Memorial Day weekend has a particular quality to it. The light shifts, the pace changes, and something inside you quietly asks: when did it become May already?

Whether you’re preparing for a proper European summer or simply carving out a long weekend within driving distance, this is the time of year when vacation and summer become synonymous. Which means it’s the right moment to talk about the part nobody tells you: how to actually prepare to step away.

Last week, I wrote about the research behind why true psychological detachment from work during vacation matters, and I admitted something that many of you recognized in yourselves. Even when we understand the evidence, even when we believe rest is essential, stepping away still feels hard.

I think that’s because we’ve spent years learning how to perform at a high level. We know how to optimize, execute, and deliver. What most of us were never taught is how to stop. How to leave without the low-grade hum of guilt. How to trust that the things that matter will still be there on Monday, and that the distance might actually make us better at all of them.

So in support of all of us trying to vacation a little better this summer, here is what I’ve found actually works.

1. Be intentional about when you travel

One of the most overlooked elements of a restorative trip is timing, and I don’t mean finding the right season for the destination. I mean mapping your travel against the rhythms of your work life.

If there are predictable windows of the year that consistently require everything from you: launches, board cycles, major deliverables, fundraisin, build your travel calendar around them rather than against them. Think in a rolling 12 to 18 month view and identify the seasons that reliably take the most.

This isn’t about perfection. It’s about reducing the likelihood that you spend your vacation mentally somewhere else entirely.

And once travel is booked: communicate early. I’ve found that flagging absence about a month out gives clients, colleagues, and teams time to prepare naturally, rather than scrambling when the OOO message goes up.

2. The week before you leave is rarely peaceful. Plan for that.

This is something almost no one talks about, and it catches people every time.

The days immediately before a trip are often the most compressed of the entire year. Everything accelerates. Inboxes fill. The mental load of wrapping things up competes directly with the mental load of actually preparing to go.

The most useful thing you can do is stop treating trip preparation as something that happens in the margins of an already full week. Block time for it. Intentional space for packing, wellness appointments, errands, and the practical details that make leaving feel manageable rather than chaotic.

For my travel clients, I build a pre-departure timeline, includng what to handle a month out, a week out, a few days before. Because how you leave shapes how quickly you actually arrive.

3. Stop treating the flight like a productivity session

I have accomplished a genuinely impressive amount of work on airplanes over the years. I’ve also learned that functioning outlets, reliable Wi-Fi, and uninterrupted focus are bonuses, not infrastructure.

And without fail, the flight where you absolutely must send something important is the one where the satellite fails somewhere over the Atlantic.

Build margin instead. Anything mission-critical should be completed before you leave the ground and not balanced on the hope that the Wi-Fi cooperates. The plane is not the office. Let it be the transition.

4. Boundaries are not a burden, they’re what makes the trip worth taking

If you do need to work during a trip, transparency matters far more than most people realize.

Your travel companions chose to use their time — their actual, finite, irreplaceable time off — to be somewhere with you. Few things create quiet resentment faster than just one quick call becoming the recurring theme of the week.

The same applies if your work overlaps with content creation. If you document professionally or creatively, name that upfront. Carve out intentional moments for it rather than allowing it to drift over the entire experience.

Most importantly: decide your boundaries before you leave. Maybe it’s an early morning hour before the day begins. Maybe it’s a single daily check-in aligned to another time zone. Whatever it is, establish it clearly: with yourself first, then with the people you’re traveling with, and then honor it.

The boundary isn’t the constraint. The absence of one is.

5. If you lead people, model the behavior you want to see

Leadership has a long shadow, and nowhere is that more visible than how you handle your own time off.

If you take calls from the beach, your team learns that real rest isn’t actually expected. If you send emails at midnight before a holiday, you quietly establish that boundary as performative rather than real. The cultural norms around rest in your organization will largely reflect what they see you do, not what you tell them to do.

So before you leave, do the work of setting the standard clearly. Designate a delegate. Name the person, explicitly, who has authority to make decisions in your absence, and make sure both they and your team understand the scope of that role. Then communicate your emergency protocol: not as an open door, but as a clearly defined threshold. What constitutes an actual emergency? And if one arises, what’s the right channel? A direct call or text? Through your Executive Assistant? An email that gets checked once a day at a specific time?

The goal isn’t to be unreachable. It’s to be appropriately reachable and to remove the ambiguity that causes teams to either over-escalate or under-communicate when something genuinely goes wrong.

Here’s what I’ve found to be true: teams that have clear protocols rarely need to use them. Teams that don’t almost always do.

6. Rest is not a reward. It is part of the work.

I said this last week. I’ll say it again because most of us still have to be reminded.

You do not earn rest only after you’ve reached some level of exhaustion that justifies it. Rest is part of sustaining a life that’s worth working hard for in the first place.

The most important thing a vacation can do is return you to yourself, to be more present, more creative, more capable of the things that actually require your best thinking. That only happens when you actually let it.

Next in the Out of Office Editions: how to re-enter without needing a vacation from your vacation.

If this resonated, I’d love for you to share it with someone who needs to hear it. And if you’re ready for travel designed around your actual life: your rhythms, your wellbeing, your standards, I’d be honored to help you plan it. Send me a message or book a planning call here.