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. But there are business reasons to take a break. They include rejuvinating your energy, getting a new perspective, and detaching to let your non-conscious mind work on stuff.
Another business reason is that the prep you do might just 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. 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.
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 might have them continue to do it after you get back – and free yourself to do more CEO related activities. Who knows, they might even do a better job than you. And that’s a good thing.
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.
Decide what can’t wait. Winston Churchill was famous for taking naps, and he told people not to interrupt him unless it was an emergency. But then he was clear to define what he considered an emergency (the building being on fire or the armed invasion of the Brittish Isles). I suspect your definition will be different. I usually say don’t call 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 might be 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.
NOTE: It’s been snowing in Pittsburgh for 18 hours as I write this – though we’re getting off easier than the Northeast which is expecting a blizzard of historic proportions. So I chose this image of a warm vacation from https://commons.wikimedia.org/wiki/Category:Files_from_Martin_Robson_Flickr_stream