Finding Calm in the Holiday Swirl: A Leader's Guide to the Final Stretch
Every year around this time, the pace quickens. Deadlines tighten. Priorities multiply. Calendars fill—both at work and at home—as if all the world agreed that December should be a sprint.
Even in the most flexible work environments, it’s hard to escape the swirl. There are goals to close, projects to land, budgets to finalize, performance conversations to prepare for… all while navigating holiday programs, elf shenanigans, gifts, travel, winter concerts, crowded stores, and the sudden realization that you still haven’t bought wrapping paper.
It’s the season where must-dos and want-tos tangle together like holiday lights. And for many leaders and their teams, that collision can feel overwhelming.
Add in the mental countdown to December 31—the invisible clock that seems to tick louder with each passing day—and even small tasks can take on unnecessary urgency. It can start to feel like everything needs to be finished before the ball drops.
But here’s the truth most of us need to hear right now: Finishing strong doesn’t mean doing it all. It means choosing what matters and giving yourself and your team grace for the rest.
As we move through this last stretch of the year, here are a few gentle reminders to help you protect energy, keep perspective, and create space for a more joyful and realistic finish.
Reminder 1: Give Yourself—and Your Team—Some Grace
This season carries equal parts sparkle and responsibility. People are juggling school breaks, sick days, delayed flights, holiday gatherings, emotional milestones, and the complicated mix of joy and exhaustion that December brings.
Grace isn’t a soft skill right now. It’s a survival skill.
A few things worth remembering:
Not everything needs to make it onto this year’s “done” list
Some projects will be stronger with January clarity
Your team is carrying more than what shows on their calendars
Encouragement goes further than pressure—especially now
Offering grace doesn’t lower the bar. It lifts the people who are trying to reach it.
Reminder 2: Protect Your People’s Energy (and Your Own)
Everyone feels the year-end push differently. Some teams are sprinting. Others are planning. Most are operating with shorter weeks, added stress, and inboxes filled with last-minute requests.
Your team doesn’t need more urgency or pressure. They need steadiness, understanding, and maybe even a little breathing room.
A few supportive gestures that go a long way:
Ask what feels heavy - and help them prioritize
Offer flexibility where it's possible
Celebrate effort, not just output
Hold your own boundaries so they feel permission to hold theirs
Protecting energy now sets the stage for real momentum in January.
Reminder 3: Celebrate the Season (Whatever That Means for You)
Amid the push to wrap up the year, it’s easy to forget that this is also a season of meaning. Reflection. Nostalgia. Connection.
Even small moments of celebration can shift the tone for an entire team:
A quick pause to acknowledge wins
A heartfelt thank-you
A moment to laugh, breathe, and regroup
A chance for people to be authentic—not just productive
Celebration isn’t a distraction. It’s a moment of light in a very full season—one that reminds people why the work matters, and why they matter to each other.
The Year-End Crunch Doesn’t Have to Break Us
Yes, this season is full. Yes, the pressure is real. Yes, the countdown can make everything feel more urgent than it truly is.
But when we choose intention over frenzy, clarity over clutter, and grace over pressure, we don’t just get through the year-end crunch.
We finish strong. We begin stronger. And we show our teams what it looks like to lead with heart in a season that asks a lot of everyone.
This is the kind of leadership WorkWell believes in. And the kind we’re honored to support—now and in every season ahead.