Honoring the Endings We Fear Most

The wound is the place where the Light enters you.

— Rumi

In the last few months, I ended a 12-year romantic partnership. I never imagined I would choose this ending. But here it is. For years, my greatest fear in life was losing this relationship. In hard moments, I would hear an old voice inside me: Matt, never forget. Everything you love will be taken away from you. And now the thing I feared most has happened. And I was the one who chose it.

When I first arrived at the clarity that ending the relationship was the healthiest path—for me and for my children—I spoke with a longtime coach and friend. He said something that surprised me:

Grieve it. But don’t grieve it too much. Because while there is sadness here, what you are moving toward is actually wonderful.

I didn’t fully understand what he meant at the time. But with each passing day, I do more.

There has been real grief. No way around that. And alongside it, something else. Grace. The clarity the ocean brings as I step into the cold Pacific each morning. The steady presence of friends who reflect back truths about my life that I could not fully see on my own. The unexpected peace of walking into my home now. A home that, just months ago, held a very different shape.

Last week, a CEO I work with reached the painful clarity that she needs to part ways with her co-founder and close friend. Her fear and conviction brought me back to my own experience of asking a close friend and co-founder to leave our business (which I wrote about here). It also clarified something I’m living right now: when we act from deep internal conviction—when we do the hard work to see clearly and choose what we believe is right for ourselves and the people we love—life begins to move with us. The path lights up. Not because it’s easy. But because it’s aligned.

I’ve felt this at the most consequential moments of my life. When I stepped away from my identity as a founder and CEO to become a coach. And now, in the wake of this ending as well.

As I listened to this CEO, I found myself hoping that she—and her co-founder—might eventually experience the same thing. That beyond the grief, there is support. That beyond the loss, there is a kind of unfolding. Because I could hear in her voice, and had witnessed, that she had done the work. She knew, as best she could, that this was the right decision. And that is all any of us can do.

As a coach, I’m trusted with the things people don’t say out loud. And what I see, over and over, is this: most people are holding something back from someone they love or lead. We do it because we’re afraid. Afraid of hurting someone. Afraid of change. Afraid of loss. It took me years to arrive at the clarity I needed—and the courage to speak it. The alternative is to hide. And hiding has a cost.

For me, it showed up as feeling small, depressed, and out of place in my own life.

This past year has been a recommitment for me. To speak from the heart. Even when it’s uncomfortable. Even when it’s messy. Even when it’s hard. Because what I’m finding on the other side is this: peace. Peace with myself. And, more often than not, peace with others too. The wisdom that wasn’t modeled for many of us is this: real connection requires truth.

If you’re holding something back today—from someone you lead or someone you love—I’d invite you to consider: what conversation is waiting to be had? What truth is asking to be spoken?

What I’m living right now, and what I sense is possible for others, is this: when we step into our truth, as hard as the outcome might be, life meets us there. The future we fear most is not always barren. Sometimes, it’s full of wildflowers. Blooming in the most unexpected places. And sometimes, from the loss we most try to avoid, comes the very grace, connection, and growth we’ve been longing for.

If I can support you in finding or speaking your truth, reach out. I’d love to talk.

-Matt

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