What to Do When Success No Longer Feels Like Success

Gordon Gekko speech from Wall Street

At some point in your career or your life, you start asking different questions.

Not How do I get ahead? But What am I building?

Not How do I lead others? But Am I leading in a way that actually feels like me?

This shift rarely happens overnight. It develops gradually, often through fatigue or underlying restlessness: There’s got to be more than this.

You might know the feeling.

You’ve done the work, built the resume, and earned the respect. Maybe even hit every milestone you set out to achieve. And yet… something inside you feels out of sync. Like the life you built no longer matches the person you’ve become. What are you still trying to prove? Maybe you’ve noticed it too, how success starts to demand parts of you you’re not sure you want to give anymore. The long hours, the unspoken pressure, the impact on your health and family.

That’s what happened to me. Years ago, I was running divisions at a large public company. On paper, I had made it. Title, compensation, influence, everything I thought I wanted. But something had been brewing for a while.

Then one evening at a board dinner, the CEO stood up and gave what could only be described as a Gordon Gekko speech from Wall Street, a tribute to “greed is good.”

I leaned over to a colleague and said, “I’m out of here.”

That was the moment, the final straw. I realized I couldn’t keep building a version of success that no longer aligned with who I was, and I changed my life.

Since then, I’ve come to recognize that same turning point in others, especially in the leaders I coach and the guests I’ve interviewed on my podcast.

What follows are the stories of three remarkable individuals: Bruno del Ama, Maryann Bruce, and Jack Swift, who each hit their own inflection point and made the brave decision to stop chasing someone else’s definition of success and start living in alignment with their own.

Bruno del Ama, founder of GlobalX, shared how he had built a wildly successful firm, with billions in assets under management, but still found himself stuck on a treadmill of milestones that never quite satisfied. He began asking deeper questions. What was all this achievement for? What was it costing him? He had an interesting observation:

“There was an interview … a few years ago with Elon Musk—he was the richest person in the world at that time—and he asked him about death. And Elon’s response was, ‘I think it will come as a relief.’ Even if it was a throwaway comment, it really shows the state of mind of somebody in the midst of ultimate success.”

Bruno didn’t turn away from success. He moved toward his true self.  He co-founded Sangha, a conscious leadership community, and now helps others move from external achievement to inner alignment.

Not everyone around you will understand when your questions change. Sometimes the hardest part isn’t letting go, it’s being the only one in the room who no longer believes in the game you helped win.

Maryann Bruce had her awakening on US Airways Flight 1549, the “Miracle on the Hudson.” Floating in a freezing raft, she realized she had built a successful life guided by Purpose and Passion, but she had overlooked something vital: Perspective.

That moment realigned everything. Today, she serves on mission-aligned boards, advocates for women in business and sports, and invests her time in work that reflects her deepest values, not just her resume.

Jack Swift quit his high-powered corporate job running Janus Henderson’s institutional business. He had made it to the top of a prestigious firm, but something wasn’t sitting right. Then came the 2008 financial crisis. His startup was on the brink, and beneath the business stress was a deeper fear: What if I fail the people who believe in me?

Rather than retreat, Jack slowed down and asked why. Why the fear? Why the pressure? And what did leadership look like when it came from the heart, not the ego?

“No way a guy from financial services should be doing that,” he said, referring to co-founding a logistics company that sold to Shopify.

“But these are things that emerged on my path because I was open, because I followed my heart.”

Maybe your moment won’t come after you survived a plane crash, but it might come on a Zoom call on a Tuesday morning, when you can’t ignore your inner voice anymore for the truth to surface.

That’s what happens when the questions change.

We stop chasing someone else’s idea of success. We begin creating something that genuinely feels like ours.

We open ourselves up to bigger opportunities.

Not bigger because of titles or money. Bigger because of the impact on others, on the world, and on the parts of ourselves we’ve kept quiet for too long.

I thought stepping away would feel like loss. And yes, there was grief and fear. But there was also space for something more honest to emerge. My work didn’t get smaller. It got deeper and more aligned with who I wanted to be.

Allow the questions to arise:

·      What do I want to build that outlasts me?

·      What kind of leader do I want to be when no one’s watching?

·      And what would change if I trusted that I’m already enough?

·      What part of me have I been leaving out of my success?

These are the kinds of conversations I have with leaders every day, people who are still in it, still successful, and still wondering if this is all there is. If that’s where you are, I’d love to hear what’s moving in you. Sometimes, just naming it out loud is the start of something real.

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