When Winners Should Quit (And Why That’s Not Failure)

Written By: Brad Pedersen

In 2008, I stood at a crossroads that would test everything I believed about persistence, success, and what it meant to be an achiever.

For ten years straight, I had lived the dream as our company doubled annually in revenue. The growth was intoxicating; each year brought new milestones, bigger orders, and - what seemed like - validation. I was doing what every entrepreneur is told to do: grow fast, scale hard, and build something meaningful.

Then reality hit.

By 2006, we had discovered that it was possible to grow too fast. Without having the right balance sheet, people, and systems, I learned that even the most promising business can collapse under its own weight. 

We went through a "restructuring;” a fancy word for bankruptcy. However the restructuring gave us fresh capital, and for two years, we tried every angle to turn things around. We added new product lines, cut costs, and worked ourselves to the bone. 

However after all that effort, we came to a stark realization: the problem wasn't a lack of funding, it was a broken business model.  We had no choice but to quit…..and simply uttering that word felt like a betrayal of my beliefs, my identity and my values.

The Lie We've Been Sold

From the time we're young, we're fed quotes about persistence. "Winners never quit and quitters never win." "Success is just on the other side of one more try." These mantras become part of our identity as founders. It is a badge of honour to have an ability to push through pain and we celebrate those who kept going despite impossible odds.

But here's what few are willing to admit: sometimes quitting is the smartest, bravest, and most strategic decision we can make.

I learned this the hard way, costly in both dollars and years. In hindsight, I stayed in my original business far too long. The data and my gut said quit, however my ego kept whispering: just one more push, one more launch. 

I was convinced that my past growth meant future potential, while at the same time blinded to the fact that so much of my identity was attached to the business.

The Trap of Sunk Cost

Annie Duke, a research psychologist and former poker player, wrote an entire book on this subject called Quit. Her conclusion is uncomfortable for those of us who pride ourselves on sticktoitiveness and grit: by the time we're wondering whether to quit something, we're probably already too late.

The culprit? Sunk cost fallacy. It's the belief that we must continue investing in something simply because we've already invested so much time, money, or energy into it.

I fell into this trap completely. 

By 2008, I had invested over a decade into building this company. I had raised money from friends and family, sacrificed time with my wife and kids, and poured every ounce of energy into making it work. Walking away felt like admitting those years were wasted.

But that's exactly how the fallacy starts to get entrenched into our beliefs.

Duke suggests asking ourselves: "Knowing what I know now, would I make the same decision today?" When I finally asked myself that question honestly, the answer was clear. No. 

The model had become outdated, the market had shifted, and I was throwing good money after bad. I had not been willing to heed the safe advice of Warren Buffett who said: "Should you find yourself in a chronically leaking boat, energy devoted to changing vessels is likely to be more productive than energy devoted to patching leaks."

I was not only trying to patch leaks in a boat that was already underwater, I had compounded my problems by using a bailing bucket full of holes.

When One Door Closes

After we shut down the business in 2008, I was emotionally and financially depleted. I felt like a failure as so much of my identity had been attached to the company.

But here's what I soon discovered: quitting opened up space for something better.

Within months, I worked with my partners to imagine a better business model. We took the lessons learned, the relationships built, and the market knowledge gained, and channeled it into a new venture with a viable model from day one. 

The resulting company became infinitely more successful and personally more satisfying than my original venture.  If I hadn't been willing to quit the first company, I never would have created the space for a new opportunity to emerge

The poet Rainer Maria Rilke wrote, "Perhaps all the dragons in our lives are princesses who are only waiting to see us act, just once, with beauty and courage."

Quitting, when done strategically and courageously, isn't running from the dragon. It's recognizing the obstacle (the dragons we face) might actually lead to a new opportunity that we may not yet see.

The stigma around quitting is one of the most destructive narratives in entrepreneurship. We celebrate the founder who pushed through and succeeded, but rarely talk about the founder who pushed through and failed anyway, wasting resources and years of life. 

Real grit isn't about never quitting. Real grit is knowing when to quit, having the courage to make the hard call, and having the resilience to start again with the lessons learned. Every ending is also an opportunity for a new beginning!

Over the years, my ability to come to this realization has not only allowed me to rebuild within the toy business but also to transcend it, by stepping into new industries, co-founding the DTC brands Pela and Lomi.

None of that would have happened if I hadn't learned when to quit.

Final Thoughts

If we're wondering whether it's time to quit something, simply by wrestling with that question, we probably have the answer. By the time we're asking, we're usually months or years past when we should have already decided. 

It is so common to hang on too long because of sunk costs, and what we believe others might think.  We often confuse stubbornness with strength.

So this week, ask yourself: 

What am I holding onto that I wouldn't start again today? 

What data am I ignoring? What could I redirect toward something with better potential?

Remember, quitting the wrong thing isn't failure, it's demonstrating wisdom, strength and courage.  It's choosing to invest the limited time and energy we have, where it can create the life and impact we desire.

If you're ready to move from striving to thriving, and from self-focus to purpose-driven living, visit www.fullspectrumlife.com to explore our Guided Mastermind. It's not for everyone, but it is for accomplished business leaders who are ready to go beyond success and step into a life of true significance.

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