How to take a vacation (and actually do it)

Over the coming weeks, I’ll be posting a few compilations of starred articles I’ve accumulated for clients but never posted. Some have been lurking in my files for a while. Lots of good topics ahead. First up: how to take a vacation….and actually do it. Read on for somewhat rambling summaries from five great pieces. If you’re in a rush, here are the key points.

  1. How to leave the office (make a plan, and then stick to it)

  2. How to come back from vacation (allow time to transition) [If you only click one link, I recommend this first.]

  3. Why vacation matters (hold space for yourself)

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How to leave the office

We all know that vacation matters in theory. Actually creating time to rest, restore, and connect with those outside your professional network is something many find challenging. IMHO, learning to leave the office is one of the most critical leadership skills. It not only shows that you have built a capable team, but reinforces that you trust them to operate independently. Any time you are away from the office, your team has a chance to flex its muscles, experiment with its current capabilities, and identify areas for further development.

As many of you know, I worked alongside HBS Professor Linda Hill for many years. Linda loves collecting leadership aphorisms. She came home from a trip to Korea with one that we all found memorable:

“The organization will thrive when the leader is lazy.”

After many years of discussion and debate, I’ve decided this is about giving your team a chance to test itself, succeed/fail, and adjust accordingly. With this in mind, leaving on vacation — and really leaving — is a critical step in building a sustainable enterprise. Especially if you want it to succeed beyond your tenure.

What I learned from taking Fridays off

Creating a structure that functions in your absence cannot be done overnight. I loved Dorie Clark’s March 2021 essay in Fast Company about making her goal of taking Fridays off a real one. In it, Dorie articulates the work required in advance. As she writes, “Here are four things I learned in the course of carving out—and, even harder, maintaining—a “Fridays off” policy. It’s my hope that you can apply them to claim more personal time in your own schedule, or at least lay the groundwork for a better and less frenzied way of working.”

  1. Set your start date well in advance (My favorite line: “The key is to start planning at the “horizon line” where nothing is scheduled.” Given sufficient notice, people won’t object.)

  2. Build in “admin time” on Thursdays

  3. Identify how you want to spend the time

  4. Know when to stand firm and when to be flexible

The Big Work Lie: “Out of Office”

Once you plan to leave, then the trick is to actually do it. Years ago (2014), I flagged this post on LinkedIn by Richard A. Moran because it rang so true. Two paragraphs stuck with me the most:

No one believes out of office status any more. No matter where we are, what we are doing, and whom we are with; we all sneak time to check and respond to email. Worse, we all expect others to do the same. No place is safe and no one believes that you are not checking emails, even whilst on vacation. It could be the tragedy of today’s workplace but it is the reality and it is not a good thing.

[When you receive an OOO response, it] raises lots of eyebrows and generates lots of questions, mainly, “Do we believe that response? Is he or she really out of touch? With today’s devices, is it even possible to be really out of the office and out of touch? Does that mean the recipient is really not checking? Is it true that people are truly addicted to email? So let’s wait and see….

Invariably, it’s up to individuals to “take the status to heart and personally reinforce it.” This is so hard. So, practice in small chunks and work up to it. Loved this note I got recently from a colleague: “Hello All! I am diving deep into my creative work and am checking email once per day sometime around mid-morning. I will get back to you. If this is urgent or time-sensitive, please call or text me.”

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How to come back from vacation

This article deserved its own category.

Why it's so hard to come back from vacation — and how to do it better

Just as preparation enables vacation, it allows for a smooth reentry. While on holiday recently, I was very glad to revisit this article by Sarah DiGiulio on how to improve one’s skill at “vacation recovery.” Disclaimer: she quotes my mentor Alexander Caillet throughout! If you are planning to be OOO, I highly recommend it. Key points I highlighted:

Shift in pace is hard (in both directions)

The issue is that you’re making a shift from the daily rhythm of vacation mode (sleeping, waking up, and eating when and where you want to) to work or home mode (getting places on schedule regardless of whether your body particularly wants to or not), explains Dawna Ballard, Ph.D., Associate Professor in the Department of Communication Studies at the University of Texas at Austin. She studies what drives our paces of life and its impact on organizations, communities and individuals.

“That shift is a point of friction, and it is frequently experienced as gloom. It’s just ‘Blue Monday’ on a different scale,” Ballard tells NBC News BETTER. They’re two very different paces of life and we usually need an adjustment phase to shift from one to the other.

WAYS to ease the transition

“So, DiGiulio asks, “is there a way to make the transition back to the “real world” any easier?” Luckily, yes!

  1. The first step is don’t go beating yourself up for feeling a little sad after returning from vacation.

  2. Prep before you go (clean the fridge; tidy up so you don’t return to a mess. So strikingly similar to how to leave the office in the first place!)

  3. Give yourself a buffer before re-entry. (allow time to keep “living in that fluid state of mind where you’re making your own decisions”)

  4. Savor the good times and let those feelings linger

  5. Put your recharged battery to use (“Take advantage of the renewed energy that vacation leaves you with, and do those things that allow you to engage with the world in a more thoughtful, productive, and constructive way.”)

  6. Bring a little bit of vacation home with you (A great trip gives you a heaping dose of feeling competent, in control and connected. Look for activities one you are home that inspire that carefree, best-you version of yourself active at home, too, Caillet adds. “Make it a part of who you are.”)

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Why Vacation Matters

Loved these two pieces, and expect I’ll continue to reference them in the years ahead.

How to hold space for yourself first

I really enjoyed this summary from Heather Platt. As leaders doing the often stressful and time-consuming work of holding space for others, Platt has practical suggestions for how to hold space for yourself. “This isn’t necessarily easy,” she notes, “but it is imperative.” A great read (along with Platt’s original post about “holding space” for anyone.) Her seven recommendations:

  1. Learn when to walk away.

  2. Let the tears flow. “tears are the window-washer of the soul” 

  3. Let others hold space for you. 

  4. Practice mindfulness. 

  5. Find sources of inspiration. 

  6. Let other people live their own stories. 

  7. Find a creative outlet for processing what you’re experiencing. 

Stress Management for Leaders Responding to a Crisis 

Thanks to Michel Buffet for highlighting this 2-page primer from the American Psychological Association regarding evidence based techniques for leading while handling stress. Unlike generic articles, this honed in on critical leadership competencies, and offers advice that can be applied to all sorts of circumstances.

Five key areas where stress takes a toll on a leader’s personal well-being and effectiveness.

  1. Decision-making

  2. Over-control of the situation

  3. Isolation

  4. Sleep deprivation

  5. Negative mood.

Seven techniques offered by psychologists to help leaders manage their stress while handling high-pressure situations:

  1. Recognize the physical warning signs of stress

  2. Pause before making decisions, public announcements (“It’s easy for leaders to get sucked into the frenetic nature of a crisis, feeling they always need to be fully responsive. However, pausing to reset and focus can contribute to better reception of a message or critical update. Leadership communication requires messages delivered with calm confidence, and a few minutes is enough for leaders to take a break, take some breaths, and consider next steps.”)

  3. Prioritize self-care

  4. Sleep

  5. Build time into the daily schedule for breaks, connection

  6. Have trusted professional relationships, support.

  7. Celebrate small wins and larger victories  


Nov 2024 PS: Why You Need Unplugged Time from Work and How to Get It by Diane Shannon ’85, MD, MPH, co-author of Preventing Physician Burnout: Curing the Chaos and Returning Joy to the Practice of Medicine, published in 2016.


Nov 2024 PS: Love this reframe from Roberto Ferraro