Yep, that’s me; I’m the silver-haired 58-year-old badass nomad of five decades who decided to tackle my wildest adventure yet: overcoming my fear of water & learning to sail.

The challenge was that I had never sailed–or set foot on a boat before. I had never read navigation charts, used a compass, seen a barometer, heard the word bilge, held a sextant, put out a fender, made a nautical knot, or understood nautical miles.

I am night blind, afraid of the water, and don’t know how to swim.

These qualities would ensure my unwavering dedication to remaining firmly on the boat and would transform me into an exceptional sailor.

Armed with the only sailing knowledge I had acquired, and that from a song by the English new wave band, The Fixx, “red skies at night?—?should have taken warning,” and a Sailing for Dummies book, I found myself on a 41’ sailboat, circumnavigating Vancouver Island; and thus began The Adventures of a Reluctant Sailor.

What Brought Me To Sailing Life at 58

We had arrived at the idea of sailing, not by mutual consent, but by mutual misunderstanding, when I had arranged a surprise birthday outing for my boyfriend of crabbing and deep-sea fishing off the Oregon Coast.

That evening, we found ourselves in a cozy Air BnB, protected from the wind and rain, ensconced in the warm embrace of Bourbon and Brubeck, reveling in the day’s events. We caught Ling Cod and crab, which we cooked, cracked, and ate while basking in the shadow of the Newport Bridge.

We felt the rolling of the waves as the land slowly disappeared from our view, and the ocean spray on our faces invigorated us to our souls. It was a perfect day, and as we lay in each other’s arms, words danced across my mind and escaped my lips: “Wouldn’t it be fun to get a sailboat and cruise around…” And then sleep came.

My dreams were filled with visions of us sailing the bay on weekend excursions, pulling into a bar with an ocean-themed name like The Jammin’ Salmon or The Virgin Sturgeon. We would partake in equally nautically named cocktails, such as the Maritime Martini or The Shark Bite, dance under the stars, and then return to life on land, refreshed and renewed.

My boyfriend’s dreams had been different. In his mind, it would be fun to ‘get a sailboat and cruise around… the world.’ His dreams were filled with sails and keels, waves and whales, nautical knots and charts. We would dance under the stars and then return to life on the sea, refreshed and renewed.

It was an innocent enough misunderstanding that had remained unspoken until now as we stood on a shaky dock, looking into the dark, cavernous belly of what was liberally being referred to as ‘a boat’.

The First Sailboat

Lapworth 36 in Disrepair. Credit: Heather Jacks

“Just be careful of those batteries,” the owner called up to us.

Looking through the doorway, the entire floor below was covered in lead acid batteries?—?each connected to the other with a jumble of wires and jumper cables. Our senses were assaulted by diesel and gasoline.

“That’s OK. We’ll just wait up here.” We exchanged glances while our eyes surveyed the boat or what remained of it.

That morning, Chris had been actively pursuing Craigslist, Facebook, and a host of other online ads for Boats for Sale. He had struck upon this; a Lapworth 36 in Winchester Bay, Oregon. It came with a resume of spectacular voyages and oceanic cruises, seaworthy, comfortable, and priced right at $8k. And now, a mere 2 hours later, we had arrived at this; a pile of floating firewood.

The young gent, with a man bun and Birkenstocks, who had greeted us, called up. “I’ll fire her up and we can take a sail around the bay.”

In unison, Chris and I both yelled back; “No. No. That’s O.K. Whatever you do, don’t fire her up!”

Later that afternoon in Reedsport, Oregon, we ate fish and chips, drank beer, and reviewed our key learnings of the day; the biggest was we needed professional help. I was thinking of the kind of help where we complete questionnaires, fill out assessments to evaluate our mid-life crisis mind states, and uncover hidden secrets; help along the lines of Ken Coleman or Dr. Phil.

Kiwi was thinking ‘help’ as in learning every detail about sailboats, sailing and beyond.

The next six months would take us on what Tommy Lee Jones called a ‘hard target search of every farmhouse, henhouse, outhouse and doghouse’, for that perfect boat. A search that took us down the entire West Coast of the United States to Mexico and back.

A search that took us on boats in New Zealand and prompted us to download the Zoom app to check out boats in France, Jamaica, and beyond.

In this search, we would come across our much-needed ‘professional help,’ Mike Mullenberg, aka: Mully Sails.

We were on an adventure, not of the Ernest Shackleton level, but of the Frodo sort?—?although, that story wasn’t a Frodo story at all?—?it was a Samwise Gamgee story. Sam, the little hobbit that followed Frodo on the Gandalf-directed adventure with a heavy yet hearty heart. He was truthful, optimistic, fearless, and courageous. But most of all, he followed Frodo out of loyalty. The story is a testament to love and friendship.

On this journey, I was Sam, following out of love and hoping against hope that my Frodo would come to his senses and realize the lunacy of the idea. To me, Krakens and Orcs were interchangeable. Davy Jones and Sauron were the same.

Have an amazing day. Thanks for reading!

If you dig this story–you might want to check out Trading Our Life on Land for A Life at Sea!