“If I gave you $10,000 to go on a cruise, where would you go?”

The groundhog is always wrong. Six more weeks of winter? No thanks.
I’m ready for new weather. More sun. A new season.

And seasons, whether in weather, life, or leadership, change more than we think.

Leadership

In my keynotes, I often ask the audience a simple question:
“If I gave you $10,000 to go on a cruise, where would you go?”

People immediately start picturing warm destinations. Friends. No kids. All the kids. Adventure. Rest.

Then I ask, “How many of you, when I said cruise, thought… do not put me on a boat?”

The laughter comes. Hands go up.

Because we want it how we want it.

But here’s the deeper point. What we want is deeply tied to the season we’re in.

If that cruise had been 15 years ago, some of us would have wanted late nights, packed excursions, and nonstop energy.
If it’s 15 years from now, we might want slower mornings, meaningful conversations, fewer decisions.

Same person.
Different season.
Different priorities.

The season of life really does matter. And it absolutely shows up at work.

Early in our careers, we often chase titles, promotions, visibility, and rapid growth. We want to prove ourselves. Build momentum. Say yes to everything.

Mid-career, life expands. Families. Aging parents. Community commitments. Health considerations. Success may begin to look more like flexibility, stability, or impact over prestige.

Later seasons shift again. We think about legacy. Mentorship. Influence. Sustainability. Contribution beyond ourselves.

None of these are better. They’re simply different seasons.

Yet in leadership, we often assume everyone wants the same cruise.
The same promotion.
The same pace.
The same definition of success.

When we ignore seasons, we misread people.

Strong leadership requires awareness that seasons shift and engagement shifts with them.

The person who was hungry for the spotlight five years ago may now be hungry for balance.
The steady performer may not want the next title but may want deeper meaning.
The emerging leader may be ready for stretch in a way they weren’t before.

If we lead everyone as though they are in the same season, we create friction.
If we lead with curiosity about the season they’re in, we create momentum.

A simple double check.
Am I offering everyone the same cruise?
Or am I paying attention to the season they’re actually in?

Because when leaders recognize seasons, they create space for people to show up fully in the one they’re living right now.

Life

And seasons don’t just shape what we want at work.
They shape who we think we are.

I recently heard a woman describe her first few months of retirement. At first, it was bliss. No alarm clock. No inbox. No meetings. No deadlines. No one urgently needing her opinion.

She basked in it.

And then something shifted.

She felt restless. Almost anxious.

Because without the structure, the urgency, and the colleagues depending on her, she realized how much of her identity and even her personality had been tied to her work. She had been fast and furious for decades. Needed. Busy. In motion. And when it all stopped, it felt disorienting.

That hit me.

Not because I’m retiring anytime soon, but because this happens quietly over time. Our calendars fill. Our titles grow. Our responsibilities expand. And without meaning to, our identity can slowly become synonymous with our output.

Eight years ago, when my husband and I started intentionally chasing joy, it wasn’t some grand identity reset. We were just tired. Burned out. We wanted something on the calendar that wasn’t an obligation. Something that didn’t require performance or productivity. Something we would enJOY.

What we didn’t realize was that we were gently untangling who we are from what we do.

We created a joy list (a dozen things we used to do, could do, want to do).
We added our joy items to the calendar.
We started tracking moments that made us feel alive, made us laugh, made us feel rested and playful.

It gave our life dimension beyond deadlines.

What if you didn’t wait until retirement to notice where your identity is anchored?
What if you could work hard and play hard (and play…that can mean rest too!)?
What if your personality wasn’t fueled only by urgency, but also by intention and enjoyment?

If you haven’t created a Joy List yet, this is your nudge.

Write down the activities that make you feel like you. The small things. The silly things. The restorative things. Then put them on your calendar like they matter. Because they do.

And if you can’t think of anything, email me. Truly. Sometimes when we’ve been running fast for a long time, it’s hard to remember what we enjoy. I’ve got plenty of ideas to help you flip that switch.

If you’d like a structured way to start, my Joy Workbook was designed for exactly this. It walks you through creating your joy list, building your joy calendar, and measuring what fills you back up so your life isn’t defined only by responsibilities.

You happen to the world, not the other way around.

The real question is, who are you becoming outside of your job? Hit reply and let me know!