Whew… we made it.

I just got home from a 9-day adventure trip to Madeira with 13 incredible women.

Our days were filled with hiking rugged trails, canyoning waterfalls, mountain biking switchbacks, paddle boarding along the ocean, laughing through Portuguese dinners, and soaking in the beauty of saying “yes” to life.

It was one of those trips that reminds you how alive you still are.

I only knew five women before I left, including Jody, our fearless organizer and self-proclaimed queen of games.

Name That Tune, trivia, dice games, card games… if there was an opportunity to play, she found it.

And honestly?

That playful energy set the tone of the whole trip.

We played on the bus rides. On the hikes. At rooftop bars, over long dinners.

And somewhere between the laughter and competition, the walls started coming down.

One night at dinner, we were playing a card game with reflective life questions.

Simple questions. But the kind that quietly cracks people open.

As we went around the table sharing our answers, something struck me.

Here was this group of extraordinary women in their 50s and 60s – women who had spent decades raising families, building careers, navigating marriages, divorces, aging parents, loss, reinvention, uncertainty, and change with incredible resilience.

Women who, from the outside, looked confident, accomplished, capable, and strong.

And yet the card game revealed that every single one of them could relate to the fear of not being enough.

The fear of being an imposter.

Negative self-talk.

Second-guessing themselves. Wondering if they measured up.

It stopped me in my tracks.

Because isn’t it wild how the stories we carry about ourselves can survive long after we’ve proven them wrong?

Here’s what I kept thinking about.

Mindset doesn’t change because life tells you you’re worthy.

Mindset changes when you begin collecting new evidence about who you are.

And sometimes that evidence comes in the most unexpected ways:

Trying something that’s difficult.

Laughing until your stomach hurts.

Jumping into cold water.

Being seen. Being honest. Being in community.

Playing again.

That’s the thing about play, adventure, and shared experiences.

They interrupt the old narrative.

They remind us we are still growing. Still capable. Still becoming.

Maybe change doesn’t always start with fixing yourself.

Maybe it starts with putting yourself in environments that help you remember who you are.

Play on!

Your friend and coach,

Jan xo