What to Do the Week Before You Leave for Vacation

(Photo: Julien Belli/Flickr)
(Photo: Julien Belli/Flickr)

In our frenetic corporate culture, even claiming your vacation time is a small victory. But with 24/7 expectations increasingly commonplace, it’s essential to lay the groundwork for a successful vacation prior to leaving town, to ensure your time off isn’t interrupted by pseudo-emergencies and coworkers trying to “keep you in the loop.” Here are four things you should arrange in the days before you depart to maximize your vacation experience.

Triage Time-Sensitive Matters. Depending how long you’ll be gone, you’ll want to line up every project or obligation by due date. Then, complete or delegate anything that falls within the dates of your vacation, or a few days afterward (because you’ll likely be playing catchup on email, meetings with colleagues, etc.). For instance, before leaving on my last vacation, I made a point of paying all my bills, because stressing out about a missed payment is the last thing you want to do on the road.

Set Email Expectations. Unless you’re headed to the middle of the Amazon, you’ll likely still have access to a smartphone—and therefore could, theoretically, be checking your email every day. It’s important to clarify a plan upfront with your coworkers. Will you check it once a day? Or tune out entirely? Will someone else be monitoring your inbox? Your autoresponder will likely clue in most people that you’re away, but it’s almost certain someone won’t pay proper attention. It’s useful to arrange coverage or at least set expectations so you won’t be penalized if you “miss” something while you’re away.

Create a Contingency Plan. Hopefully it’s unlikely, but there may be emergencies that arise. Check in advance if your cell phone will work (some carriers function overseas and others don’t), and create a backup plan just in case someone needs to reach you in the case of a genuine problem (such as sharing your itinerary, including hotel phone numbers, with at least one colleague). It’s also useful to specify what type of situations warrant getting in touch. In The Four-Hour Workweek, Tim Ferriss famously recounted his decision to authorize customer service representatives at the company he ran to make decisions on expenditures up to several hundred dollars. It cost him money, but saved him a ton of stress and hassle—and most of the time, their decisions about refunds and other issues matched what he would have done, anyway.

You may also decide to outsource crisis management entirely, as my colleague Steve did a number of years ago. He was a solo consultant headed to Central America, and suspected as the trip approached that 1) his cellphone wouldn’t work; and 2) one of his clients might be hit with a negative story in the press. He arranged with me and the client to ‘cover’ for him, paid me a portion of his monthly retainer, and I handled the emergency which did, in fact, arise. Many solutions work here – but for your sanity, it’s important to plan them in advance.

Set Expectations with Your Traveling Companion. Understandably, most of the pre-vacation focus is about what needs to happen at work before you depart. After all, you’re leaving the office behind and will be focusing on your partner, family, or friends for the next week or two. But leading up to your departure, it’s important to set expectations with them, just as you would with coworkers. During a month I spent traveling in India a few years ago, I put several monthly client retainers on hold and didn’t submit a new business proposal that I was invited to, because I was committed to taking time off and spending it with my then-partner. The cost? At least $20,000 in booked revenue, and perhaps up to $50,000 if I’d won the new business pitch.

I thought I was over-indexing on being a devoted girlfriend —but when I decided, over the course of a month, to take two hour-long business calls to talk about possible speaking engagements, I endured days of withering silence because I was “prioritizing work” instead of our relationship. Perhaps needless to say, we’re not together anymore—but if we’d clearly set expectations upfront about how much time we were spending together and what an acceptable mix of work and pleasure looked like, perhaps we’d have had fewer fights (or found more compatible traveling partners).

Vacations are increasingly rare in these hurly-burly times. If you’re going to take one, you can ensure you enjoy it more and aren’t constantly pulled back into banal office concerns by triaging the urgent upfront, setting expectations with both coworkers and your traveling companions, and ensuring that if a true crisis does emerge, you can be reached—or they at least know who else to call.

Dorie Clark is a marketing strategist who teaches at Duke University’s Fuqua School of Business. She is the author of Reinventing You and Stand Out. You can receive her free Stand Out Self-Assessment Workbook and follow her on Twitter. What to Do the Week Before You Leave for Vacation