Check In Before Checking Out: Tips for a Worry-Free Vacation

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Getting ready for a weekend and getting ready for a vacation have a lot in common for me. I like to look around, clean up, and clear out so I can get away.

Looking at the next month or so of your life, are you planning to leave town, take some time off or just enjoying a weekend at home with friends and family? If so, consider getting your “stuff” together so you can break away, easily and completely.

There are three things that I do before I feel “great” about going/getting away from work: 


Review the Outstanding Business
It takes about an hour a week (and, if I’m leaving town, away from my computer/office for more than four to six days, I usually plan about three hours for this) to review my outstanding business. Specifically, I review my “Sent Items” in email, my “Waiting on” inventory of things that other people are doing for me, and my “Projects” list.

I like to go through and scan the last seven to ten days of sent items in my email. While I’m doing so, I will forward emails that are still outstanding and delete emails I no longer need. This keeps me current in my agreements and waiting-for items, as well as manages the “size” of the overall email system that I am keeping.

I keep a separate waiting for lists of items I ask people by phone, in meetings, or with a hand-written note. Of course, I look at this several times per week (like just before calling someone or meeting with them face to face). But, once per week, I really review. I’m looking for anything that I need to follow up on, or something that I need to “take back” because I feel that the owner of that piece is not going to follow up/follow through for me.



This “objective” system makes it much easier to know how strictly I need to “watch” other people’s agreements. If it’s one thing I’ve learned over the years it is this: People tend to over commit! 

Review My Upcoming Calendar
I review the next twenty-one to forty days on my calendar. I do this with a piece of paper nearby, as my calendar is a digital one (I’ve used all kinds of digital systems, one of my favorite is set up in the Outlook Dashboard view). I go day-by-day and look at any daily reminders as well as the timed appointments I’ve set up. I tend to use my calendar to only hold onto meetings and events (not a lot of to-dos, those are over in my tasks area of my own organizational system). When I come to something that reminds me of something else, I make a note of it on the paper. When I’m done reviewing the next month or so, I then use the paper to go back and add things to my calendar and my task lists.

It may seem like “double entry” to write it on paper, and then type it in the computer. Here’s my experience: I want to stay “in the flow” of the calendar review. When I go from the calendar, to the task lists, and back to the calendar, I tend to distribute and tax my focus. I don’t move as completely through the review and on occasion I get so distracted by the growing task list that I stop doing the review altogether.


Make a Top Five List
In the days before I leave for vacation (and for the weekend, as I generally do my weekly debrief on Thursdays) I write a “Top Five” list. Of course, I’ve learned that I need to keep the top five to five items. I once worked with a client who had over twenty items on his top 5 list!

These are the five things that must be addressed before I get away so I can get away! They might be people to talk to, projects to finish, or goals to work toward.


Once those are done, I can walk out the door and feel guilt—and commitment—free.

When you know it’s time to check out of work mode for a few days, what do you do so that you’re not feeling the itch? Let us all know in the comments. 


By Jason Womack of DumbLittleMan

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