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When Losing Hurts More Than Winning Feels Good

June 13, 2025

The Problem: Too Nice to Be Taken Seriously

You win the pitch. Land the client. Get the award. Revenue climbs. Recognition flows.

And yet… it doesn’t feel like it should.

Maybe you feel relief more than pride. Maybe the high of the win lasts a few hours, but the sting of a loss lingers for days. You obsess over the missed opportunity, the dead project, the rejection. You celebrate in a whisper and mourn in a scream.

BillH Headshot

By Bill Hoogterp

Sound familiar?

For many high achievers—especially entrepreneurs, creatives, and competitive professionals—this imbalance can quietly erode their energy, culture, and joy. Left unchecked, it creates a workplace (and a life) where progress feels like pressure and success is something to survive, not savor.

Why It Happens: The Psychology of Pressure

This emotional pattern isn’t weakness. It’s wiring.

People who care deeply about their work are often driven by fear of mediocrity, of complacency, of letting others down. Ironically, that same drive—what makes them excellent—can also rob them of the ability to feel joy in the wins. In many ways, it’s not even about being “unhappy,” it’s about being unable to process success emotionally before mentally moving the goalposts.

And here’s the risk: when leaders operate in this space, their teams start to mirror them. They learn to chase achievement but never pause to enjoy it. The culture becomes one of anxiety and anticipation, not celebration and growth.

The Solution: Emotional Time-Boxing

The most effective solution I’ve seen? Time-box your emotions. Create rituals. Name the rhythm.

Let’s look at a few practical examples:

1. Time-Boxing the Loss

A professional golfer once told me that after hitting a bad shot, he gives himself three seconds to let it out. Yell, grunt, curse—whatever helps. But only for three seconds. Why? Because dragging it out poisons the next shot.

In the NFL, teams will enforce a 20-minute “mourning period” after a loss. You’re expected to be upset. But once that 20-minute mark hits, a captain puts on music or cracks a joke. The message: it’s time to reset—because your family is waiting, and they don’t deserve your emotional hangover.

You don’t have to be an athlete to apply this. Whether you're alone or with your team, decide: How long do we sit with a loss? What’s our process for moving through it, and moving on?

2. Celebrate Like It’s a Skill (Because It Is)

If your wins fade fast and your losses haunt you, flip the script. Create longer, more intentional celebration rituals.

Ring a bell. Share a toast. Take a team walk. Make a “win wall.” Or just pause and let the moment land. The goal isn’t fanfare—it’s feeling it. Let your team see what pride looks like. Let them know it’s safe to feel joy before chasing the next challenge.

I often tell leaders: celebration should outweigh commiseration at least 3-to-1. That’s not soft. It’s sustainable.

3. Train Your Brain to Look for the Good—First

Before analyzing what went wrong, start with what went right. This isn’t forced positivity—it’s mental conditioning.

If you only ask, “How can we do better?” you’re reinforcing a deficit mindset. If you also ask, “What did we crush?” you’re reinforcing growth and momentum.

Start every post-mortem with the positives. Make that the habit.

4. Lead with Purpose, Not Just Performance

Research from organizational psychologist Adam Grant shows that people who chase happiness rarely find it—but those who pursue purpose and impact tend to experience more happiness as a byproduct.

In other words: Don’t obsess over feeling good. Focus on doing meaningful work, building strong teams, and delivering value. Happiness follows purpose.

One Last Tip (From the Golf Course)

Legendary golfer Nick Faldo once told me, “When you grip the club, use a 3 out of 10 pressure. Not 10. Never 10.”

That advice? It’s golden for leadership too.

Hold the club—your business, your ambition, your pride—but don’t strangle it. Loosen the grip, and you’ll swing freer, farther, and with more joy.

Final Thought

There’s nothing noble about wallowing in defeat, just as there’s nothing arrogant about celebrating a win. Both are part of the emotional rhythm of work. If you want to build a resilient culture—and a healthy inner world—ritualize both. There is a time to strive, a time to grieve, and a time to celebrate. Create the space for all three.

Bill Hoogterp is a bestselling author, entrepreneur, and one of the world’s leading executive coaches. He is also a contributor to Fortune, where he answers real questions from executives striving to become better leaders.

Explore His Fortune Column

If you or your team are struggling to stay motivated, celebrate wins, or shake off the sting of a loss, you’re not alone—and you don’t have to figure it out solo.

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