268: Sabbaticals—Especially for Non-Academics—as Regret Insurance | Harvard Lecturer DJ DiDonna

DJ DiDonna is a Senior Lecturer at Harvard Business School, where he teaches entrepreneurship. In 2019, he founded The Sabbatical Project to define, explore, and research sabbaticals, and he has since advised organizations ranging from nonprofits to Fortune 50 companies on how to design sabbatical policies. His work on sabbaticals has been featured in outlets including The Atlantic, Time, Fast Company, The Wall Street Journal, CNBC, Fortune, and NPR. Before his work on sabbaticals, DJ co-founded EFL Global, a fintech social enterprise that helped enable more than $2 billion in capital for underbanked businesses and individuals across more than 20 countries. On his own sabbatical, DJ walked 900 miles on pilgrimage in Shikoku, Japan, and ran a poverty research lab at Notre Dame. DJ's is also the author of the book, Big Time Off: The Transformative Power of Sabbaticals and How to Take One

In this episode we discuss the following:

• Sometimes we need to zoom out before we can know whether we should keep going. DJ had his  dream job, but over time, it stopped being fulfilling. So he took a sabbatical.
• Sabbaticals are different from vacations. On vacation, the work is often still waiting, and part of our brain is still running in the background. But on a true sabbatical, we step far enough away from normal life to see more clearly and focus on what is important, not just what is urgent.
• Sabbaticals also give us room to experiment with different versions of ourselves. When we’re younger, we have socially acceptable ways to do that — school, internships, missions, study abroad, gap years. But as adults, those opportunities become less common, and we often stop experimenting altogether. We get on a track, stay in the lane, and assume the next thing should look a lot like the last thing. The sabbatical helps us break out.
• I love DJ’s phrase that sabbaticals are “regret insurance.” Maybe we can’t take a sabbatical tomorrow. But what are we doing five years from now? What would we regret never having done? And what would it look like to start planning now?