Great Escapes — or, Why I Sail
By Randy Kaufman
with research assistance from Dustin Lowman
In the depths of winter, with lakes frozen and boats shrink-wrapped, I ask myself why I love to sail. My attempt to answer that question follows. Spoiler alert — it’s not about the warm weather, and it’s not about sailing’s similarities to the high seas of investing.
Roots
Born in the dark days of February, with Russian blood pulsing through my veins, I abhor the heat. Sun fries my porcelain white skin. Summer — not my thing.
Vermont beckoned for undergraduate training. As if 4 years in Middlebury, VT didn’t sate my appetite for extreme cold, I chose Chicago for law school instead of sunny California. Testing my mettle, temperatures stayed well below zero my first Chicago January, shutting the city down and even delaying our sacred pizza deliveries.
“I can and I will deal with this,” I said. And I did.
Later in life, I lived a delightful 15 years in upstate NY, never stepping foot on a sandy beach, never taking an ocean plunge. Put me in the mountains, I always begged; put me on skis, I always beseeched. Happiness was plummeting down a snowy hill, the wind in my hair, my eyes tearing. Be they sunny bluebird powder days, be they gnarly whiteouts and howling winds — I loved them all.
In the cold, I layer up. Warmth avails if I dress properly. In the heat, my body drips, and makeup melts down my face. Sand chafes and tunnels to every body part. There are only so many clothes to jettison. And, besides, who knows what lies beneath the ocean’s surface.
For sailing, an activity that necessitates heat and sun, exploring how explains my why.
Adventures
I love adventures — bring ’em on, I say. In 1973, traveling to France alone at the age of 14, standing in the airport with my red-cloth-striped suitcase in hand, sheepishly looking around for someone who fit the description of my new French family, decades before the cell phones ruled the earth, in the massive Charles de Gaulle airport — what could go wrong?
In 1984, I traveled around the world with my law school roommate. I had more than a few crazy nights in Bangkok, rode elephants in the Tiger Tops jungle of Nepal, cycled for three weeks in mainland China, camped in Tibet, and trekked to the Annapurna base camp.
The 1990s: I rock climbed in the Gunks and heli-skied in British Columbia.
“Sure,” I always say. “Why not?” I always ask, especially if an adrenaline rush awaits. Adventures are my antidote to work stress. I’ve regretted none of them, in spite of the fact that at times, I wasn’t sure that I’d survive.
In 2015, a date asks me to go to East Hampton to try sailing. “Yes,” I say.
Later
Powering through a fear greater than the dark — the ocean — I continued to date the guy. When he encouraged me to race small boats in New York harbor, I took the bait. When he invited me to race with semi-pros in Oyster Bay Long Island, I did. The thrill and the speed simultaneously frightened and seduced me (along with the guy), and I was introduced to the warmth of a sailing community.
To my delight, the guy kept up with me on black diamond Colorado ski slopes, thus earning a promotion to “boyfriend.”
A year later, we joined a crew for an overnight race from Stamford to Martha’s Vineyard. Remnants of a hurricane lingered. After a lovely day of sunshine and sweet winds, the weather turned gradually, and then quickly. Cold rain poured down, blasting our faces like sandpaper. When the boat heeled violently, our pro-skippers took over. We grabbed our foul weather gear and sat on the rail, freezing and huddled, staring into the darkness, praying our 28-year-old skipper, teeth clenched, eyes ahead, and iPhone in hand, would keep us safe from the notorious rocks that litter Long Island Sound.
The boat arrived safely at 1:30 a.m. I was chilled like I’ve never been before. I Ubered home and took the longest and hottest shower of my life — gripping a hot coffee cup in my hand, trying to not let the shower water dilute my precious, steaming black coffee.
And then, I decided I’d do it again!
Trips to the British Virgin Islands and Tortola awaited. Drama did not.
So, a few years later, foolishly believing all Caribbean sailing resembled floating in a turquoise bathtub, I agreed to charter a French racing boat in Martinique, a vessel meant to be crewed by a party of six, without a pro skipper on board. Dolphins, white beaches with wild horses, and spectacular scenery delighted.
Abnormally high winds also awaited on a sail from St. Lucia to Martinique. A 60 mph squall, bright white and very wet, approached. I gripped the wheel in my hands. I gave the helm to the boyfriend, looked into the whiteout, clutched my tether, and channeled my father, the man who always had enough, who was grateful for each and every day.
