How To Take A Two-Week Vacation Guilt-Free

Most American professionals don’t take two consecutive weeks off, but it can be done–and it feels awesome.

How To Take A Two-Week Vacation Guilt-Free
[Photo: Unsplash via Pixabay]

Europeans may spend the entire month of August at the beach, but Americans tend to think of vacations as week-long events at most. The average full-time worker gets 10.2 paid vacation days after 3 years on the job, according to the Bureau of Labor Statistics, and even professional workers with a decade of service average just 16. But even with that limited time off, most people won’t take most of it at once because they worry about the ramifications if they do.


Yet some busy people do manage to take real vacations–at least two consecutive weeks off. Here’s how they do it, guilt-free.

Create A Vacation Action Plan

“It’s a lot easier to feel comfortable taking a couple weeks off if you’ve had a longer time line to plan,” says Josh Warborg, district president at Robert Half in Seattle. He often takes two weeks off over the winter holidays, and this summer will be taking a two-week trip to see the Tour de France, with a “vacation action plan” in place so business does not stop.

A good rule of thumb several vacationers mentioned is to start planning at least a week ahead of time for every business day you’ll be gone (e.g. 10 weeks for a 2-week trip). Since you may need to give this much notice to claim vacation time during busy stretches, it doesn’t take much extra work to think through processes while you’re asking for dates.

Make Sure There Is Someone To Cover You

We all like to think we’re indispensable, but in well-run businesses, that shouldn’t be the case. Brian Scudamore is the founder and CEO of O2E Brands, the banner company for 1-800-GOT-JUNK? and other firms. His employees get five weeks of vacation, he says, and are encouraged to use it, but they must have backup for the time they are gone. Cross-training at least one other person on each person’s job means that no one can become a bottleneck. That’s good for vacations–but also if people get sick, called for jury duty, or quit unexpectedly.

Melisa Rett, assistant director of operations for the Sentinel Operations Center at the Harvard Pilgrim Health Care Institute, recently visited the Azores for two weeks with her husband. “A few weeks before, I made sure the colleagues and collaborators I work with daily were aware of my vacation,” she says.

“Then I made a list of my responsibilities that couldn’t be put on hold, found a backup to cover for me, and spent a little time making sure my backups had all of the information needed either via a brief meeting or writing a detailed email.”


She canceled any meetings she normally ran or designated a backup. “Fortunately I could spread around my responsibilities to a few different coworkers so it wasn’t too much of a burden for any one person,” she says. If you’re doing that, make sure you list each person’s function in your out-of-office email contacts section.

Expect Pre-Vacation Madness

Maureen Anderson’s family took a two-week road trip over the winter holidays. Because she and her husband run a syndicated radio show (Doing What Works), they had to produce several extra episodes ahead of time. “We often joke that if we didn’t take a vacation we wouldn’t need one,” she says. But it helps to keep your eyes on the prize: weeks with nothing on your plate but fun.

Limit The Check-Ins

Scudamore takes six weeks off each summer, hitting such places as Provence, or Kenya. “I completely disconnect from email, completely disconnect from social media,” he says. To make sure he sticks to staying disconnected he asks his assistant to change his passwords. “I can’t control myself,” he says and “you can’t fully recharge if you’re thinking about business.”

That’s one way to go dark, but there are others. If you are worried about being completely off the grid, you can give one trusted person the cell phone number of your spouse or a travel companion, with instructions to call in an emergency. Most things won’t reach that bar. You can also give people a personal email address for emergencies and only check that, so you don’t see routine work matters.

Some people decide that they do want to do a bit of work, but if so, you can limit the mental overflow by checking in for a few minutes in the morning before your travel companions wake up. Then you unplug for another 24 (or 48) hours until the next check-in.

Reduce The Amount Of Email You’ll Come Back To

If you get 150 emails a day–a pretty average number–then being out of contact for 10 business days means there will be at least 1,500 messages waiting for you. This can be agonizing for fans of Inbox Zero. That’s one reason some people don’t take two-week vacations, but it doesn’t need to be one. Likely, only 10-15 emails a day will be important, and half of those will be overtaken by events (or your work buddy will have dealt with them in your absence).


Inbox 50 is more manageable than Inbox 1,500. Indeed, most of those 1,500 messages will be so obviously unimportant you can delete them instantly. If this takes you one second per deletion, that totals 25 minutes of cleanup. It’s not nothing, but it’s not a reason to skip a vacation either.

If possible, you can also have someone you trust (e.g. an executive assistant) clean up your inbox in your absence. Scudamore’s assistant sets a goal of dealing with all his emails, and summarizing all news into a single message. “I don’t come back to hundreds and thousands of emails,” he says. “I come back to one.”

Brace For Push-Back

Ideally, everyone would cheer your vacation. You’ll come back relaxed, recharged, and happy to cover for your colleagues, which you should do (a souvenir gift is a nice touch, too, for anyone who’s provided heavy coverage). Unfortunately, that does not always happen. Some people report snide remarks, even notes in performance reviews, about extended vacations.

You can’t change other people’s mindsets, but you can also decide it’s worth it. With just a one-week vacation, “the first two or three days you’re shaking off whatever you left behind, and for the last couple days you’re gearing up for whatever’s waiting in your inbox,” says Anderson. “That leaves you with–what?–two days of actual rest.”

Whereas a two-week vacation gives you closer to double digits of days to truly unwind. You can make memories that will sustain you until your next vacation.

About the author

Laura Vanderkam is the author of several time management and productivity books, including I Know How She Does It: How Successful Women Make the Most of Their Time (Portfolio, June 9, 2015), What the Most Successful People Do Before Breakfast (Portfolio, 2013), and 168 Hours: You Have More Time Than You Think (Portfolio, 2010). She blogs at