Turning tough lessons into stronger leadership

This post was originally published on Forbes Nonprofit Council.

“Sometimes you win; sometimes you learn.” My colleague Nicole introduced this mantra into our work culture, and I’ve since found myself repeating it across my diverse roles—from CEO to mentor to mom. It came to mind again recently as I reviewed notes from a mentoring brainstorm, reflecting on how much of our leadership style is shaped less by triumph than by trial.

Inspirational leaders who saw our promise and encouraged our growth deserve credit. But our most lasting lessons often come from more difficult experiences: the bad bosses, the misaligned teams, the moments when our values were tested. These aren’t just hard moments; they’re formative. They ask us: What kind of leader do you want to be? And even more, how do you want others to feel under your leadership?

Mid-career, I remember raising concerns with a supervisor about the unsustainable pace of my work and travel. His response—one he likely meant as praise—was, “Patty, you’ve always been worth two people.” I smiled and replied lightly, “Thanks. Where do I pick up my second paycheck?” We both laughed, and the conversation moved on. But I left the room unsettled. To this day, I believe he thought he was giving me an authentic compliment. It took me years to fully understand why I heard it as a sting. At face value, it was acknowledgment, but it also revealed an uncomfortable truth: I was being rewarded for overextension, not for balance or sustainability. That moment stayed with me. It taught me that recognition without support is not a compliment; it’s a warning.

Over time, I realized what I had been allowing—in the name of loyalty, commitment or the quiet hope that things would improve on their own. Experiences like these now shape how I lead. The peer who undermines instead of collaborates reminds us to foster trust and culture. The colleague who avoids responsibility reinforces the need for clarity and accountability. The boss who views overperformance as baseline effort challenges us to set healthier boundaries.

In my own leadership today, I push my organization to pursue excellence, but not at the cost of well-being. We don’t conflate burnout with dedication. When someone proposes something new, we ask, “What are we taking off the table?” or “What support do you need to make this happen?” These aren’t merely nice questions; they intentionally signal our belief in building systems that empower, not exhaust.

We still strive for the exceptional. But we do so with our eyes open, aware that ambition must be met with infrastructure, and that motivation thrives when people feel seen, supported and valued.

That “you’ve always been worth two people” comment is still with me. It reminds me to look beneath praise and question systems and our expectations of people. And to never confuse someone’s output with their worth.

Nicole’s mantra holds true: Sometimes you win, and sometimes you learn. In leadership, we don’t always get to choose our lessons. But we do get to decide what we carry forward and how we model it for others.