休假如何改变一切：三种休假者原型与实用指南

👋 Hey there, I’m Lenny. Each week, I share deeply researched product, growth, and career advice. For more: Lenny’s Podcast | Lennybot | How I AI | Become an AI-Native Builder and other favorite AI/PM courses

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This newsletter wouldn’t exist if I hadn’t taken a sabbatical.

Seven years into my stint at Airbnb, I took a three-month break. It was the first time I’d taken more than two weeks off in my more than 15-year career. I spent those months tinkering, reading, and traveling—and even snuck in a 10-day silent meditation retreat. At the end of it, I realized my heart wasn’t in the work anymore and that it was time for something new. So I left my job without much of a plan and spent the next six months exploring. Those six months turned into a year, that year turned into this newsletter, and the rest is history.

Looking back, I can say those were among the three most important months of my life, because they led me to what I do now—the most interesting, fulfilling, and impactful work I could have imagined.

Life makes it hard to get off the default path and back onto a road of your own design. Sometimes that looks like leaving your job, like I did. Other times, it means reconnecting to why you’re doing the work you’re already doing. Either way, in my experience and that of many friends, significant time away from your day-to-day is necessary for the mental, physical, or emotional shift that will reveal what’s next. What you need is what today’s guest author DJ DiDonna calls “Big Time Off.”

DJ is the founder of The Sabbatical Project and an early guest contributor to this newsletter, and today DJ’s book Big Time Off comes out! It’s a beautifully written, deeply researched book on the value of taking time off, with tangible advice, real-world case studies, and practical considerations for anyone who wants to shake things up. Below are some excerpts from his excellent book to help you start thinking about what a sabbatical might look like for you now or down the road.

I’d always wished there were a guide to help me think through that decision and make the most of this precious time off. We finally have one.

DJ will be in person in San Francisco at the Commonwealth Club on Thursday, July 23 (also streaming live online), interviewed by NPR podcast host Aarti Shahani. As a bonus, all Lenny’s readers are invited to the afterparty at Barebottle in Bernal Heights (8–10:30 p.m.)—your first drink is on DJ.

Also, for anyone who wants support on this journey, DJ has created a private WhatsApp community for Lenny’s readers. There he will host a live AMA on August 4 at 5 p.m. PT, as well as maintain an ongoing asynchronous forum for sabbatical questions, concerns, and ideas—click here to get your invitation.

Let’s get into it.

Almost 10 years ago, I stepped away from my dream job—a fintech company I’d co-founded—to spend a few months prioritizing the important over the urgent. I walked a long pilgrimage, cared for my mother during an illness, and knocked out some smaller items on my list, like writing a song and remodeling my kitchen.

Like Lenny, I came back changed. The time away made it clear that my old life no longer fit who I wanted to become.

So I left my company and set out to learn if my experience was unique or part of something bigger. I spent two years interviewing hundreds of sabbatical alums, which became a peer-reviewed paper and the foundation of my book, BIG TIME OFF: The Transformative Power of Sabbaticals and How to Take One.

Making sabbaticals accessible to everyone—not just the lucky few like me—takes rigorous evidence: evidence to convince business leaders (many of you included) to create supportive workplace policies, and policymakers to create supportive public policies. In this book, you’ll find plenty of evidence with which to make a business case.

But human stories of change are also necessary to convince the part of you that thinks taking time off would be irresponsible or impossible. That’s why personal journeys like Lenny’s matter, and that’s what’s at the core of the book: inspiration, permission, and a blueprint for the experience of a lifetime.

I’ve included excerpts from two practical chapters below to help you figure out how to approach your sabbatical, and how to avoid some common mistakes from the start. I hope it’s helpful.

Excerpt from Chapter 4: Catalysts, Archetypes, and Barriers

The three archetypes of sabbatical takers

The type of sabbatical you choose depends on your life stage, job status, and a variety of other factors, such as personal responsibilities and desires. A 45-year-old father of three will not have the same considerations—or priorities—as a 30-something who just sold her company or a 26-year-old between jobs. That being said, a sabbatical doesn’t have to map perfectly with your age or the expectations of others. A gap year, for example, can make as much sense at 55 as it does at 18.

On top of what you’re able to pull off logistically, it’s important to consider your intentions for your time off in the context of who you are and what you really need. Which part of you is planning your sabbatical—is it your exhausted work self, your internal productivity monster, or the creative version of you from deep down? Understanding your tendencies doesn’t just give you a lens to help choose the most suitable sabbatical; it also provides a mirror to help you see the life that warrants reexamination. Ultimately, understanding the various types of sabbatical intentions will help you align your sabbatical to what you need and to return with greater self-understanding.

Over the course of my work, I have come across three archetypes among sabbatical takers: Achiever, Seeker, and Explorer. Recognizing yourself in these archetypes can help you make the best of your hard-earned break from routine. (You will likely identify with more than one of these archetypes, and that’s completely normal. In fact, many folks experience all three during their time off.)

Understanding what each archetype hopes to gain and into which traps they’re likely to fall will also allow you to take advantage of the experiences of many alumni who have gone before you. You’ll be better equipped to know when your work-obsessed self may be taking over. For example, sometimes you can redirect a competitive, work-obsessed mindset into a beneficial sabbatical activity, like volunteering your time for others or whipping yourself back into shape with gusto. Other times, you may realize that it’s this mindset itself, not your chosen activities, that you need some time away from.

The Achiever

The first and most common archetype is the achiever. Achievers view their sabbatical first and foremost as an opportunity to get things done.

Achievers are easy to recognize. They’re looking to make up for lost time by trying to squeeze years of life goals into a few months. They’re primed to view their sabbatical from the perspective of what they got done instead of how it made them feel. Don’t judge—most people initially conceive their sabbatical this way. Because we so rarely have freedom over large swaths of our life, it can be hard not to think about a sabbatical as a prime opportunity for productivity on the personal front.

What this archetype wants: