Stephen J O'Shea

I remember the silence as we sailed into our first storm. From the middle of the Gulf of Mexico, we were 300 miles offshore. We’d never had the budget to purchase life rafts or survival suits before leaving Pensacola, and we were far beyond the reach of any Search and Rescue team. We were sailing for survival.

Nobody mentioned this, though. Nobody mentioned that we were in the middle of hurricane season, either: or that it was one of the most active seasons of all time. Instead, we held our breath—staring down the wall of black hurtling toward us—and tried not to hurl up the food we forced down.


The months leading up to our departure were less ominous. Taylor and I had raced to get the boat ready for September—we needed to reach Cape Horn, a whopping 5,000 nautical miles from Florida, before March if we’re going to have any hope of rounding it—and yet, despite the ticking clock, we’d always find ourselves marveling at how everything seemed to just “fall into place.” It was as if the universe was conspiring in our favor – like we were onto something bigger.

Paul Coelho called it the “Principle of Favorability,” or beginners luck, in his novel The Alchemist. It’s the idea that everyone’s Personal Legend begins with a stroke of good fortune – that, without a set of very unlikely circumstances, nothing extraordinary would ever happen.

Our luck began when Taylor and I reconnected during my trip to Guam, and it persisted throughout the next year – the way our schedules aligned with him getting out of the Navy while I wrapped up a PhD; the circumstances leading to our purchase of the Ole Lady; refurbishing the boat in time; and finishing my PhD early enough to leave by our departure date. We even managed to leave on schedule, despite a crucial crewmember backing out just days before.

To quote Taylor at the beginning of Hurricane Waters, there was “no reason not to go.” We cast off our lines and, with just three crewmen, steered for the heart of the Gulf. In the middle of hurricane season.


We’d reefed our sails well in advance of the storm. Our jib (the forward sail) was a triangle the width of my arm, and our main sail was in its third reef (cut down to the smallest surface area possible). I was manning the helm when it hit. At home, when a system like that sweeps overhead, you hear the wind howling and the rain smattering against windowpanes. Or maybe you're driving your car—you might feel some resistance at the wheel, maybe even drift in the lane a bit—but when you’re at sea during a storm, manning the helm means life or death.

Getting hit by that night was a lot like running into a wall. Wind and sea spray slammed against the beam (side) of our boat when two seconds before it had been coming off our bow (the front). My shoulders flexed to turn the boat into the wind, but our mast was already dipping to just feet above the water. Our boat was tilted at a precarious angle, waves broke over the railing, and water washed across the deck, but no matter how hard I twisted—no matter how hard I gripped the helm—the wheel wouldn’t budge. I thought the steering cables had tangled or, worse, snapped. When we finally came over the crest of a swell large enough to break our rudder from the current, our mast looked like a fallen tree. I hauled us into the wind, and we angled straight for the worst of the weather: dead into the storm.

It’s a strange sensation, pointing your bow toward a black hole. Wind was howling in our ears like the scream of a jet engine, and the whole while it felt like our boat was going snap against the face of each swell. But turning into the wind was the only way to immediately reduce our speed. With the mainsail still up, we were as likely to break our boom jibing downwind as we were to capsize in the turnaround. Not that cutting upwind was any easier. With the wind as strong as it was, I had to hold an angle so steep that our bow was angled straight into the swells.

We were flying over the crests of each wave, hovering for a moment as our weight shifted forward, only to pitch forward again, crashing into the next trough. We needed to take a broader angle into the swells, but to do that we had to lower the main sail.

I was hardly aware of the mechanics at that point – this was my first storm, and I was focused solely on keeping our mast out of the water. So when Taylor said, “Alright,” clapping his hands on his knees, the last words I expected to follow were: “Let’s bring down the main.”

I didn’t grasp the magnitude of his words right away. Waves were crashing over our bow, splashing against the bimini, and we were heeling at an almost 45 degree angle. But Taylor stood up all the same, stepping out of the bimini. Kell followed without hesitation, their years in the Navy a wordless communication saying that, unless we moved now, we were going to die. There was no time to say anything. No time to dig up harnesses or run a safety line up the deck. No time for life jackets or mayday calls or last minute messages from the Garmin. There was only the storm and our boat, battered by the wind and swells.

Taylor and Kell moved out of the cockpit up the side of the boat. They hadn’t even reached the mast when a wave broke over the bow. It was the kind of wave I’d only seen in movies: the one that salty old captains describe as a wall of water rising black out of the sea. It was like diving into a pool. Water slammed into Taylor and Kell. It washed over the bimini, blinding my view completely. I thought our whole boat had gone underwater, that the wave had flipped us onto our backs.

