“When I saw the Horn at 3 o’clock this morning it gave me chills,” John Kretschmer said in a grainy video from the deck of his Kaufman 47 Quetzal in mid-December, hanging on the starboard shrouds and beaming with Cape Horn in the background. “It looks exactly like it did 40 years ago.”

Forty years ago, on January 25, 1984, John rounded Cape Horn to starboard in the Contessa 32 Gigi. On that very same day, I was born.

Besides this weird serendipity, John’s second rounding of the Horn one month before I turned 40 had me pondering the value of mentors. He surely didn’t know it, but John was to become a mentor to me from the first time we corresponded. I’d always been drawn to his writing, and in 2006, I contacted him about my dad, who had been at sea during Hurricane Lenny, the “wrong way” storm John immortalized in his book At the Mercy of the Sea. Were it not for a broken shroud on a brand new boat that forced my dad and crew back to Bermuda, he may well have been part of John’s book, I’d written to him back then.

John sent me a thoughtful reply, thus beginning a 15-years-and-counting mentor/protégé relationship that has has done more to shape my career than any other influential bond besides those with my parents and Mia.

I modeled my career on John’s, starting with deliveries—free at first for experience and later as a paid skipper with Mia along as my mate for most of them. Heck, Mia and I even did our own version of Cape Horn to Starboard when we sailed our first boat, Arcturus, across the far North Atlantic in 2011. I didn’t write a book about it, but it’s the voyage that kick-started our path in ocean sailing.

I’m not sure if John would even consider himself a mentor to me, and I’m not sure I’ve been given any sort of special treatment over any of his other fans, shipmates, or former students. We never had any formal arrangement, nor did we ever really acknowledge it. Instead, anytime I send him an email, pick up the phone, or bump into him in a foreign port, he is there with a reply, some advice, or a glass of wine in Quetzal’s cabin.

Even now that our business, 59° North, technically competes with John, he remains a mentor and a friend. Most recently before our Greenland passage on Falken last summer, John gave me coordinates to, in his words, “the greatest anchorage of my career.”

I feel a debt of gratitude to John, and Mia and I have tried to pay that forward ever since we started 59º North in 2015. Developing folks interested in making a career on the sea has been a core belief of ours, thanks to John, and almost from the start we’ve had our own apprenticeship program to accomplish this. I wanted to create opportunities that the 21-year-old me would have gone bananas to find and that really don’t exist, particularly in offshore cruising. Falken has an extra pipe bunk in the staff quarters that is reserved for apprentices; eight apprentices sailed with us in 2023, and we’ve been interviewing for this year’s slots.

Mentorship offers knowledge that can’t be bought. Mentors give you essentially unlimited access to their expert’s mind, and yet it requires responsibility on the part of the protégé to ask the right questions. Yes, there’s all the practical stuff—like learning celestial nav—but the real value is in transferred experience. In other words, the “I learned this the hard way so you don’t have to” lessons. Unlike formal course studies, mentorship has no curriculum, no grades, and no real conclusion. At its best, it’s an ongoing form of sharing education and experience.

John continues to inspire me and countless others, and watching him round the Horn 40 years later only adds to the mystique. And it gives me confidence, too; if he can do it, so can I.

So, here’s to John the sailor for accomplishing, for a second time, a feat that all offshore sailors dream about yet few dare to attempt. And here’s to John the mentor for unintentionally enabling my career path into offshore sailing.

To aspiring and even experienced sailors, I encourage you to reach out to your heroes—the sailing world is uniquely filled with characters you might find surprisingly willing to help, even if just recreationally. And to the would-be mentors out there, I encourage you to share your knowledge and skills with the next generation. 

March 2024