How to Delegate the Admin of Your Vacation to Your EA

If you’re not planning on utilizing your EA for your upcoming summer vacation, you’re doing it wrong.

And I don’t mean having them book flights, etc - I mean the actual admin of your trip.

What would it look like for them to own all the logistics, enabling you to truly disconnect?

Most founders are resistant to this - we want to draw lines between “work” and “personal”.

Except your brain and body don’t do that. You’re one person - there are no severance procedures in real life.

Which means, if you spend your vacation doing admin work (confirmation numbers, flight times, transportation bookings, restaurant reservations)…

And fail to actually rest.

Then that same “vacation admin” will work in to work the following Monday morning exhausted instead of refreshed.

What’s the ROI on that?

Last week when I was in Mexico, I got a taste of what it’s like to really step away. Even from vacation admin.

How I nearly missed my flight — and didn’t even know it

My wife and I were in Playa del Carmen, totally unplugged. No kids, no inbox, no Slack. Just each other, a few books, and tacos/margs on repeat.

We were supposed to return home on Wednesday.

So on Tuesday, I coordinated at late checkout with hotel staff as our flight was at 6:15pm which meant we’d be picked up from the hotel at 3:30pm.

Except I had it backwards and didn’t know it.

We were to be landing at 6:15 in Austin.

The flight was to depart Mexico at 3:30.

If we had stuck to my plan, we’d have rolled up to the airport at 4:45 - for a flight that was long gone.

But since my EA, Jed, was in charge of owning the logistics of our travel, she checked on the status of our flights, hotel and car service the day before on Tuesday.

She noticed the problem and fixed it without me even knowing.

After the fact, she sent me a text on Tuesday:

“Heads up, your flight tomorrow is at 3:30pm so I re-scheduled the car to pick you up at 12pm.”

She saved me before I even knew there was a problem.

Delegating your personal logistics isn’t indulgent. It’s a strategic investment in your clarity and energy.

Want to travel like a founder, not a flight attendant?

Here’s where to start:

• Build a Travel Playbook: Document what needs to happen before, during, and after every trip. Make it repeatable.
• Have your EA create a chronological itinerary: My EA built out a Notion table with all dates/times, confirmation numbers, phone numbers & addresses. It gave me step by step directions on where to be, when. Plus, this meant she always knew where I was and what I was doing on a given day.
• Give your EA full ownership: Don’t just hand off tasks - hand over the outcome. Let them be the point person for flights, cars, reservations, and backups.
• Define what counts as urgent: Set up an escalation protocol so you’re only pinged if it’s truly necessary.

The real flex?

Coming back from vacation better than when you left — because you didn’t spend it triple-checking details.

If your next trip still depends on you to run smoothly, then you’re not resting - you’re working in disguise.

Want to build a system where your life runs without you?

Let’s talk.

‍