C-Suite Advisory

The Right Way to Prepare for Stress-Free Time Off

Americans are notorious for leaving vacation time unused each year. In 2019, 768 million days were left unused, and it’s only gotten worse since pandemic-induced remote work and travel restrictions (and hesitation) became the norm. Now that work and life are happening in the same space for many of us, practicing self-care and taking intentional breaks are more important than ever before.

Due to unrealistic expectations and overcommitted workloads, it’s no surprise that we’re so reluctant to step away from the laptop and shut down for a few days. Instead of looking forward to relaxing days off, we anticipate inevitable work emergencies and returning to a mountain of requests. As a result, just the thought of taking time off induces stress.

Fortunately, it doesn’t have to be that way. It is possible to unplug during PTO without feeling overwhelmed, it just takes some intentional preparation. 

The best time to start preparing is a few weeks before you plan to put up your out of office message and disconnect.

Build your bench

If your upcoming time off is only a few weeks away, it is likely too late to begin this critical step. However, building a trusted support staff is a critical component to taking stress-free leave. Whether your team includes an executive assistant, chief of staff or other key roles, identify which leaders within your organization can stand in for you when needed. If you assess your current team and recognize knowledge or skill gaps, it could be time to prioritize a new hire or hires that have the expertise available to provide coverage when you are away from the office.

Assess your to-do list

A few weeks prior to your scheduled time off, take stock of current projects and initiatives. Scan your project management system and check in with your direct reports. Then, create a quick, high-level list of everything that could require your attention during your time away. Your next step is to ruthlessly prioritize each of these projects and communicate expectations with your team. 

As your PTO dates draw near, it’s important to have a stopping point in mind for each project 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 continue working through your PTO. When you’ve articulated what “done” or “enough” means for each project, you decrease the time spent worrying about work you could be doing while you’re away.

Set boundaries

The key to enjoying your time off and avoiding burnout during PTO requires you to set boundaries in advance and clearly communicate them. Don’t wait until day one of your time off to consider your boundaries. If they’re not clear and haven’t been communicated, they might as well not exist. Instead, ask yourself prior to departure:

  • 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, not only are you taking a step to combat decision fatigue, but you’re also much more likely to hold firmly to them when something does inevitably seek your attention.

Automate and Delegate your Out of Office communication

While we’re no stranger to the Out of Office message, most automated responses do a poor job of communicating expectations. Instead of simply setting a message letting recipients know you’re out of the office, consider providing the following information:

  • When you will return
  • Whether you’ll be checking or responding to messages while away
  • Expectations for when you will respond
  • Who they should reach out to for assistance in your absence

If you communicate regularly with different groups of individuals, for example, current clients, prospective clients, vendors or a board of directors, provide expectations for when you will respond to each group in the automated message. This makes it crystal clear when someone may expect a response from you and can decrease the number of follow-up messages to enter your inbox.

In addition to communicating expectations through an automated Out of Office message, create  a one-page document with frequently asked questions to share with your support staff. Equipping your team with answers to commonly asked questions can reduce the possibility that you’ll be interrupted during your time away.

Yes, it is possible to unplug, disconnect, and step away during your upcoming PTO totally stress free. It just takes a little bit of prep, clear communication, and setting clear boundaries with yourself and others.


Written by Anna Dearmon Kornick.

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Anna Dearmon Kornick
Anna Dearmon Kornick is head of community at Clockwise, a leading smart calendar software company that’s changing the way people work and organize their time through artificial intelligence that automatically organizes calendars. Anna is also a time management coach who helps busy professionals and business owners master the skills needed to stop feeling overwhelmed and start spending time on what matters most. She even hosts a podcast, “It’s About Time,” that discusses work and life balance, as well as time management tips, productivity strategies and real-life advice to help her listeners make the most of their time.


Anna Dearmon Kornick is an opinion columnist for the CEOWORLD magazine. You can follow her on LinkedIn. For more information, visit the author’s website.