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You’re not “too busy”: The best time to schedule OOO time

scheduling out of office
The Robin Team
Published on

We chatted with time management expert Laura Vanderkam on the ideal time of year to schedule vacation time.

Summertime, and the workin’s not easy. Beyond the neverending projects, half your team already scheduled vacation time this season. Productivity already feels like it has taken a hit. When are you ever going to be able to take time off? Sounds like you may be desperate for some expert scheduling advice on the best time of year to disconnect.

We synced up our own schedules with Laura Vanderkam, bestselling author and speaker on time management, career development, and work-life balance. She provides two easy solutions for you to detach from your 9-5 for a few days or a few weeks. It’s time to throw the excuses out the window.

Option 1: piggyback vacation time on company holidays

Laura Vanderkam tells us why it works:

In general, the easiest time to take a vacation is when the opportunity cost is low -- that is, most people aren't getting much done anyway, and you have some official holidays so you can take a long vacation with few "real" vacation days.

Obvious examples: the days around the 4th of July -- this year it was on a Wednesday, and a lot of people had M-T-W off, so if your office had summer Fridays (half days) you could take a 9-day trip for the price of 1.5 vacation days (given the weekends on either side). The same phenomenon can occur around Christmas.

Use the piggyback tactic if:

  • You don’t have a lot of vacation days to begin with
  • You have a crazy workload and need to take time when other people are mellowed out

Don’t use the piggyback tactic if:

  • You’re looking for a break when you’re in the midst of full work week busy periods
  • You’re competing with colleagues for vacation slots and cannot duplicate time off requests

How to check what your options are:

  • Check your company vacation policy. Do you follow stock market holidays or a custom list of days? You likely have several Mondays off throughout the year with the two more popular holidays in the middle of the summer and winter.
  • Check what dates your colleagues have already requested off, either through Outlook or Google Calendars or in an HR platform like BambooHR.
Humanity Why You Should Take Vacation
Whatever you end up doing, stop NOT scheduling vacation. via Humanity.

Option 2: request time off during standard work weeks

Laura Vanderkam says:

There's much to be said for taking a vacation when other people aren't. You get a real break, and then get to relax on the lower-key work days around holidays.

Use the standard work week tactic if:

  • You have a lot of vacation days to begin with
  • You’d otherwise be competing with colleagues for extra days around existing holidays
  • You want to disconnect in addition to the existing holidays

Don’t use the standard work week tactic if:

  • You don’t have a lot of vacation days
  • Your workload is too heavy consistently throughout the standard work weeks

How to check what your options are:

  • Check your company vacation policy. Do you have three weeks or more? You should be able to take five to ten days off and get out of the office.
  • This is a big one - be smart about your workload schedule over the course of the year. Check your project calendar. Do you have slower periods during the year that wouldn’t disrupt major projects you’d be contributing to? Sometimes immediately after a big project or event is the best time to take a vacation, when you put in a lot of work up front and would just be relaxing back at work afterward anyway. Different roles or industries typically have a standard for this (i.e. accounting, roles with month-end or quarter-end goals)
Humanity Use It or Lose It Vacation Days
Use it or lose out on it, whether or not you can roll over, via Humanity.


No matter what, don’t feel guilty. It’s necessary to disconnect to recharge your brain and contribute more positively at work once you’re back. And if you schedule things right as well as prep for your time out, things should be all gravy at the office while you’re gone.Bon voyage!

Robin Vacation Post Call to Action

Sources: Laura Vanderkam, Humanity, Vecteezy

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