But the Ole Lady broke through, and when she did we went surfing down the back of the swell at fifteen knots. Water drained off the deck, off the bimini, and I knew then that I was alone. Taylor or Kell were gone. There were no headlamps flashing in the dark. No silhouette’s moving across the deck. There were no sounds. No calls or cries to come about. Taylor and Kell had been swept out to sea.

With the wind as strong as it was, and the main sail full and ready to burst, there was only one direction I could hold without capsizing. I’d sink the boat trying to turn around... but I had to try.

I pivoted in my seat—gripped the wheel to whip the bow around—when a speck of light glinted off the jib sail. It was a storm so dark, with rain so thick, that I knew it couldn’t be anything else. My grip slackened and then, together, a single body in motion, Taylor and Kell rose from the deck floor.

They’d been swept off their feet, knocked to the ground and thrashed about, but both of them had somehow grabbed the standing rigging before being washed out to sea. They were alive.

“Turn into the wind!” Taylor shouted. He was already at the mast, untying the halyard (the line that pulls up the main sail). The boat was heeling hard after I’d shifted position, so I had to brace my feet against the gunwale to haul the helm about. She broke through, my eyes glued to the wind indicator, and I held her there, dead into the wind.

Taylor and Kell began lowering the main by hand. Jibsheets lashed them across the back like corded whips, rain and sea spray stinging their eyes, but neither of them flinched. They were machines, pulling down the sail even as it slapped them across the face. Meanwhile, we were crashing into waves so hard that the two of them were being knocked off their feet every minute.

They had her all but locked away when the jib backwinded. (*This happens when the wind comes across the bow and fills the forward sail from the wrong direction. The sail and the lines holding it cross over the deck, pulling the boat sideways.)

I’d been holding our bow into the wind for as long as I could, but the swells were too big, our rudder too small against the current. We began to turn sideways. I cranked the engine, the wheel countered all the way to starboard. But after the jib reversed on itself, we were turned perpendicular to the wind. We were sitting ducks for each breaking swell. Then our main sail shot up the mast. It filled with wind, and the whole boat heeled for the waterline again.

I remember seeing Kell swing off of his feet, a single hand wrapped around the boom as his feet grazing the waterline. Taylor was screaming at the top of his lungs. “Into the wind!” he shouted, his headlamp the only beacon of light. “Turn her into the wind!”

I tried, but I couldn’t. Waves were breaking over the side of our boat, only this time we weren’t soaring over them. The Ole Lady was rocking so hard that the jib sail dipped into one of the swells, scooping at a dose of ocean water. Three-hundred miles from the closest shoreline, from any hope of rescue, and we were utterly hopeless.


Since Taylor and I announced our plans to circumnavigate South America, we’ve had a lot of people try and convince us not to. The least expected being our third crewmember, a cinematographer who volunteered to join us for the journey.

I’d just finished a book about veterans returning to civilian society, and Taylor was using this trip as a kind of Odyssey to facilitate his return from the Navy, so it seemed only natural to use our journey as a means to spread awareness about the difficulty veterans face returning home. The most immediate and popular medium for reaching people is video, and to film effectively we needed a third crewmember.

We’d had a number of people express their desire to join us on this trip. Most of them would say something along the lines of, “It’s my DREAM to sail around the world. You are so LUCKY to have the opportunity.” But in searching for an addition to our crew, Taylor and I were incredibly selective. We would have to spend upwards of a year with this person, in a very small, enclosed space. They would have to contribute towards our mission, carry their weight around the boat, and not bail when things got rough.

In the end, we only considered three people. In every case, we’d feel out the candidate before inviting them to join. We wanted to make sure it was feasible for them to come; that they were earnestly interested; and finally, we wanted this trip to advance them in some way: we wanted to give them an opportunity to chase down their dreams.

The first two candidates turned us down. Their excuses were different, but the theme was consistent. Both of them were comfortable in their current lives. They weren’t happy—they weren’t pursuing their “personal legends”—but they were scared to lose what little they had. Like the crystal merchant in The Alchemist, or Tolstoy’s rendering of Anna Karenina, it was the surreality of their fantasy that appealed to them – not the realizing of it.

