What Vacation Taught You About Leadership (And You Didn't Even Know It)

A silhouette of a family walking along a beach shoreline during a vibrant orange sunset, symbolizing taking time off and stepping back to gain retail leadership perspective.

Taking a vacation can teach many leadership lessons, often without us even realizing it.

You look forward to a vacation, yet at the same time you fear what you're going to walk back into when you get back. Sound familiar? I hear so many people say that when they get back from vacation, there's so much catching up they need to do that it often feels like it wasn't worth taking the vacation. That's just not the way it should be.

Vacations should be about relaxing, disconnecting, and recharging. The more you work toward that over time, the lessons you've learned so far - even early in your career - can help you get to a point where you can truly enjoy your vacation. You can come back and feel like you haven't missed a beat, and your team feels like they were in charge and weren't concerned about how long you were gone.

Imagine one day being able to take two or even three weeks off and not worrying about what you're going to come back to at the end of it. What would it take in order for that to be true? Let's look at some of the leadership lessons that can come from taking vacations to help you get to that dream outcome.

Letting go of control

The hardest part of the first day of vacation is usually not sitting still or setting your phone down. It is accepting that the business is running without you standing there making sure of it.

This may not be something anyone wants to hear, but it is something every leader must face. If the place falls apart the second you leave, that is not a compliment to how important you are. It is a sign you have not built a team that can run without you.

A vacation forces you to find out, whether you like it or not, whether your team can handle things on their own.

The leaders who come back from a week away and find everything mostly fine are usually the ones who spent a lot time training their people and trusting them to make decisions. The ones who come back to a mess usually never let go of enough control to find out if their team was ready.

Getting distance to see what actually matters

When you are away from the store, your brain finally gets some space. You stop thinking about the distracting details of every day reality. And when that happens, you start to see which problems at work are actually big deals and which ones just felt big because you were standing too close to them.

Distance gives you a strange kind of clarity. The stuff that felt urgent on a Wednesday afternoon often looks small a few days later from a beach chair or a hiking trail. The problems don’t change, your perspective does. Not to mention, you are thinking with a clearer mind and not driven by the stress of the moment. You now have some time to look at things from new angles.

Good leaders use this. They step back on purpose sometimes, even without a plane ticket, because they know being too close to something makes it hard to judge how much it actually matters. Even a long weekend, where you can truly disconnect, provides these types of benefits.

Do you ever recall having some time where you really were able to “be away” and then came back full of new ideas and fresh outlooks on the problems? That is the true benefit of a vacation.

Learning what drains you

Vacation also teaches you something about your own energy that you cannot learn while you are in the middle of a normal work week. You start to notice what you actually needed a break from. Maybe it was not the job itself. Maybe it was the constant interruptions, or the same three conversations you have every single day, or just never having a quiet minute to think.

Paying attention to what you feel relief from on day one of vacation tells you something important about where your energy leaks out during a normal week. That is useful information. It means you can go back and actually protect some of that energy instead of just running on empty until your next vacation bails you out again.

Another thing I’ve found is that taking a vacation helps you step away from your routines. I will always shout the benefits of solid routines and how they assist in planning and supporting your needs. But we do still need breaks from them as well. Vacations give you a chance to understand where your routines help you, and where they might hold you back or drain your energy. When I come back from vacation, it is rare that I don’t make at least some minor adjustments to the routines I follow each day. That time away helps you appreciate both the good and the frustrating parts of what you do every day.

Working without your usual systems

On vacation, you do not have your normal tools. You are not working with the same applications, you may have a different computer (if you have one with you at all), or everything is just arranged in an unfamiliar order. If something goes wrong, a flight gets delayed, a reservation falls through, you have to figure it out with whatever you have got in front of you.

That kind of improvising is a leadership skill too. Being able to solve a problem without your usual systems and structure is exactly what happens on your worst day at the store, when the register goes down or half your team calls out. Vacation gives you low stakes practice at staying calm and figuring it out without your normal safety net. It ends up building a resilience muscle that you may not always notice in your normal home or work environment.

Real time with people

Last, and maybe most importantly: vacation usually means real, uninterrupted time with people you care about. No phone buzzing every five minutes. No half listening while you think about tomorrow's work activities. You have the time to be present in the moment with the people you’re with and whatever you are doing (even if that is just lounging by the pool).

We’re probably kidding ourselves if we think our family doesn’t notice when we aren’t fully committed and fully present. Vacations aren’t just time away from work, they’re time with friends and family. Be fully present. Take advantage of that and the joy that comes with it. Everyone has examples of what that feels like, so keep it in mind and keep coming back to it.

It really does make a difference in the relationships you can build and strengthen, whether with your family, your kids, your partner, or a good friend. Those moments help you see things through a different lens, and they matter. You recognize this more and more as you get older and have more experiences like these.

Don’t take these vacations for granted. They’re a chance to be committed to what you’re doing in the moment, not what’s happening back at the workplace. Enjoy the time, and be intentional about enjoying it.

Bringing it back

You do not need to wait for your next vacation to use any of this. Start noticing this week whether you are giving your team enough room to run things without you hovering. Pay attention to whether you are too close to a problem to judge it fairly. Notice what is actually draining your energy day to day. And the next time you are having a conversation with someone on your team, try giving them the same attention you would give someone across the table from you on vacation. Turns out that week away teaches you more about leadership than you probably realized while you were busy enjoying it.

What leadership lessons have you learned while taking vacations?

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