“When you arise in the morning, think of what a precious privilege it is to be alive — to breathe, to think, to enjoy, to love,” rang the Marcus Aurelius-penned words in the voice of my beloved father.
Thankfully, that wasn’t my day. I didn’t blame the boyfriend. As great a sailor as he is, he could not predict squalls. Instead, I cast my commitment fears aside and the boyfriend was promoted twice more — first to fiancé, ultimately to husband. I pleaded with him to get the dogs he said he’d never own again.
He convinced me that we should get a boat of our own. Now, we own two wonderful labradoodles (or do they own us?) and a claret-red sailboat, named “But Luckily,” harkening to all the sailing stories we hear: “Our boat pitchpoled in front of a ferry, and it looked like we were about to get run over, but luckily the ferry turned sharply away at the last minute.”
Or, take the inscription of our wedding bands: The two jaded 50-year-wealth advisors were convinced they’d never find love again, but luckily, they found one another.
Back to The Why
You might assume that the similarities of sailing and investing are what drew me to the seas. Countless pages have been penned on their metaphorical similarities. During my Boston decade, long before I knew the difference between a tack (turning upwind) and a jibe (turning downwind), I’d read these blogs, understanding nothing. But immediately upon holding up a sheet in my sore, cracked hands (for the non-sailors among you, a sheet is a fancy word for a rope attached to a sail), the analogies jumped to life. You cannot sail straight into the winds to reach your destination. Sailors chart a course, and sail with the winds dealing with the unexpected (waves, cruise ships, hurricanes, oyster farms, and on and on).
These non-linear paths and non-obvious approaches enable sailors to reach their ports. Like great investors, sailors must stay agile and calm in an uncertain world. Sailing, like good investing, flourishes with superb risk management and good processes. How you react to unexpected challenges portends your success or failure. With focus, determination, a clear head and good steering (my favorite role on a sailboat by the way), ports are reached, goals are achieved.
More than Money
But, for me, it’s not about investing. It’s about the 4Gs. As one of my favorite poets and musicians, Leonard Cohen, said: “If you don’t become the ocean, you’ll be seasick every day.” Author Chris Hubber sums it up:
There’s something about sailing that can make one feel comfortable with everything happening in their lives and in the world, at least for a little while. Where there is peace, though, there is also the mighty strength of the sea that can bite back at you when you least expect it, throwing your boat and your life together into chaos.
My Growth mindset thrives on a sailboat. The sport confounds and confuses regularly. Knots — beyond my reach except for a few. Navigation — a huge challenge. Not a sail goes by in which I don’t learn something. I have no doubt that that will remain the case for the rest of my sailing days.
Grit — oh boy, the times I just “grit” my teeth and power through, hoping I’ll survive and not go overboard in crashing waves as they wash over the deck of a heeling boat, or as a boom slams in high
winds, barely missing my un-helmeted head. I tamp down my fears. I carry on. I survive to sail another day.
Grace — little could be more graceful than the rainbows we see, or the sun rising as we leave a port to catch the tides.
And, my favorite: Gratitude, always, for the amazing life I’ve led, for my dear family and many friends, and for the adventures I’ve had.
Ski slopes thrill and amuse, but nothing compares to being in the middle of the ocean, in a tiny plastic boat, to remind you that the world is vast, and we, small. Our lives are but a nanosecond on the spectrum of all time. Our daily perseverations won’t matter in the long run. There may be a better reminder to focus on the present (see the meaning behind my logo, Aker Advisors here: akeradvisors.com), but not that I know of. There may be a place to feel more humbled and more grateful for being alive, but it isn’t known to me. There may be a better way to learn how much (or how little) you really need; alas, I know of none.
If you’ve enjoyed this blog and if sailing (or just awesome music) appeals, check out one of my all-time favorite songs: [Wooden Ships by CSNY], and consider pairing it with another classic by the same band, Southern Cross.
To the sailors among you, I wish you safe seas ahead.
ABOUT THE AUTHOR
Randy Kaufman, formerly a corporate tax attorney and investment banker, is now a wealth advisor who prides herself on focusing on what matters most: clients’ peace of mind, family dynamics, and getting enough, not more. Randy is a passionate student of impact investing, strategic philanthropy, and behavioral psychology (while not a psychologist, she occasionally plays one in the boardroom). She is dedicated to helping the underprivileged, and is a proud member of global venture fund Acumen's advisory board. A thinker, learner, and pursuer of overarching truths, she is always eager to discuss big ideas about money, and its off-and-on associate, happiness.