“Take the Risk or Lose the Chance”

I saw this on someone’s T-shirt on a train in Italy last week when I finally reserved some time for a 2-week vacation to explore Europe with my wife. It’s just a simple phrase—but even on vacation there can be unexpected insights that make us think and inspire us. This certainly did for me!

Perhaps like many of you, I’ve spent most of my working life planning for retirement while putting off living like I’m retired. Even as I’ve thought about and written about a phased approach to retirement—scaling back hours, taking longer breaks between projects, saying no to things that used to feel non-negotiable—I still find myself hesitating. Do I really have enough saved? Should I wait one more year? What if the market shifts?

But as I sat on that train, watching the hills of Tuscany roll past, I realized: the greater risk may be waiting too long.

For those of us entertaining a phased retirement path, the process is gradual by design. We’re not leaping off a career cliff—we’re walking down a winding, thoughtful path. It’s a smart strategy. But even when the numbers make sense, our mindset can lag behind.

There’s always a temptation to keep pushing the goalpost:

• “Just one more year of work.”
• “Just until the mortgage is smaller/paid off.”
• “Just until the next market rebound.”
• “Just until Medicare kicks in.”

That’s how years slip by. That’s how people end up with a healthy bank account but a backlog of unlived dreams.

Retirement doesn’t have to begin with a farewell cake. The mindset can begin with a two-week vacation we never used to make time for. It begins with turning down a project that doesn’t spark interest. It begins with choosing time over money—not recklessly, but intentionally.

This trip wasn’t only a vacation, it was a bit of a test drive for the life I say I want: slower pace, deeper presence, more experiences, less hustle. And it reminded me why the phased retirement road intrigued me in the first place.

The point of retiring in phases is to make room for what matters now—not just someday.

Let’s be honest though: the fear of taking the risk never fully goes away. Even with a plan, a spreadsheet, and a cushion, there’s always that voice asking, “Are you sure?”

But at some point, the fear of not living becomes louder than the fear of not earning.

So, here’s the gentle nudge I wish someone gave me a few years ago: you don’t have to be 100% ready to start living like you’re retired. You just need to be ready enough.

If you’re on the phased retirement path, you don’t need to upend your life tomorrow. But maybe it’s time to:

• Block off that long weekend you keep postponing.
• Cut back your weekly hours and see how it feels.
• Say no to the project that drains you—and yes to the one that excites you.

Because the truth is, this isn’t rehearsal. Life doesn’t pause while we wait for “enough.” It’s unfolding now, whether we lean into it or not.

So, take the risk. Try the shift. Book the flight. Say yes to what your retired self would.

Take the risk—or lose the chance.