Show Notes
Burnout, career uncertainty, and midlife stuckness have become increasingly common, but stepping away may be the key to moving forward.
In this episode, Chip Conley sits down with DJ DiDonna, Harvard Business School senior lecturer, entrepreneur, and author of Big Time Off. After reaching burnout while running his dream company, DJ took a four-month sabbatical that transformed his perspective on work, success, and life.
In this conversation, DJ shares: Why burnout is often a sign that something needs to change How sabbaticals create space for clarity, growth, and reinvention The role of travel, pilgrimage, and reflection in personal transformation Why midlife is the perfect time to reassess your priorities Practical advice for planning a sabbatical, even if it feels out of reach
If you're feeling stuck, overwhelmed, or ready for a new chapter, this conversation offers a powerful reminder that sometimes the most important step forward is taking a step back.
Listen now and discover the transformative power of time away.
Timestamps: (01:47) Introduction & DJ’s New Book (02:53) Burnout That Led to a Sabbatical (04:42) The Freedom of Having No Structure (06:18) Why Pilgrimages Transform People (10:47) What Changed After Four Months Away (13:08) Sabbaticals Inside Organizations (16:20) Do Employees Leave After Sabbaticals? (20:40) How Sabbaticals Improve Retention (22:20) The Value of Floating Managers (24:20) Fear, Burnout & Quiet Quitting (25:51) Why Midlife Needs Sabbaticals (31:00) Creating Midlife Inflection Points (32:20) The Three Sabbatical Archetypes (35:30) How to Take a Successful Sabbatical (39:40) Planning for Sabbaticals Financially (41:10) Sabbaticals as Regret Insurance (42:40) Wisdom Bumper Sticker
Learn more about MEA at https://www.meawisdom.com/
#Sabbatical #MidlifeReset #PersonalGrowth #CareerChange #BurnoutRecovery #Midlife #LifeTransition #SelfDiscovery #WorkLifeBalance #PurposeDrivenLife #PersonalDevelopment #CareerReinvention #TimeOff #ChipConley #MidlifeChrysalis
More from The Midlife Chrysalis
“Stay positive” can feel hollow when cancer returns, someone you love dies, and your marriage is ending.
You can build a successful life and still reach a point where you need to rebuild yourself.
Your first love can stay with you for decades. So can the story you keep telling yourself about it.
Watch a great film, then share dinner with the person who made it. That’s the spirit of the MEA Film Fest, where stories on screen spark conversations and connections in real life.
After decades at the top, John Donahoe found himself starting over at 65.