How as CEOs We Can Truly Relax and Enjoy the Holidays

For most people, the holidays are a signal to slow down. Having worked with many CEOs over the years, they often do the opposite. Even when the calendar says “time off,” the reality is that responsibility doesn’t magically disappear. The business is still there. The pressure is still there. 

I’ve found that what makes holiday periods like Christmas particularly hard isn’t just the time away itself, but everything that leads up to it. In the weeks before a break, I notice myself trying to anticipate every possible issue, make every decision in advance and strive to set the business up so it can’t possibly need me. That preparation is sensible but it comes with a hidden cost.

By the time the holiday actually starts, I’m often already carrying tension. My body is there with my family, but part of my attention is still at work. Small things irritate me more than they should. My patience is thinner. And underneath it all there’s a quiet frustration: I wanted this time to be restorative, and yet I can feel myself struggling to be fully present.

Why We Carry the Pressure With Us

Over time, I’ve come to see that this isn’t a personal failure. It’s baked into the role.

As CEOs, we sit at the point of greatest consequence. When things go wrong, it always seems to land with us. That sense of responsibility doesn’t shut off just because it’s a holiday. Many of us are also deeply attached to our companies, not just financially, but emotionally. We’ve built them and stayed with them through moments of huge uncertainty and risk. Turning that vigilance off isn’t a switch; it’s a process.

There’s also a paradox in how we prepare to take time off.  Personally, the harder I try to eliminate every risk before stepping away, the more aware I become of how many risks actually exist. Instead of calming my mind, I sometimes end up amplifying the very anxiety I was trying to reduce.

What To Do Before Taking Time Off

I’ve learned that presence during a break is earned in advance.

Before stepping away, I now ask myself what needs to be true for me to relax. For me, that usually comes down to clarity. Who owns what while I’m away? Which decisions need my involvement and which ones don’t? If I haven’t made this explicit, my mind stays on-call and feeds my anxiety.

So rather than trying to finish everything, try focusing on closing open loops by documenting them. Writing down the current state of play, key risks and active decisions helps calm the mind and gives a sense of control. The work doesn’t need to be complete, but it does need to be contained.

Another important step is to set expectations with my family ahead of time. I let them know it may take a day or two for me to properly decompress, or I may need to do some email or take a few calls early in the mornings. Naming this reduces the pressure to instantly relax, which ironically makes it easier to do. 

Finally, decide in advance what “being available” actually means. If I check my email or do a few calls before the day starts, how will that allow me to be more relaxed and present for the rest of the day? It's a tradeoff that you may be willing to make.

What to Pay Attention to During the Holiday

Once the holiday starts, I avoid forcing total disconnection. I’ve found that rigid rules often backfire. Instead, I aim for what I call “contained connection” where I can be predictable for my family, while still being connected if really needed. 

I try to monitor where my attention is going. So if I catch myself mentally solving problems or rehearsing future conversations, I don’t judge. I simply bring my focus back to what’s in front of me. Presence, for me, isn’t something I achieve once; it’s something I have to work at and return to again and again. For me especially, physical grounding helps more than willpower. So walking, exercise, time outside and unstructured time with my family all help settle my nervous system enough to be truly present.

A Simple Holiday Presence Checklist for CEO’s

Before the holiday begins, here's a short checklist to lower the mental load:

Before you step away:

• Have I clearly handed over ownership for anything that might arise?

• Have I documented the current state of the business so my mind doesn’t have to hold it?

• Do I know exactly how and when I’ll check in, if at all?

• Have I set expectations with my team and my family?

• Have I decided what “good enough” presence looks like?

During the holiday:

• Am I getting pulled into imagined future problems?

• Do I need reassurance right now, or can I gently bring my attention back to this moment?

• Have I moved my body or been outside today?

This isn’t about perfection. It’s about giving yourself a way back to presence when your attention drifts.

Redefining a Successful Holiday

For CEOs, taking a break isn’t a reward for having everything under control. It’s a requirement for leading well over the long term. 

So try not to judge a holiday by whether or not you stopped thinking about the business entirely (That's an impossibility for most of us). Reframe it: success looks like enjoying moments of genuine connection, moments my family notices, even if I still think about work occasionally. And eventually returning after the break with more energy, clearer judgment and a little more patience than when I left. 

Happy Holidays!

Dermot

Photo by sina rezakhani on Unsplash