A Leader’s Vacation Guide

Ah, vacation…

A magical time to disconnect, relax, and forget the horrors of meetings that should have been emails.

But let’s be honest—if you’re a manager, the idea of taking time off can feel… stressful.

What if something goes wrong?

What if people keep calling you?

What if your team realizes they don’t actually need you? (Kidding! Kind of…)

The truth is, preparing for a vacation when you’re in a leadership role takes some planning.

But if done right, not only will you enjoy your time away guilt-free, but your team will also thrive in your absence. Here’s how to prepare like a pro.

1. Understand Why Leaders Struggle with Taking Time Off

Let’s start with some psychology. Many leaders struggle to step away because of something called over-responsibility bias. Research published in Harvard Business Review found that leaders often believe the company (or team) can’t survive without them—even for a week. Spoiler alert: it can.

Daniel Pink, in his book Drive, explains that autonomy is one of the biggest motivators for employees.

Translation? Giving your team the freedom to handle things while you’re away might actually boost their performance—not hurt it.

If you’re worried about things going wrong, remind yourself: the goal of leadership isn’t to do everything yourself; it’s to empower others. Vacation is your ultimate leadership test.

2. Delegate Like a Boss (Before You Leave)

No, delegating doesn’t mean dumping all your work on your poor team.

It means setting clear expectations and ensuring the right people know what they’re responsible for.

Here’s how to do it:

Make a List of Critical Tasks: What absolutely must get done while you’re gone? Be realistic. (Hint: That one report you tweak 20 times before sending? Not critical.)
Choose the Right People: Assign tasks based on strengths. If your assistant is amazing with schedules, let them handle the calendar chaos. If your team member is great with problem-solving, let them troubleshoot.
Write It Down: No one likes vague instructions. Use tools like Asana or good old email to document responsibilities. Make it idiot-proof, even if your team is full of geniuses.

Pro Tip: Don’t forget to include a “point person” who will act as your go-to while you’re away. This person should know how to handle emergencies—or at least know how to make it look like they handled them.

3. Communicate Your Plan (Don’t Ghost Your Team)

Taking a vacation isn’t a secret mission. Let your team (and maybe even your clients) know when you’ll be away and what to expect. Be clear about:

Your Availability: Are you completely off the grid, or will you check in once a week? Don’t be that person who says, “I’ll be unavailable” and then replies to every email at 2 AM.
Who’s in Charge: Make it crystal clear who’s handling what in your absence. This prevents everyone from panicking and sending urgent Slack messages about printer ink.
Your Trust: Reassure your team that you trust them. A little vote of confidence goes a long way. Say something like, “I know you’ve got this!” And mean it.

4. Set Boundaries (and Actually Stick to Them)

The vacation starts when you unplug. Not when you reply to “just one email” or secretly peek at Slack “for a second.”

According to a study by Project: Time Off, employees who fully unplug during vacations are 30% more productive when they return. So, do yourself a favor:

Turn off email notifications.
Use an auto-responder with a bit of personality, like: “Hi there! I’m currently recharging my batteries (and probably eating too much ice cream). I’ll get back to you on [date].”
Tell your team that unless it’s an emergency involving fire, blood, or lawsuits, they shouldn’t contact you. (And make sure you define “emergency” because people have…creative ideas.)

5. Prepare Your Team for the “What Ifs”

One reason leaders stress about leaving is the fear of what if something goes wrong? The good news: most “what ifs” can be solved with preparation. Here’s how to troubleshoot ahead of time:

Emergency Scenarios: What’s the protocol if a client has a major issue? Or if the Wi-Fi goes down? Create a simple playbook for these situations.
Decision-Making Guidelines: Encourage your team to make decisions without you. Use a rule like: “If it costs less than $500 or takes less than 5 hours, go for it.”
Backup Contacts: If something truly catastrophic happens, have a trusted colleague as your backup. Just make sure you ask them first.

6. Organize Everything (Yes, Everything)

The more organized you are before you leave, the less chance of chaos. Start by:

Your Inbox: Flag important emails, archive the junk, and set up filters. Coming back to a clean inbox feels like winning the lottery.
Updating Documents: Make sure important files are easy to find. Use shared drives like Google Drive or Dropbox to store everything neatly.
Creating a Cheat Sheet: Leave behind a “cheat sheet” with key details—passwords, deadlines, and contacts. (Just don’t write your passwords on a Post-it note stuck to your laptop.)

7. Test the System Before You Go

Here’s a fun experiment: Take a mini-vacation before your actual vacation.

For a day or two, step back and let your team handle things while you observe from a distance.

This will give you valuable insights into:

What systems work well (hooray!).
What needs to change before you disappear for a longer period.

Think of it as a vacation rehearsal. If you’re feeling fancy, call it a “leadership simulation exercise.”

8. Mentally Prepare Yourself to Let Go

Let’s face it: the hardest part of taking a vacation isn’t organizing tasks—it’s trusting the process and actually relaxing.

A study in The Journal of Happiness Studies found that people enjoy their vacations more when they fully detach from work. Easier said than done, right? Try this:

Reframe Your Thinking: Instead of worrying about what could go wrong, think about how this break will make you a better leader. Burnout benefits no one.
Set Fun Goals: Challenge yourself to NOT check your email for 7 days. Reward yourself with something fun if you succeed—like that overpriced drink with a tiny umbrella.
Focus on the Big Picture: Remind yourself that leadership isn’t about micromanaging. It’s about building a team that thrives even when you’re not there.

9. Re-Entry: How to Handle Your First Day Back

Your first day back from vacation can be overwhelming. But if you plan ahead, you can ease into it:

Block Off Your Calendar: Give yourself a buffer day before diving into meetings. Use this time to catch up and prioritize tasks.
Tackle the Big Stuff First: Resist the urge to reply to every email. Focus on high-impact tasks instead.
Reflect and Improve: What worked well while you were away? What didn’t? Use these insights to make the next vacation even smoother.

So, plan your vacation, pack your bags, and remember: the world will survive without you for a week -or seven.

And when you return, you’ll be rested, recharged, and ready to lead with fresh energy.

Bon voyage, leader—you’ve earned it!

I am incredibly grateful that you have taken the time to read this post.

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