Out of Office: The Leadership Test No One Talks About
Why the way you “vacation” says more about your leadership than your LinkedIn profile ever will.
Most people don’t take real vacations.
They take their job somewhere with a better view.
Laptop. iPad. Phone. Early email sessions. Mid-day “quick calls.” All in the name of being too important to unplug.
Here’s the truth:
If you can’t step away, the problem isn’t your job—it’s you.
I learned this the hard way.
My wife once told me I gave her the worst vacation of her life. She wasn’t wrong.
I was working the entire time. Thought I was killing it. I was actually killing the vacation.
Eventually, I changed. It took some trial runs, a little trust, and a hard look at how I led. But now, I take actual vacations. No laptop. No meetings. Just presence.
The Wake-Up Call
It was a trip to Miami. Our first vacation after our son was born.
I spent most of it on the phone—making deals, putting out fires, convinced that no one else could handle it.
At the end of the trip, my wife didn’t sugarcoat it.
“We just wasted a bunch of money so you could work remotely. This was the worst vacation I’ve ever had.”
And she was right.
The Half-Measure Phase
After that, I tried to do better.
I worked during “off hours.” I answered emails early in the morning. I tried to sneak in calls while she was doing something else.
What I really did?
I just got better at working vacations.
I was still cheating myself out of the mental space I needed.
Still cheating my family out of time they deserved.
Still pretending I had balance, while my phone sat between us at dinner.
The Shift
Eventually I realized:
I didn’t want to work on vacation—I wanted to stop thinking about work altogether.
So I tried something radical.
Before my next trip, I told my team:
“I'm going on vacation. I'm not bringing my laptop or iPad. I’ll have my phone—but only for emergencies. (And I mean real emergencies. Like the building burned down.) I trust you to make the call. I believe 99% of the time, you’ll make the same decision I would—and for the other 1%, you can call me.”
Now, I did bring the laptop and iPad that first time—but I never touched them.
I checked email a couple times on my phone - but didn’t respond.
And after a few days, I stopped checking altogether.
The Payoff
That was 7 years ago. And I’ve never looked back.
I was present. I relaxed. I reconnected.
And I realized how many years of family experiences I’d diluted by trying to be “just available enough.”
So if you’re still taking your job on vacation with you, here’s the hard truth—and the good news:
5 Things to Remember Before Your Next Trip
You’re not that important.
If you won the lottery and quit, would the business fail? No? Then it can survive a week or two without you.If you’ve built a strong team, act like it.
Trust them. Empower them. They’ll grow from it—and you will too.Almost every decision is fixable.
Even the bad ones. Don’t let fear of mistakes be the reason you miss your life.If you’re a micro-manager, get help.
And I’m not joking.If you’ve got FOMO, ask yourself why.
That’s not hustle. That’s insecurity in a nicer suit.
Vacations matter.
Your body needs the rest. Your mind needs the space. Some of my best ideas have come after I stopped trying to think about work.
So, next time you write “Out of Office” in your email signature…
Mean it
.
Gotta call it like I see it! 😉
That’s insecurity in a nicer suit. ~ Love that!