The Trips You'll Never Regret

A few days ago, Nicole and I spent time in Savannah, Georgia, with some great friends. Andy and Lesley Peters hosted us at The Ford Plantation, and Lucas and Elissa Howard joined us as well. We spent our days fishing, hanging out by the pool, exploring downtown Savannah, enjoying incredible meals, and laughing harder than we had in a long time. We caught everything from stingrays to sharks, sat through a few passing storms, shared stories over long dinners, and ended one evening at a comedy show that left all of us wiping tears from our eyes.

It was one of those trips that reminds you how much life can happen in just a few days.

As I sat on the plane heading home, I realized the things I'll remember most won't be the fish we caught, the places we visited, or even the photos we took. It'll be the conversations. It'll be sitting around a table with people we care about. It'll be hearing stories that reminded us where we've been and talking about where life might take us next.

On paper, none of it sounds extraordinary, but that's exactly what made it extraordinary.

If I'm being honest, it almost didn't happen. I could have found plenty of reasons to stay home. My energy still isn't completely back, and there was a part of me that wondered if this was the right time to take the trip. Looking back now, I'm incredibly grateful I went. After the last few months, getting away with friends felt less like a vacation and more like a reminder of what matters.

For years, I thought life would slow down eventually. I thought there would be a season when the calendar opened up, the responsibilities eased up, and there would be plenty of time for the things that mattered most. What I've learned is that life rarely works that way. It keeps moving. Calendars fill up, responsibilities grow, kids get older, and seasons change. Before we know it, years have passed.

One of the things I love most about the 10-Year Letter process is that it forces people to stop and think about the life they're actually trying to build. Not just the business. Not just the goals. The life.

When people write their letters, they rarely talk about having attended more meetings, answered more emails, or worked a few extra hours. They write about relationships, experiences, adventures, memories, and the people they love. They write about a life they would be excited to wake up to.

That's what this trip reminded me of.

Life isn't waiting somewhere in the future.

It's happening right now.

Many of the moments that end up meaning the most happen because someone simply decided they were important enough to put on the calendar.

As I headed home, I kept thinking about one question: What have I been meaning to schedule that I keep telling myself I'll get to someday? For you, it might be a trip you've talked about taking for years. It might be dinner with friends you've been meaning to reconnect with. It might be a conversation you've been putting off or an adventure you've convinced yourself can wait until life settles down. Whatever it is, don't wait for the perfect time. In my experience, perfect timing rarely arrives. Life has a way of filling every open space we leave available, and before we know it another season, another year, or another decade has passed.

Ten years from now, you probably won't remember another ordinary week on your calendar. What you'll remember are the experiences that became stories, the people you shared them with, and the moments that reminded you what really matters. Those moments rarely happen by accident. They happen because someone decided they were important enough to make time for.

Before this week ends, schedule something worth remembering and put it on the calendar.

Your future self will be glad you did.

Have you written yours yet?

Ready to create a future you're excited to live?

The 10-Year Letter Workshop and my coaching programs help people gain clarity, reconnect with what matters most, and intentionally author their next chapter.

If you're ready to align your actions with what matters most and build a life you're excited to wake up to, I'd love to help.

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