What I Learned About Letting Go (From my 2 week vacation)

I hate the advice "just delegate more."

It sounds great in theory. But when you're the creative vision behind your work, letting go feels impossible. What if they mess up? What if the client notices? What if everything falls apart while you're gone?

I just got back from two weeks in Europe with family. Red-eye from New York to Germany, for my wife's cousin's wedding, then a cruise through Santorini, Turkey, Mykonos, and Naples. But here's the thing. I almost didn't go because I couldn't imagine being away from client work for that long.

The night before we left, I was scrambling to finish projects, brief my creative friends who'd cover me, and set up systems so nothing would slip through the cracks.

Then reality hit.

Day one in Rome: we're starving, find a restaurant across the street at midnight, and I'm thinking "this is fun but I should check emails." Day three in Santorini: we're hauling a stroller up cobblestone stairs that feel like they were designed to punish tourists, and I'm still refreshing my phone between cable car rides.

Day five in Turkey: my bank blocks all my cards. Can't call because of the time difference. I'm stuck on a beach in Kusadasi with my family, and for the first time in years, I literally can't work even if I wanted to.

That's when something shifted.

By the time we hit Mykonos, I was laying in the shade at Ornos beach, actually napping while my wife and kids played in the water. Not thinking about client deadlines. Not planning the next project. Just there.

Here's what two weeks away actually taught me:

• Your business reveals its weak spots when you step away. The stuff that "only you can do" is often just the stuff you haven't taught anyone else to do yet.

• Trust isn't built overnight. I've been building relationships with other creatives for years. When I needed coverage, they showed up. That network didn't happen by accident.

• Lower stress = clearer thinking. I felt physically different in Europe. Better. Calmer. Not because of the food or scenery, but because I wasn't carrying the weight of every single decision.

• Process beats perfectionism. My friends didn't handle things exactly like I would. But they handled them well enough. And "well enough" kept clients happy and projects moving.

By our last stop in Naples (birthplace of modern pizza), we had to hit Pizzeria de Michel. I realized something. I'd spent more quality time with my family in those two weeks than I had in the past few months back home. Work always gets in the way. Life always gets in the way.

But being forced away from the daily grind reminded me why I'm building this thing in the first place. It's not just about the work. It's about having the freedom to disappear for two weeks and know everything's still running.

The truth? I'm still not there yet. I want to close my eyes for a month and know everything's running smoothly. That's my goal before summer 2026.

But this trip proved something important: the world doesn't stop when you step away. Your business doesn't crumble. Your clients don't leave.

Sometimes the best thing you can do for your work is to stop working on it for a while.

What about you? When's the last time you truly stepped away? Hit reply and let me know. I'm curious what's holding you back.

-Matt

P.S. — I picked up a Fujifilm X100VI a few weeks ago and it's been incredible on this trip and client work. Sometimes the best creative tools are the ones that just get out of your way. You can see some of the photos I used for this post here.