Finding My Luck on Cloud Nine
Meet my sailing friend and mentor, Captain Roger Swanson, A true One of One
"Travel is the realm of the improbable adventure, the quick fix, the ship passing in the night. It entitles you to meet interesting people whom you would otherwise never meet even if you laid traps or advertized for them."
Lawrence Millman- "Last Places"
As we get closer to the Okoboji Writers Retreat coming up soon Sept 28 - Oct 1, I’ve been trying to introduce my Subscribers, followers and readers to my life, and career, as I proceed down the Substack journey with the Iowa Writers Collaborative. Maybe this will help going into the retreat where I will do my best in workshops and panels over the very busy days on the Iowa Lakeside Laboratory campus. I hope some of you are coming to the inspiring event where we have time to meet and chat. OWR Link
In one of my last few stories before the retreat, I wanted to introduce you to Roger Swanson, my mentor who took me to the sea and changed my life. Part of the reason in doing so is to make you all ponder your own lives and the people who are special to you who have opened doors and created opportunities. I also want to explore the concepts of being lucky versus creating your own luck. We will discuss this in my workshops.
There are so many people that pop in and out of our lifetimes. Sometimes we take notice and act to create further contact and form relationships, and sometimes we don’t. As I look back on my life and people I have met, I regret not acting so many times to pursue further contact and explore these potential opportunities. My ocean sailing career came down to luck, and making luck happen. I did not want this certain ship to pass through the night and out of my life. It had to be boarded.
People constantly ask me how I began my ocean sailing career. The answer is easy; I met a Minnesota hog farmer, and the rest is history. No kidding. I really did meet my mentor, Roger Swanson, 35 miles north of Lake Okoboji on his century farm in southern Minnesota. The retired naval seaman’s home port was Dunnell, population 165, not exactly the mental picture I had created in my vivid imagination.
I first heard of Roger Swanson in the late 1980’s when I was working on building out the displays of old black and white photographs for the creation of the Iowa Great Lakes Maritime Museum in Arnolds Park. It was a huge labor of love and the process tried my copy work and printing skills to my very core back in the old film days.
There was an interesting volunteer for the museum that I met who grew up near the little town of Dunnell, MN, and she knew I was a sailor and adventurer. One day I was struggling with lighting all the photos and she said I needed to go up north and meet Roger’s son Steven who was an architect and a specialist with environmental controls and lighting systems for museums.
Steven and Roger had built an underground vaulted museum on his farm for all the charts, artifacts and collections that Roger had obtained throughout his circumnavigation on his sailboat named Cloud Nine. She could introduce me to Steven. I made the contact and traveled north to the farm where I was greeted by him at the door. His father was off sailing around the world again and would not be back for quite some time.
The interior of the home itself was like a museum with photos of dreamy, exotic locations and nautical charts from all over the world. And then there was the basement. First you entered through a huge old bank vault door which opened into a climate controlled dreamworld, dripping of world travel, nautical history and collections of cultural and historical artifacts . It was amazing. I was overwhelmed. Steven and I chatted about the layout of the room, displays and lighting while my mind was racing to far off destinations.
The conversation soon shifted to adventures and sailing. Steven asked me about my background and I told him that I was a professional photographer, a racing sailor and adventurer. He asked me if I was interested in potentially sailing with his father on Cloud Nine. This was the opening, my chance of a lifetime I had been waiting for, and here it arrived on a hog farm in Minnesota.
It would be almost another year before I could meet Roger with his busy travel schedule. When the time arrived I discovered that the process of meeting him would also involve a lengthy interview. Roger graciously met me at the door. He was small in stature, quiet and a bit reticent. We immediately bonded however on scow (a particular kind of small dinghy sailboat) racing on Lake Okoboji. It turns out he knew some of the older sailors there on the lake. I knew them all and the conversation quickly evolved from there.
