Don’t spoil your vacation worrying about returning from vacation. Use these principles to come back in control and with peace of mind.


Two days before composing this post, my wife and I returned from a week’s vacation in New England. I made a conscious decision not to take my laptop. After all, it’s a vacation. But would I get behind? Wouldn’t I face an avalanche of work after returning form vacation?

I’m proud to say that after a couple of days back on the grid I’m 100% up to date with email. I have no pressing deadlines. Best of all, I’ve navigated my return stress-free. I even decided to add something to the agenda…compose this post and the accompanying podcast and video for you, outlining how I did it. Will what worked for me work for you? That’s our focus.

Prepare for your absence

Let people know you will be gone. If they are going to be counting on you for something, give them a deadline of when you need their requests. Anything that gets to you before the deadline will be handled. Everything else must wait until your return.

I put an out-of-office announcement on my email. For more on that concept, check out the post I did in conjunction with Brittany Naylor for the Evernote blog and this site. Letting people know I would be gone, including that out-of-office response, cut down considerably on the email I would receive during the trip.

Work ahead

What can you do ahead of time leading up to the trip? We all have recurring deadlines. During the time I would be gone, I had four of them that come around each week

  1. I offer an online course geared for school administrators in my state. The course consists of a book study with supplementary material and exercises accessed through the course portal. Every Saturday, I email the present cohort. Each of those weekly emails parallels a chapter in the book. I would be out of town during the time for one of them to go out. So, I wrote the email ahead of time and used Gmail’s “send later” feature.
  2. Every Tuesday, I send content to my email list. Composing this email is something I do each Friday. Having several days of cushion is nice. If an opportunity presents itself, I like having a cushion of several days. If Friday’s usually busy, I still have several days available to handle the task. So before the trip, I wrote that email early and scheduled it to release on the appropriate day, even though I would be out of town at that time.
  3. Likewise, the content you’re enjoying right now releases on Tuesday, but it’s composed weeks in advance. My goal is to have the content for the entire month, composed, recorded, edited, and scheduled before the month begins. In this particular case, I’m recording on Friday and scheduling the release for Tuesday. What was scheduled for this week and for the remainder of the month has all been pushed a week into the future.
  4. I write a weekly newspaper column and have a deadline of Thursday for submission. Since I hate bumping up against a deadline, I submit my article each Wednesday.  Since I arrived in town late Wednesday evening. I still could have made the Thursday deadline. But no, I wrote the article, attached it to an email to the editor, and scheduled it to send on the date I normally would have sent it anyway.

Use little windows of wait time.

Every trip comes complete with “hurry up and wait” segments. During the trip, I used that time to triage email. I was able to do the following:

  1. Delete what’s of no interest.
  2. Snooze items of interest until several days after my return. (I love the snooze feature in Gmail.)
  3. Handle important items that require only a quick reply.

When we stepped on the plane to fly home, my email inbox contained exactly one email. That single email was the flight information.

Don’t be the bottleneck.

After our flight and the drive home, it was time for bed. The next morning, it was time to get to work.

But with so much that had been postponed until my arrival and so much else that is arriving, where do I start?

Rule #1 is, “Don’t be the bottleneck.” Just like in tennis or basketball, you want to get the ball out of your court and into the other person’s court.

What are other people waiting on from me?  They can’t move forward until they hear from me. That’s not a situation where you are I need to be. You find yourself answering phone calls and emails from people asking for a “status report.” 

First up was the online course I mentioned. We are moving into the final weeks and some participants are turning in their final projects. They need feedback from me on how they did. I handled those first.

Next was data related to a project involving a dozen or so schools. For schools that had submitted their part before the trip, it was all handled. For those who missed that deadline and needed to wait until my return, I wanted to get that turned around quickly.

When the bottleneck is someone else

In two other areas, I am waiting on information from others before I can move forward with the projects. No issue. I have plenty else I can do. But, I do want to get them handling their parts so that when I am ready to work on those projects, I’ll have the information.

So, next up is sending emails letting people know what I am waiting on. That usually gets things moving.

Breathing room

Now that I am not the bottleneck and have also made strides to remove the bottleneck others are causing, I have some breathing room. I can enjoy reestablishing some balance.

I’ve snoozed emails over the last week. Some of them are receipts from the trip. It’s time to assemble and record all the receipts from the trip, both paper and digital.

I always keep a zippered pouch in my briefcase. It’s great for holding all the paper receipts my wife and I accumulate. Currently, we print our receipts so all receipts are in paper form and can be matched to the credit card statements. At some point in the future, we’ll likely hit a tipping point where most receipts are arriving digitally and digitizing the rest becomes the better option.

Between these paper receipts and printing the ones sent to me digitally, we have all receipts from the trip. It’s also a prime time to leave good reviews for the bed and breakfast where we stayed on our trip.

The emails I snoozed during the trip will be returning over the coming days. Each one takes very little time. Often, it’s those little things that fall through the cracks and cause problems later. Keeping the system clean is important. I want every piece of paper in its place, every email handled, my Evernote inbox empty, and my task list in good order.

New opportunities

One of the benefits of being organized is when new opportunities present themselves, you’re ready. My first day back, a podcast episode released, one on which I was a guest. I want to be able to take time to promote that post through my social media channels and include it in the weekly email to my subscribers.

Next, a wonderful review of Get Organized Digitally! appeared on the MiddleWeb blog. I had no idea that one was coming. I want to be able to promote that review as well as send thanks to the reviewer and to the MiddleWeb blog.

Big projects

All the content for my blog, podcast and YouTube channel is complete and scheduled for the rest of the month.  Because of the post you are reading now, one I decided to compose and add after the trip, I pushed the content for the remainder of the month back a week. Now, I have the first episode for October handled as well! I can now tackle something big.

I mentioned a book study earlier. That book study is on Get Organized!: Time Management for School Leaders. Because of its popularity, I am going to create a similar book study to accompany my latest book, Get Organized Digitally!: The Educator’s Guide to Time Management. The target release is January 1, 2023. But I want to have the majority of the work completed by the end of September so I can begin promoting the course during the last quarter of the year.

That’s the formula for returning from vacation stress-free

So that’s my formula for taking a vacation and not spending the whole time worrying about my return

  1. Prepare others for your departure.
  2. Work ahead of deadlines before you leave.
  3. Triage email while you’re gone.
  4. Don’t be the bottleneck.
  5. Follow up with others to break the bottleneck.
  6. Handle the little stuff so you can clear the decks.
  7. Take on something big with total control over your time and the peace of mind that nothing is falling through the cracks.

You earned that vacation. Enjoy it. With the right planning, you won’t spend your vacation worrying about your return.

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