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Learning This One Thing Changed My Work, My Relationships, And How I Live My Life


The nausea hits me imperceptibly at first—less like the proverbial “rogue wave” that you read about in sailing books, and more like an invisibly rising tide. But the symptoms are the same: the sweats, racing heart, and finally, the inevitable salivating.

The timing isn’t ideal. I’ve just arrived in the Bahamas last night and I’m about to embark on a week-long, live aboard, learn-to-sail adventure in the remote out-islands of the Exumas. The motion of the ocean, however, isn’t what’s making me feel queasy.

The more pressing problem is the other boat docked in front of us, whose $1.4 million bow looks precariously like it’s about to crash into ours. I’d volunteered to “fend off” as we pulled out of Palm Cay Marina. Now, it looks like I might just sink us all before we even leave the slip.

“Five feet!” I shout from the foredeck, counting down the distance to impact. “Three feet! Two feet . . . !”. Averting my eyes, I wait for the sound of fiberglass crunching.

Then, suddenly, as if obeying some unseen magnetic field, our 40’ Lagoon catamaran, Never Say Never, hard stops, full reverses, and nonchalantly swings to starboard (right), whiffing the other boat by an arm’s length, and heads for open water.

When I turn aft (backwards), our boat captain and instructor, Tim Jenne, gives me a wide-smiled thumbs up from the helm. I’ve just learned rule #1 of operating a sailboat: “Don’t hit shit”.

The “Writer’s Life”—under sail

Courtesy of Nautilus Sailing

I’ve always wanted to take a few years off of life and go “cruising” on a sailboat.

I got close once in my mid 20s. If being a writer was really nothing more than experiencing the world and writing it down, where better to find inspiration than island hopping around the equator mixing with the locals? Living on a boat also turned out to be one of life’s dirty little real estate secrets: notwithstanding the food, fuel, rum, and repairs, it was basically free.

So, after college I moved to Key West, Florida and bought a beat-up 30’ sailboat named No Paine. For the next three years, I fixed her up while living aboard, painstakingly learning how each system worked and how to live on the water so that we could safely cross an ocean together. I also developed a voracious appetite for books with titles like Fatal Forecast and Where There Is No Doctor, filling my head with enough technical jargon that at times it felt like it was gaining weight.

The around-the-world voyage I envisioned in my 20s never happened. I eventually helped crew a 44’ yacht across the Southern Ocean from New Zealand to Argentina in my 30s. But, by the time I arrived in Nassau, I hadn’t done any real sailing in decades.

Our week-long, live aboard sailing course begins with light wind and the opportunity to get to know … [+] our boat, a 40′ catamaran named Never Say Never

Courtesy of Peter Lane Taylor

The author preparing to learn to sail (again) in the Exumas in the Bahamas

Courtesy of Eliza Riley

My girlfriend, Eliza, on the other hand, never got seduced by the urge to cruise. Despite being a former SCUBA instructor, she’d always been content to sail with a little wine and cheese closer to shore. Until recently.

Now, with one son finally in college and her second a year away, the idea of a having a 5-star, fiberglass hotel suite that floats around the world has started to sound far more soul satisfying than an empty nest. So, last year we decided to take our first step towards making that vision a reality by learning to sail together as part of a professional, accredited live aboard course. That’s how we found Nautilus.

The third student on our trip this week is a former Mormon-turned-sailboat racer from Texas named Diana, who’s spent the past few years fastidiously building up her sailing resume with the goal of crossing an ocean herself one day.

Eliza and our captain and instructor, Tim Jenne, prepare to get underway on Day 1 of our week long … [+] live aboard sailing course

Courtesy of Peter Lane Taylor

Nautilus Sailing was founded in 2010 by a California surfer-cum-Colorado transplant named Tim Geisler, who originally took up sailing as a means to scout out remote South Pacific reef breaks.

His start-up story is a classic spin on mining opportunity from adversity. When the Great Recession hit in 2008, Geisler lost his job as VP for a global non-profit, which eventually forced him and his wife to foreclose on several investment properties when their tenants stopped paying rent. They also lost the dream home they were building outside of Crested Butte.

“The good news,” recalls Geisler, “was that the recession gave us the chance to pause and re-invent ourselves. So, we decided to combine our passions for sailing, education, and adventure into our next endeavor. Nautilus grew slowly at first. But, somehow, we kept adding new clients and destinations. Our biggest challenge soon became cashflow. A few times, I had to sleep in my car at the airport because I couldn’t even afford a hotel room.”

