Five Tips for a Good Night’s Sleep When Work is on Your Mind

Sleeping easy has never been harder. How to balance your work stress when you can’t turn it off.

A number of years ago, I set out on a business trip to support a senior leader who I admired very much. We were heading on an extended trip where I’d write his remarks for a wide variety of engagements and audiences, partner with his admin on his outrageous schedule, and generally run interference on the gamut of things that came his way. I knew it would be a grueling few weeks, but I felt up to the challenge, and excited for the opportunity.

We waited out a delayed flight in the airport lounge, and battery power began to dwindle. “I’m plugging my computer in — don’t let me forget it!” was his ask as he went out in search of power. It turned out I wasn’t as up to the job as I thought.

We boarded the plane, and twenty minutes after takeoff I could see him heading from executive class towards my seat at the back of the plane. “I left my laptop, damnit!” Dread set in. The flight crew called back to the airport and tried to find it, but it was gone.

We immediately worked to repair the situation, investigating any chance of finding his laptop. And when that failed, getting a new one shipped out. It wasn’t the start to the trip that either of us had imagined. I felt beyond terrible and was losing sleep over the stress of it all.

But my feelings about it were just that: mine. He wasn’t making me feel bad about it — just the opposite, in fact. He could have been furious, possibly even fired me. But instead, he taught me a great lesson: the importance of compartmentalization.

As a leader, you need to be able to compartmentalize. Or everything will consume you.

This was his perspective when I asked how he had so quickly moved on. I was grateful that he wasn’t making me feel any worse than I already did, but I truthfully couldn’t see how he wasn’t consumed by this mishap. Years later, I now realize that being able to compartmentalize is a critical skill of leadership — it just doesn’t work the way I thought it did back then.

I used to imagine compartmentalization as the ability to ignore issues and stress. And while that may be true for some, the way I now see it is that being able to compartmentalize means just that: keeping everything in its place.

I visualize stress in an Ikea cabinet with uniform boxes lining its shelves, each full of a different category of things to think about. I group my common areas of concern into those boxes and I fill up positive boxes to balance them out. When all those imaginary boxes are equally full and in balance it’s impossible to fixate on a single point of stress. Instead, I tuck all my worries away in favor of a good night’s sleep.

Struggling to put your work stresses to bed? Here’s how you can give this strategy a try.

1) Make sure your “wins” box is always full.

You know the saying “give credit where credit is due?” I give myself credit and make a mental note of it when things go well. Whether it’s saying the right thing in a meeting, a colleague thanking me for my support, remembering to wish someone a happy birthday, or simply sharing a laugh with a peer, I’m consciously and constantly adding to the box labelled “good job, me.”

2) Let your wins balance the “failures” box — which is the one to really watch out for.

It’s easy to focus on the misses, and so I very deliberately stack them up against my wins. When I beat myself up over the email I should have worded differently, I think about 25 others I’ve sent that day that aren’t weighing on me. When I think of the things I could have done better, I roll through the list of achievements in my wins box.

All those things I’ve filed under “good job, me” balance out self-diagnosed shortcomings that might otherwise become a focus.

3) Keep a box of “things I didn’t get to” and accept that it will always be at capacity.

I think of work as “daily triage.” There’s no way I’ll get to it all, and I don’t try. That permission to leave a list at the end of the day might take some time to get comfortable with, but it’s vital.

The trick is to know that you did the things that needed to get done — and to accept that the rest of it will still be there tomorrow. Having a system to stay organized and manage this reality is another key to falling asleep at night.

4) Designate a box for “mild concerns.”

Give yourself permission to sweat things that aren’t perfect, but only a little. When I’m stressing about something, I ask myself if it will be a big deal a week from now.

Will anyone else remember this incident? Will this issue have any impact at the end of the year? Will I even remember my own stress over this in a few weeks? If not, I put it in its appropriate “mild concern box” and just giving it that label allows me to move on and not give it more attention than it deserves.

5) Put work itself in a box.

Compartmentalizing within work is critical — so too is compartmentalizing work itself. Let’s be real, you’re not forgetting about work the minute 5:00 PM rolls around on Friday. But, that is a good time to let all the other worries you’ve been keeping in their own box all week take over.

Rather than focusing on pushing your work stresses down, bring your life lists up. What vacation do you need to plan? Is your home “to do” list out of control? Make a list of all the things that you need to do that aren’t work-related. Just looking at that all in one place should do the trick!

Getting started: Organize your mind and minimize your work stress.

So, that’s the trick. Define the right boxes to store the wins, the failures, and everything in between, and then fill and balance them to put your mind at ease.

You may want to label your “boxes” differently than I do — go for it! Grab a pen and make a list of all the things keeping you up at night, and then group them in a way that makes the most sense to you.

Perhaps it’s negative comments from your boss which are the toughest to let go. Try putting those in a box and then filling a box full of positive things you hear from colleagues as a counterpoint.

Maybe you’re struggling to get comfortable leaving your list unfinished at the end of the day? Explore Task Apps like Zenkit or Microsoft To Do to see which solution might be right for you. And don’t just look at what’s outstanding — take a moment to review the items you’ve crossed off, as well. Those checkmarks are no small feat, and the credit you give yourself for those accomplishments is a great balance against lingering tasks.

And let’s be real: Keeping anything in its own compartment has never been harder than while this pandemic continues to linger. Who could have anticipated our loved ones would become our co-workers and water cooler companions? Or that a home office, home gym, home school, and home life would all exist as one? With day-to-day life converging in so many unexpected ways, a mental strategy to keep worries in check has never been more timely — or necessary.

So back to that ultimate goal of a good night’s sleep.

Which box do you stress about, and which one do you need to fill to balance it? Instead of minimizing the things keeping you up, balance them out and let all of the boxes fade into the distance. Now get back to sleep.