475. “Think of Sabbaticals as Regret Insurance” | The Power of Time Off with DJ DiDonna
Jul 20, 2026
DJ DiDonna is a senior lecturer at Harvard Business School and the founder of The Sabbatical Project, where he studies how extended time away from routine work can reshape our health, identity, and direction. In his new book, Big Time Off: The Transformative Power of Sabbaticals and How to Take One, he draws on years of research to show why sabbaticals are far more than extended vacations.
We explore how stepping away gives us enough distance to recover from burnout, reconnect with neglected parts of ourselves, and consider what we want from the next chapter of our lives. DJ explains the three common sabbatical archetypes: the achiever, the explorer, and the seeker. He also shares why duration, disconnection, and journaling matter more than creating the perfect itinerary.
Our conversation offers a practical way to think about time off, even when family, finances, and professional responsibilities make it feel impossible. A meaningful sabbatical may require years of preparation, but the first step is deciding which experiences are too important to leave undone.
The Biggest Helping: Today’s Most Important Takeaway
Treat a sabbatical as regret insurance. Make space to identify what you would regret never doing, then begin moving the financial, professional, and logistical pieces needed to make it possible.
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