Nautilus Founder, Tim Geisler, started his company during the Great Recession as a way to combine … [+] his passions for sailing, education, and adventure. It’s now one of the largest ASA accredited sailing schools offering courses in the Bahamas, Mexico, Tahiti, Spain, Croatia, and the Grenadines

Courtesy of Nautilus Sailing

Our Nautilus instructor, Tim Jenne, combines decades of sailing experience, a contagious love of the … [+] ocean, and an innate ability to teach and connect with his students

Courtesy of Peter Lane Taylor

Geisler’s next biggest problem as he scaled became finding enough experienced instructors who also possessed the right temperament to teach.

“All of my instructors back in California were crusty old sea salts who had no idea how to connect with students,” Geisler remembers of his own early days learning to sail. “Mostly, they were just good at yelling. So, it was obvious to me that the real opportunity for Nautilus was starting a sailing school with instructors who had equal passions for teaching and the water. Back then, no one was really targeting 30 to 55 year old women and men in their prime earning years either. I knew that if we combined really nice boats with learning to cruise in amazing destinations like the Bahamas, Tahiti, and Mexico, we’d have a business that would be successful.”

Fast forward fourteen years, Nautilus is now one of the most respected and prolific American Sailing Association (ASA) certified schools in North America, offering dozens of live aboard courses each year ranging from Sailing Made Easy 101 to “bluewater”, open ocean passaging.

Eliza crams above deck for our first ASA 101 Sailing Made Easy exam (she scored a 98%)

Courtesy of Peter Lane Taylor

After our near miss leaving Palm Cay, Jenne steers Never Say Never out of the channel on a heading of 155-degrees south-southeast. For the next five hours, our course will take us 35 miles over the shallows of the Exuma Bank to Norman’s Cay, a long, crowbar-shaped island that was once the Medellin cartel’s primary cocaine smuggling hub between Colombia and America.

Today’s forecast is for light to non-existent winds. So, instead of hoisting sail once we hit open water, Jenne takes the opportunity to familiarize Diana, Eliza, and me with the anatomy of our boat and its “feel” underway through a series of engine, steering, and maneuvering drills.

First, we take turns yanking the wheel hard left, then hard right, learning Never Say Never’s “turning radius”. Next, we gun the twin diesel engines full forward, then full reverse, getting a sense of how fast we accelerate and how long it takes to stop. Finally, we practice man-overboard recoveries with an inflatable buoy named “Pepe” who’s got a nasty habit of getting drunk and falling in the water. As we scramble around deck, Jenne is constantly observing our communication and teamwork. He’s also quick to offer well-timed advice and reassurance.

“Repeating skills and running scenarios are two of the most important things we’ll do this week,” he explains as we pull Pepe from the water one last time. “If you’re the helmsman, do you know exactly what to do if someone falls overboard? What if it happens at night? How fast can you turn or stop to avert a collision? When something unexpected happens, knowing what to expect from your boat can make all the difference.”

That evening we anchor in the lee of Norman’s Cay, a deep mango sun setting into the water as if dissolving into still, blue ice. Over the dunes behind us, a nearly full moon rises in mirror-like symmetry on the opposite side of the earth. The only other object on the horizon is a silhouetted superyacht anchored a few miles away.

“This is my favorite time of day,” Jenne remarks, as he settles into a beanbag chair on the aft deck. “Too bad you three have to study.” Wink.

Eliza enjoys the calmer side of learning to sail after anchoring at sunset in the lee of Norman’s … [+] cay

Courtesy of Peter Lane Taylor

Jenne’s meticulous attention to detail and knack for teaching are matched only by his passion for … [+] the ocean and love of sailing, thanks in part to five years serving in the U.S. Coast Guard

Courtesy of Peter Lane Taylor

Jenne is the kind of person writers love to write about.

At first, he comes across a little on the reserved and unexcitable side. Yet, as I quickly learn, he’s stealthily gregarious and easy to laugh, with a clever sense of humor belying the encyclopedia of life experiences in his head. Physically, he’s lithe and kinetic, accompanied by a mind that never stops thinking about the next move. His love of the ocean is contagious.

Jenne’s first experience sailing was when he was 13 growing up in Washington State in a small boat that he and a neighbor launched from a local beach. As it caught wind, Jenne marveled at how it magically started to float beneath them. “Then, all of a sudden, once we lowered the centerboard and leaned back,” he recalls, “We were flying. It was the most exhilarating thing I’d ever done.”

