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August Experiment: Your Sailing Adventure

This is #8 of 12 experiments for the year, offered to get you inspired, thinking creatively, and organized in the pursuit of bold life ambitions of deep personal meaning. (Click on the numbers to read the January through July experiments for 2023 1, 2, 3, 4, 5, 6, 7 .)


Our 2023 experiments to this point have focused on the process of interpreneurial planning. That is (and as with any startup), what is my dream, why does it matter, who cares most, and how do I get organized and launched? This experiment focuses on something much more meta: the personal balance required within if your interpreneurial ambitions have any chance at success. Onward!

A trinity of strengths

If you’re enjoying this 2023 series of Life Leap experiments you’re likely embarked on a daring life adventure, or considering one. Successful journeys requires 3 things: a sturdy vessel, the energy to power it, and a map to your destination. To have any chance of realising your Life Leap - regardless of your well of talent, the thrilling dreams you envision, or the masses waiting with arms wide open - a healthy respect for this trinity of strengths is required for success. Let’s look at a helpful maritime analogy.

Maryland’s enchanting Eastern Shore

I used to sail on the Eastern Shore of the Chesapeake Bay with my dad and brother during summer holidays. My dad would rent a boat and we’d take up residence at the historic Robert Morris Inn for a week. Mom and the sisters would join as well, but they weren’t as keen on tacking around the bay all day.

My dad selected well-made sailboats - 30-some foot Ericsons or Pearsons, typically - and there was always a thorough set of nautical maps in the cabins. Each morning we would meet at breakfast praying for good wind: not a howling gale; not a listless draft; just a steady, powering breeze. Where are we heading to today boys?

Dad was not one for the aimless sail. Tilghman Island; Saint Michaels; Trippe Creek; there was always a destination set for the day as we motored out on the Tred Avon River, sailed down the Choptank, and then into the greater bay. We had the charts to go anywhere and knew how to read the winds. Out by 9, sandwiches for lunch, back by 4 and a bucket of steamed blue crabs to hold us over until dinner. These outings marked some of my warmest life memories. Truly blissful.

Sailing provides the perfect analogy for a successful life leap. The key ingredients are a sturdy ship, a steady wind, and a well-plotted map. If any single one of these is missing you’ll commit endless time and boatloads of resources on a disappointing journey. The ship is your physical body. The wind is your passion for the journey. And the map is your Interprize Plan.

Consider the handicap of missing any one of the 3:

  • A sturdy ship. You may have a steady wind and know where you want to go, but a leaky ship can’t get out of the harbor. If you don’t honor your physical health and maintain a strong vessel, you’ll struggle and exhaust with each advancing year. Find exercises that suit your interests and lifestyle. Try different things. Commit to the ones you love. A sturdy ship will help you ride out choppy seas. Stay robust.

  • A steady wind. You may be jacked up, buffed out, and know where you want to go, but with no wind in your sails you’re dead in the water. Emotional resilience is every bit as important as physical robustness. Mindfulness and meditation; the best rituals for building positivity (or happiness if you prefer); maintaining close friendships: these are just a few practices that build emotional resilience and will see you through some foreboding weather. Adopt the ones that suits you best. A positive outlook will keep your sails full. Stay resilient.

  • A well-plotted map. Your ship is strong and the wind is blowing, but you have no clear direction. You tack from shore to shore but don’t have a fixed heading. Where is your North Star? These 2023 experiments are designed to guide your design of that map: your Interprize Plan. What is the grand ambition that will feed your passion and fill you with purpose? How do you most effectively pursue it? Not clear, … then please work through Experiments 1 through 7 again. They will help. Build that map: x marks the spot. Know where you’re going and how to get there.

The Trinity of Strengths

Finding this balance is not something you suddenly achieve, it’s something you continually pursue. The critical takeaway is that these 3 pillars are elemental to a grand life pursuit of deep personal meaning. Constantly work to strengthen them. Our Life Leap Workshops are designed to do just that: instill the best practices of interpreneurial planning while immersing in rituals and routines for the body and soul.

If you want to know more about the art of interpreneurship and the work we do at the Interprize Group, contact me through the site or at I’d love to hear from you.

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