A Leader’s Vacation; The 5 Keys to Vacationing Like a Leader!

It’s a sad truth so many leaders and employees are actually nervous to take their oh so precious Vacation Time. Anxious of what will happen to their inbox, the fires that will ensue, the calls and emails they’ll get while at the beach, not to mention the vacation they’ll need from their vacation as spending countless hours of travel with their family proves to be more challenging than initially thought… sound familiar? I’ve even heard of people cutting their vacation short to attend to organizational issues, or simply thinking about work while on vacation and thinking about vacation while at work! I can go on, but you get the point. The gist of A Leader’s Vacation is… vacations are necessities, not luxuries! They don’t all have to be a trip to Disney or a cruise around the world… they can be small, they can be big, or they can be a Staycation at home. However, they must have all 5 Keys to vacation like a Leader… So, what are they?

Make It!

This first Key may be simple for some and the hardest for others. Some Leaders and Front-Line Employees will fight you to the death and are willing to quit their jobs if they don’t get the time they requested off; whether for their annual vacation with family or simply the time they requested with last-minute notice! While for other Leaders & Employees, it’s not that big a deal and they’ve stockpiled endless days and have to be forced to use it before they lose it! This can be for several reasons… perhaps it’s a part of their culture and now a part of their DNA. I think of my father, as a child I actually thought the man slept in a suit, Lol! I remember him leaving the house in a suit, returning in a suit, sat at the table in a suit, and I remember my mom jokingly (but seriously) saying he could call-off or take a vacation, “The bank won’t burn down without you.”. My Father-in-Law, the same way… old school and country strong; there are no days (or minutes for that matter) off!

Some leaders and employees struggle to take vacations because it’s in their DNA as I just mentioned; while others struggle because no one can do their job like them, they believe the ship will sink, and all heck will break loose. If any of this is true, there are bigger issues to address within your leadership, modeling, coaching, shadowing, and trusting your people. Or perhaps you’re in an organization that grinds their people into the dirt until they have nothing left to give and there’s never a good time to take your vacation due to ongoing crisis or growth… Believe me, the people under you are watching… if they think what you’re doing is what it takes to be successful and/or advance; why would they want to?

The point here is to “Make It” (time for your vacation) and set it into your calendar and your life; enhancing both your Leadership & Work/Life Harmony!

Take It!

This is simple yet powerful! You’ve scheduled your vacation… the time is here… and you now have every reason why it’s not a good idea or a good time to go. Newsflash, there are better times to take a vacation than others; however there’ll always be a noble reason not to go: a crisis came up, someone’s out sick, a deadline is approaching, an important client or bigger boss is coming to visit, etc. “Take It” refers to taking the vacation you scheduled and said you needed all those months ago. When taken correctly, in addition to the following keys I’m about to share, your future self will thank you!

Not to mention, do you really want your significant other and kids getting used to you not being around? It happens faster than you think, and it doesn’t take long for people to get used to anything! It’s a truly sad day when the person that’s been absent (YOU) decides to be present and quickly realizes they don’t fit in anywhere. Your spouse has an established flow and now you’re in the way. Your kids have a flow… and their friends and interests are now more important than you. So back to work you go… More likely off to depression you go… Be Mindful!

Protect It!

Now that you’ve “Made It” and “Taken It”… it’s time to Protect it! Protecting it is three-fold:

  1. Prepare your staff for you to be gone. Do they know when you’re leaving and when you’re returning? Have you asked what questions they may have or are anxious about… and helped them with possible solutions? Have you passed-off necessary tasks and duties to the correct person and connected them with the necessary people for elite follow-through? Have you made the person under you aware of their Authority Span… do they have the same amount of decision-making power as you or is it up to a certain point… and does the team know that?


  1. I’ve found it a great idea to protect your vacation by using a travel service. Of course, this won’t be necessary when you’re “Staycatioing” but for anything else it can prove to be an asset! Some people are born planners and organizers. My wife is just that… she can plan a vacation down to the minute and do a great job doing it… but the stress of planning it and following through with it, although successful, can make her and everyone else feel like they need a vacation from the vacation! Therefore, we started using Beebe Travel and have partnered with them as a business to further impact organizations, leaders, employees, and their teams.

Employees are going to take vacations anyway… what if they can be concierged for them and for you… all thanks to your company? Whether it’s getting you annual Disney trip planned and arranged, a car-service to take you and “The Fam” to the beach, or an Air B&B planned for you. What a load off and a great perk!


  1. Lastly, protect yourself from anxiety by being more self-aware! Some leaders and front-line employees go on vacation, turn work off, and don’t think about it until they literally walk into the office or crack open their laptops on their day return. That’s not me!

As a professional speaker and author, I absolutely love what I get to do for a living… writing, making videos, creating, and connecting. Protect yourself by knowing yourself and create time to satisfy your passion without neglecting your loved ones! While on vacation, I still wake up my normal time of 5:45am (before the world or at least those in my world are up) to post my content, create a bit, and make connections via social media. Then I’m done for the day and can enjoy my wife, my life, my kids, and vacation.

Reflect It!

At some point during your vacation, “make time” and “take time” to reflect on all you have, all you are, and how you want to return from vacation as a person, partner, professional, and parent! This is a truly amazing moment that doesn’t have to take a lot of time, but will allow a personal and professional evolution! For me, when I couldn’t afford to go to the beach… I sat on my front step and pondered this. Now, I get to do it on a beach, a cruise, or some fancy hotel… the point is, my vacation and your vacation will be pointless without this reflection period. Do you know how lucky you are to have the job you have, a vacation, the people you’re on vacation with, the opportunity to go back and actually be of increased impact and make a difference? Not everyone can say this… so be mindful to Reflect, Enjoy, and Evolve!

Preface It!

So many companies act as if they didn’t know you were away on vacation and expect you to walk in the day of returning with old work done and new work almost completed… What the heck!!! Before you leave for your vacation and after returning, it’s so important we “Preface It”… preface what you need to return from vacation like the elite leader you envisioned.

When you’re in a position of leadership, preface with your team your time for availability upon return. This is a great opportunity to enhance not only your leadership, but also that of those you’re leading! Yes, there may be a line outside your door waiting for you, or your emails have hit mass quantity, etc. Be sure to know what you need: Time to review with Direct Reports on how things went in your absence… the great, good, and ugly… as well as a plan of how you both will lead through it better for next time! Time to catch up on emails, 1-on-1 Meetings, what meetings to attend, put on hold, or send someone in your place.

If you’re more a Middle Management to Front-Line, upon your return it may be great to suggest or ask for “Email & Issue Time”… a time to catch up on emails and best prioritize what to attack the first few days post-vacation. It may also be a great idea to know if meetings on your first day or week back can be “Optional”… either by asking someone else to go in your place, attend the portion concerning your team, or recording the meeting to watch it later. Discussing this with your company pre-vacation is proactive leadership and something your boss may wish they had thought of!

These are the 5 Keys to Vacationing Like a Leader? Which Key stood out for you most and why? What will you apply, starting NOW, for yourself and your team?

“So many companies act as if they didn’t know their employees were away on vacation and expect them to walk in the day of returning with old work done and new work almost completed… What the heck; this is not leadership… Be Mindful!!!” – Andre Young

Written by: Andre Young

Click www.youevolvingnow.com to connect, chat, and to find out more about Andre Young’s Leadership & Work/Life Harmony Trainings, Speaking Engagements, Books, and more; evolving your organization, your leaders, employees, and teams!

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