How We Became (A Little More) Impervious to Failure

When my brother and I were 11, our father designed a 17-foot boat for sailing around the world. He’d never ventured more than a few miles from the U.S. He’d never sailed, or designed a boat before.

Dad bought a book, “Skene’s Elements of Yacht Design,” and a RadioShack computer. Then he spent a year programming the computer to produce the optimal shape for a sailboat hull. The unloveliness of the result was proof of its genius: where most hulls curve up at the stern and bow into a smile, ours curved down into an oval.

After another year drawing in by hand each joint and winch, our father drove the family across the state to meet a naval architect. My brother and I played catch in the parking lot while he went in. He came out an hour later, defeated.

The architect had said that such a small boat wouldn’t have enough wind in the open ocean, where the mast would dip below the level of the swells. But then Dad spent most of the family’s savings buying a boat of the exact same size.

From Here, You'd Spend the Rest of Your Life Swimming for Shore

Now we had to learn how to sail it. From home, he'd call a Coast Guard hotline for small-craft advisories, announcing each as an opportunity to learn reefing or heaving-to. Once we passed the first channel buoy, he relished reminding us how cold Puget Sound was by saying “From here, you’d spend the rest of your life swimming for shore.”

For landfalls, he built a dinghy in the exact shape of our tiny cockpit, so it could fit inside it like a matryoshka doll. The dinghy had room for only one person, but he attached a fishing line to it, reeling it back for a second passenger. When I got in for the first time, water began spilling over the sides until I sprawled across the bottom to distribute my weight.

I learned from this to be careful, which doesn’t come naturally to me. I learned other things too: that people will endure any hazard, such as coming about in a strong wind, if you can calmly explain first what will happen. From squalls, jibes and other sudden calamities, I learned you don’t always get to decide when you've got to make a decision.

I learned that looking miserable was a family betrayal, even when we came sputtering past all the other boats at the the dock near midnight; this has been useful to remember when I’ve felt like the only unsuccessful person in a room.

I learned that to win a race, you have to develop a feel for the trim of the sails, freeing your eyes to scan the waters for wind-shifts; in any competition, it’s easy to spend too much energy sorting yourself out, and miss the world around you.

And I learned from being becalmed so many times that all of us, even carseat-bound infants in a traffic jam, like going anywhere much better than going nowhere, a tendency that can lead you astray.

But mostly I learned about the power of delusion. After years of boom bashings, lee shores, near-misses from container ships, hypothermia and passengers’ hollered prayers to God, I was shocked to see that our dad's log consisted entirely of entries like “Successfully crossed Strait of Juan de Fuca. Arrived Port Angeles 0200.”

How to Resist Growing Up

These delusions became my world. Growing up is mostly the process of having to acknowledge the differences between your world and the whole world. Bizarre displays of affection for the family pet or bedtime stories deep into adolescence only become embarrassing -- only begin to die -- the first time someone else sees them.

But part of what our father taught us was how to resist growing up, how to keep seeing things the way only our family did. After a young adulthood trying to get him to see the world for how it really is, my brother Wes and I have come back to the way our dad is, realizing that it’s sometimes our job to see the world as it could be, as we want it to be.

Any New Enterprise Is a Sustained, Collective Delusion

This is what I try to do at work, insisting that Redfin is still growing up too; what after all is a startup if not a sustained, collective delusion? And this is what my wife and I do dragging the family out for a two-mile hike, telling the grumblers in the backseat that the Seattle rain is refreshing.

It turns out that you can recognize a delusion’s a delusion and still refuse to give it up. On an overnight crossing to Dry Tortugas, my dad and Wes got caught in a squall. “I wasn’t scared,” Wes said, “until the storm cleared, and the moon showed the waves towering above the boat.” He saw our father at the tiller, happy as ever. It was the same for me in Bellingham Bay, when Dad tried to reassure me about the water gushing into the cockpit by explaining the center-board’s rising moment arm and the changing force vectors on the sails.

Back on shore, I told him I had begun to think he was nuts. He just laughed. It was the sound an only child makes, raised Jewish in Depression-era Texas, who never tried fitting in, and who probably always knew he was never going to make it around the world.

My mother has died, and my father, 81, now lives alone in Florida. He still has a boat filled with his jury-rigged inventions. He struggles to maintain it, and I barely know how to operate it. He has decided the boat's too dangerous for his dog, but seems puzzled that I spend so much time trying to find the life preservers for our small children. We go out, with no one on the ocean to tell us how foolish we are, on every visit.

Glenn Kelman is the CEO of Redfin, a next-generation real estate broker. Follow him on Twitter @glennkelman. My father says he never really thought he'd make it around the world, but just wanted to visit Belize.