Manny was younger and more reckless. He was a mutual friend of ours, and when I asked if he would come help us shoot a promotional video for our trip, he volunteered to join us for the whole thing. Taylor and I liked his decisiveness. “That’s the kind of attitude we want!” said Taylor over the phone. I was in New York trying to find an agent for my book; Taylor was in Pensacola refurbishing the boat; and Manny – our final candidate – was in Los Angeles, attending a masters programme at UCLA for cinematography. He’d already requested a year’s leave, and was receiving nothing but encouragement from university faculty to join us. So, over the course of a single week and a few long-winded Skype calls, we concreted Manny’s position in our crew. We began planning around his attendance. We invested thousands of dollars in camera equipment (instead of a hydrovane or weather radars), in extra food and provisions (instead of safety gear)—and, finally, we funded his flight to Florida to show him the boat and plan out the adventure.

As our departure drew near, Manny became more and more evasive. We were trying to coordinate the release of our “hype” video, but he was unresponsive. He wouldn’t return our phone calls. He wasn’t “reading” our messages on FB, even though we'd watched him come “online.” We were a week out, just days before our scheduled departure, and he’d gone AWOL.

Four days before we were set to leave, he sent us a text message. The content was organized and well thought-out. It was a well-marinated message—the kind you spend days, maybe even weeks, preparing—and in it, he listed all of the many reasons why we shouldn’t go on this trip. At the end, he declared that we were ill-prepared. Then he laid down an ultimatum. Unless we were willing to spend another year making preparations—another year of slip fees that we couldn’t afford; another year of subscriptions to satellite GPS and Garmin InReach that we couldn’t sustain; another hurricane season in Florida when we'd barely escaped the last, and another year of corrosion which would just as likely damage our boat at harbor as being on the open water—unless we were willing to cancel our trip just four days out, Manny wouldn’t be able to “cross that line” with us.


Taylor and Kell managed to pull down most of the main sail before the jib backwinded, but it was too full of wind to finish now. Not to mention every swell knocked them back to the ground. Kell had taken to sitting down on the ground. He had his ankles crossed, swells crashing against his back as they broke over the beam. We were stuck there with a backwards jib, the wheel pulled all of the way to starboard, and twenty-foot breakers lining up to flip our boat.

There was only one thing I could think to do, only one possible action besides sitting there and waiting for a rouge wave to sink us. It was act or be acted upon, and if we were going out I wanted to go out swinging. I grabbed the helm and spun the wheel hard to port, turning the boat downwind as hard and as fast as I could. Wind pushed our sails out and waves began crashing over our stern. I reached behind me and grabbed the mainsheet, pulling with all my strength as the wind came across our back. The boom swung hard across in a shudder of movement, the jib whipped back to its proper position, and—after almost dipping our mast in the crest of a swell—we leveled out and began to move again.

We'd come all of the way around and were angled back into the wind. It was a maneuver I didn’t even know existed, pulling a near 360 without tacking (and it's far from recommended!). But, by some miracle, it had worked. Taylor and Kell were able to finish tying off the main, hanging precariously from the boom as we broke through swell after swell. I was able to hold a course of 30 degrees into the waves, a (relatively) comfortable angle, and Taylor and Kell returned to the cockpit. They were drenched and panting with exhaustion. We sat in silence for a long time, catching our breath and soaking in what had happened. Then Taylor laughed. “Holy shit!” he said, and the rest of us joined in. We were riding a high, surfing down swells of over 25 feet, but we’d done it. We were alive.


The storm didn’t end that night. With just a sliver of jib out, we were hurtling along at six knots (top speed with both of our sails full - on a good day). The swells were a steady 25 feet, and the storm raged on another 30 hours. When it broke into a relative calm, we were drained and exhausted, blown off course, and still hundreds of miles from Mexico. Our backs and bodies ached, we hadn’t slept in days, and the weather was by no means “clear.”

Looking back, it’s tempting to ask myself if we could’ve been more prepared for that moment. For instance, a more prudent move after the jib backwinded might’ve been to tack the jib sheets, rather than spin the boat around completely. Would another year of preparations have helped us in that moment, through that storm? Would our crossing the Gulf been safer, or less threatening, if we’d maybe conjured up money for weather radars, autopilot, a life raft and survival suits?

It’s possible. But there’s an expression that almost every sailor knows by heart. It goes, “If you wait until you’re ready, your boat will never leave the harbor.” There is always more money that could be spent, more time sailing around local bays and harbors, and there are always going to be a million reasons not to set sail.  But there is only one way to experience the open ocean; and you only need one good reason why to overrule the why-nots.

Could we have been more prepared for that storm? Yes. But when the sun rose two days later, after hours and hours of restless, delirious sailing, I experienced a level of ecstasy and fulfillment that I hadn’t felt in years – maybe ever. We had just pushed ourselves past the limits of what we thought possible, what most people think possible, and we had survived. New boundaries had been set – new borders for the rest of our trip, for our futures – and the implications were boundless.


Watch the full episode of our Gulf crossing here: