Is The Deepening For You?

Ever felt that uncomfortable ache when you’re caught between what was and what could be?

That tension between holding on to what’s familiar and stepping into something unknown?

Sometimes, it’s obvious—a career change, the end of a relationship, or a life event that flips everything upside down.

Other times, it’s quieter.

A subtle feeling that the life you’ve been living doesn’t quite fit anymore. A restless ache for something more.

A growing restlessness about who you are and where you are in life.

Deep down, you know something more is available but you're not quite sure how to access it.

Whether the shift is loud or soft, one thing is certain: it’s rarely easy.
These moments stretch us, pulling up more questions than answers.

This is what I call the sacred in-between—the space between what was and what will be.

It’s uncomfortable, yes. But it’s also brimming with possibility.

I know this space well.

When I left the NFL, I held on tight to everything that made me feel successful, even though deep down, I knew it wasn’t serving me anymore.
​
Letting go was messy, loud, and disorienting—so I resisted.

Eventually, I found myself stuck.

I was fighting to hold onto what felt safe, even though it was keeping me from moving forward.

From the outside, everything looked fine. But inside, I was burned out, restless, and frustrated.
​
​I thought I needed another milestone or achievement to fix it. But what I really needed was to stop fighting and learn how to hold the tension of the in-between.

And that changed everything.

This in-between space isn’t just discomfort—it’s a threshold. A threshold to a life that feels more real, aligned, and fulfilling.

But here’s the thing: crossing this threshold doesn’t happen by accident.

Without the awareness on how to navigate it, it’s all too easy to retreat to what feels safe, even if it no longer serves you. (Hello, self-sabotage.)

The shift for me came when I stopped running from the discomfort and started working with it.
​
I stopped pushing for answers and learned to stay present in the unknown.

Slowly, the life I’d been striving for stopped feeling like a burden and started feeling like a gift.

This is the heart of The Deepening.​

It’s not a quick fix or a new strategy to hustle your way forward.
​
It’s a space to slow down, go deeper, and explore the tension of the in-between—not to fix it, but to expand your capacity to hold it.

Because when you do, that space becomes the birthplace of new potential, deeper purpose, and real transformation.
​
​It’s where you realize that the answers you’ve been searching for aren’t out there. They’ve been within you all along.

This isn’t for everyone, but if it’s for you—it will change everything.

So, if you feel that stirring, that sense that the life you’re living no longer fits who you’re becoming, I’d love for you to join me.
​
Because this isn’t just a day. It’s a turning point.​

Here’s to trusting the in-between and the unfolding that follows.

As always, I’m rooting for you. We’re in this together.

-Caleb

PS. If you're interested in this but rather do it in a group over the course of a few weeks, sign up and I'll send you more information.