Roger interviewed me about my background and interests. I told him that I had a longtime dream to sail around the world but had never been ocean sailing. He then offered me an opportunity. If I was up for it, I was to meet him and his sailboat in Cape Town, South Africa, halfway around the planet, in a year. Our rendezvous would be at the end of October 1991. I would be a crew for the 6000-mile sail across the South Atlantic Ocean if I was up for it. I said I would be there.
“How will I find you and Cloud Nine in Cape Town,” I inquired. “Just get there, come down to the main boat harbor and you will find us,” he stated with a wry smile and a twinkle in his eye. Everything was a test and a challenge with Roger. Getting to Cloud Nine with with all my gear, 10,000 frames of film, 30 hours of video tape, 5 cameras and all my sailing gear while navigating through the scrutiny of the waning Apartheid apparatus of officials and intelligence officers is a story for another day.
A year later I was literally on Cloud Nine, Roger’s beautiful yacht, for the sail of a lifetime. I never looked back. This would be the first of many voyages over sixteen years with Roger Swanson, the gentleman who changed my life and took me to the sea and allowed me to fulfill my dreams on the ocean.
Roger Swanson, both highly intelligent and methodical, seemed to have all the best attributes for a life spent at sea. In addition to being able to handle the daily drudgery of farming, he had an innate and immense curiosity. As a businessman, he invented several successful products, including the fiberglass truck topper, and with his father had perfected a mathematical method of cracking safes, among other (legal) pursuits. But when he lost his first wife to illness, their daughter, Lynn, challenged him on his 50th birthday to “sail around the world like you always said you would do.” What followed is one of the great sailing stories of all time.
Roger sold his business and purchased Cloud Nine, a 57-foot Bowman ketch-rigged (two masts, four sails) sailboat. She became a legend. According to Cruising World Magazine in 2014, “the top American Cruising Yacht in history may well have been Roger Swanson’s Cloud Nine.” That is still true in 2025.
In 1981, Roger and his two sons made a 28-month, 37,000-mile circumnavigation of the world. (Lynn was too seasick to complete the entire voyage.) Roger went on to complete two more circumnavigations (the last with his second wife, Gaynelle).
He logged 220,000 nautical miles over 40 years and took 310 different people to sail the world’s oceans during his career. I was fortunate enough to be one of them, beginning in 1991. I sailed with Roger on three Atlantic crossings, once below the Antarctic Circle and twice to the Arctic, including the successful transit of the Northwest Passage. Nine major voyages, nearly 40,000-nautical miles over sixteen years 1991-2007.
Roger received the Cruising Club of America’s prestigious Blue Water Medal in 2000 and was named the “preeminent American offshore voyager of the last three decades.” Captain Swanson was a good mentor, indeed.
On Christmas Day 2012, at the age of 81, Roger sailed over his last horizon. In a final update to my sailing blog at the time, I wrote:
“It is with a very heavy heart that I post tonight. My friend and bluewater sailing mentor, Roger Swanson, has passed into the deep after a hard-fought battle with illness. Roger was a great mind, strategist and adventurer.
Because of his willingness to accept ‘greenhorns’ on his sailing vessel, hundreds of lives were changed forever, including mine. I sailed all over Planet Earth with Roger. By seeing the remote regions of the world by sailboat, and working hard to get there, I was privileged to experience the environment in a unique and nuanced manner that shaped my life and views of ocean ecology and our earth’s climate system.
Roger opened doors that only he could have opened. There will never be another one like him. One of One. Fair breezes, Captain. Godspeed, and thank you always for taking me to the sea.”
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I cannot begin to relate the extravagance my mind experienced while reading this substack. Your brief story about your sailing mentor, Roger Swanson, was stirring. Your sailing adventures must be other worldly. Oh, and the photography is superb. Thankyou David!
Thanks David! My life, too, was greatly changed by Roger including sailing across the South Pacific in 1982/83, to Antartica in 1988 and meeting other sailors whose boats I would adventure on. I’m very thankful for his generosity.