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May 17, 2016

Office Hours: How to Take a Vacation Like a Pro

PSA: despite everyone’s favorite Game of Thrones tagline, winter isn’t coming. Summer is the season actually speeding our way, and it’s dragging the memories of sweet, sweet three-month vacations in its wake.

As a young professional fresh enough out of college that I still refer to the period of time between Christmas and New Year’s as “winter break”, I empathize with the struggle to transition from a student’s mentality to one that doesn’t involve twelve annual weeks of unstructured free time.

Vacationing while employed requires far more thoughtfulness and preparation than it did as an undergrad. Luckily, we’ve got you covered. Here’s how to get out of the office and onto the beach in six easy steps.

When you first start thinking about a vacation….

  1. Consider waiting at least three months. Starting a new job means learning new names, a new employer history and modus operandi, new engagement platforms, and plenty more. You’re figuring out your new daily routine and trying to impress your manager and the rest of the office by showing them exactly how committed you are to helping your company thrive. This is not the time to road trip across America, embark on a Eurotrip, or try to hit up every country between South Africa and Morocco. Waiting three months before you start checking Google Flights during your lunch break is a good rule of thumb — by this point in time, you’ve (hopefully) established your presence and dynamic on the team.
  2. But if the vacation’s been planned since before you accepted your offer, this is the exception to the rule. A pre-planned vacation is something to discuss with the hiring manager or your future team lead in the last stages of the hiring process. Be forthcoming about the time and duration of travel, although you do not need to be specific about the reason. This is part of negotiating your new position, so consider being flexible with your start date. Try: “What do your needs look like during the week of XX/XX? I have a pre-planned vacation at this time, and want to make sure that the work I do and the team’s work will not be unduly affected.”

Once you’re ready to relax….

So you’ve been at your new job for three months and two days, the office dog makes a beeline for you when it wants a walk, and you’re starting to generate and pursue your own leads. It’s still too soon to aim for that two-week sabbatical, but a four-day reprieve is now probably warranted. Planning for a vacation can be tough for many reasons; like a parent or the proud owner of a Neopet, you now have more to worry about than just yourself. Your vacation shouldn’t involve stressful back and forths about who was responsible for what component of a project—for you or your team. So:

  1. Ask for those days off! Have this conversation in person, but it’s good practice to follow up in an email afterward. Let your manager know that you’re thinking of taking some days off, and when you’re hoping to do so. Especially as a junior team member, avoid taking extra time off around busy periods or already-scheduled holidays. During this discussion, check in with your manager about email — are you expected to be on-call, or can you just screen your emails?
  2. Before you leave, check in with your manager and team. When you’re out of office for more than a few days, emails and tasks will pile up. Make this inevitable deluge easier on yourself and your office by speaking with your coworkers about where you are on your projects, what needs to be done while you’re away, and who will be filling your shoes while you’re out. (This person should be listed on your out of office responder, which you should not forget to set up!) Put your time off on the team calendar and your personal calendar, and send a reminder in advance to update your manager and collaborators on where you are in your workload and where you expect to be before you leave.

When all that’s done, go forth and enjoy your well-deserved time in the sun!

And when it’s time to come home…

  1. Don’t schedule meetings the first morning back! This may not be in your control — and if it isn’t, try to plan your travel to allow for time either the night before or earlier than usual the next morning. If you can, however, try to block off your first morning back. Coming back from vacation only to be bombarded with emails, requests to respond to emails, or questions about your uneven tan lines can be a little distracting and stressful—but it’s not so bad if you‘re prepared!
  2. Ease yourself away from the beach and back into the office. Take an hour or two to respond to emails, plan out your day and the rest of your week, catch up on what’s happened while you were gone, and reacquaint the office dog with your scent by bribing him with strips of jerky.

And that’s it! Now you’re ready to vacation like a pro(fessional).

VFA Has Ceased Operations


Since its first cohort in 2012, Venture For America (VFA) has championed entrepreneurship, innovation, and economic growth across the nation. As of August 6, 2024, VFA has ceased its operations. While this marks the end of an era, it also provides an opportunity to reflect on the extraordinary accomplishments and lasting impact that we have achieved together.

Please click here to read the full update.

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