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My trip to Hawaii is looming. Looming? I mean, “Yea! I’m traveling again!” but it’s all coming back to me now, the work it takes to have a real vacation. It’s really worth it and it takes work. It’s now June 9. I leave June 29. I’ll be gone for 10 days. If I want a real vacation, I have many things to turn over in the different areas of my life. All the projects, responsibilities, management, etc. that I tend to each week.

What do I mean by a real vacation? I mean one where you are not required in the areas of your usual, day-to-day life. Vacation comes from the word Vacate. By a real vacation, I mean one where you have done the work to set up your life to be able to vacate it. Vacate it?






A real vacation is going to happen when I have set up my company, my passion projects, and the groups I’m a part of. When I’ve set them up to be “deprived of an incumbent”. That incumbent is me! I will not be “occupying” my roles for 10 days.

Now, you could just dump and run. You could just set the auto-responder and call a few people and say, “I’m going on vacation. I’ll be back July 10.” And you could then return to a mess.

Part of going on a real vacation is that when I’m there, I don’t have to be worried about returning to a mess. I don’t have to be snorkeling while pondering “I sure hope it doesn’t all fall apart while I’m gone.” I don’t have to be in the outdoor massage cabana with the ocean in the background while hoping the invoicing goes well and wondering if there’s money in the right account for payroll. This freedom is the payoff of the work I’ll do over the next 20 days.

I’m starting my list of what needs to be turned over and to whom. Who will cover the different bases? What do I need them to do while I’m away? How do I need them to do it? If they have questions, or get into the weeds with it, who is a resource they could turn to (that is not me!)? What do I need from them when I return, so that I’m set up for a smooth re-entry?

So, my trip to Hawaii is looming. There is snorkeling, sundresses, lazing in the sun, and homemade banana bread with lilikoi cream cheese from a small farmer’s market in my future.

When is your next vacation? What’s the work you need to do to have that be a Real Vacation?