Don’t Forget the Sunscreen
It’s the season when lots of people take vacations. So I thought I’d share a bit about how to do it when you’re a business owner.
Why?
The first question (always – about almost anything) to ask is why do it at all? Presumably you’ll enjoy a vacation for personal reasons. Your business should be in service to your life, not the other way round, so that’s reason enough. But there are also benefits to your business when you take a break, if you do it properly. They include rejuvenating your energy, getting a new perspective, and detaching to let your non-conscious mind work on stuff.
But the best benefit is that the prep you do could change how the company works even after you return.

Step 1 – Replace Yourself.
Too many entrepreneurs I know think things will go to hell if they leave. And too many are right. So the first step is to figure out what you do that can’t wait while you’re gone, and train someone else to do those tasks. By “do those tasks” I mean produce the outputs you were producing. After all it’s not doing the work that’s important, it’s producing the results.
I said train someone, not just dump the responsibility on them. Most of the time, you only have to do this with tasks that are non-CEO tasks: stuff you’d hire someone else to do if the company were 3 or 4 times the size it is now. So think about what outputs you’re producing that ultimately you’d like to have done by someone else.
CEO Tasks can usually wait till you get back, because they tend to be non-urgent (though very important). So this becomes a good opportunity to take stock of the many hats you wear and get some people cross-trained. If they do a good enough job, you should have them continue to do it after you get back – and free yourself to do more CEO related activities, or just work less. Who knows, they might even do a better job than you. And that’s a good thing.
When you get back – don’t jump into the same old routine. Have the people who took over what you were responsible for continue doing so. This will ratchet up your company.
Step 2 – Communication While You’re Away
If you need to check in regularly (and sometimes you do) set specific times that you’ll be calling in. Tell people who you want to talk with, in which order, and what you want them to be prepared with. Set this up before you go.
When Should they Interrupt?
Decide what you want to be interrupted about. Winston Churchill was famous for taking naps, and told people not to interrupt him unless it was an emergency. Then he defined an emergency as the building being on fire or the armed invasion of the British Isles. I suspect your definition will be different. I usually say don’t call me unless there’s fire or blood. But whatever your criteria are, be sure to let people know in detail when to interrupt you and when not to. This exercise is also something you can carry on after your return.
Step 3 – What to Tell Your Family
Before you leave, tell your family (presuming you’re vacationing with them) when you’ll be checking in with work so they can plan when you won’t be available. Then STICK TO YOUR PLAN! Don’t tell them you’ll be on a call from 10-11 and have it stretch out till 11:10 or 11:15. Better to under promise and over deliver. Also let them know ahead of time that there might be an emergency, so they don’t feel betrayed if one comes up. If it does, explain what happened and why it was so urgent.
Step 4 – Capture Your Thoughts
Since getting out of your routine triggers your non-conscious mind to come up with lots of ideas, you want a way to capture them that will be as effortless as possible. Some of those ideas will be great – though most won’t be. Don’t analyze them till you return – just capture them for later review.
Record them to your phone (and get them transcribed), or carry a pencil and note cards. Use anything you can do consistently, because those ideas happen at weird times. That’s how your non-conscious works. Then when you’ve captured the ideas, you can get back to enjoying your vacation.
Step 5 – When You Return
Ease back into it. It’s common to return a day or so before anyone knows you’re back and while your email still says you’re out of the office. Use that time to review the thoughts you captured, solidify any insights you had about how you want to function differently, plan new projects or kill old ones.
What would it be like if every day were a vacation? That’s something to ponder.
And don’t forget to pack the sunscreen.