Sailing quickly took over Jenne’s life. Outside of school, he spent all his free time learning about boats and building experimental models out of Styrofoam blocks with bed sheets for sails. Then, when he was 16, he decided that he wanted to save lives. So, in 1984 he joined the U.S. Coast Guard, eventually specializing in search and rescue (SAR) in the notoriously dangerous ocean waters off of the Pacific Northwest coast.

“The problem with SAR missions is that they normally don’t happen in good weather,” recalls Jenne of his five years on active duty patrols. “That got me into some pretty scary situations. 60 knot hurricane-force winds. 45-foot waves. Sailors strapped to IVs because everyone’s throwing up from dehydration. But those experiences made me good under pressure. They also taught me never to overreact when things get sketchy.”

One of the keys to learning to sail is getting out of your comfort zone, challenging yourself, and … [+] coming to terms with the unknown

Courtesy of Nautilus Sailing

“Slow is smooth, smooth is fast”. Jenne’s calm and effective teaching style has been honed over a … [+] hundred Nautilus courses

Courtesy of Peter Lane Taylor

Those experiences also helped sculpt Jenne’s soft touch, “slow is smooth, smooth is fast” teaching style which, for Geisler, was so hard to find in his instructors years earlier.

When we’re practicing skills, for instance, Jenne is never barking us through our paces. When we’re overwhelmed, he encourages us to talk through what’s happening in real-time. And at the end of each day, there’s always a window set aside to discuss what’s working, what’s not, and why—so adjustments can be made.

Most importantly, Jenne has a steadying air about him that naturally puts people at ease. Wind and water are formidable forces. Boats are, too. So, when things go wrong, the repercussions can be intense. As a result, says Jenne, a big part of learning to sail is learning to overcome fear.

“Sailing and the ocean will always be full of unknowns,” he explains. “But to experience the magic of anything new in life you have to overcome the fear of doing it in the first place. Learning to sail is no different. It’s about challenging yourself. And a significant element of that is letting yourself get out of your comfort zone.”

The Bahamas “Sun Salutation”: one of the greatest things about learning to sail is beginning every … [+] day on the water

Courtesy of Peter Lane Taylor

Day 2 of our course dawns cloudless with a light easterly wind painting the water corduroy at just past high tide. Jenne’s already been up since sunrise, checking lines, prepping sails, and scoping out the weather on his iPad. Diana, Eliza, and I are too busy down below cramming to notice.

At 8:00 am, Jenne drops our first ASA sailing test on the cockpit table with an audible slap. Along with the #2 pencils to fill in the answer sheet, the whole examination vibe gives me temporary back-to-school hives.

I’m also acutely aware of the stakes here: assuming the three of us pass today’s test and three subsequent ones over the course of this week, Diana, Eliza, and I will each officially be certified to charter a sailboat virtually anywhere in the world. There’s a certain absurdity to the entire proposition when you actually think about it: Who in their right mind is going to throw me the keys to a multimillion-dollar sailboat right now and say, “See you in a week”?

Yet, as I open our first test and start filling in the bubbles, I quickly realize that I already know way more than I thought did.

If you grow up by the water, there’s a good chance that sailing runs in your DNA. Our anchorage at … [+] Warderick Cay at the headquarters of the Exumas Land and Sea Park

Courtesy of Peter Lane Taylor

The author at the helm of Never Say Never, “discovering” himself as Captain of the Day

Courtesy of Eliza Riley

People learn to sail for a lot of reasons.

If you’re raised by the ocean, for instance, it probably runs in the blood. For countless others, boats are simply the mechanical means to a recreational end, like fishing or scuba diving. More old school, less ambitious types just like the ascot, yacht club culture.

Then, there are those like Jenne, Diana, Eliza, and me who sail to push their limits and discover themselves.Not surprisingly, most Nautilus students are similarly the fast driving, steep skiing, soul searching kind. Professionally, they’re also frequently CEOs, entrepreneurs, and start-up founders looking to hone their leadership skills and build better teams.

“The people who sign up for our courses are typically very successful in their fields,” Jenne tells me. “They like doing challenging things, and their desire for freedom is a huge driver, which is why many of them are entrepreneurs in the first place because they thrive on autonomy and self-determination. At certain points when you’re crossing an ocean no one can rescue you. So, the risks and lessons in sailing and start-ups in many respects are the same.”

