When Success Isn’t Enough: Redefining What Truly Matters

We spend our lives chasing success, climbing the corporate ladder, making more money, and proving ourselves. In midlife, we question what to do once we achieve it, or why we keep pursuing it when we haven’t.

You tell yourself that after the next raise, the next title, the next bonus, you’ll finally have the freedom to do what you actually want to do. But the target moves.

This is not about quitting or retirement. This is about living and working on our terms.

For many of the leaders I’ve coached, that realization is not apparent, but there is a feeling: success hasn’t given them what they expected.

Over the past year, I’ve spoken with many leaders who have faced that turning point and chosen to look inward rather than outward. In my latest podcast episode, I share key insights from Jack Swift, Brett Wright, Bruno Del Ama, and Keith Lawrence on how they built impressive careers and, more importantly, how they aligned with their values.

Facing Fear and Listening Inward

When the financial crisis hit, Jack Swift had just raised capital from friends and family to launch a financial services firm. As markets collapsed, so did his sense of control. Nights were spent replaying worst-case scenarios, what if he lost their money, their trust, his reputation?

That fear bled into everything. He stopped showing up as the husband and father he wanted to be. “It put me in a really dark place,” he told me.

Then he started asking a different question: What am I actually afraid of?

Jack realized most of his fear wasn’t about money; it was about judgment. “What will people think if I fail?” he said. Once he could name it, the fear started to lose its grip.

He calls it sorting fear into three buckets: failure, success, and judgment. Naming which one you’re in turns a loop into a learning experience. “Once it’s approachable,” he said, “you can ask what it’s teaching you.”

That practice reshaped how he thinks and leads. It also gave him the conviction to walk away from roles most people would hold on to, first at Janus Henderson, then at TIFIN, after realizing they no longer aligned with his values. “Listening to your heart,” he said, “will bring you more success.”

Leading with Questions, Not Answers

Brett Wright learned his version of that lesson through leadership. A former Penn State football player, he grew up believing strength meant never showing weakness.

It took years to unlearn.

“The most powerful thing I can say as a leader,” he told me, “is I don’t know. Let’s find out together.”

That shift, from proving to connecting, changed how he led teams. Instead of showing up with answers, he began asking better questions, especially one he uses often: How might we?

That simple phrase reframes leadership as a shared process. It opens space for collaboration and creativity instead of competition.

“First, seek to understand before being understood,” Brett said. “Don’t come in to be heard. Come in to make sure others are.”

Stuck on the Treadmill

For Bruno Del Ama, the realization came after hitting his own business milestone.

When Global X reached two billion in assets, it should have felt like success. For a moment, it did. Then his mind went to three billion. Then five. “I caught myself,” he said. “That’s when I realized there’s no end to that chase.”

It’s what psychologists call the hedonic treadmill—you adapt to each achievement and move the posts again. Bruno began asking different questions: What does success mean if it always needs more?

He discovered that meaning doesn’t come from growth metrics but from connection. “We all want to be seen,” he said. “When someone sees potential in us that’s bigger than what we see in ourselves, we grow into it.”

That’s what good leaders do: they see, trust, and challenge people to rise. “When you trust people, they step up,” he added. “When you don’t, they shrink.”

Designing What Comes Next

Keith Lawrence works with executives facing what happens when the work that once defined you starts to end.

He often sees clients whose identity is entirely tied to their career. When that role goes away, they lose their compass.

“While you’re still working,” he said, “start figuring out what the next chapter looks like. What would you love to do next?”

That’s harder than it sounds. It requires slowing down, asking questions, experimenting, and setting boundaries.

Keith prefers to focus on fulfillment rather than happiness. “Life isn’t about constant comfort,” he said. “Fulfillment is about being able to handle both the good and the hard.”

He’s seen the cost of not doing that work early. “Most people,” he said, “run out of meaning before they run out of money.”

And when he talks about wealth, he’s not talking about dollars. “The real currency,” he told me, “is time.”

Redefining Success on Your Own Terms

Each of these leaders reached a point where traditional success no longer made sense. They learned to listen inward, lead with curiosity, and define success through alignment rather than external validation.

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