193: Sabbatical Planning with DJ DiDonna
Free Time with Jenny Blake
Building a Business to the Point You Can Step Away From It for an Extended Period of Time
Jonathan Ive: How we're working is just something that we take for granted. Can you build a business to the point where you can step away from it for an extended period of time? And like I view that as the ultimate measure of success as an entrepreneur. If somebody listening or me were to create a sabbatical, what is the ideal amount of time?
The average American worker gets 11 days of paid vacation per year. Among those with unlimited paid time off (PTO), the average person takes 19 days off per year, yet 48% of Americans say they still check their work email while away.
What about business owners? Although it seems like we have more free time, the reality is that life as a business owner can be a 24/7 unceasing, all-consuming task. Even if you’re not at the computer, your passing thoughts probably drift toward what you need to do, projects to tackle, revenue gaps to make up for.
Today’s guest, DJ DiDonna, is an advocate for taking more abundant time off—ideally measured in months, not days or weeks. By DJ’s definition, sabbaticals should go beyond recovering from burnout; instead offering extended time to learn more about yourself in unstructured, even “unproductive” ways.
More About DJ: DJ DiDonna is a Senior Lecturer in the Entrepreneurial Management Unit at Harvard Business School, where he teaches the required first-year course: The Entrepreneurial Manager. In 2019, he founded The Sabbatical Project to define, explore, and research sabbaticals. He is currently working on a book based on this research, called Time Off Well Spent: A Sabbatical Manifesto.
🌟 3 Key Takeaways
- DJ defines a sabbatical as: Measured in months not days or weeks; taken intentionally; no specific outcome in mind (i.e. not working or trying to achieve anything); where you are exploring and learning something new about yourself.
- Three archetypes of sabbatical-takers: Explorer, Seeker, and Achiever. You might toggle between all three during your time off, switching modes from working holiday (passion project) to free dives (exploring the world), to more personal quests (existential discovery).
- Sabbaticals ideally start slow, with extended time to heal: sleeping in, eating healthier, and reconnecting with family or friends. When sabbaticals serendipitously unfold from recovery to exploration to putting that learning into practice, they can “lead you to a really radical new self.”
📝 Permission: Take four to six months off, even if it’s two years from now to give you enough time to prepare. Entrepreneurs often grasp their role in their companies too tightly, and inadvertently create a business that will fail without them.
✅ Do (or Delegate) This Next: Look for the area of your business that would fail without you. What small step could you take today to bolster that area for the future?
🔗 Resources Mentioned
- DJ on the web, Twitter, LinkedIn, The Sabbatical Project
- Quiz: What’s your sabbatical style?
- Videos: TEDxEVHS—DJ’s Sabbaticals: Time [off] well spent, TED—Stefan Sagmeister’s The Power of Time Off, How Bug Soup Becomes a Butterfly, David Foster Wallace This is Water Commencement Speech.
- Course: Sabbatical Basecamp
📚 Books Mentioned
- Time Off Well Spent: A Sabbatical Manifesto (Coming soon!) by DJ DiDonna
- Clockwork, Revised and Expanded: Design Your Business to Run Itself by Mike Michalowicz
- Reboot: Leadership and the Art of Growing Up by Jerry Colonna
- The 4-Hour Work Week: Escape the 9-5, Live Anywhere and Join the New Rich by Tim Ferris
- Free Time: Lose the Busywork, Love Your Business
- Pivot: The Only Move That Matters Is Your Next One
🎧 Related Episodes
- SPARKED: How to Take a Life-Changing Sabbatical with DJ DiDonna and How I Took a Month Off to Write & Make Art (and what REALLY happened)
- Good Life Project: Jenny Blake | How to Create More Free Time
- The Tim Ferris Show: How to Reboot Yourself with Jerry Colonna
- Free Time: 166: Crashing into Quiet Time, 146: New? Help Us Welcome the Next You (A Message for Your New Team Members), 044: Are You High Net Freedom?
- Pivot: 124: Penney & Jenny Show — Embracing Liminal Space (the In-Between), 45: Happy Launch Day!! Pivot for the Podcast: James Altucher Interviews Jenny
📝 Check out full show notes from this episode and share it with a friend: https://itsfreetime.com/episodes/193
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