A New Way to Think About Your Vacation Time

Photo illustration; Image sources: C Squared Studios/RICHARD EDEN/Getty Images

In late 2019, I got an idea: I would plan the entire next year’s vacations at once.

There were a few reasons I thought this was a brilliant approach. First, my husband and I could block the same dates that our kids weren’t in school, so all our days off would coordinate. Second, it allowed for better interfamily PR; the ski faction wouldn’t grumble about spring break beach plans, since they knew we had a booking in Colorado over Christmas. And finally, research finds that anticipation accounts for the bulk of the happiness associated with any vacation — so planning far ahead meant we would have a lot to look forward to in 2020.

By thinking of the year holistically, and then managing your “portfolio” of vacation time, you can maximize your enjoyment, whatever life dishes up.

Look at the whole year at once

While vacation time varies wildly, most workers have a reasonable number of days to play with. According to the Bureau of Labor Statistics, the average U.S. worker with five years of experience at a company has 15 paid vacation days. Add in the major holidays when many offices close (a few days around Thanksgiving and Christmas, New Year’s, Memorial Day, the Fourth of July, Labor Day) and many people are looking at 20-plus days to allocate in the portfolio. By strategically stacking vacation days with holidays and weekends, you can score multiple longer chunks (for example, nine days around Thanksgiving for the price of three vacation days if your office closes for that Thursday and Friday). You can also pepper the calendar with smaller bits of time off where they’d do the most strategic good.

So look at a calendar of the whole year. Look at your kids’ school calendars. Map out what time would make sense for the big chunks — maybe spring break, a few days around the Fourth of July, and Thanksgiving week. Or maybe you’re not beholden to school schedules, and you can take a week off in February and October.

Consult your bucket list

At the same time, think about options. I recommend making a List of 100 Dreams — a bucket list of sorts of anything you might want to spend more time doing in life, travel and holiday activities included. You could aim to pull one travel goal off the list each year. Some international destinations might not be available (at least in the first half of 2021) but think about what options are available closer to home. Driving to beautiful places and renting homes that allow you to stay far away from crowds works whatever the Covid situation.

Consult with your team

Discuss these ideas with anyone you vacation with, and see if you can agree on a plan. Looking at the whole year allows you to accommodate more people’s preferred vacation options, or to mix things up, and also allows you to watch the budget. If you agree on a bigger ski trip in late November, you might agree to a more affordable beach rental in July (or vice versa). Figure out your optimal logistics.

Now, in this unpredictable time, whether you go ahead and book is a personal choice. I like to lock things in, though I know this tendency can lead to concerns about refunds (or the hassle of obtaining them). In general prices are better earlier, though not always — 2020, not surprisingly, featured more last-minute availability. But here’s the key: Mentally consider the trip booked, so you can start the happy process of looking forward to it. Dreaming about that summer beach trip can make a rainy December morning far more pleasant!

Don’t underestimate the random Wednesday

A balanced portfolio of time off can include breaks that are about recharging, not travel. So reserve a few days to scatter through the year for when you’ve got a long stretch between bigger vacations.

While it might seem rational to use these vacation days to create long weekends, with lots of people working from home, Friday afternoons tend to feature fewer scheduled events anyway. You might be able to get up early and put in a full day by noon — and then log off — without taking an official vacation day. Or an even better choice, in my book, is taking a Wednesday off here and there. If work feels like a slog sometimes, then taking a random Wednesday off just for fun will break up the week nicely. You only have to work two days in a row until you get your Wednesday off or your weekend off. On any given Monday, that can give you a lot to look forward to. Especially if you requested the Wednesday months ago — like a present from your past self.

Laura Vanderkam is the author of several time management books including Off the Clock and 168 Hours. She blogs at LauraVanderkam.com.

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