The Decoder: The Archetypes of Sailing with Angels

It was a hot, foggy dusk when I drove up to Sea Level to pick up burgers and mac-and-cheese bites for dinner. Sitting at one of the picnic tables past the seaside shack was my favorite lawyer friend, alone except for ten happy soon-to-be high school freshmen girls devouring burgers and fries at the table beside her. She asked how the Sailing with Angels launch was going, then immediately got practical.

“I need a decoder.”

Of course she did.

This is a woman who outshines me intellectually, counsels me wisely, thinks like a litigator, and approaches life as one giant evidentiary exercise with good humor sprinkled on top. She wanted to trace each character back to both its literary archetype and its real-life inspiration. Who represented what? Which classic storytelling roles were hiding beneath the Vineyard backdrop, fog stories, and harbor rituals?

So I sat down to do exactly that.

How would this book fare in the English-class exercise of mapping Jungian archetypes to each character? When you write, the story often simply flows out. It is only later, through editing and reflection, that you stop and wonder, “How would this hold up in a classroom?”

At first glance, Sailing with Angels feels whimsical and coastal. There are harbormasters and tinkerers, commodores and anglers, moonbeam voyages and fog pie. But beneath the poetry and illustrations lives something chasing the dream of an A on an AP English paper:  a story crafted with literary archetypes that have existed in storytelling for centuries. Something to make the generations of school teachers in my family proud. 

Princess Briel is both the Innocent and the Explorer. She begins wide-eyed and hopeful, then slowly realizes the generation who raised her will not always be there to guide the way. She is learning to navigate grief, but also learning what every adult eventually discovers: we carry our younger selves with us forever. She is me. Her outfit, my favorite childhood swimsuit. Her memory equal parts eclectic, nostalgic and optimistic. 

The Nurse emerged as the clear final character. She is the Hero and the Caregiver. Not because she slays dragons, but because she stands beside people in life’s hardest hours. She fights fiercely when there is still fighting to do, yet understands that love also means knowing when it is time to let go. She is inspired by a dear friend’s mother, Courtney Brady, an island EMT who found nursing later in life.

The Alchemist became the Magician archetype because of his ability to translate ideas into success. Inspired by entrepreneurial mentors I grew up around, he sees possibility before others do and encourages people to chase their magic. The two humans behind the character are Stanley Goldstein, founder of CVS, and Bob Carroll, my first employer and owner of the local hotels and restaurants of my childhood.

The Judge is my father. Wise, moral, and incapable of resisting a tease, he is equally Ruler and Jester. He governs through humor, language, rituals, and cleverness. His legendary dad pun, “A door is many things, but a jar it is not,” eventually led to the concept of keeping our memories ajar. He reminds us that wit can soften even the hardest truths.

The Harbormaster is the Connector, also with a smidge of Jester. Inspired by Barbara Nevin and the magnetic personalities who seem to hold entire communities together, sometimes shocking them with good humored antics. She represents the people who instinctively know that life is meant to be shared and enjoyed. She orchestrates parties, remembers names, introduces generations to one another, and somehow makes everyone feel included. “When they’re passing tarts, take a tart” is not really about pastries. It is about saying yes to life and to each other.

The Tinkerer, inspired by Bill Brine, became the Creator and Jester rolled into one. Every harbor town has a pied piper of possibility, the person behind the crazy idea, the impossible contraption, or the adventure everyone remembers twenty years later. He reminds us that imagination is not frivolous. It is fuel. 

The Commodore is inspired by Ted Dixon and the old guard of harbor life such as Bailey Norton, Ted Morgan and many others, he is the Sage and the Ruler, the grandfather to all. A keeper of ceremonial dress, traditions, cocktails, and harbor lore, he is the kind of man who can cut through the fog with a sweet distraction, and a perfectly timed story. His socks, red and green for port and starboard.  Life needs markers. 

The Whaler Mom is another kind of mother figure, the one driving the carpool and keeping the kids in line when your own mother is not around. Inspired by Betty Hayman and the other mothers you loved and feared all at once, she is loud, entirely self-sufficient, and impossible to intimidate. She can steer her own boat well into her late 80s, teach you how to sail, and tell you to toughen up as she needlepoints. My favorite Easter egg in the book is the alligator she is stitching, a nod to the next book, Sailing with Alligators, about navigating the jerks in this world.

The Anglers are the sparkling stoics of my childhood, an amalgamation of all the angles of strong New England mothers who taught us manners, classic style, humor, and competitiveness in equal measure. In literary terms, they are part Caregiver, part Hunter. Beautiful, poised, capable women who taught us how to host, flirt, laugh, pull up our bootstraps, and keep sparkling anyway.

What I learned while cross-referencing the final story was what I had intuitively known from the start: I was raised by, and sailed alongside, Sages and Jesters who cared deeply for their communities. As my first reviewer observed, “this book [Sailing with Angels] is reminiscent of The Little Prince, except that in this book, all the characters are likeable.”

In reflection, Sailing with Angels evolved into a modern fable layered with settings, songs, symbolism, and characters drawn from real life, some singular, some stitched together. It also became a poem because poetry trims away my tendency to wander, helping the story feel less memoir and more universal. Beneath the harbor rituals and fog stories is a simple hope: the people who shape us never fully leave us. Their lessons, quirks, and spirits continue to sail alongside us long after they are gone.

The book may be about grief, but the characters are really about inheritance.

Not financial inheritance. Emotional inheritance.

The people who teach us how to sail before we ever realize we are learning.

The Archetype Decoder

Princess Briel - Innocent, Explorer

Queen Marjory - Sage

The Judge - Ruler, Jester

The Commodore - Ruler, Sage

The Whaler Mom - Rebel, Caregiver

The Alchemist - Magician, Sage

The Harbormaster - Connector, Jester

The Tinkerer - Creator, Jester

The Anglers - Caregiving Hunter

The Nurse - Hero, Caregiver