Hello lovey humans,

If you've ever had a childhood dream that seemed too crazy to imagine coming true, then this one is for you. This one is about a boy who dreamed of owning an island in a lake. This is Randy's story.

The Dream

Randy's family has been on Long Lake in Naples, Maine. Since the 1960s, when his grandparents built Ricker’s Resort, summers have been spent on the water, winters ice fishing and snowboarding at Pleasant Mountain. He learned to swim in that lake. Learned to fish in it. Knew its shoreline the way you know your own hand.

And every meal of his childhood, framed dead center outside the dining room window, sat Pine Island. He fished around it. Swam around it. Snorkeled its ledges. In fifty years he never once set foot on it. It was private. It was always just out of reach.

Somewhere around the age of eight, he started telling people he was going to own it. Just matter of fact telling. He didn’t know how, didn’t know the cost, didn’t know if it would ever sell. He just carried the fact.

Time Flies

Meanwhile he did what you’re supposed to do. Ticked all the boxes. Married Jamie-Lynn, raised two kids on the North Shore of Massachusetts. Built the forever home. Filled it up with all the stuff.

For most of his working life, Randy Bernard's job was to make a room believe in what they were selling. He led go-to-market teams for software companies. He was steeped in the world of quotas, pipelines, and the machinery of scale. He was very good at it too. He was good enough at it to write a bestselling book on it and be a regular keynote speaker. Randy had a gift, and it was: transferring enthusiasm from one person to another.

By every reasonable measure, he’d arrived. Then, for the first time in his lifetime, Pine Island came up for sale.

He knew what that meant. Whoever bought it next would hold it for a generation. This was the window, and it wasn’t going to open twice. So he sat his wife down and asked her the most question: Do you trust me? She said yes before he’d finished. Then he told her the plan — sell the dream house, move the kids into an apartment so they could finish high school with their friends, and put everything they had into an island.

His own words: "It sounds crazy, and honestly, it was."

The island hit the market in February. On his fiftieth birthday, April 28th, they went under contract. Two weeks later it was theirs.

The Second Harvest

The version of Randy’s story is the one that makes a good documentary — man reinvents himself, chases the impossible dream, wins. Roll credits. But that’s not what happened. Randy didn’t reinvent himself. He didn’t become someone new at fifty. He went back to the kid staring out the window at that island. Together with his wife, they sold the forever home, the safe life, not to trade up, but to return to the thing he knew in his heart. The island was not a new ambition. It was the first one. It predated everything on his résumé.

I’ve been thinking about this more than usual, having recently sold my house and donated almost everything I owned. On the surface, downsizing, or subtraction, can feel like loss. But below that layer is something more meaningful. It's about clearing away the thing you thought you had to do to get back to the thing you must do to remain true to yourself.

Everything Changes, Nothing Changes

A few weeks ago we visited Randy and his family on the newly opened island. It's really is dreamy. No screens, no neon signs. Just swimming around the island, fishing off the rocks and sunning our bodies on the dock. It truly feels like stepping into a bygone summer seen in faded postcards.

Today Pine Island Retreat hosts reunions, weddings, creator retreats, offsites, and the occasional private concert because Randy is obsessed with music. Every week Randy watches people step off the boat carrying the whole weight of their ordinary lives, and every week he watches them leave lighter than they came.

And the coolest part is that nothing about Randy's gift has really changed. He's still doing the only thing he's ever done. Every week people step off the boat onto Pine Island with the childish enthusiasm of arriving at a dream destination. Maybe even leaving behind the masks so they can just be themselves again. He's still just transferring enthusiasm from one person to another.

Yours in the work,

Richard & Devon