For so many CEOs and business owners, taking time off is a major point of friction.
They have hardworking teams that depend on them, and they want to set the best example by working just as hard and ensuring they’re always there to help the team with any questions or concerns.
When they do manage to go on vacation, they bring their work laptop and don’t bother to enable “do not disturb” mode. The Slack messages or Teams notifications just keep buzzing away.
But being so indispensable at your organization that you can’t even take a vacation is a sign of mismanagement, not great leadership. The best CEOs are those who take their vacations on time and without guilt.
If everything depends on you, you’ve built a bottleneck. The strongest, most well-oiled companies aren’t the ones where CEOs put in countless hours every week, but the ones that can easily function independently of their leader. So if you don’t feel great going on vacation, maybe one reason is that you don’t have a contingency plan.
When someone on our team takes paid time off, we don’t simply hope everything works out. We create a coverage plan, reassign responsibilities, and ensure every question has a clear point of contact.
Our philosophy is simple: Take all the time off, as long as we don’t feel your absence.
The same rule applies to me, as it should to every firm leader. Before I go on vacation, I make sure I delegate the work I handle to people I know can handle it, so that, barring a massive emergency, I can actually log off during my downtime.
But what if you do everything you think you can before your vacation and yet it turns out the company was still in a bit of a free fall while you were gone? Congratulations, you’ve just exposed weaknesses in your firm that you can get to fixing now that you’ve returned, refreshed and reenergized.
Because on top of being useful and even necessary, vacations are essentially free stress tests. The goal of any firm should be resilience and excellent operations regardless of any one person’s presence. Vacations are a great way to test if yours is actually built for that.
So as you can see, taking a vacation isn’t about escaping your responsibilities.
First, it’s about proving you’ve built systems, leaders, and processes capable of carrying them. If your business falls apart every time you step away (or anyone on the team does), then you know you need to reorganize how things are done.
And second, it’s to get your strength and energy back before you continue being the leader you are for the majority of the year. Rest and relaxation aren’t the opposites of hard work. They’re essential parts of it.