Plotting routes, programming Never Say Never’s instruments, and learning the names of all of the … [+] lines and rigging that control the sails are some of the essential practical skills we learn underway during our week long course

Courtesy of Peter Lane Taylor

After acing our ASA 101 test (everyone scored 95% or better), Diana, Eliza, and I pull up anchor and point Never Say Never almost exactly 180 degrees due south.

We’re still on the tail end of a high-pressure dome that’s been parked over the Bahamas for a week, so instead of attempting to sail in light winds again we elect to motor along the inside edge of Exuma Bank for another day. After stopping at Shroud Cay for lunch, we’ll continue south in the afternoon on to Warderick Cay where we’ll check-in to the Exuma Cays Land and Sea Park for the rest of our trip.

Along the way, Jenne teaches the three of us some of the more practical skills we’ll also need to master this week on top of the theory and rules of the road, like programming Never Say Never’s instruments and managing the multi-colored linguini of lines leading back to the cockpit that controls the sails.

Nautilus live aboard sailing courses lean heavy on the reading and even heavier on the skill … [+] building—even at sunset

Courtesy of Peter Lane Taylor

By the time students complete a Nautilus live aboard course they are proficient with everything from … [+] tying basic knots to understanding international maritime rules and regulations

Courtesy of Peter Lane Taylor

One of the enduring ironies of sailboats—despite all of the knowledge and expertise that’s required to operate one safely—is that the only thing you need to buy one is money. That fact puts asymmetrical pressure on voluntary education when it comes to safety and order on the water compared with learning to fly a plane or drive a tractor trailer, both of which require extensive training and licensing.

As a result, Nautilus’s live aboard sailing courses lean heavy on the reading and even heavier on the skill building, starting with how to tie basic knots all the way up to decoding the complex cryptography of buoys and lights telling sailors where to go and what to avoid. Jenne personally is also masterful at teaching his students sailing’s more “artful” skills, like reading the wind and water and using the clouds to forecast the weather.

“Time on the water was all that the early mariners had to understand what was happening around them,” explains Jenne, gesturing to the array of touchscreens crowding Never Say Never’s helm. “Now, we’ve got all of this technology feeding us satellite data in real time so that we can make split second decisions. But there’s still no substitute for experience, instinct, and feel.”

Our anchorage at Warderick Cay is a tropical paradise devoid of humanity with the exception of a few … [+] other boats

Courtesy of Peter Lane Taylor

The summit of Boot Hill with its hundreds of driftwood plaques left by cruisers who have passed by … [+] here before ys

Courtesy of Peter Lane Taylor

Later that afternoon, we glide into Warderick Cay amid a small armada of other charter boats moored along the anchorage’s main channel. After stowing our sails, the four of us hike up to the island’s highest point, a scrubby, sun-bleached summit called Boot Hill which is festooned with hundreds of driftwood plaques honoring the names of other cruising boats that have passed by here before us.

It’s a gnarled and fitting memorial to humanity in an outpost largely devoid of it. And yet, what hits me most potently on the way down is that the privilege and exclusivity of this place has little to do with money. Every other boat around us took the same risks to get here. That democracy and solidarity, Jenne tells me, is unique among sailors.

“We all look after each other out here,” he says. “Knowing someone is a sailor and has experienced places and moments like this, you automatically know a lot about them and what kind of person they are, no matter how big their boat is. Mariners are special in this way. We’re more like a tribe.”

Eliza carefully navigates Never Say Never out through the narrow cut south of Warderick Cay and into … [+] open water as Jenne makes sure we keep a safe distance from the reefs on either side

Courtesy of Peter Lane Taylor

The next morning, Diana, Eliza, and I emerge from our cabins to a high-pitched whistle emanating from Never Say Never’s web of rigging holding up the mast—a telltale sign that the wind is picking up. Jenne is already on deck, smiling out over an anchorage of whitecaps.

Our destination today, roughly forty miles south, is Staniel Cay and Thunderball Grotto, where the infamous underwater cave scenes from the eponymous James Bond movie were filmed. There’s also a marina on the island with a quirky, Jimmy Buffett-esque bar and restaurant, so tonight will be our first and only night eating out.

With a brisk breeze blowing steadily for the first time all week, we decide to sail on the outside of Exuma Bank today. That means we’ll finally be sailing with full canvas up and officially out in the open water, where the underwater shelf drops off and there’s nothing to decelerate and dampen the waves.

