September brings a familiar shift across many workplaces: summer flexibility gives way to busy fall calendars, Q4 planning ramps up and taking vacation suddenly feels at odds with the mad dash to end the year strong. Despite what the return of the pumpkin spice latte suggests, summer isn’t over until September 22, and Labor Day hardly marks the last chance to take a meaningful break before year-end. Long weekends, fall breaks and holidays offer plenty of reasons to use paid time off (PTO) along the way.

However, taking the time is only part of the challenge. For many workers, the anxiety starts well before the vacation does.

Among workers who don’t use all the paid time off available to them, Pew Research found that 49% worry about falling behind at work. Similarly, a 2025 FlexJobs report found that 43% of workers said their workload was too heavy to justify taking time off.

And once someone does decide to take time off, many professionals put considerable mental energy into making their absence manageable for others: write handoff notes, agonize over the right out-of-office response and ensure nothing catches fire before the flight takes off.

Most of that preparation is focused on the time away from the office , even when much of the stress stems from anticipating the first days back : an accumulated workload, marathon meetings and a case of the Sunday Scaries magnified by every day the inbox went unchecked.

One deceptively simple strategy addresses both.

The Future Self Brief: How Leaders Can Reduce Work Stress After PTO

As a workplace wellbeing strategist, I often encounter a persistent tension across organizations: how can people perform at a high level in demanding environments while making recovery a meaningful part of how they work?

One longstanding practice changed my own experience of taking time off and has since become one I regularly recommend to leaders: the Future Self Brief.

The idea owes something to my childhood love of Bill Watterson’s Calvin and Hobbes, and a particular storyline that always stuck with me. With homework due the next day, Calvin decides his future self can handle it. He climbs into his cardboard-box time machine and travels a few hours ahead, expecting Future Calvin to have finished the assignment. Instead, he discovers Future Calvin has been counting on Past Calvin to finish it first.

It’s a surprisingly apt metaphor for how leaders typically prepare for PTO. We leave thoughtful instructions for everyone navigating our time away, but rarely think to leave any for ourselves when we’re back.

The Future Self Brief fills that gap. It’s a one-page briefing written to yourself capturing the current state of work and high-level preparation for the first week back.

The distinction is simple: an out-of-office response tells others when to expect a reply. Handoff notes equip colleagues to handle what needs attention and ownership.

The Future Self Brief is designed for ourselves.

And there is another benefit: knowing that information has already been captured can make it easier to actually leave work behind. A 2025 meta-analysis published in the Journal of Applied Psychology found that psychological detachment from work during vacation was among the factors most strongly associated with greater well-being.

While the Future Self Brief can’t guarantee work never crosses the mind, it can create that mental distance by providing reassurance that the important details are accounted for and there’s a plan for the first days back.

How Leaders Can Write a Future Self Brief Before Taking PTO

The most useful Future Self Brief will look different for every leader based on the realities of their profession, organization and responsibilities. A CFO will almost certainly write a different brief than a salesperson, physician or consultant.

However, a few sample prompts can help provide the structure:

1. Current State of Business

For each active workstream, client or project, note the last meaningful development, the next milestone or response expected and who is responsible for it. Essentially, preserve the details that would otherwise require digging through a week of Slack messages and meeting notes to refresh your memory.

  • What are the last substantive developments on each key priority?
  • Which response, approval or next step may need follow-up when you return?
  • What context would be difficult to find later in an email thread?

Record what a project tracker cannot. Document an honest snapshot of your judgment and emotions upon departure.

  • What still feels unresolved?
  • What are you most concerned about?
  • Where do you feel particularly confident or optimistic?

Establish the first week’s priorities before a full calendar and overflowing inbox start setting them for you.

  • Look at the Calendar : Write out light preparation and context for the most important meetings and calls.
  • Map Your Follow-Ups: Which colleagues, clients or other stakeholders do you need to communicate with first? Where useful, draft the message before leaving. If it still makes sense after time away, it is ready to send.
  • Create Your Action Plan: Write out the first three tasks you will tackle when back in office while the context is fresh.

One final step can make the Future Self Brief considerably more helpful: protect time on the calendar to use it. After a longer trip, that might mean a buffer day; when that isn’t realistic, even a meeting-free morning creates time to actually execute the brief. Otherwise, a first day back can quickly become a succession of meetings scheduled by people who understandably have their own priorities.

Takeaway: Keep it to one page. The idea is to create a useful document that takes minutes to scan on the first morning back and relieves stress while you write it rather than becoming another pre-vacation assignment of its own.

The Future Self Brief: The Strategy That Belongs in Every Leader’s PTO Plan

The Future Self Brief can be useful regardless of the PTO length. Whether for a two-week vacation, a long weekend or a few days over the holidays, the practice creates space to mentally disengage from work and experience the benefits of the time away.

The point Calvin missed all those years ago was simple: Future Calvin just needed Past Calvin to leave better instructions.

Fortunately, everyone else can learn that lesson without climbing into a cardboard box.