A 7-point checklist to prepare for holiday PTO so you can truly unplug during your time off

A 7-point checklist to prepare for holiday PTO so you can truly unplug during your time off
Anna Dearmon Kornick says setting boundaries is important to be able to really enjoy your time away from work.Anna Dearmon Kornick
  • Anna Dearmon Kornick is the head of community at Clockwise, an intelligent calendar assistant tool.
  • She says the key to relaxing time off is planning ahead and setting boundaries with your colleagues.

Picture this. Your out of office auto-responder is on. Your laptop is closed. You're ready to step into your PTO completely present, and the only thing on your to-do list is to enjoy the holidays. Sounds like a dream, right?

But then, the nightmare begins. A client has an emergency, a coworker has an urgent question, and your phone vibrates with a Slack message. Suddenly, you realize you didn't finish that one thing on your list. You close your eyes, and take a deep breath. Out comes your laptop as your dreams of peaceful PTO vanish into thin air.

Fortunately, this doesn't have to be your reality. To truly unplug during the holidays without feeling overwhelmed, it just takes a little preparation. The best time to start preparing is a few weeks before you plan to put up your out-of-office message and disconnect. Then, follow this checklist.

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1. Assess your to-do list

A few weeks before your scheduled time off, take stock of your current projects that are in motion. Scan your task list, your project management system, and create a quick, high-level list of everything you're working on.

2. Check in with your boss

Priorities tend to shift around the holidays. For some, this means that work slows down to accommodate busy schedules. For others, it means ramping up and moving even faster. Talk with your manager in advance to make sure that you're aligned on priorities. That way you're focusing your days prior to being on leave on the projects that matters most.


3. Talk with your team

If any of your current projects require collaboration with coworkers, vendors or other partners, you'll want to incorporate your team's availability into your Out of Office plan. Communication is key, and definitely don't assume that you're the only one with plans to be offline during the busy holiday season.

4. Set boundaries

The key to successful PTO begins with setting boundaries in advance and clearly communicating them. If they're not clear and haven't been communicated, they might as well not even exist. Here are questions to consider:

  • What am I willing to do during my PTO?
  • What am I NOT willing to do during my PTO?
  • What constitutes an emergency?
  • What can wait until I return?

When you identify and articulate your boundaries in advance, you're much more likely to hold firmly to them when something does inevitably pop up.

5. Decide what 'done' looks like

It's so important to have a stopping point in mind in order to combat Parkinson's Law. Parkinson's Law states that "work expands to fill the time allotted." If you don't decide in advance what "done" looks like, you'll be tempted to keep working through your PTO or you'll spend your precious days off worrying about work you could be doing. Nip the worry in the bud by deciding what "done" looks like.

6. Reverse engineer your wrap-up plan

Working backwards from your last day in the office, put together a simple plan for each of your projects that incorporates your team's availability for collaboration and helps you arrive at "done" on time and ready to close your laptop.


7. Set your out-of-office autoresponder and update your calendar to reflect your days

When you set your out-of-office message, be sure to communicate:

  • When you'll return
  • Whether you'll be checking or responding to email while you're away
  • Expectations for when you will respond
  • Who they can reach out to for assistance in your absence
  • Pro Tip: Include a recent blog post, news mention, or other piece of content that they can check out in the meantime.

Yes, you really can — and should — unplug, disconnect, and step away during your upcoming PTO stress-free. It just takes a little bit of prep, clear communication, and setting clear boundaries with yourself and others.

Anna Dearmon Kornick is the head of community at Clockwise, an intelligent calendar assistant tool. She also hosts It's About Time, a podcast about time management and work/life balance.