(Really) Risky Business

Wes Skiles is one of the leading practitioners of what may be the world’s most hazardous sport: underwater cave diving. There is no injury rate for mistakes made in an underwater cave — only a mortality rate. So why does Skiles keep diving?

It was in the Yucatan’s Grand Cenote cave system that underwater explorer Wes Skiles, 42, a veteran of more than 3,000 descents into water-filled caverns, made his greatest escape from the gods of risk and chance. It went something like this.


Looking as if he’s prepped for a long day’s journey into inner space — with a pair of scuba tanks strapped to his sides and an assemblage of regulator hoses, lights, and guidelines hooked to his harness — Skiles plunges 60 feet down into Cenote’s Web of underwater caves. He swims 1,000 feet into the system, intent on wrapping up a mapping survey of Cenote’s aqueous labyrinth of tunnels and chambers. On this day, he intends to check out the last of the system’s unexplored side tunnels.

Skiles swims up to a restriction — a chimneylike shaft that’s not much wider than a Subaru tire. He hesitates, knowing that he could get trapped like a bug between the cave’s ceiling and floor. But he decides to push on. He has come upon many such passageways before and discovered that they often open up into virgin caves where no explorer’s light has ever shone. But not this time.

He unclips his scuba tanks from their side mounts. Dragging one tank between his legs, he pushes the other tank ahead of him like a battering ram and squeezes into the shaft. Digging his fingertips into the tunnel’s limestone floor, he pulls himself forward an inch at a time. With great effort, he muscles through the restriction — only to jam himself into a dead-end hole that’s no larger than a coffin. His face is pressed hard against a wall of rock; his feet are crunched above him at a 45-degree angle. He can barely move, and he has only a finite number of breaths left to find his way out.


“I’ll die in here,” he thinks, “and no one will ever find me.”

Trying to remain calm, he realizes that his only hope is to make himself smaller — to strip off gear so that he can turn around and push himself back through the tight passageway. He struggles out of his side-mount harness, works free from his fins, and gains a foothold. In a Houdini-like maneuver, he manages to find a little slack. He wriggles around until finally, he’s facing the way out. He collects himself and formulates an escape plan: Squeeze back through the restriction and then swim like hell. One tank is almost spent; the other is half-empty. He must make it to the cave’s opening before he runs out of air.

He struggles back into his gear and jams himself through the restriction. He’s ready to make a run for it, but he can’t. Horror-struck, he realizes that the tank containing most of his air has slipped away from him and rolled back into the restriction. “I’m so screwed,” he thinks. He plummets back into the passageway, gropes desperately in the dark for the tank — and finds it. If the tank had dropped into the hole, he would have run out of air and drowned. Even now, with both tanks clipped to his sides, he has just minutes of air remaining as he makes it out of the system. Like Prometheus, who stole that ball of fire from Zeus, Skiles has defied the gods and survived.


Cave diving is arguably the world’s most hazardous sport. There is no injury rate — only a mortality rate. In northern Florida alone, more than 300 people have drowned in underwater caves. With each dive into the belly of the earth, skilled aquanauts such as Skiles make the ultimate bet, putting up their very lives as collateral as they push to illuminate new discoveries. Make a bad bet in business — on an ill-conceived strategy or on a poorly designed investment — and you might lose your job or your company. But in the world of cave diving, the downside is 6 feet under. It is absurdly easy to take on too much risk, panic, and drown.

“If you take average, experienced divers and put them in an underwater cave environment, you expose them to all sorts of risks that they don’t understand and that they’re not prepared to deal with,” says Skiles. “They would certainly die. And it would be a hard, terrifying death.”

In his much-acclaimed book Against the Gods: The Remarkable Story of Risk (John Wiley & Sons, 1996), economist Peter L. Bernstein writes that the word “risk” derives from the early-Italian risicare, which means “to dare.” Thought of this way, risk is not a fate but a choice — something that we choose to assume in our work, in our careers, and in our companies. That is why we have tracked down Wes Skiles and his diving partner, Peter Butt: They have dared to make fresh discoveries about the nature of risk and the art and science of choice. In caves such as Cueva de Fuego, Devil’s Eye, Grand Cenote, and No Way, Skiles and Butt have learned how to read risk, evaluate it, weigh its consequences — and get out alive when things go terribly wrong.


Why Risk It? Tales From the Downside

Beneath the white clapboard churches and pink ranch houses of north-central Florida lies an awesome world of underwater caves and caverns. This complex waterscape was formed over millions of years, as rain percolated down through the region’s porous limestone and chewed through the soft karst, braiding a riverine Web of underground passageways. Today, this immense latticework of tunnels, dubbed the Floridan Aquifer, contains as much water as all of the Great Lakes combined.

For the past two decades, a small band of master divers, centered on the area around the rural town of High Springs, have limned many of the Aquifer’s speleological riddles. Hole by hole, tunnel by tunnel, they have pushed through its culvert-sized passageways and broken into its diamond-clear underwater rivers. Wes Skiles is among the most experienced of this skilled tribe of cave divers. A barrel-chested man with a high-domed forehead and an accent as thick as a Florida heat wave, Skiles probed his first cavern when he was just 15 years old. Seven years later, he helped design many of the safety procedures that now regulate the National Speleological Society’s cave-diving certification program.

