On Taking a Vacation from Work

Those of you who heard my 2010 presentation at EECI Leiden or EngineSummit 2 may remember a story about a client I had about a year ago. It was a big client, a 5-digit-income-a-month client, which is nice for a small development shop like Encaffeinated. The story I told revolved around losing that client due to non-performance of some contractors I hired for the project. You might think that losing that client was the worst part about that particular project, especially for reasons that were somewhat out of my control. If so, you are incorrect.

The worst part about that project was the week-long trip my family took to Disneyland toward the end of that contract. Disneyland was great, and spending time with my family was invaluable. But every night after the kids’ bedtime and every day during naptime, I was immediately on the laptop, working away. It gets worse: I had to take one planned conference call and several unplanned emergency calls from the client while in the park with my family. Imagine telling your family you’ll find them in an hour as you struggle to hear 10 people on the other end of a conference call while “It’s a Small World” rings over and over in the background. There is no way to find anything positive in that, from any perspective.

Last week, I went to Las Vegas with my wife. My parents had the kids and this was our first real opportunity to enjoy time with each other away from work and the kids in years. I decided early on that I’d not be dragging the laptop and iPad along on this trip. I work hard, Heidi works hard, and we needed to get away from *everything*. And that is just what we did. And it was fantastic.

I set this trip up with my clients by casually mentioning the trip purposely in phone, email or Basecamp conversations in the weeks preceding the trip. This removes the element of surprise and panic from clients when you email them a reminder right before you leave. I think this was the most vital step I took. It allowed my clients to think ahead and mentally prepare for Encaffeinated being closed for a week.

I set up an email address, 911@encaffeinated.com, as its own email account on my domain. Then, the week before I left, I crafted an email as a reminder and BCC’d it to all of my active clients:

We’ll be taking a vacation for the week of May 30th and our offices will be closed. We will be completely offline and won’t be checking work email or voice mail. You are welcome to leave a phone message or send email to our work addresses as you normally do, and we will get caught up on those messages upon returning to work the following week.

If you have an emergency, you can email 911@encaffeinated.com, which will be monitored daily. However, we request that you respect our family time out of the office and only email this address if there is truly an emergency that needs quick attention. Thanks for your understanding.

Thanks for the continued opportunity to work with you. We love our clients!

This gave them a more concrete reminder of the vacation, as well as dates, and most importantly, a way to contact me incase of an emergency. This set the expectation perfectly, in my opinion. I set up a vacation voice mail message on my way out of the office and felt like I had covered my bases. We embarked on our trip with nothing but iPhones, and while on the shuttle to the terminal I opened the settings for my work email account and switched the Email setting to “off”. I then added the 911 email account and the stage was set.

We had a wonderful vacation. Quality time with no distractions. Sure, we teased our friends on Facebook and Twitter with pictures and comments from poolside. I read NetNewsWire along with physical magazines while drinking island drinks by the pool (there’s that teasing again), we checked our personal email and I checked 911 email a few times a day. So, we stayed online recreationally, but the only work interaction I had was a 911 email from one of my developers in need of some access information for a client site. That was quickly handled and the only work I got near in a week.

Most importantly, I never even thought about sneaking a look at email. In the spirit of Merlin Mann’s Inbox Zero, my head wasn’t in my inbox when I wasn’t physically looking at it. I had planned well and part of the plan was to enjoy time with my wife, for both our benefit.

Upon our return, over this past weekend, I casually filtered through my work email. About 2/5 of the email I got were newsletters or other immediately deletable messages. Of the remaining 3/5, about 50% were Basecamp or other notifications that could also be deleted after review. The remaining messages were actionable. I starred them in Gmail and put it away until today (Monday). By 3pm I had answered them all or moved them over to Things tasks. Inbox Zero. The other kind. Unsurprisingly, none of my clients went out of business and none of their websites blew up while or because I was gone.

And all that just reenforces my decision to do it exactly the same way in August when our next vacation is planned. You should too.