All episodes of How to Be Awesome at Your Job

How to Be Awesome at Your Job · 2026-07-23 · 36 min · 6,923 words

1169: Tapping into the Transformative Power of Sabbaticals with DJ DiDonna

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Part of navigating through life and and navigating your identity is What are you good at? What are you not good at? What do you like? What do you not like? And I think about sabbaticals as regret insurance. Because

You get to try things on for size that you would have regretted not doing. at the end of your life. That's DJ Dadonna. He's a senior lecturer at Harvard Business School and the founder of the Sabbatical Project. For the past six years, DJ has been researching and exploring the role of sabbaticals in modern life, as well as aiding organizations around the world to design and implement sabbatical policies. He writes about this and more in his latest book, Big Time Off, The Transformative Power of Sabbaticals.

And how to take one. Child one. How to convince your boss to let you take a sabbatical? Two, how sabbaticals can act as regret insurance, and three how How to plan for a truly fulfilling sabbatical.

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