When You’re Not Winning, You’re Learning: Leadership Lessons from Adversity
As a lifelong athlete, I have lost over and over again. From kids’ soccer to college volleyball to rec league “just for fun” programs, it’s inevitable that one team always loses. While losing is never fun, I’ve had many great leaders remind me of this important lesson that has carried well into my professional life:
Growth often happens when you’re not winning.
Whether you’re leading a team, managing a project, or navigating challenging business cycles, moments of challenge are opportunities for deep learning. I saw this firsthand during my time as a buyer for Nordstrom—especially when slower sales forced us to rethink, rework, and innovate.
When business was tough, the urgency pushed us buyers to:
Test new products with speed and creativity.
Dive deeper into data, exploring trends and insights from every angle.
Refresh merchandising strategies to better align with customer needs.
Hone negotiation skills to protect margins under pressure.
Stay resilient and avoid a downward spiral in team morale.
Collaborate relentlessly with partners to turn things around.
Each of these actions became a lesson and a tool that we not only used in the moment but could lean on as creative ideas to boost business in the future. Of course, we did some of these activities when business was booming, too—but not nearly at the same pace.
Just like losing in sports, every down cycle in business is a deep learning opportunity. It's a chance to test new approaches, analyze things differently, and work in new capacities you didn’t think possible—incredible lessons for any professional.
No one wishes for adversity, but leaders who have struggled through adversity again and again gain something invaluable: hard-earned experience, sharper instincts, and an improved toolkit for navigating future challenges. If you’re in a down cycle right now, this is your chance to learn, grow, and bounce back more resiliently than ever. Lean into the moment, dive into your toolkit, and trust that you will come out better for it.
For more leadership insights, follow Nova Founder Maggie Olson on LinkedIn.