Why We're So Bad At Taking Time Off

Did you know that one of the biggest regrets of the dying is, “I wish I hadn’t worked so hard”?

That line always hits me. Not because it’s dramatic, but because it’s painfully ordinary. So many of us are living in a way that makes rest feel like a reward we have to earn instead of a basic human need. And if you live in a place with a proper summer, like I do in Toronto, it can feel especially absurd to work your way through the season while the good weather slips by in a blur.

I find myself thinking about all the hours we spend inside, staring at screens, telling ourselves we’ll slow down next week. Or next month. Or when things calm down, which is a hilarious little fantasy because things are never exactly calm, are they?

The summer we keep missing

How many of us are barely making time to enjoy the warm weather we wait all year for?

I keep thinking about lakes, gardens, morning coffee outside, campfires, long walks, and the kind of summer evenings that make you feel like a person again. Not a productivity machine. Not a calendar with legs. A person.

And yet, many of us keep pushing through, even while our bodies and brains are waving tiny white flags.

There’s a reason burnout is so common. We’ve been trained to think our worth is tied to our output. That rest is what happens after the work is done. But for a lot of people, the work is never really done. The inbox refills. The tasks multiply. The guilt shows up wearing sensible Birks.

Vacation anxiety is real

For many of us, time off comes with its own weird little sidecar of anxiety.

What will happen if I go away?

Will the project stall?

Will someone else get ahead?

Will I come back to a mountain of work and immediately regret leaving in the first place?

So we overprepare. We work longer hours before the break. We leave ourselves less and less spacious. Then we return and immediately dive back in, trying to catch up on the thing we were never really allowed to step away from.

It’s a terrible bargain. You spend the first half of your vacation unwinding and the second half dreading your return. Not exactly the restorative escape we were promised in all those glossy summer fantasies.

What helps

There’s no magic fix, but there are a few things that can make this whole mess more manageable.

1. Be honest about how important you actually are.

This one stings a bit, but in a useful way. Most of us are not as indispensable as our anxious brains would like us to believe. The work will continue. People will cope. Things will get handled. It may not be perfect, but perfection is not the requirement here. Being absent for a few days does not make you irresponsible. It makes you human.

2. Name what makes time off hard.

If rest makes you anxious, get specific about why. Is it unfinished work? A fear of disappointing people? Worrying that no one else will take care of things properly? Once you know what’s underneath the anxiety, you can actually do something about it. Delegate. Ask for help. Set up coverage. Make a re-entry plan that doesn’t feel like walking back into a fire.

3. Set one boundary and keep it.

Start small if you need to. Maybe weekends are not for work. Maybe you stop checking email after dinner. Maybe you create an autoresponder that reminds people you’ll respond on Monday and, yes, your weekend is protected. Boundaries are not dramatic. They’re just the structure that keeps your life from spilling everywhere.

I once decided that weekends would not be for work, and honestly, it changed things more than I expected. There was guilt at first. Then anxiety. Then, eventually, freedom. Funny how that works. Once I stopped quietly betraying my own intentions, I started to feel more rested, and more productive when I did return.

A better way to say it

Your autoresponder doesn’t have to sound like a legal disclaimer from 2004. It can sound like you.

Something like:

Weekends are for lake dips, garden coffee, long walks, and a very respectable amount of doing absolutely nothing. I’ll be back in your inbox on Monday, probably after a walk and my first coffee.

That says the thing without sounding like a robot with a permission slip.

And if you work for yourself, scheduling content ahead of time can take some of the pressure off. It’s one of the few places where being a little strategic actually helps you rest more, not less. I know. Suspicious behaviour.

If you can’t take the whole summer off

Not everyone can disappear to Italy for two months with a linen suitcase and a romantic lack of urgency. Sad, but true.

So instead, consider what a smaller version of relief might look like. A few remote days somewhere new. A workcation. A longer lunch. A Friday off every now and then. A real weekend. A protected morning. A pocket of time that belongs to you and not to your obligations.

The point is not to do rest perfectly. The point is to stop treating it like a luxury item reserved for later, after you’ve earned your way into being a person who deserves air.

A little permission

Here it is, in case you needed it: you are allowed to close the laptop. You are allowed to step away. You are allowed to go outside without making a productivity case for it. You are allowed to rest before you collapse. You are allowed to enjoy the season while it’s here.

Because honestly? Life is short. Summer in Canada is shorter. And the inbox will survive without us for a minute.