Episode Details

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 work and money
• Why functional workaholism is the thing most of us are living with
• What AI has to do with the case for stepping back, and why learning from a place of fear versus curiosity makes all the difference
• How Jessi's own three-month hiatus from the workplace, during which she wrote a book and raised a newborn, turned out to be a sabbatical she didn't know she was taking
• How to start planning for a sabbatical five years from now, even if taking one today feels impossible

Follow DJ DiDonna and Jessi Hempel on LinkedIn.