There’s a moment in midlife when the old maps stop working.
All the strategies that got us here (striving, accumulating, proving, optimising) don’t seem to point us anywhere meaningful. We don’t feel lost exactly. But we don’t feel like we’re going anywhere.
Chip often describes midlife not as a crisis, but as a calling to edit. It’s an invitation to let go of what really doesn’t fit anymore and make space for something new. Over the past 13 years of building The Happy Startup School and my own midlife transition, I’ve learned that this editing process doesn’t begin with answers.
It begins with listening.
Why insight alone isn’t enough
Many of us are addicted to insight.
We read the books. We geek up on podcasts. We integrate the frameworks.
And yet, we still feel stuck.
In our work with midlife founders, professionals, and creatives, we see a pattern: people know something’s not quite right, but can’t name what right is.
That’s not an insight problem.
It’s an inside problem.
Modern life keeps us in our heads. Midlife requires us to return to the body, to place, to relationship, and to time that isn’t optimised within an inch of its life.
Which is why one of the most powerful exercises we use is deceptively simple.
The Postcard from the Future
When working with people in transition one of the things we love to do is to dream without the filters.
We invite people to write a short postcard (three years from now) from a version of themselves that feels deeply alive and fulfilled.
Not wildly successful.
Not finally “sorted.”
The instruction is gentle:
- Imagine waking up in a life that fits you.
- Where are you?
- How are your days shaped?
- Who are you with?
- What no longer feels heavy?
This exercise isn’t about manifestation or goal-setting. It’s about re-connecting ourselves to what aliveness actually feels like.
Because when people do this, something surprising happens.
They don’t write about titles or exits.
They write about pace.
About belonging.
About doing fewer things, better.
And with people they trust.
The future self isn’t louder.
It’s calmer.
More grounded.
More honest.
It’s the archetype of the modern elder.
And crucially: it becomes a compass.
Once you’ve heard that voice (even faintly) it becomes much harder to keep living in ways that contradict it.
This exercise forms the heart of our Designing Your Midlife Reset work, where participants begin by identifying what drains their energy, what nourishes them, and which core needs will guide the next chapter of their lives.
Why place matters in midlife transitions
Here’s the thing we’ve learned the hard way:
You can’t edit your life when you’re in the thick of it.
Midlife transitions need containers.
They need slowness, beauty, and other humans asking the important questions.
This is why people come to MEA in Baja and Santa Fe.
That’s why, alongside our online work, we (The Happy Startup School) host the Midlife Reset Retreat in Girona, Spain. It’s an intimate, in-person gathering for people who find themselves between chapters and want to think clearly again.
Not jumping head first into the next venture.
But understanding who you are becoming in this next season of life.
Many followers of Chip’s work tell us the same thing:
“I love this work… I just wish there was something like this closer to home.”
If you’re in Europe (or simply drawn to doing this work away from the noise) Off-Grid Girona offers something rare: space, nature, unhurried conversation, and a chance to practise the wisdom we often only read about.
We’ll walk.
We’ll write.
We’ll eat together.
We’ll let go of what’s heavy.
And most important of us, we’ll listen — to ourselves, to our ideas and to each other.
A quiet invitation
If the idea of writing to your future self stirred something in you, that’s not accidental.
You don’t need a dramatic reinvention.
You don’t need another productivity system.
You may simply need time, place, and permission to hear what’s already true.
That’s the work of midlife.
And it’s work that’s better done together.
You can read more about our approach to midlife transitions here, or explore the Midlife Reset Retreat in Girona if you’re curious about experiencing this work in person.
Wherever you do it: may the second half of life feel less like optimization, and more like coming home.
-Carlos
Carlos is co-founder of The Happy Startup School. He helps midlife founders and professionals gain clarity, make confident decisions, and redesign work that feels more like them. His retreats and programs turn reflection into practical next steps.