Last December, I took a one-week trip to Vienna. I usually make a solid plan for working on vacation (see the tips, below), but that time I didn’t.
I was teaching an online course and my “Plan A” was to get up early from Monday to Friday and spend 30 minutes logged into the university’s learning management system to monitor the students’ progress. Then, on Saturday and Sunday, I planned to spend two hours each day logged-in to review and respond to their weekly posts. I had paused all my writing and consulting work for the trip and only committed to the course. Seven hours work should have been manageable.
On my first day in Vienna, I woke-up early, made coffee, and got down to work; just like I planned. After I was logged-in for two minutes, I lost the hotel WIFI connection and didn’t get it back for another ten minutes. The two minutes on and ten minutes off WIFI connection continued for the next six days. Instead of completing seven hours work, it took fifteen hours to get about two hours of work done.

Not making a solid plan meant spending less time enjoying Vienna, disappointing my students, and disappointing myself.
If you need to work on vacation, follow these tips to get it right.
#1 Set expectations early
Friends and family
Most of the people we go on vacation with would rather we didn’t work at all, or work only during times that are good for them. Making them miserable will make you miserable, so you need their support. Weeks before you leave, everyone needs to agree on what kind of work you’re going to do, and how much. If you get agreement early, no one should be surprised when you step away from the conga line to take a call, or check your email before the morning swim. And, you will continue to have their support when you keep your word to only work during the agreed times.
Boss, clients, and business partners
Most people are less productive when they’re away from their primary work location and also not able to communicate as quickly. So, if your boss, client, or business partner, is expecting you to work on your vacation, tell them the days and times you’ll be on email or available by phone. If you won’t be available in real-time, tell them your delay for responding to messages—24 to 48 hours is reasonable.
In your out-of-office reply on your email and voicemail, say how long you’ll be away, if you’ll be returning any messages, and who they can contact in your absence. If you do plan to return messages, only do it during the days and times you’ve already agreed to. If you start communicating outside of those times, then people will expect you to be available all the time.
#2 Chunk-it-out and prioritize
Since you’re probably not going to get as much done as you want, breaking your work into meaningful, smaller chunks will help you stay on top of the important stuff. Maybe you’ll only create an outline for that presentation, and do the final draft when you get back in the office. Instead of responding to all email and voicemail, maybe you’ll only answer the top three before breakfast.
If all goes well, you’ll probably get more done than you expected.

#3 Plan the work, work to the plan
Once you have support, managed everyone’s expectations, chunked-it-out and prioritized, it’s time to schedule your work.
Schedule your vacation work time like you would any other meeting: choose the time of day, place you’ll work, and the resources you’ll need. Most importantly, don’t try to schedule work on-the-fly or at the last minute. Make your schedule before you leave and make sure the time and place are agreeable to your vacation buddies.
Lastly, avoid working on days when you’re travelling between places. On those days, you’ll be busy checking in and out of hotels, packing and unpacking, and arranging transportation.
#4 Re-evaluate your plan and have a “Plan B”
More unexpected things happen on vacation than during the rest of the year, so be prepared to re-evaluate your plan and adjust your work times and expectations. A Plan B for bad hotel WIFI, can be getting up early to work at a local coffee shop that has great WIFI. A Plan B for a noisy hotel might be working at a library.
If you can’t get as much done while following Plan B, that’s okay. As long as you have chunked-out your work and prioritized, you’ll still get the most important stuff done.
#5 Keep everyone informed
At the end of every work session, let your vacation buddies, boss, client, or business partner know your plan for the next session. If your plan isn’t working, tell them you had to move to Plan B and might not get as much done as you and they wanted. Keep managing everyone’s expectations about your work throughout your vacation. People will be more understanding when they see that you have a solid plan and are working to the plan.
Check-out these other articles on defining your own work-life balance and the difference between workaholism and healthy immersion in meaningful work.
Do you have any tips for planning vacation work? Please let me know by leaving a comment, below. Or, you can connect with me and comment on Facebook, LinkedIn, and Twitter. Also, please share this article with your family, friends, and coworkers.
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Great but vacations should be to re-charge your battery if at all possible.