On taking time off

Lenny's newsletter opens with his own sabbatical experience and then hands the floor to DJ DiDonna, founder of The Sabbatical Project, who has interviewed over 250 people about extended time off. DJ argues that sabbaticals are rarely regretted and can be transformative, but people tend to take too little time and fail to truly disconnect. He recommends at least two to three months, ideally around six, because it takes weeks to shed work identity. He also covers disconnecting through travel, somatic activities, and nature, and answers FAQs about working during a sabbatical, career impact, and taking time off with a partner or kids. The piece matters for PMs and leaders weighing a break, and for managers deciding whether to grant one.

01Key takeaways

• Plan for at least two to three months off, and ideally about six, so you have time to truly rest.
• Expect the first several weeks to be spent shedding work anxiety and identity before real rest begins.
• Disconnect deliberately by uninstalling apps, setting auto-replies, and traveling somewhere unfamiliar.
• Use physical, hands-on activities and time in nature to reconnect with your body and creativity.
• Avoid doing work-like tasks on sabbatical, since even a few consulting hours tends to expand and defeat the purpose.
• Structure time off as disconnection, exploration of your curiosities, and integration through journaling and reflection.

02Key sections

Why sabbaticals are worth it

DJ reports that the people he interviewed almost never regret taking time off, and describe it as a peak life experience. Lenny shares how his own sabbatical led him to start the newsletter.

Take enough time

Two to three months is the minimum, and about six months is ideal. Most people need several weeks just to stop feeling anxious about work and to rediscover who they are outside of it.

Actually disconnect

Travel, physical activity, and time in nature help break the ties to routine life. Digital boundaries are needed too, and in-person relationships often become a highlight.

Common questions

Working during a sabbatical undermines the benefits, though experimenting with a new craft is fine. Sabbaticals can strengthen a career story, and partners and kids can join with planned time apart.

Structuring your time off

DJ suggests three phases: disconnection, exploration, and integration. Integration includes journaling and reflection, since learnings surface gradually over time.

03From the post

“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…”

04Frameworks mentioned

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.