Don’t Let Your Dreams be Dreams

by Tom Benson, Pilot Knob STEM Magnet School,


Dear Friends,

As you may know, I am out sailing for a year on Faith Afloat, my Catalina 350 sailboat, with my two boys Luke, 12, and Liam, 16. But many of you don’t know the back (and back, back)-story to this #PrincipalSailingEdventures. So, let me take you back a few years and show you how my dream was ignited and how it became reality more than 40 years later.

Back Story …

My dream to sail began when I was a teen. I read the book “The Dove” and saw the 1974 biographical film based on the story of Robin Lee Graham, a 16-year-old who sailed around the world alone from 1965 – 1968. The book and articles in National Geographic hooked me and created my dream to become a sailor. This trip is the achievement of that dream.

For those who want to know more, here is the Back, Back Story …

In 1974 was a 6th grader living in St. Cloud, MN. St Cloud is about as far away from an ocean as you can get (and surely not a tropical location). I happened to watch a National Geographic special about Robin Lee Graham, a 16-year-old boy who sailed out of Marina Del Rey, CA in 1965 to become the youngest person to sail around the world. The documentary made such a powerful impression upon me that I clearly remember sitting on the red indoor/outdoor carpeting in our basement (a memory which singles me out as a baby boomer) and watching it. I was spellbound, and from that moment on I was fascinated with sailing and determined to become a sailor, adventurer, and explorer.

We all need role models and supporters; fortunately, I had both. My parents supported my dream and my mom bought us a small Snark sailboat. A Snark sailboat is nothing more than a large piece of Styrofoam with a sail – but you need to start someplace. After many capsizes and rescues I got a little better at sailing the Snark. I also had teachers who shared their passions. I clearly remember Mr. Bruce Moberg, my high school social studies teacher, and the times we spent sitting in his garage looking at his sailboat as he told stories of sailing in The Lake of the Woods. Mr. Moberg fanned the flames of my sailing dreams while showing me the powerful impact a teacher can have on a student’s life. If there are any teachers reading this, please tell your stories and share your passions; “Telling story,” as Hawaiians call it, is a compelling tool.

The next big step towards my dream came while living and going to university in Portland, Oregon, a location I chose specifically because of its proximity to the ocean. Portland’s nickname is “Bridge City” due to the rivers which crisscross the city. Whenever I could, I sailed 27’ – 30’ boats on Portland’s rivers and through the Columbia Gorge. One summer, my friends and I chartered a 40’ Islander sailboat in the San Juan Islands off the coast of Washington. We sailed to Canada and explored the islands that we came across along the way. The excitement of sailing to a foreign country, landing on an island, exploring, looking for shells and driftwood, and learning about the local history was fascinating to me. Seeing Killer Whales and all the ocean life exceeded my expectations beyond belief, and confirmed my dream. I knew for certain that sailing was something I wanted to do more of.

In 1986 I left Portland and moved to Los Angeles, California, to begin my career as an inner-city teacher in South Central LA. At first people laughed and doubted that a teacher making $24,000 a year could have a sailboat. But dreams are powerful things to mess with and I spent all my free time searching through marinas in Southern California for a boat I could afford. Finally I found a 27-foot, 1968 Santana/Schock sailboat sitting under a layer of dust and grime at a working marina in San Pedro, California. I called the owner and learned that the boat had been the pride and joy of a man who tragically died before completely finishing the boat. I purchased the boat from his widow, who was pleased to know that I would love, cherish, and restore the boat, completing her husband’s work while creating my own dreamboat. When finished, I named the boat The Roy after my grandfather who loved the water. I learned through trial and error – mostly errors! — how to sail The Roy. Again, something for teachers and students: I raced the boat and at first I was such a terrible sailor that all the boats finished hours before we finished. But, we practiced and learned more, and finally won the race series (Growth – Mindset and Effort = Achievement).

As a teacher I wanted to share my love of sailing with my students (biking too) and encourage them to dream, “paying it forward” like Mr. Moberg had done with me, so I taught some of my 3rd grade students to sail. These were African – American and Hispanic students who lived only eight miles from the ocean, but rarely, if ever, made it to the beach, let alone on a sailboat. It was gratifying to teach them, although I began to question my teaching skills when, after sailing for an hour or so, one of the students asked where the motor was and why didn’t he hear it. So much for my teaching skills, though I like to believe that they have developed considerably since then.

I eventually left behind the ocean, but never left behind my dream. Fast forward to 2003; while working for the Minnesota Department of Education I met Jay Haugen, a fellow co-worker. We bought a boat together, which allowed me to sail once again. I shared my dream of sailing full-time with Jay, and we hatched a plan to take a sabbatical (I like to call it a seabbatical) to go and sail. Jay, his wife Janet, and their children Kaetchen, 15, and Kimberly, 10, headed out for a year of sailing “The Great Loop,” down the river system to Florida and up the East Coast. They had a great trip that was life changing. I wanted to follow in Jay’s wake, but was unsuccessful at getting a sabbatical to support the trip. As each year passed Jay encouraged me to get going despite the lack of funding, but the time was never quite right. I would often sit over a craft beer with Jay and have him recount his adventure; now I am looking to tell the story to others who will also take the trip or pursue their dreams.

Fast forward again to 2017, when a combination of events vividly illustrated how life and circumstances can change in an instant; I realized that time could run out before I achieved my dream. Around the time of that epiphany, I saw “Don’t Let Your Dreams Be Dreams” written in the bathroom of The Thirsty Pagan Brew Pub. This became my personal motto; I decided to cast off the bow lines and take a chance that it would all work out. Thanks to the support of my wife Sandy, daughter Nicole, Mom and Dad, along with Mr. Visa, Mrs. Chase, and their son Discover, we headed out on Faith Afloat on August 1, 2017 for a year of sailing. I call this year long journey my “Principal Sailing Edventure,” because it combines the fulfillment of my own dreams with the desire to share my experiences with students, just as Mr. Moberg did with me, to encourage others to dream and follow those dreams — regardless of how long it takes.

As I finish writing this I am at anchor just outside of St. Augustine, Florida with my two boys Liam 16, and Luke 13, living our dream. We are continuing our adventure down the Intracoastal Waterway and heading to the Caribbean. We are excited that you are following our sailing adventure. You may follow us via FaceBook and Instagram at TomBenson777. If you would like to reach me in person, please feel free to call at 651-262-9197, or email at

Tom Benson

S/V Faith Afloat

Pilot Knob STEM Magnet School Principal



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