CEO Coaching: How to Do Vacations

I need a two-week vacation with frozen libations?

And flip-flops propped up and a view?

Of a wide-open ocean where the world's in slow motion?

An umbrella, two blue chairs, and you?

—Zac Brown Band, Two Blue Chairs and You

Many of my clients over the years have sucked at vacations. Some didn’t take them at all. Others worked through the entire thing. Many just couldn’t relax. I’ll be honest—I wasn’t great at them either (I even went a few years without one at one point) when I was an executive. But now? I’m a PhD-level vacationer. So, I thought I’d share what works for me and what those clients who’ve mastered the art of vacation are doing. Here are some vacation guidelines you might consider.

1. Boundaries Are Your Best Friend

Your board member might want to meet in the middle of your scheduled vacation, but if it’s going to upset your family or mess up your plans, say no (politely). If you have a boss or board who constantly interrupts your vacations, either you’re allowing it, or you work for a jerk.

2. Set Expectations

Give your team and any other VIPs a heads-up that you’ll be away. Have a process in place for emergencies, and let everything else wait.

3. Check Messages Sparingly

I’ve always liked work, so checking messages once a day isn’t a problem for me—but if you start responding, you’ll just get more of them! “I’m on vacation, back with you in 10 days” is a good response. Better yet, have your assistant respond to as many as possible.

4. Mixing Work and Pleasure? Go for It

If you can effectively mix work and pleasure, good for you! I have Starlink in my trailer, and just last week, I did a 90-minute video call with a client while camped in a national park on a fishing trip. My first cocktail was within arm’s reach.

5. Don’t Obsess Over Work

You’ve probably figured out by now that you can’t just tell your brain to “stop it!” when thinking about work. However, you can replace those thoughts with other thoughts. Don’t dwell on work. Dwell on the great time you had last night at dinner or today in a foot of fresh powder!

6. Plan Major Trips in Advance

Spur-of-the-moment trips are great, but put some major trips on your calendar and plan for them. It’s fun to look forward to them and indulge in an occasional daydream about what they’ll be like. I typically have a few teed up at any given time.

7. Ease Back into Work

I learned this one from our founder at Kinko’s when I was an executive there. I used to have my assistant drop off my mail (back when most of it was hardcopy) at my house, and I’d work from home on my first day back. This way, I cleared up the busywork and was able to be present and more relaxed when I got to the office. If you work from home, block out the first day and tell people you’re unavailable.

8. Start Each Day with Gratitude

You’ll have a much better vacation if you start each day with a gratitude exercise. Who wants to be angry on vacation?

9. Incorporate Fun Weekly

Put some fun and interesting events on your calendar each week. Even an hour or two can increase your energy and clear your thinking.

Bonus Point: Jimmy Buffett and good beer.

I assure you, you’ll be a better boss, a better spouse, a better parent, and a better human if you learn how to do vacations well! Go plan one now!