Why a Break From Work Might Be the Best Career Move You'll Ever Make

Why a Break From Work Might Be the Best Career Move You'll Ever Make

July 20, 2026 · 30 min

About this episode

DJ DiDonna discusses the benefits of taking a break from work and how it can positively impact your career and life.

Most of us approach a long break from work with some anxiety. Whether it’s a layoff, parental leave, or a season of caregiving, there’s tension around if and when we’ll return to work and how we’ll explain the gap on our résumé. DJ DiDonna, senior lecturer at Harvard Business School and author of the new book Big Time Off, wants to change that. This week, he joins Jessi to make the case that stepping away from routine work — for whatever reason, for however long — is one of the most strategic things you can do for your career and your life.  Jessi and DJ discuss: What a sabbatical actually is, and why two-thirds of them happen because of a negative catalyst, not a choice Why immediately job-searching after a layoff is like grocery shopping while hungry The difference between a vacation, a corporate "sabbatical," and the real thing, and why it takes six to eight weeks just to feel like yourself again What DJ calls "fertile emptiness," and why most of us never let ourselves get there How to use a sabbatical to run experiments on possible future versions of yourself The story of a CTO who went to Norway, built a text-to-speech app, and redesigned his entire relationship with…

People in this episode

Host: Jessi Hempel

Guest: DJ DiDonna

Topics covered

Keywords

Mentioned in this episode

Organizations: Harvard Business School

Books & works: Big Time Off

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