👋 Hello, I’m Lenny and welcome to a ✨ once-a-month-free-edition ✨ of my newsletter. Each week I humbly tackle reader questions about product, growth, working with humans, and anything else that’s stressing you out at the office.

Q: I’ve always wanted to take extended time off from work – a sabbatical – but have never mustered up the courage to do so. Is it a good idea? How do I get the most out of my time off, and what pitfalls should I avoid?

I took a sabbatical while at Airbnb and it was one of the most transformative experiences of my life. I wouldn’t be doing this newsletter if not for that experience.

I took three months off (after seven long years), and did all the cliche things—traveling, reading, a 10-day silent meditation retreat. Also a lot of days of nothing at all. I had every intention to come back to work after it was over, but by the end of it, it was crystal clear to me that I was ready to move on to a new adventure. I vividly remember checking my email about halfway through the sabbatical and distinctly feeling my heart dropping. My heart was no longer in the work. I didn’t yet know what I wanted to do next, but I knew it was time to shake things up.

After leaving, I planned to take 6 months to explore and tinker. That turned into a year, and that turned into the newsletter that you’re now reading. There is a 0% chance this newsletter would have emerged if not for the space that this time off created—the space to tinker, to research, and to write. To chase my happy.

Though this worked out well in the end, I frequently wished I had a guide to help me make the most of my time off. And I’m not alone—my friends and former colleagues often ask me for advice about taking time off and I have nowhere to point them to. I’ve also noticed a big uptick in questions and discussions about sabbaticals in our subscriber Slack group. This may have something to do with the intensity of the past year 😭

Thus, I’ve decided to devote an entire issue to the topic of sabbaticals, and I couldn’t imagine a better person to help us all learn about taking time off effectively than DJ DiDonna, founder of The Sabbatical Project. I was introduced to DJ by my friend Nick Soman (thanks Nick!), and after chatting with DJ it was clear that he had a lot to teach us. With that, I bring you DJ’s amazing guest post on Time (Off) Well Spent. Enjoy 🙏

For more from DJ, you can help his research, share your own sabbatical story, and get notified when DJ’s upcoming book comes out. DJ also takes on a limited number of clients for sabbatical coaching—email him here.

Sabbaticals: Time (Off) Well Spent

by DJ DiDonna

Q: I’ve always wanted to take extended time off from work – a sabbatical – but have never mustered up the courage to do so. Is it a good idea? How do I get the most out of my time off, and what pitfalls should I avoid?

First, you’re on the right track—I’ve interviewed more than 250 people from all walks of life, and I’ve never spoken to anyone who regretted taking time off. (And this includes people who got divorced while on sabbatical as well as those who spent most of their time off caring for a dying loved one.) 

Instead, people call their time off transformational, life-changing, and one of the best decisions of their lives.

This near-universal reaction is what spurred me to transition from a fintech founder to starting a research and advocacy organization on extended leave: The Sabbatical Project. Our academic research suggests that sabbaticals are a “peak life experience,” right up there with having a baby, getting married, and other life-defining moments.

BUT, considering how bad we are at taking time off from work in general*, there are two lessons to learn about how to best take advantage of such a unique and powerful opportunity:

1. Take enough time off

2. (Actually) disconnect 

After going into detail about what these lessons mean for your future sabbatical, I’ll also address three common questions prospective sabbatical-takers have for me:

1. Is it okay to work while on sabbatical?

2. How will it impact my career?

3. What if I have a partner and/or kids?

Let’s dive in.

1. Long enough to “be”

One of the most common questions I get is: “What’s the minimum amount of time I could take off to get the benefits of a sabbatical?” 

The short answer is: Two to three months minimum, six-ish months ideally, and up to twelve is great. 

The shorter answer is: sigh. I get this question a lot, and I understand where it’s coming from, especially for those who take time off (and work) like Americans. But...

A sabbatical is not something you do, which can be optimized to do more efficiently. Instead, think of it as a space where you can be. It takes a while—a lot longer than you’d think—to disentangle yourself from your work identity. Just think about how long it can take some evenings after work to transition from executive to mom, from boss to creative hobbyist, or from product manager to loving partner.

Most people in our study described needing at least six weeks(!) just to lose the anxiety around tasks piling up, phantom phone alerts, and old responsibilities that were no longer theirs. Take this quote from a US Treasury employee on a sanctioned six-month leave of absence:

“I finished work on a Friday, and was on a plane on Monday, so it really was a seamless transition, work-wise. But it was surprisingly hard to get into the hang of being ‘off’; It felt weird to not have to check my emails every single day. I think that first month was about just understanding that work was no longer my life anymore, and I had to re-learn what my life meant outside of work. Like who I was, and what my purpose is without work giving me that purpose. Especially coming from a job that really had a mission.”

Why does it take so much time? In our study, we found that sabbaticals create a safe, “liminal space” for transitioning across identities. This “identity workspace”—think of it like a yoga room or dojo for your personal development—allows us to reflect upon, and experiment with, our lives. For example, one of our interviewees spent several months working at an ecolodge in Hawaii to see if that was an attractive pre-retirement goal (it wasn’t).

All of this to say: don’t short circuit your ability to fully rest, recover and experiment. Assign a block of time during which you will give yourself permission to be “off” from routine life. And yes, if you’re taking a sabbatical between jobs, commit to abstaining from job-searching. Opportunities will be there when you return and you’ll have a better story to tell if you give yourself time to do it right! Take this former attorney’s story:

“I was willing to relocate to a place where I didn't have any connections, and I was willing to start a brand new program without the requisite background in academia. I was willing to work with different communities I never really identified with. These are all things that I probably would've been too scared to do before taking the sabbatical...I no longer feel the same pressure to do things the way that other people have done them.”

