October 13, 2026 | Issue Archive
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Sometimes the Right Ending Still Hurts
Moving forward doesn’t mean you have to stop loving what you left behind.
This weekend, I looked out our hotel window in Nashville and saw a building that took me back more than thirty years.
I even took a picture of it.
It was the Loews Vanderbilt Hotel. The first place I ever stayed in Nashville, when my parents brought us to town for a Sawyer Brown fan club breakfast in the early 1990s.
Back then, I had no idea Nashville would become my home for nearly thirty years.
Or that one day I’d be looking at that hotel from a city I’d had to leave behind.
My wife, Megan, and I were in town to see Jack White. It was her gift for my 50th birthday and it was a great one! It was an amazing show and a really special weekend.
If you've seen me speak, you’ve heard part of my story: I moved to Nashville at 17, chasing dreams of making music. I went to Belmont University, built my career, made lifelong friends, and called it home.
Then, in 2023, we moved to Ohio.
I know we made the right decision. But this weekend just reminded me:
I still miss Nashville. A lot.
The places that become part of us
Before the show, we spent some time driving around the city.
Down 21st Avenue. Through Hillsboro Village. Past Belmont. Over to 12South and 8th Avenue South.
Streets I hadn’t driven since we moved away.
Familiarity, certainly. Nostalgia, probably. But more than anything, it felt like home.
I remembered the dreams I’d had there. The neighborhoods where I’d imagined someday owning a house. The places I’d been. The people I’d known.
The city has changed, of course. Our hotel sat on the site of an classic Nashville café where I once ate. Buildings disappear. New ones go up.
But so much of it is still right there. The same streets. The same corners.
Close enough to drive. Far enough to miss.
Sometimes the right choice is still a hard choice
We moved for reasons that still matter.
That hasn’t changed. Neither has how much I love what we left behind.
I think we sometimes misunderstand what it means to move forward.
We imagine that once we’ve made a decision, accepted a change, or closed a chapter, we’re supposed to feel good about it.
No looking back. No second-guessing. No wishing things could have been different.
That’s not how life works.
Sometimes you can be certain you made the right decision and still wish you hadn’t needed to make it.
Sometimes you can be grateful for what a new chapter makes possible and still grieve the one that ended.
Sometimes the right ending still hurts.
And that doesn’t mean it was the wrong ending.
When the change isn’t yours
Maybe you’re navigating a change at work right now.
A restructuring. A new leader. A different role. The end of a team you loved being part of.
Or something more personal. A move. A relationship. A dream that didn’t unfold the way you’d imagined.
You might understand why it’s happening. You might even see the good that could come from it.
That doesn’t mean you have to pretend you’re happy about everything you’re leaving behind.
Something mattered to you. Of course you’re going to miss it.
Acknowledging that isn’t staying stuck in the past. It’s refusing to shrink what was good about yesterday to make room for something good tomorrow.
THIS ENDS NOW
Is there something you’ve been telling yourself you should be over by now? Something you still miss, even though you know life needed to move forward?
Maybe you don’t need to be over it.
Maybe you just need to choose what you carry.
THIS MOMENT MATTERS
What will you carry forward?
We don’t always get to choose what changes.
But we always get to choose what we carry forward.
Nashville helped shape who I am. The dreams I chased there. The friendships I made. The lessons I learned.
None of those things disappeared when I crossed the state line into Ohio.
They came with me.
An ending doesn’t erase what came before it.
You can honor what was. You can miss what was. And you can still choose to move forward.
All three can be true.
That’s why I took the picture.
Not to hold on.
To carry it forward.
Up we go—
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P.P.S. We’re putting the finishing touches on an updated speaking demo. If you’re lining up speakers for a 2027 kickoff, conference, or leadership offsite, hit reply with the event date and I’ll send you an early look.