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

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

Author: How to be Awesome at Your Job July 23, 2026 Duration: 34:54
DJ DiDonna makes the case for why taking more extended time off helps professionals get further in their careers–and shares tricks for actually snagging that time. — YOU’LL LEARN — 1) How to convince your boss to let you take a sabbatical 2) How sabbaticals act as “regret insurance”3) How to plan a truly fulfilling sabbaticalSubscribe or visit AwesomeAtYourJob.com/ep1169 for clickable versions of the links below. — ABOUT DJ — DJ DiDonna is a senior lecturer of business administration at Harvard Business School, where he teaches MBA courses on entrepreneurship and building meaningful professional and personal lives. He has spent his career translating social science research into real-world tools for positive change. In 2019, DiDonna founded The Sabbatical Project to define, explore, and research the role of sabbaticals in modern life. He has helped organizations around the world—from nonprofits to Fortune 50 companies—design and implement sabbatical policies.His work has been featured in The Atlantic, Harvard Business Review, Time, Fast Company, The Wall Street Journal, and The New York Times. Previously, DiDonna cofounded EFL Global, a fintech company that enabled more than $2 billion in capital to underbanked businesses and individuals across twenty countries before its acquisition in 2018. DiDonna earned his MBA from Harvard Business School. On his sabbatical, DiDonna walked nine hundred miles on pilgrimage in Shikoku, Japan, helped lead the Wilson Sheehan Lab for Economic Opportunities at his undergraduate alma mater, Notre Dame, and unskillfully remodeled his kitchen. Outside work, you can find him plotting how to be in the Big Outdoors.• Book: Big Time Off: The Transformative Power of Sabbaticals and How to Take One by DJ DiDonna• LinkedIn: DJ DiDonna• Website: TheSabbaticalProject.org• Website: djdidonna.com— RESOURCES MENTIONED IN THE SHOW — • Tool: Voice Dream Reader• Book: The Three-Body Problem (The Three-Body Problem Series, 1) by Cixin Liu• Book: Working Identity: Unconventional Strategies for Reinventing Your Career by Herminia Ibarra— THANK YOU SPONSORS! — • Shopify. Sign up for your free trial at Shopify.com/awesomepod• Monarch. Get 50% off your first year with code AWESOME at Monarch.com See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Ever feel like there's a gap between the work you're doing and the work you know you're capable of? That's the space where How to Be Awesome at Your Job lives. Hosted by Pete, this long-running podcast digs into the practical, often overlooked tactics that transform good performance into remarkable impact. Rather than abstract theory, each conversation with accomplished thought-leaders and results-getters focuses on extracting specific, actionable insights you can apply immediately. You'll hear real stories and candid advice that sharpen universal skills-like clear communication, strategic thinking, and effective collaboration-which are essential for any role that involves working with others and solving problems. With over 25 million downloads and recognition from places like The New York Times and Forbes, the podcast has become a trusted resource for professionals seeking more than just a checklist. It’s about cultivating a more fulfilling career, finding more meaning in your daily tasks, and yes, creating more wins and financial reward along the way. Tune in to discover how small shifts in approach can lead to significant gains in your performance, your well-being, and your overall enjoyment of the work you do.
Author: Language: English Episodes: 50

How to Be Awesome at Your Job
Podcast Episodes
1145: How to Flourish in Chaos and Build Adaptability with Anne Grady [not-audio_url] [/not-audio_url]

Duration: 41:01
Anne Grady shares expert tips for developing your capacity to adapt, change, and grow during times of uncertainty.— YOU’LL LEARN — 1) Why to seek out the (second) greatest threat to your brain2) How to optimize your thre…
1143: How to Build a Career that AI Can’t Replace with Aneesh Raman [not-audio_url] [/not-audio_url]

Duration: 37:22
Aneesh Raman guides you on how to use AI and turn it into a competitive advantage. — YOU’LL LEARN — 1) Why you shouldn’t see AI as competition 2) How to make the most out of AI in your workflow3) What AI can’t replicate–…
1141: How to Stop Burnout Before It Starts with Guy Winch [not-audio_url] [/not-audio_url]

Duration: 40:04
Guy Winch shares the simple strategies for taking back control of your mind, energy, and attention from work.— YOU’LL LEARN — 1) How to stop rumination loops2) The trick to dealing with difficult situations beyond your c…