The Cost of Winning by Kristy Mast

In my work with leaders, I often hear a surprising phrase:

“I don’t feel like I’m winning.”

What makes this so interesting is that the people saying it are often breaking records, hitting goals, and surpassing milestones. On paper, they’re winning. So why don’t they feel that way?

Growth Doesn’t Equal Easy

One reason is that winning almost always brings new challenges. Growth creates complexity. Systems that once worked begin to stretch. What used to feel manageable starts to break under the weight of more people, more conversations, more risks, and more responsibility.

Many leaders assume business will get easier as it grows. This is rarely the reality. Bigger usually means heavier. The stakes get higher, the risks get larger, and the problems become more complex.

But here’s the shift: growth is opportunity.

• Opportunity to strengthen.
  
  
• Opportunity to reinvent.
  
  
• Opportunity to solve problems you’ve never solved before.
  
  

The key mindset change is subtle but powerful: it’s not “I’m winning, but everything is falling apart.”
It’s “I’m winning, and I have the opportunity to…”

That single word swap—from but to and—reshapes how we experience growth.

The Gap vs. The Gain

Another reason leaders feel like they’re not winning comes from what Dan Sullivan and Dr. Benjamin Hardy call the gap and the gain.

High achievers often measure success against the future—where they want to be next. But that line is constantly moving. As soon as one milestone is reached, another is set. The result is a  nagging sense that it’s never enough.

The solution is to shift focus from the gap to the gain. Instead of fixating on how far we still have to go, we look back and measure how far we’ve already come. That perspective fuels motivation instead of discouragement.

Choosing Gratitude

So how do we stay out of the trap of chasing “enough”?

For me, it comes down to one practice: an attitude of gratitude.

We can’t control every challenge, but we can always control our perspective. Gratitude shifts us:

from lack to abundance, frustration to perspective, and from overwhelm to opportunity.

When our kids were little, Wes and I used a call-and-response with them: we’d say, “Attitude,” and they’d reply, “Of gratitude.” If their ice cream order was wrong, the lesson wasn’t about the ice cream—it was about perspective. Instead of focusing on what was missing, they could be grateful they had ice cream at all.

The same principle applies in business. The wrong hire, a missed goal, or a stretched system can be discouraging if we only see the gap. Gratitude reframes the moment. We see the gain: we’re growing, we have opportunities, and we’re still in the game.

The True Cost of Winning

Winning always comes at a cost. The work gets harder, the weight gets heavier, and the risks get real. Gratitude ensures that the cost pays dividends—not just in what we achieve, but in how we experience the journey.