The Importance of Working Hard on a Sailing Yacht

“My little pirate.” That’s the nickname Michael has given me this summer, as it feels like many of my corporate (client) income boats have burned these last few years. At the same time, he says he has never seen me so happy and free. “You’re not in a raft anymore,” he said. “You’re in a sailboat. You don’t want to be in the big cruiseliner anyway.”

Not to be confused with Sailing the Sea of Shiny Shoulds (I clearly love ocean metaphors!), today’s episode is all about embracing the agility and freedom that small business owners have to Sail the Free Time Seas. Heck, even one of the richest men in the world, Jeff Bezos, chose to buy a sailing yacht (albeit the world’s largest) rather than the more mechanized superyacht.

🌟 3 Key Takeaways / Goldilocks

• Three business vessel metaphors: the superyacht or cruise liner (large corporations), the sailboat (agile small-medium businesses), and the raft (struggling micro-businesses); the Goldilocks ideal lies somewhere in the middle.
• Relationship with Risk: A super yacht-like small business, due to its size and resource intensity, may be less willing to take risks, akin to how a super yacht cannot afford to take on dangerous waters. On the other hand, a sailboat-like small business can quickly change its course and can be more open to taking smart risks, seeing them as opportunities for learning and growth.
• Sail la Vie! Celebrate and embrace the full autonomy you have to set your own course—what you work on, with whom, and how you get there.

📝 Permission: Embrace your agile sailing yacht status as a Free Timer—we don’t all need to be (or buy or build) a superyacht :)

✅ Do (or Delegate) This Next: Celebrate how far you’ve already come from your earliest days in the rickety raft stage of running a business to where you are now.

🔗 Resources Mentioned

• Articles: New Yorker—The Haves and The Have Yachts, NYT—5 Deaths at Sea Gripped the World. Hundreds of Others Got a Shrug.
• TV Shows: Below Deck and Below Deck Sailing Yacht
• JB’s Secret Substack: http://itsfreetime.com/secret
• App: Substack (for reading others you subscribe to)
• Community: BFF (promo code PODCAST)

📚 Books Mentioned

• Love with a Chance of Drowning and The Worrier’s Guide to the End of the World by Torre DeRoche
• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One
• Life After College

🎧 Related Episodes

• SPARKED: JB on SPARKED with Jonathan Fields (Spotify playlist)
• Pivot: 304: Through the Crux—Pivoting from Acting to Entrepreneurship with Ryan Devlin
• Free Time:
• 050: Business-Building Metaphors—Are You Running a Machine, House, or Restaurant?
• 028: When the Financial Tides Recede
• 138: ⛵️ Stop Sailing the Sea of Shiny Shoulds

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