Mile Marker № 002
With an Open Hand.
July 5, 2026

"So why love anything at all? If the higher I fly, is the further I fall… why love anything at all?"
There are songs that become companions for a season. I love music. And I tend to listen to the same songs on repeat for weeks at a time. Not because they're so profound every time I hear them. More because they quietly and melodically put words to things I've been carrying for a while.
This one did that for me.
It also made me think about another quote I heard recently.
"Entrepreneurs are often found at the blackjack table, not the chess table."
At first, I laughed. Then I realized this one wasn't really about gambling. It was about uncertainty. About people willing to make decisions without guarantees. It's about those who understand that certainty is a luxury life rarely offers.
The more I thought about it, the more I realized maybe that's true of more than entrepreneurship or business. Maybe it's true of love. Maybe it's true of faith. Maybe it's just true of living in general.
Listen. I love Bubble Craps. For anyone who doesn't know what that is, YouTube it. And just don't roll a seven.
Now, some people probably hear that and think it's because I enjoy gambling. Maybe. Maybe I do enjoy gambling. Responsibly, of course. But I think there's something deeper than that, that's actually been an outlet for me over the past year. There's something fascinating about the moment you smash the button and the dice "leave your hand".
You've made your decision. You can't take it back. You can't manipulate the outcome. You simply watch. Just praying it's not a seven.
Life has felt a lot like that lately for me. I left a stable job. Started two businesses. Raised capital. Bought real estate. I'm back to writing publicly. Preparing to date again. And over the coming days I'll be following God into some new places where I couldn't even see ten steps ahead just a year ago.
Nothing I've set out to do over the last year has come with any sort of guarantee. If anything, it was 100% risk. When I talk about incredible highs and lows, there's not a much better way to put it. And maybe that's why I've been thinking so much about these lyrics.
"Why love anything at all?"
For most of my life, I've unknowingly treated love like a transaction.
If I loved well enough. If I worked hard enough. If I became enough. Maybe I'd receive what I was hoping for in return.
Marriage. Friendship. Business. Even faith.
I don't think I realized how deeply that way of thinking had taken root until recently. I'm beginning to wonder if love (or just living) was never meant to be transactional in the first place. Maybe neither one is something we leverage to secure an outcome. Maybe it's just participation.
Participation in the very character of God. He gives freely. He pursues relentlessly. He remains faithful. Not because everyone responds. But because that's simply who He is.
And that changes everything.
It means I don't have to live and love because I know how the story ends. I can do both because both are worthwhile.
I know this because the lesson wasn't theoretical for me, it still isn't. It was forged in the middle of a divorce I never wanted. There were mistakes. Some mine, some not. For a long time I replayed every decision, wondering what would've happened if I'd chosen differently.
Eventually I realized something. For one, therapy saved my life. But also. I don't regret loving. I don't regret trying. I don't regret believing something beautiful could be built. The outcome wasn't what I hoped for. But love isn't measured only by outcomes. Sometimes it's measured by whether you were willing to offer it freely in the first place.
That's changed the way I think about dating and relationships. Even recently, I re-connected-ish with someone who reminded me what simple, honest connection feels like. At least on my end. It didn't become the relationship I had quietly hoped it might, dating back to a while ago even. But here's the thing about my own growth: years ago, I would've viewed that as a failed investment. Now I just see it as a gift. For a brief moment, our paths crossed again. I laughed. I learned. I gave. I initiated. I led. I was vulnerable, open, honest. And I walked away loving Jesus a little more than I did before as a result.
That doesn't feel like failure. That feels like participation. Maybe that's true of all of life. That doesn't mean I wasn't disappointed. But again, it's not about the end result for me anymore outside of who I am becoming. And the ability to love people deeply, freely, and without demanding an outcome is a dangerous gift.
Friendship. Parenthood. Business. Faith. Even these words you're reading. None of them come with guarantees. You can build something that fails. Trust someone who leaves. Pray prayers that seem to go unanswered. Pour yourself into something only to watch it unravel.
Or…
You can spend your whole life trying to avoid those possibilities.
I'm just not convinced that's living.
These days, I'm far less convinced faith is about eliminating uncertainty. I think it's more about becoming the kind of person who can love in the middle of uncertainty and through the disappointment and the "wasted time", still smile, and genuinely say: it is well with my soul.
To live with an open hand. To stop asking every experience, "What will this become?"
And instead ask, "Who am I becoming because of it?"
Maybe that's why God keeps inviting us instead of demanding from us. Participation can't be forced. Only accepted.
So why love anything at all? Because the point was never avoiding the fall. Maybe the point was learning that the flight was always worth it. And always will be worth it.
And maybe, years from now, you'll look back and realize the moments that broke your heart became some of the very stones that reminded you God had been walking beside you all along.
I'll see you farther up the trail.
Reflection
Who am I becoming because of it?
Grace and peace,
Caleb
Continue Along the Way
Three more mile markers

Mile Marker № 003
Room for Both
Forty-eight hours after a judge finalized my divorce, my daughter drew our family on the wall of our new home. I'm learning there's room for both grief and joy.

Mile Marker № 001
Farther Up the Trail
A letter to a younger self — written from another trail, not from a mountaintop. On dependence, softness, and the quiet stones we leave behind.