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Vitaly Gariev via Unsplash

Every Career Has 4 Phases. Here’s Why Reliving The First Can Make You a Better Leader

I recently returned to Disney World—this time with my grandchildren.

I’ve been there many times before. When my kids were young and we lived in California, we went to Disneyland at least twice a year. We moved through the park like a well-oiled machine, never missing a favorite ride.

Twenty years later, I got to see it again through fresh eyes.

Call it a stretch, but Disney World has me thinking about the working world. Experiencing this famous theme park might be a great metaphor for our development as leaders. Consider these phases:

Phase one: open-eyed and awe-filled.

The first time you walk into the park, everything feels magical. Even the teacups are a thrill. You’re soaking in the music, the colors, the characters.

Early in your career feels the same way. You say yes. You stay late, and you absorb everything. It’s not about status yet—it’s about discovery. That openness builds your foundation and fuels your energy.

Phase two: young and restless.

Soon enough, you chase the biggest thrills—the rides with warning signs on the map.

In your career, this is the season of stretch assignments, advanced degrees, and bold risks. There’s adrenaline in proving yourself, and you push your limits.

Phase three: aligned and advancing.

You find your rhythm. You know which rides matter to you and which don’t, and you move through the park with efficiency.

At work, you’ve earned perspective. You’re less reactive and more strategic. Others look to you for guidance. It’s often your most visible and productive season.

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Phase four: grounded and intentional.

You’re less concerned about being first in line and more concerned about whom you’re standing beside.

You know your lane, and you’ve experienced the thrills. Now you find joy in helping others navigate theirs and in celebrating their success.

This time, you might have seen me in Mickey ears. Because at every phase, what matters most is something children do naturally: experience awe, wonder, curiosity, and joy without self-consciousness.

Research tells us that making room for experiencing awe restores us. It lowers stress. It expands our perspective, and it reminds us we’re part of something bigger than ourselves. But you don’t need a theme park to experience that.

You might find it on a quiet morning walk or in a sunset you didn’t plan to notice. Perhaps you watch someone you’ve mentored step into their own success. On this trip, I got to borrow those moments of awe while I witnessed my grandchildren seeing something for the very first time.

As leaders, we spend a lot of years chasing the next ride—the next title or milestone. And there’s nothing wrong with that. Those seasons build meaningful careers. But at some point, the deeper reward shifts.

You realize the real joy isn’t being first in line. It’s standing beside someone else while they take their turn. It’s choosing presence over pace. When I walked through Disney World this time, I wasn’t studying the map. I was studying my grandchildren’s faces.

Because the goal isn’t to relive the thrill of the ride. It was to remember the wonder that made you step on the ride in the first place. And no matter which phase you’re in, that kind of wonder is worth holding on to.

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