Failing Retirement

PUBLISHED JULY 2025

When I retired from a long and rewarding career in financial services earlier this year, I thought I had a solid plan. After all, I had spent decades advising others on how to pre-pare for retirement—surely, I could manage my own. But just a few months after stepping away, I found myself back at work, fully re-engaged in an exciting new executive role.

When attending a board meeting for one of our fine Kansas City arts organizations, a fellow board member said: “Scott, I see you failed retirement.”

That comment stuck with me—not as an insult, but as a spark. It got me thinking: What does it mean to “succeed” at retirement? And why did I, someone who prepared diligently, find retirement unfulfilling?

The Four Dimensions of Retirement

We often treat retirement as a finish line. But in truth, it’s more of a pivot—one that demands thoughtful consideration across four critical dimensions: financial, structural, psychological, and purpose-driven.

Financial Readiness: Let’s start with the obvious. A successful retirement requires a strong financial foundation. That doesn’t just mean having a big number in your 401(k). It means understanding your future lifestyle, health-care needs, legacy goals, and philanthropic aspirations—and ensuring your plan is flexible enough to adapt over time.

While do-it-yourself financial software can be helpful, I believe deeply in the value of a trusted financial adviser. Good advisers don’t just crunch numbers; they serve as fiduciary partners, helping you balance risk and reward, spending and saving, giving and investing. The earlier you engage one, the better. Retirement is not just about living off your savings—it’s about managing your financial life with the same rigor and discipline you brought to your career.

Structural Shift: The day after retirement, the structure you once took for granted vanishes. No more calendar full of meetings, no deadlines, no Monday-morning huddles. At first, it’s liberating. But over time, the lack of structure can be disorienting.

I’m an early riser by nature, someone who used to hit the gym before dawn. But without a job calling me out of bed, I found myself slipping—“I can work out later” often became “I never quite got to it.” And while lunches with friends were wonderful, I missed the rhythm and accountability that came with the workday. For extroverts like me, the office is more than a place of business—it’s a source of energy and identity.

Psychological Identity: I underestimated how much of my identity was wrapped up in my work. It wasn’t about title or power—it was about relevance. For decades, I was part of an ever-evolving conversation in finance, philanthropy, and civic life. Retirement created a void I hadn’t anticipated.

Yes, I filled some of that with volunteer work, board service, and family time—all of which I treasure. But I missed the intellectual stimulation and strategic challenge of work. I missed being part of a team. I missed, in a word, growing. As a lifelong learner, the thought that my skills might atrophy was more unsettling than any market correction.

Purpose and Legacy: As I wrestled with whether to stay retired, I thought deeply about purpose. I’ve always believed in civic engagement—not just because it’s good for the soul, but because it’s good for business. Connecting the great people I’ve worked with to the great causes I care about has been one of the joys of my life.

Ultimately, that desire to stay engaged—to make a difference—led me back to work. When I was offered a role that allowed me to combine my skills, passions, and community commitment, I said yes.

The Gift of Being Wanted

One of the unexpected gifts of this journey was realizing that people still saw value in what I had to offer. There’s a unique satisfaction in knowing your experience is still relevant, that your insight still matters. In a world increasingly focused on youth and speed, it felt good to be wanted—and even better to feel useful.

A Final Thought … 

If you’re contemplating retirement, I encourage you to think beyond the numbers. Reflect on what brings you joy. Consider how you’ll stay relevant, engaged, and healthy. Take the time to design a life—not just an exit strategy.

And if you find, as I did, that retirement doesn’t quite fit—don’t be afraid to pivot. There’s no shame in “failing” retirement. In fact, sometimes failing is just another way of finding your next calling.

Enjoy the journey—wherever it leads.