The holiday season always reminds me that there is such a thing as too much of a good thing. My kids start winter break thrilled—new toys to play with, days at home, permission to veg out. But by the time the new year rolls around, they’re itching to go back to school, eager to show off their favorite holiday gifts and dive back into their routine.
It got me thinking: why don’t we, as adults, approach returning to work after a vacation with that same positive energy?
More often than not, coming back from time off stirs up feelings of anxiety. For some, it reaches the point of canceling out any lingering benefits of the break. Others overcompensate by overworking upon their return.
Just as kids head back to school after winter break with renewed energy and a few shiny new accessories, we can return to the office with a sense of anticipation instead of dread—and without burning out right away. It all comes down to planning ahead and making smart use of the AI tools in your toolbox.
Here are some of the strategies that I use and share with employees at Jotform to help ease back into work after time away.
Automate the admin so you can focus on what matters
After spending the holidays with my family in the Turkish countryside, one of my favorite parts of returning to work is catching up with colleagues—swapping stories and photos from our OOO adventures. But I wouldn’t have the time or energy to do that if I were buried under the tedious busywork of easing back into work mode.
That’s why I use, and encourage our employees to use, AI to automate as many manual administrative tasks as possible. It starts with an audit of your typical back-to-work routine, ideally before you leave the office, so you’re prepared ahead of time. Make a list of every task in a normal day and all your responsibilities. You’ll likely spot several that can be partially or fully automated with AI—like scheduling status meetings with Motion or Clockwise; taking meeting notes (and sending follow-up emails) with Fireflies.ai or Otter.ai; and managing your inbox with Superhuman, Shortwave, or Microsoft Copilot.
When you let AI handle the busywork, you create space for diving back into activities that you enjoy, like more meaningful creative work and reconnecting with your team.
Use AI to zoom out and see the big picture
Research shows that nearly half of American workers don’t take all their paid vacation time. One of the main reasons is that they fear falling behind. That worry isn’t entirely misplaced; stepping away from the daily grind does mean falling out of the loop for a bit. But it’s important to zoom out and keep your break in perspective.
Rather than focusing on the week-to-week, imagine that time off in the broader context of your year. Viewed this way, your vacation isn’t a setback, but rather, it’s an investment in your long-term productivity. Studies consistently show that professionals who take regular breaks enjoy better sleep, higher job satisfaction, greater engagement, and stronger performance.
Compiling quarterly recaps is a great way to maintain that big-picture view and track progress toward annual goals. AI can do it for you. Tools like Notion AI, ClickUp Brain, or ChatGPT can take your company data and summarize project updates, highlight milestones, and visualize your progress, without you having to manually compile the reports.
Seeing your progress and achievements laid out explicitly can help you keep OOO time in perspective and eliminate the stress of “falling behind” when you return.
Reignite curiosity and your momentum
One of the biggest challenges of getting back on track after time away is momentum. When you’re in the rhythm of work, collaborating with colleagues, or tracking project progress, productivity and ideation feel almost self-propelling. But after some much-needed R&R, getting that momentum back can feel like pushing a boulder uphill.
This is where AI can step in as a creative partner. Tools like ChatGPT can spark fresh ideas during brainstorming sessions, or analyze data—like marketing reports or customer feedback—to generate insights and actionable takeaways. By handling some of the initial heavy lifting, AI can help reignite the curiosity and creative energy that makes returning to work fun.
Finally, this may sound obvious, but give yourself time to ease back into work mode. Schedule some downtime, especially during the first week. Stagger your meetings, and resist the urge to burn the midnight oil right away. This can help prevent “reentry shock”—that disorienting jolt from relaxation to chaos. With a little thoughtfulness and some helpful AI tools, leaders and their teams can painlessly get back into the swing of things.
