had clung to tenure just because it was comfortable, none of that would have happened.
The Problem with “Never Quit” Thinking
Blind commitment to anything—whether it’s a job, relationship, business, or idea—can be a trap. It’s easy to fall victim to what behavioral economists call the sunk cost fallacy, the tendency to stick with something simply because we've already invested time, money, or effort into it.
We've all seen it:
The entrepreneur who refuses to pivot, even when the market clearly rejects their product.
The employee who stays in a dead-end job out of fear of losing seniority.
The athlete who plays through a career-ending injury just to “tough it out.”
In these cases, the refusal to quit isn’t admirable—it’s destructive. It doesn’t demonstrate perseverance; it demonstrates stubbornness at the expense of progress.
What Winners Do Differently
The best decision-makers don’t just endure—they adapt. They assess their circumstances objectively and aren’t afraid to walk away from things that no longer serve them. This is where legendary poker champion and decision-making expert Annie Duke offers a crucial insight:
A good decision isn’t judged by its outcome; it’s judged by the quality of the decision at the time it was made.
Think about that for a second. If we only judge our decisions by their outcomes, we’ll be fooled by randomness. Bad choices sometimes lead to good results, and good choices sometimes lead to bad results. Sometimes, bad decisions, turn out to be lucky. The key is not to evaluate success based on whether things worked out, but on whether the decision made sense at the time, given the available information.
I had no certainty when I quit my safe and secure job for an unsure opportunity. All I had was a sound decision-making process, a vision, and the courage to act on it. And that’s what winners do.
Let’s say you’ve been going to the same gym for the past two years. You signed up for a year-long membership, convinced that this would be the key to your fitness transformation.
At first, you were motivated. But over time, you started noticing some problems:
The gym is too far from home, making it inconvenient to get there.
The equipment is always crowded, forcing you to wait or rush your workouts.
The personal trainers aren’t helpful, and the overall atmosphere doesn’t inspire you.
You find yourself dreading workouts, making excuses, and skipping sessions.
Still, you don’t want to quit. Why? Because you already paid for the membership. Because you’ve been going there for two years. Because you feel like quitting means failure. But here’s the truth: You are not quitting fitness—you are quitting a bad system. A smarter move? Quit the gym and find a better alternative.
Maybe a gym closer to home makes it easier to stay consistent.
Maybe switching to home workouts fits your lifestyle better.
Maybe trying a new fitness class makes exercise more enjoyable.
By quitting the ineffective approach, you free yourself to find a better solution.
This is exactly what winners do. They don’t blindly persist just because they made a past decision—they reassess, adapt, and move forward. So, the next time you hesitate to quit something, ask yourself:
Am I holding onto this because it’s truly working? Or am I just afraid to let go?
The answer might change everything.
The Art of Knowing When to Quit
So, how do winners know when to quit? Here are a few guiding principles:
1. They Quit When the Evidence Says They Should
Winners are not romantic about their past decisions. They rely on evidence, not emotions to determine if something is worth pursuing. If the signs point to a failing venture, a toxic relationship, or an unsustainable habit, they cut their losses—quickly.
2. They Quit When Opportunity Cost Becomes Too High
Every moment spent on a losing endeavor is time that could be spent on something better. Winners are obsessed with maximizing their return on time and effort. If an investment isn’t paying off, they reallocate their energy toward something with a better chance of success.
Nassim Nicholas Taleb, an author known for his work on randomness, risk, and decision-making, has a unique way of looking at opportunity cost—one that goes beyond traditional economics.
In conventional terms, opportunity cost is the idea that every choice you make comes at the expense of another choice. If you spend $100 on a dinner, that’s $100 you can’t invest in stocks. If you spend an hour watching TV, that’s an hour you didn’t spend reading or exercising.
But Taleb takes this concept deeper. He emphasizes optionality, meaning the ability to have flexibility and better choices in the future. The higher your optionality, the lower your opportunity cost.
For example, if you commit to a rigid career path too soon (e.g., locking yourself into a corporate job with no room for innovation), you lose the optionality to explore entrepreneurship, freelancing, or other emerging industries. By contrast, if you keep your options open—developing diverse skills, staying adaptable—you reduce the opportunity cost of committing too soon to the wrong path.
The takeaway? Avoid situations where you are stuck and cannot pivot. The more trapped you are, the higher your opportunity cost. He also warns that not all opportunity costs are obvious. Sometimes, people don’t see what they’re losing because the cost is “silent.”
For example:
If you stay in a stable but unfulfilling job, the opportunity cost isn’t just a higher salary elsewhere—it might be your mental health, creative potential, or long-term happiness.
If you stay in a failing business too long, the opportunity cost isn’t just the money lost—it’s the time you could have spent on a better, more scalable idea.
