How to Prepare for a Summer Vacation at Work—So You Can Actually Enjoy It (Yes, Really!)🌞✈️

My husband and I "on vacation" a few years ago. Yikes!

Does the idea of a relaxing summer vacation sound more like a fantasy than a reality? You know the drill—your OOO message is barely set before the emails start piling up, your phone buzzes with “quick questions,” and you spend half your trip worrying about the avalanche waiting for you when you get back. Sound familiar? If so, you’re not alone.

Why Taking Real Time Off Feels So Hard

Here’s the thing: even though 75% of professionals say their bosses encourage taking PTO, a whopping 71% still feel pressured to keep up with work during their vacation. Only 1 in 4 executives truly disconnect while away. It gets worse—almost 60% say they return to a more stressful workload, and nearly a quarter report the positive effects of vacation vanish immediately upon returning. So, what’s going on?

In my over 20 years as an executive coach, I have noticed a pattern: high-achievers aren’t just busy—they’re indispensable (or at least, they think they are). That’s why the thought of unplugging feels risky. But here’s a little secret: the real risk is not taking a proper break. Burnout is real, and the World Health Organization now classifies it as a workplace hazard. If you want to lead well and climb higher, you need to recharge fully.

So, how do you prep for a vacation that doesn’t leave you dreading your return? Here are the steps I share with my clients—executives who, just like you, want to enjoy their summer and come back to a manageable inbox.

The Pre-Vacation Game Plan: No Surprises, No Chaos

1. Start Early—Way Earlier Than You Think

Don’t wait until the week before your trip to start prepping. As soon as your PTO is approved, block your vacation on all relevant calendars and let your team know. This isn’t just a courtesy—it’s a signal that you’re serious about your boundaries.

2. Map Out Your Coverage (and Make It Bulletproof)

Create a detailed, written coverage plan using our ILS Vacation Hand-Off Plan. Assign clear points of contact for every major responsibility. If you lead a team, make sure each member knows who’s handling what. Share this Plan with everyone who might need it—colleagues, clients, even vendors. Contact me for the ILS Vacation Hand-Off Plan at Anna@ILSInt.com.

Extra tip: Schedule a hand-off meeting the week before you leave. Walk through ongoing projects, deadlines, and “what if” scenarios.

3. Get Ahead, But Don’t Overdo It

Look at your calendar for the week you return. What deadlines are lurking? Can you move them or delegate? Finish up as much as possible before you leave, but don’t try to do three weeks’ work in one. That’s a recipe for exhaustion, not relaxation.

4. Set Clear Boundaries—And Communicate Them Loudly

Your out-of-office message isn’t just a formality. Be explicit: “I will not be checking email or voicemail during this period. For urgent matters, contact [Name].” Specify what counts as an emergency, and make sure your backup is empowered to make decisions.

Consider removing work apps from your phone and silencing notifications. If you’re feeling bold, leave the laptop at home. Yes, really.

5. Remind, Remind, Remind

A week before you leave, remind your team and key contacts about your upcoming absence. The day before, send a final nudge. People forget—help them help you by making your boundaries crystal clear.

The Return: Beat the Post-Vacation Blues

You know what’s almost as important as prepping before you go? Planning your first few days back. Most professionals feel overwhelmed by the workload that greets them after vacation. Here’s how to avoid that fate:

• Leave yourself a “welcome back” to-do list. Jot down priorities and next steps before you leave—future-you will thank you.

• Block off your first morning back for catch-up. No meetings, if possible. Give yourself space to get oriented.

• Don’t try to clear your inbox in one sitting. Triage ruthlessly—respond to what’s urgent, file the rest for later.

A Few Real-World Tangents (Because Life Happens)

Let’s face it—sometimes, despite all your planning, things go sideways. A client once told me about returning from a beach holiday only to find a crisis had erupted on day two of her trip. Her backup handled it beautifully, but only because she’d been given authority and context. The lesson? Don’t just name a backup—train and trust them.

Also, consider this: it takes most people three to four days to stop feeling stressed about work while on vacation. If you only take a long weekend, you might not get the full benefit. But if you’re gone for a week or more, don’t be surprised if you need a few days to truly unwind—plan your travel and activities accordingly.

Quick Actions for a Smoother Summer Break

• Block your vacation dates on all calendars—early and often.

• Complete and share the Vacation Hand-Off Plan. Request this from me at Anna@ILSInt.com.

• Delegate tasks and create a written hand-off plan.

• Set a clear out-of-office message, naming a single emergency contact.

• Remove work apps and mute notifications.

• Prepare a “return to work” list and clear your desk before you go.

• Schedule downtime for your first day back—no meetings, just catch-up.

• Remind everyone (twice) that you’ll be unreachable.

The Bottom Line: Your Vacation Is an Investment

Here’s what I tell every executive I coach: taking a real break isn’t just good for you—it’s good for your team and your company. Only 25% of professionals truly disconnect on vacation, but those who do come back more creative, focused, and ready to lead. Don’t let guilt or habit rob you of the rest you’ve earned.

This summer, give yourself permission to step away. Prepare well, set boundaries, and trust your team. You’ll return not just rested, but ready to tackle whatever comes next—with energy, vision, and maybe even a little sand still between your toes.