Personal DevelopmentRejuvenation

5 Keys to Taking a Vacation You Don’t Regret Later

Have you ever needed a vacation from your vacation? I have. On my first Monday back in the office, I’ve found myself wondering why I spent all that time and money in the first place. 

It took me years to realize that vacationing is a skill. And just like any other skill, it takes practice. The best vacations require work, but not the kind of work you imagine. With a little effort, you can prepare to step away—and not regret it later—by planning a vacation with these five keys in mind.

Key 1: Vision

When Gail and I first started vacationing together, it didn’t take us long to realize we had mismatched expectations. Gail loves to sightsee. She wants to wander through museums, tour local landmarks, eat at all the top-rated restaurants, and explore wherever we are. At first, she’d build out complicated itineraries to make sure we had the best experience possible. There was just one problem. Her idea of vacation sounded exhausting to me.

On vacation, I love to relax. I love a good meal, and I want the opportunity to explore. But I also love my afternoon nap. I love leisurely conversations. I love an itinerary with white space we can fill as the mood strikes us.

Gail and I had a vision problem. To solve it, we had to begin intentionally discussing what we wanted and working together to build an itinerary that met both of our needs. Without a shared vision, we weren’t in alignment. Our misalignment led to conflict.

You need a vision for your vacation, too. Even if you’re vacationing alone, you should take time to slow down and clarify what you want. Otherwise, you might end up going on the vacation you think you should have, only to find out it’s not at all the vacation you needed. 

Can you really visit Rome without seeing the Parthenon? Can you really pay to stay in an all-expenses-paid resort and then spend a whole day just lying by the pool? If it’s what you need—yes, you can.

Key 2: Your Why

Every good what has a great why. Vacations don’t have deadlines the way your work does. They’re easier to put off. Maybe that’s why Americans left 768 million paid vacation days unused in 2019. Without clarity about what makes your vacation so important, your vacation days are much more likely to pile up.

Ask yourself a few questions. Why does it matter? What will this vacation mean for you? What’s at stake if you don’t take your vacation?

If you’re having trouble answering these questions, here are a few reasons to get you started:

  • Vacations help refresh your energy and excitement.
  • Regular vacations help prevent long-term burnout.
  • Vacations improve your attitude at work.
  • Vacations help you reconnect with who you are apart from what you do.

In the words of Anne Lamott, “Almost everything will work again if you unplug it for a few minutes, including you.” Imagine what it would make possible to spend not minutes or hours, but whole days away from the demands of work. 

Key 3: Planning for Rest and Rejuvenation

Nature abhors a vacuum. If you don’t have a plan for how you’ll spend your time, you’ll drift back into work.

Your plan doesn’t have to make you busy. Sleeping in, slow mornings, and lounging around can all make the list. But you need to take the time to make your plan explicit. 

Your plan should be tailored to fit your personality, preferences, and location. What does rest look like for you? Where will you eat, and with whom? How will you disengage from work?

Your plan doesn’t need to be exhaustive, but it needs to be clear. Without it, your time away is less likely to be restful.

Key 4: Closing Open Loops

It’s hard to rest when you’re afraid of letting others down. You need to proactively close open loops, so you know your team is taken care of.

My assistant, Jim, is really helpful when it comes to open loops. He’ll look at my calendar and ask, “What needs to happen for Michael to be able to step away from the business for a month-long sabbatical?” We schedule podcast recordings in advance. He finds others to cover events or webinars I’ll miss. He requests adjustments to project timelines.

For some of you, the idea of a month-long sabbatical seems impossible right now. Start where you are. If you didn’t take off any time last year, start with a week. If you’ve taken a week, try two or three. Then, ask yourself what needs to happen in order for you to be able to fully step away during that time.

At our company, team members fill out a status update for their teams and supervisors that provides information on the projects they’re working on, including links, instructional videos, and any information that might be helpful in their absence. 

This is also the moment to designate who is responsible for which decisions in your absence. But beware—if you fail to respect those decisions, you’ll undermine your team’s trust.

Key 5: Activating a Departure Plan

Creating a plan isn’t enough. You need to communicate it.

Meet with the key stakeholders to walk through the status of projects you’ve been working on and the key action items they can expect in your absence. Block off time to close any additional tasks that arise during the meeting. You’ll also provide guidance on how to react in case of an emergency.

Start by defining what constitutes an emergency. It should be a high bar. In the case of my company, only situations like major lawsuits and significant cash-flow issues are worth an interruption to my vacation. Then, identify what should happen in each case. I direct my team to Jim, who will know how to get in contact with me.

You may also need to communicate with stakeholders outside your team, like major clients. Notify them of your upcoming vacation, clarify your expectations, and give them a path. Ask, “Do you anticipate you’ll need anything from me? Let’s get it taken care of right now.” Tell them who to contact in case they need timely solutions.

Then, unplug. Remove the work-related apps. I even automatically delete work messages while I’m gone, because most issues will be solved by the time I return. You can find the auto-responder message I use in this post. This way, I return to work refreshed, without a flooded inbox.

Your time off is just as valuable as your time on. Rest makes work possible. If you want a tool to walk through each of these features for your upcoming vacation, visit Then, design the vacation of your dreams.

Last modified on October 10th, 2022 at 9:18 am

Disclosure of Material Connection: Some of the links in the post above are “affiliate links.” This means if you click on the link and purchase the item, we will receive an affiliate commission. Regardless, we only recommend products or services we use and believe will add value to our readers. We are disclosing this in accordance with the Federal Trade Commission’s 16 CFR, Part 255: “Guides Concerning the Use of Endorsements and Testimonials in Advertising.

More In Personal Development
Become a Full Focus Insider

Subscribe to the Full Focus newsletter for the latest insights, strategies, and tools from our CEO to keep you winning at work and succeeding at life!

Sign Up Now