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/

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