The point? Look beyond money. The biggest opportunity costs are often your time, your flexibility, and your ability to take better risks.
Beware of Irreversible Decisions
Taleb frequently talks about "path dependence", meaning that some choices lock you into a certain trajectory—and once you’re in, it’s costly (or impossible) to pivot.
If you take on massive student debt for a degree you don’t love, that’s a huge opportunity cost—because now you’re pressured to stay in that career that you don’t love just to pay off the debt.
If you stay in a toxic business partnership, the opportunity cost isn’t just the financial burden—it’s the future deals and opportunities you miss because you’re entangled in a bad situation.
In other words, avoid decisions that limit your ability to change course. The more irreversible a decision, the higher the opportunity cost if it turns out to be the wrong one.
The Hidden Cost of NOT Quitting
Most people only think of opportunity cost in terms of what they gain by making a decision. But Taleb forces us to ask, What is the opportunity cost of NOT quitting? What do you lose by staying in the wrong place, with the wrong people, doing the wrong things?
Understanding opportunity cost Taleb-style means thinking beyond money, recognizing hidden risks, and maximizing optionality—because the biggest cost isn’t what you lose, it’s what you never even realize you could have had… and that is a HUGE factor!
3. They Quit Things That No Longer Align with Their Goals
Success isn’t just about sticking to one thing forever—it’s about evolving. The best leaders, entrepreneurs, and athletes are constantly reassessing their priorities and letting go of commitments that no longer align with their vision.
4. They Quit When Stubbornness Is Masking Fear
Sometimes, we refuse to quit because we’re afraid—afraid of what people will think, afraid of admitting we were wrong, afraid of the unknown. Winners don’t let ego or fear dictate their choices. They recognize that letting go is often the bravest thing they can do.
Quitting as a Competitive Advantage
Some of the greatest successes in history came from knowing when to quit:
Jeff Bezos was doing exactly what society tells us to do—climb the corporate ladder, earn a great salary, and build a stable future. By his early 30s, he was already a senior vice president at a prestigious Wall Street hedge fund, making six figures and set for life.
By all conventional measures, he had "won." But then, he read something that changed everything. The internet was growing at a 2,300% annual rate—an explosion unlike anything the world had ever seen. Bezos couldn’t shake the feeling that this was the future, and that he was sitting on the sidelines.
One day, he walked into his boss’s office and told him about an idea: an online bookstore that could sell any book, anywhere, to anyone. His boss listened patiently, then gave him advice that many would consider wise:
"That sounds like a great idea for someone who doesn’t already have a good job."
Bezos went home that night and thought about it. He had a secure career, financial comfort, and a predictable future. But he also had a once-in-a-lifetime idea. Then he asked himself a question that would change his life forever:
"When I’m 80 years old, will I regret staying? Or will I regret not taking this leap?"
The answer was obvious. He quit his job, packed up, and drove across the country with his wife, working on a tiny startup from his garage. He called it Amazon.
At the time, quitting seemed crazy—leaving a stable, prestigious job for a company that didn’t even exist yet. But looking back? It was the best decision he ever made.
Elon Musk wasn’t supposed to be an entrepreneur. He was on track to earn a PhD in applied physics at Stanford, with dreams of working in high-energy physics. That was the safe path. The respected path. But as soon as he started the program, something didn’t feel right.
It was 1995, and the internet was exploding. Companies were being built from scratch and turning into billion-dollar empires almost overnight. Musk saw it happening in real-time.
And he had a choice:
Stay in academia for years, studying complex theories in a lab.
Or quit immediately and jump into the tech world, where things were moving at lightning speed.
Most people would have stayed. It was Stanford, after all. Musk? He lasted exactly two days before walking away. "Why wait? If I already know what I want to do, staying longer is just wasted time." He quit his PhD, co-founded Zip2, and later went on to launch PayPal, Tesla, SpaceX, Neuralink, and The Boring Company—fundamentally changing multiple industries.
Had he not quit that PhD program, he might have had a comfortable, well-paying career. But because he quit, he changed the world.
It is important to note that winners don’t just push forward blindly. They strategically retreat, reposition, and reallocate their focus toward more promising opportunities.
Quit Like a Winner!
The next time you feel pressure to "never quit," ask yourself: Am I persevering toward something meaningful, or am I just afraid to let go? Have I become a victim of the sunk cost fallacy?
Winning isn’t about refusing to quit. It’s about knowing what to quit, when to quit, and having the courage to do it. The real winners aren’t the ones who stick it out no matter what—they're the ones who make smart, calculated decisions that move them forward.
I quit tenure—and in doing so, I built something that had an even greater impact. The truth is, I didn’t quit. I advanced. And sometimes, that means walking away from what’s comfortable.