Issue #78 Winning the Wrong Way: The Most Expensive Kind of Success

Written By: Brad Pedersen

Growing and scaling a business takes relentless commitment. I know this firsthand—having started and built multiple companies over the years.

In my first venture, I had something to prove. I poured everything into getting it off the ground. After nearly a decade of scaling within Canada, I made the bold decision to expand into the U.S. We rented a showroom in New York and geared up for a major trade event in the fall of 2001.

This was a significant new initiative and at the time, every opportunity felt essential. Every meeting, every handshake, every late-night flight seemed like one more step toward the future I was determined to try and create.

When the World Stopped

On the morning of September 11, 2001, I was in a meeting in Manhattan when the ground seemed to tremble. Word spread quickly. The towers had been hit. Chaos unfolded around us—flights grounded, bridges closed, phone lines jammed. The city that never sleeps stood still.

In that moment, everything I had been chasing—the deals, the expansion plans, the next big move—suddenly felt small. All I could think about was getting home. But I couldn’t. I was stuck in New York, thousands of miles away from my wife and young family, with no way to reach them and no way to return.

That experience shocked more than just the city. It shook something loose in me.

Up until that point, I had convinced myself the long hours and sacrifices were all for the greater good—that the strain was temporary, that the payoff would come. But sitting stranded in that city, forced me to reflect. And in that reflection, I had to admit something hard: I wasn’t just committed to the business—I was consumed by it.

I realized that chasing business success and the resulting external validations had subtly become my sole priority, and everything else had been made to wait.

The Jenga Metaphor

In my book Startup Santa, I compare life to a giant game of Jenga.

Each block represents a part of your life—your values, your commitments, your priorities. Some blocks are foundational. These are the ones you simply can’t move without compromising the entire structure: your health, your marriage, your family, your faith. Other blocks are more flexible. They can shift, depending on your season of life, your energy, your current focus—but even those need to be moved with care.

At first, you can pull out a few pieces and still build upward. That’s how the game works. But the key is to never pull out a foundational block, while recognizing that every block you remove subtly weakens the tower. And eventually—often without warning—it all comes crashing down.

We tell ourselves it’s temporary. The long hours. The missed dinners. The constant travel. Just until we hit the next milestone. Just until we achieve the next level. And for a while, the structure holds…. until it doesn’t.

The truth is, your time, attention, and energy are always flowing somewhere—and they inevitably reveal what you value most. Over time, every action, every decision, and even every indecision begins to compound. The game we’re playing isn’t about how high we can build. It’s about ensuring that as we build, we never compromise the foundation so that our structure remains standing when the pressure comes.

The Pyrrhic Victory

In 279 BC, King Pyrrhus of Epirus defeated the Romans in battle—but at such a devastating cost to his own forces that he reportedly said, “Another such victory and we are undone.” He had won the battle, but lost the war.

Today, we call that a Pyrrhic victory: achieving success at such a steep price that the win no longer feels like one.

Modern life is full of these hollow triumphs. Founders who scale companies but lose their families in the process. Entrepreneurs who conquer markets while sacrificing their health. Professionals who build financial empires yet retire with fractured relationships and an empty heart.

Among the ten wealthiest men in the world, there have been thirteen divorces. That’s more than a statistic—it’s a flashing red light.

Keeping the Engines Running

Let me be clear: I’m not against building a business. I believe in bold dreams, meaningful work, and making a lasting impact. But I’ve learned—often the hard way—that if growth comes at the expense of what matters most, you may one day realize you traded the essential for the expendable.

That said, life comes in seasons. There are times when certain priorities demand more from us—when pushing hard at work or chasing a big goal will create imbalances. That’s okay and that's normal. The key is recognizing that it is a season and should be temporary and along the way we should always maintain some investment into our values. 

Another way to think about it, is to consider your values like the engines of your life meant to propel you into the preferred future you are designing. You can throttle them up or down, depending on the season you are in, but you can’t afford to ever shut them off entirely. Some engines—like friends or fun -- might have to go on idle for a time, but if neglected, they may not restart when you need them most.

You will need to stretch for your goals. You will have to make some short-term sacrifices. But the key is to keep all the different engines running and never shutting them off completely.  

When considering the engine of your health, there’s an old adage worth repeating: A healthy young man wants a thousand things. A wealthy old man with poor health wants only one.

The Real Bottom Line

In business, we often talk about opportunity cost—what we’re willing to give up to pursue a goal. I have come to learn that the most significant costs aren’t financial. They’re physical, They’re relational. They’re spiritual. They show up in the moments we miss, the conversations we never have, the memories we never get to make.

I’ve witnessed many leaders build impressive careers but along the way leaving their relationships in ruins. Entrepreneurs who work tirelessly to hit their business goals, only to realize that along the way, they’ve sacrificed the very things that would have given those accomplishments meaning.

True wealth isn't just measured by the size of your bank account. True achievement isn't a resume filled with awards. It's about health and vitality. It is about loving and being loved in return and knowing that the people who know you the best; love and respect you the most.

This isn’t a call to lower your ambition. It’s an invitation to align your ambition with what truly leads to a fulfilling life.

Chase your dreams. Build boldly. Reach higher. But in the process, never trade what is essential for what is seemingly so urgent in the moment but ultimately trivial in the end.

The leaders I admire most aren’t just sharp in business—they’re wise in life. They’ve learned that true, whole life success, means tending to all the areas that matter, not just the ones that show up on a balance sheet or in a quarterly review.

So as you build your empire, it is good to remind yourself: what is it for? And who is it for?

And above all, remember this: the people you’re building for—make sure they’re still with you. Still whole. Still connected. Still proud to walk beside you as you ascend to the summit.

Because a win that costs you what is most important isn’t a win at all. It’s the most expensive kind of loss there is.

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