Never Say Never finally gets underway under sail

Courtesy of Peter Lane Taylor

“Remember that this is what you came here for,” Jenne yells above the wind, as Diana and I raise the mainsail and Eliza steers the boat out through the last pinch in the channel, surgically navigating between waves breaking 20’ to either side. “Prepare for lift off!”

A few minutes later, clear into bluewater, Never Say Never catches a gust of wind, heels to starboard, and begins to surge through the ocean, propelled by some invisible convergence of physics that I’m pretty sure I’ll never understand, yet, in this moment, has never felt more thrillingly real.

I look back to find Eliza—to make sure she’s in the same moment, feeling what I’m feeling. But she’s already smiling back at me, her arms outstretched on either side, each hand cradling the opposite ends of a rainbow that’s just formed on the horizon.

“Is this it?” she asks Jenne, grinning. “Is this that magic you were talking about?”

Eliza holding the “magic” rainbow

Courtesy of Peter Lane Taylor

The bar and restaurant at Staniel Cay Yacht Club is a Jimmy Buffett-style cruiser’s paradise all the … [+] way down to the sand floor

Courtesy of Peter Lane Taylor

That evening at Staniel Cay Yacht Club, the bar is already packed with sailors from a dozen countries by the time we arrive for dinner, the collective volume rising by the minute. Some, like us, are clearly charters on a schedule. Others—more unhurried and sun wizened—look like they’ve been holed up here for months.

It’s hard at moments like this not to get nostalgic about my Key West years and to want them back. This was the sailing “world” that I’d always dreamed of writing about in my 20s. Maybe it still is. Either way, thanks to Jenne and Nautilus, I finally have a clue what I’m doing this time around compared with two decades ago.

“That’s the thing about sailing,” says Jenne as we row back to the boat, “It’s never too late. Never say never . . .”

A perfect downwind run to Nassau: “Remember that this is what you came here for”

Courtesy of Nautilus Sailing

On our last morning before returning to Nassau, Diana, Eliza, and I take our final ASA exam under the sun spokes of a clearing storm. On the downwind run back north, Jenne laces a lure to one of our fishing rods, pays out the line, and does more observing than instructing this time as the three of us sail Never Say Never home on our own.

Technically, team building isn’t part of Nautilus’s curriculum. Yet, it’s a essential part of what Jenne wants his students to learn during their time on board with him. In the Navy, distinctly defined roles and responsibilities are the foundation of order and mission success. For the rest of us, the nuances of working together towards a common goal frequently need to be learned and re-learned. In this way, becoming a skillful sailor is a lot like training a puppy. Intent is essential. Clear direction is critical. Repetition is key. To reinforce these lessons, few activities are more exhilarating and life-changing than sailing.

“Ultimately, being the captain of a boat isn’t about giving orders,” says Jenne. “It’s about perspective and understanding and, most of all, knowing when not to drive the boat. It’s also about being willing to clean toilets and knowing that nothing is beneath you. The same goes for life. If you do the same in both, you’ll have loyal friends and relationships that will follow you to the ends of the earth.”

Officially ASA certified! Diana and Eliza feeling nostalgic on the last day of our Nautilus live … [+] aboard course

Courtesy of Peter Lane Taylor

Exumas, Bahamas: Hard to get to, even harder to leave

Courtesy of Nautilus Sailing

Later that evening, after piloting Never Say Never back into our slip at Palm Cay, I’m already feeling philosophical as our trip comes to an end. For centuries sailors have sought enlightenment from the sea. Yet, what wisdom have I gained over the past week?

It’s a question Jenne loves to ask of all his students over dinner on the last night—in no small part because the responses reflect how well he’s done his own job. For me, the answers couldn’t be more clear cut:

First, don’t stress when things don’t go your way. Most things, especially when they have to do with the ocean, are beyond your control.

Second, avoid perpetual preparation. Make your plans and capture all the variables with a systematic, methodical approach. Then, untie the lines and go. You’ll figure the rest out along the way.

Third, remember that awe and wonder are the other side of inexperience. Avoid the “been there, done that” attitude.

Fourth, be open to the instruction of others. Find teachers and mentors (and captains like Jenne) you admire and aspire to be like, then learn everything that you can from them.

Fifth, be humble about what you know. Be even humbler about what you don’t.

Lastly, never say never. Dreams—even the madcap, Key West kind—only die if you let them.

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