The Holidays, Time Off, and Why Unwinding Is Harder Than It Should Be

The holidays are supposed to be a pause.
A slowdown.
A chance to reset before the new year.

And yet, for a lot of people, they’re anything but restful.

Calendars are technically lighter.
Out-of-office messages are on.
Slack is “quiet.”

But mentally? Many people are still very much at work.

This isn’t a failure of discipline or gratitude.
It’s a boundary and systems issue, and the holidays expose it.

The Holiday Illusion of Rest

December creates a strange kind of pressure.

There’s an expectation to:

• close loops

• finish strong

• tie everything up neatly before year-end

At the same time, we tell people to “take time off and recharge.”

Those two messages often collide.

So people try to do both, and neither fully works.

They take the days, but carry the weight.
They step away, but stay available.
They rest physically, but not mentally.

By January, they’re back, but not restored.

Why Time Off Around the Holidays Feels Different

Holiday time off is uniquely hard because it sits at the intersection of:

• personal obligations

• family dynamics

• financial stress

• year-end performance pressure

• planning for what’s coming next

For leaders especially, this is when the mental load is heaviest.

Even when they’re “off,” they’re:

• thinking about headcount

• replaying decisions

• worrying about what January brings

• holding responsibility they don’t know how to set down

This isn’t a discipline problem.
It’s a boundary problem.

If Boundaries Aren’t Clear, Time Off Becomes Performative

Many organizations technically support time off.

What they don’t support is disconnection.

If leaders:

• keep messaging “just in case”

• expect replies during shutdowns

• reward responsiveness over rest

• pile work up for people to return to

Then the holidays become a test of loyalty, not a break.

People notice.

And over time, they stop believing the message that rest is valued.

The Real Reason People Don’t Unwind

Here’s what doesn’t get said enough:

A lot of people don’t know how to unwind anymore.

They’ve spent years in high-growth, always-on environments.
Their nervous systems are used to urgency.

So when things finally slow down, their bodies don’t.

They feel restless.
Disoriented.
Anxious.
Guilty for not being productive.

This is why “just take time off” doesn’t work.

Unwinding isn’t a switch.
It’s a skill, and most workplaces never help people build it.

What Healthy Holiday Boundaries Actually Look Like

In organizations with strong boundaries, the holidays feel different.

Not perfect, but lighter.

That’s because:

• expectations are reset in advance

• coverage plans are clear

• work is intentionally paused, not just postponed

• leaders truly disconnect first

• returning teams aren’t punished with chaos

Time off feels restorative because the system can hold without constant vigilance.

That’s not generosity.
That’s good design.

HR’s Role at Year-End Isn’t Policing PTO

Good HR doesn’t spend December reminding people to “use their days.”

It helps the organization ask better questions:

• What breaks when someone steps away?

• Why does it break?

• Where is knowledge concentrated?

• Which roles are carrying too much?

• What signals are leaders sending, intentionally or not?

The holidays are a mirror.

If no one can unplug, something upstream needs attention.

A Better Way to Enter the New Year

Rest isn’t the opposite of ambition.
It’s what makes ambition sustainable.

Boundaries aren’t about doing less.
They’re about making space to do the work that actually matters, without burning people out in the process.

The organizations that get this right don’t rely on willpower or goodwill.

They build systems that respect time, energy, and humanity, especially when the year comes to a close.

That’s how you start January with clarity, not exhaustion.

If year-end always feels heavier than it should, you’re not alone.

We see this every December: good leaders carrying too much, unclear boundaries, and systems that rely on people staying “on” even when they’re supposed to rest.

This is exactly the kind of work we help with at The People Group, building People systems that allow time off to actually feel like time off.

If this resonated, feel free to reach out.