DJ DiDonna: Bold Time Off, What It Takes to Step Away
Send us Fan Mail About this Episode Your dream job can still burn you out, and admitting that can feel like failure even when everything looks “successful” on paper. I sit down with DJ DiDonna to get real about what actually happens when you step away from work and why that choice can be one of the most authentic, bold decisions you ever make. We dig into the illusion of certainty that keeps so many of us clinging to “safe” paths, plus the push-pull dynamic behind most sabbaticals: burnout and breakdown on one side, curiosity and meaning on the other. DJ shares what his research has found about career breaks, sabbatical policies, and the psychological permission gap that shows up as resume fear, guilt, and the worry of what other people will think. We also talk about the parts nobody glamorizes, including, grieving an old identity, hearing your inner voice get louder, and learning how to be present again. Then we go deeper into the practical side of a transformational sabbatical. DJ explains why getting out of your head and into your body can be the fastest route to healing, and he tells the story of his 900-mile pilgrimage in Japan and the confidence it gave him to “launch into uncertainty.” If you’re thinking about a career break, burnout recovery, entrepreneurship, or simply building a more meaningful life with better work-life balance, this conversation offers both encouragement and a clear way to start planning before a crisis forces your hand. In this Conversation • The illusion of certainty in “safe” career paths and why it keeps us stuck • Burnout as the push, and curiosity as the pull toward what matters • Why sabbaticals can start with grief, self-doubt, and an identity vacuum • Getting out of your head and into your body through exercise and creativity • DJ’s 900-mile Japan pilgrimage and the confidence it built for uncertainty • Planning a sabbatical like routine maintenance rather than a crisis response • Treating time off as a career cycle and building real time wealth • How DJ's new book Big Time Off grew from lived experience About DJ DiDonna DJ DiDonna is a Senior Lecturer at Harvard Business School, entrepreneur, researcher, and founder of The Sabbatical Project, an initiative dedicated to understanding the role that meaningful extended time away from work can play in our careers and lives. Before turning his attention to sabbatical research, DJ co-founded EFL Global, a financial technology company that helped enable more than $2 billion in capital for underserved businesses and individuals around the world. His work has been featured in The Atlantic, TIME, Fast Company, The Wall Street Journal, and other major publications. His new book, Big Time Off: The Transformative Power of Sabbaticals and How to Take One , brings together nearly a decade of research, hundreds of interviews with people who have taken sabbaticals, and DJ’s own experience stepping away after years of entrepreneurship. DJ's new book challenges the idea that extended time away is simply a luxury or an escape from work. Instead, he examines how purposeful time away can influence identity, relationships, creativity, career direction, and the way we think about what matters most. It also offers practical guidance for deciding when to take a sabbatical and how to design one that can create meaningful change. Additional Resources LinkedIn: @DJDidonna Website: DJ DiDonna Newsletter: Subscribe to the Sabbatical Project Get your copy of Big Time Off Support the show -------- Stay Connected www.leighburgess.com Watch the episodes on YouTube Follow Leigh on Instagram: @theleighaburgess Follow Leigh on LinkedIn: @LeighBurgess Sign up for Leigh’s bold newsletter