2. Cut loose

The reason that most successful sabbaticals include traveling at the start is because it’s the easiest (and most symbolic) way to disconnect from normal life. Take this nonprofit executives experience:

"I had to quit the job and leave the state in order for me to feel like it was no longer a part of my life. It's formal separation, a ceremonial separation. The reason I like traveling is the only constant is you. You end up in all these different cities and people, cultures and sites and smells. After a couple weeks, you are now you again. You're no longer the personality that your friends helped kind of maintain. You're a little bit more natural."

Our research suggests that two other activities can be just as crucial for disconnecting—and therefore making the most of your time off: somatic activities and time in nature.

Somatic activities are simply those which utilize your body. Getting out of your head heals you and stimulates your creativity. Whether it’s yoga teacher training or ceramics class, find a way to reconnect your disembodied “knowledge worker” self with your flesh and bones. I remodeled my kitchen by myself, and rebuilt a deck with my cousin. It was horrible. It was also great!

Time in nature by itself has been shown to have transformative effects on mood, creativity, and fulfillment. Combine this with the extended time and space that sabbaticals offer, and getting outdoors accomplishes several things at once: it activates your body, forces isolation from regular life, and provides a chance to conquer hard-won physical goals. 

Unfortunately, traveling by itself no longer ensures disconnection. Global connectivity means that you need strong boundaries around what kind of communication you receive—and when—you’ll have access to it. Uninstall those apps, and set up email auto-responses! But while you’re disconnecting digitally, make time and space for connecting in-person; strengthening relationships with loved ones stands out as a highlight for most sabbatical-takers. Your newfound time-wealth will enable you to fit into the tight schedules of all those whose schedules never seem to overlap.

—

It can be very difficult to fit a sabbatical into life, but our research suggests it’s more than worth the effort to do so. Too often, the events that spur us to reflect or grow or transform are negative—most sabbaticals are catalyzed by events such as the death of a loved one, burnout, or a toxic work environment. Take control of some of the things which profoundly shape your life by exploring yourself, the world, and those who mean everything to you by taking extended leave at points in your career. Time off is time well spent!

Have a sabbatical story to tell? Tell yours here. Or get in touch to be connected to other sabbatical-takers (or those in the planning stages) or to get guidance and coaching from myself or someone on the team.

* Especially Americans, who despite having the fewest vacation days of any developed country, still leave a few days of PTO on the table annually.

Sabbatical FAQ

Q: Is it okay to work while on sabbatical? 

A: Yes, it’s okay to work, just don’t Work. Doing anything that resembles your current job will make it more difficult to reap the benefits of time off. Even if it’s “just a few hours consulting.” Those hours will expand to fill more time, prevent you from spur-of-the-moment planning, and in general, defeat the purpose of disconnecting from your work identity. If your “work” is experimenting with a new thing altogether, like being a photographer, or sound healer, or trying to cram as many national parks in 60 days off as possible, by all means, knock yourself out. Just be careful when using your time off to start a company…

Q: I have a partner and/or kids - is it worth the effort? How should we do it?

A: Without question, some of the most inspiring stories in our research came from people traveling with their children (see picture above) or partners. It’s obviously much more logistically difficult to do so, and a takeaway from the interviews on those traveling with partners is to ensure that you carve out some time apart to tackle personal goals (and to give each other a bit of space). Remember, just because you can’t go on sabbatical next month, doesn’t mean you can’t ever do it; many of our interviewees spent years saving up and planning for their time off.

Q: How should I structure my time off? 

A: It depends. Not only is everyone different, the needs for—and roles of—a sabbatical change over time. (I identify seven lifestage-based sabbaticals in my upcoming book.) In general, I’d recommend breaking up your sabbatical into three stages:

1. Disconnection

2. Exploration

3. Integration

As I mentioned above, plan on giving yourself upwards of six weeks to heal and disconnect—the more burned out you feel, the longer it will likely take. Physical activities, sojourns into nature, visiting loved ones will help.

Next, explore what Elizabeth Gilbert calls your curiosities. Try not to put pressure on yourself to find the “next big thing,” or to double down on something that sounds cool or will impress other people; instead ask yourself what questions you’ve wanted to explore, and work them into your plans. One interviewee left his green energy job to explore civic tech in Estonia. An edtech pioneer spent three weeks deep-diving about octopuses and animal consciousness on a lark. (Pun not intended.)

Finally, give time to integrate your learnings. This includes journaling, reading, and planning how to map your learnings into the next phase of your life and career. It’s best to do this somewhat isolated from others, if only for a weekend. But it’s not a one-and-done operation; your learnings will pop up gradually over time—keep that journal handy.

Q: What will future employers think about my time off? Won’t it make it harder to get a job?

A: Most sabbatical-takers actually use the story of their time-off as a differentiator in the interview process. One of our interviewees talked about how he was able to break away from the “boring consultant” stereotype by talking about traveling to countries on the US State Department’s do not travel list. A question to ask yourself is: if an employer looked down on you for taking time off to do something that’s important to you, would you really want to work for them?

Q: As an employer, when should I allow my employees to take a sabbatical? I fear that people don’t often come back, or they come back and soon quit.

Great question! Stay tuned for next week’s post where I’ll drive deep on this topic.

Thanks DJ! Learn more about The Sabbatical Project and get notified when DJ’s upcoming book comes out.

Have a fulfilling and productive week 🙏

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Sincerely,

Lenny 👋