How to Plan Your Sabbatical [Free Time]

In this episodeJenny Blake and DJ DiDonna talk about the role of sabbaticals for business owners, why managers shouldn’t be afraid to take time off, and about how existentially important it is for small business owners and solopreneurs to carve out time away from their routine work.

Listen here.


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.

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.

Alternate: More often than not, when you step away, you’re not only giving yourself a chance to renew and refresh for the next phase, but it’s the only way to learn what works and what doesn’t in your business.

✅ 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

📚 Books Mentioned

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