No One Wins a Race That Never Ends

I used to think I should be further along by now.
But then I realized—there is no timeline but my own.
So I stopped measuring my progress against others and started asking—
Am I becoming the person I want to be?
You are not behind.
You are becoming, in your own time.

The start of my career felt like the Kentucky Derby—jockeys pressed tightly together, muscles straining, the gates bursting open as the race to get ahead began. Except in this version, the racetrack was my career, and I wasn’t just running. I was constantly glancing sideways, measuring myself against the pack. Was I edging ahead? Was I falling behind?

As a working-class kid from the North of England, I was already a little surprised to be in the race at all. I thought of that famous John Cleese, Ronnie Barker, and Ronnie Corbett sketch on the English class system, where Corbett, the shortest of the three, looks up and declares, I know my place. That belief had been ingrained in me from childhood. Yet here I was, running alongside peers who had always expected to be there, competing in a game I hadn’t even been sure I was allowed to play.

For years, I ran hard. Success was about forward motion—climbing ladders, chasing promotions, hitting milestones. I landed leadership roles in major corporations, then stepped into the high-stakes world of running a public company. We were poised for a major deal, working with Wall Street investors to fund a strategy that would lead to a lucrative exit.

And then, 2008 happened.

The financial meltdown hit just as we were about to ink an investment deal. Instead of following through, the bank turned on us, shorting our stock and gutting our company’s value. In a matter of days, we lost 95% of our market cap. The same bankers who had smiled across the table at me days before now had the audacity to sue me for their commission—on money they never even raised.

It was a moment of brutal disillusionment. Not just with the system, but with myself.

For the first time in years, there was no next step waiting for me—only silence. And in that silence, I started to question: Whose race had I been running all along?

I stepped down as CEO, staying on as an unpaid consultant for a time, trying—out of sheer duty—to salvage something for the investors. It was exhausting, demoralizing work. I felt like I had failed them. And I had failed myself.

But when I started thinking about what to do next, something unexpected happened. People kept calling, offering me new leadership roles—like none of this had ever happened. In the UK, a failed CEO is publicly disgraced. In the U.S., failure is just another line on the resume.

I nearly went back. I was a finalist for a CIO role at a Fortune 500 company—the kind of job that would have, in my old life, signified a successful return. But one weekend, I found myself standing outside my former company’s headquarters, looking up at my old office window. I had worked there for eighteen years. And yet, there wasn’t a single trace of me left—no systems I’d built, no business I’d grown, no teams I’d nurtured.

Eighteen years, and the only trace left was the one in my own mind.

Walking away from that offer should have felt like failure. Instead, it felt like freedom. Like stepping off a treadmill I hadn’t realized had been moving beneath me for years.

I sat down with pen and paper and started mapping out a different kind of future. I wasn’t just looking for my next job. I wanted a touchstone—a guiding principle that would define the work I chose from then on. And I found it: helping kids become all that they can be.

That single guiding principle led me into the nonprofit world, where I spent the next several years leading organizations focused on youth leadership and education. But even in mission-driven spaces, I found familiar pitfalls—ego-driven founders, financial mismanagement, the relentless push for growth at all costs. One founder in particular loved the thrill of convincing donors to give money for his ideas, only for those funds to be rerouted to cover the financial gaps left by reckless spending. When I uncovered some gray-area bookkeeping and reported it to the auditors, I was pushed out. Terminated for poor performance—mere weeks after receiving a glowing performance review.

It turns out, no matter where you are—Wall Street or the nonprofit world—there’s always someone chasing the next big win.

And I was done chasing.

Then, an offer came. Not the kind that made logical sense, but the kind that lit something up in me.

A friend called, asking if I would go to China for two months to teach leadership skills to university women. No pay, just travel covered. My head said reckless. My heart shouted yes.

For once, I wasn’t making a smart decision—I was making a true one.

I didn't know how, but I knew this experience would open doors—I just didn't know which ones. And sure enough, when I returned, the same foundation that had passed me over for a leadership role months before reached out, asking how they could help me find my next opportunity. Over coffee, I joked that now I had the education experience they had wanted before. It turned out the person they had chosen still hadn’t stepped into the role. What started as a short-term contract soon became a full-fledged executive director position.

This time, I wasn’t forcing my way in. I wasn’t proving my worth. The role came to me when I was already standing in my own.

Looking back, I see now what I couldn’t see then. I had spent so much of my life worrying about whether I was keeping pace, when the real question was: Am I becoming the person I want to be?

For years, I had been running, measuring, competing. But maybe life wasn’t a race at all. Maybe I was never behind—I was just on my own track.

If you feel like you’re behind, I urge you to pause. Lay out all your options in front of you—including your dreams, no matter how unrealistic they seem. And then, instead of fixating on the risks, listen for what resonates.

You were never behind. You were just becoming—exactly as you were meant to.