Today, Skiles and veteran cave diver Peter Butt, 45, own and operate Karst Environmental Services Inc. — an organization that contracts with government agencies, conservation groups, and private companies to map the Aquifer’s countless tunnels. Skiles also runs a photography and television-production company, Karst Productions Inc., which has produced science-adventure specials on underwater caves for PBS, CBS, and the Discovery Channel. Whether as a film-maker or as an explorer, Skiles has helped shotgun some of the most ambitious cave-diving expeditions on the planet.


We meet up with Skiles in his office outside High Springs on a late-spring day, as great tropical thunderheads boom outside. As Skiles launches into an animated talk about risk as it applies to cave diving, his face breaks into a Jack Nicholson-like grin, without the leer. His mood doesn’t darken one bit as he takes on the critical element in every risk equation: the downside. It is difficult to overestimate the dangers of venturing into a water-filled cavity of the earth. As a cave’s stygian gloom takes over, the environment becomes a totally alien place. A world without gravity or light. A world utterly unforgiving of careless mistakes.

A single misplaced fin kick, and you can rile up a black pudding of silt that cuts visibility to zero. Take just a couple of detours down tempting side tunnels, and the whole physical world can turn in on itself — making even an experienced diver swear that the way in is the way out. And all the while, a diver is using up precious air. Take a wrong turn, and you only have a finite number of breaths to find your way back.

“If you get disoriented in open water, you can locate the surface simply by following the ascent of your exhaust bubbles,” says Skiles. “But in an underwater cave, your bubbles are swallowed by the blackness. There is very little up and down in one’s mind: Everything could be up; everything could be down. An underwater cave is a three-dimensional space in which you have to reorient yourself to the rules of gravity. And then you have to deal with the voices in your head — voices that could, if you let them, push you into a panic. If you’re not able to calm your fears, your fears will take over.”


The folklore of cave diving is full of stories of lost divers who frantically searched for a way out until their air was exhausted. Veteran divers have all heard the story of the Florida diver who took a wrong turn at a junction of two tunnels. When he realized that he was about to exhaust his air supply, he grabbed his slate and used his last breaths to scribble a good-bye message to his family. Michael Bane, in his book Over the Edge, tells the story of a diver who became separated from her fiancé and took a long, panicked death swim down a tunnel to nowhere. The recovery team found her claw marks etched into the limestone wall.

In a 12-year span that began when he was just 16 years old, Skiles recovered the bodies of 30 divers who perished in northern Florida’s underwater caverns. Another time, he pulled three dead brothers out of a cave called Devil’s Ear, near High Springs. They were inexperienced divers who got lost, panicked, and drowned. “The three of them were holding hands when I found them,” recalls Skiles. “That was a tough one. It wiped out the family’s whole lineage. But what kills one can just as easily kill three.”

Most of those who have died lacked formal cave-diving training. But sometimes, even veteran cave divers get too cocky for their own good. And even if experienced divers take all of the right precautions, they’re still not guaranteed a safe return. One of the best, a friend of Skiles’s named Parker Turner, died at a place near Tallahassee called Indian Springs. Part of the cave collapsed, plugging the way out. Turner clawed through the debris, almost reaching the cave’s upper chamber, before running out of air. His partner followed the path that Turner had cleared — and survived.


After Turner’s death, Skiles stopped recovering bodies. The emotional toll was just too great. But Skiles still dives. The question is, Why? What makes it worth the risk?

Skiles doesn’t hesitate before answering: Underwater caves are one of the last frontiers on Earth. They are places of beauty and wonder that only a handful of people have explored. Where others see a black hole, Skiles sees what he calls the “nothingness highway” laid out before him, and he wants to be the first to cruise down that road — the first to shine a light on these underwater labyrinths and discover a new maze of tunnels, or a grave of mastodon bones. For him, journeying into a virgin cave system is like discovering the Grand Canyon — while flying.

Of the many dives during which Skiles pushed himself to the edge of human experience, one moment stands out. He was with a team that was attempting one of the first mixed-gas cave dives — using mixtures of helium and oxygen to enable them to drop more than 300 feet deep into Florida’s Wakulla Springs. (At that depth, a diver will deplete a normal tank of air in 30 breaths.) Skiles and his team had pushed more than 2000 feet into a large, dendritic tunnel that broke off into smaller and smaller passageways, like the branches of a tree. They hit a depth of 320 feet and then started up a steep slope. When they broke over the top of the hill, the divers found themselves in an enormous chamber that soared to a height of 250 feet. In the center was a 7-foot spire of boulders, capped by a pure-white rectangular stone standing on its edge.


Skiles and the other divers stared in absolute awe. “That great slab of rock was a mirror image of the monolith in the movie 2001: A Space Odyssey,” recalls Skiles. “It struck me at that moment that just like in the movie, we were using advanced technology to visit and explore an alien world. But in another sense, we were really the most primitive of beings. We all got chills. We named that place the Monolith Room.”

His Options Are Always Underwater

It’s nearly a theological concept in cave diving: Take two of everything. Your equipment is your life support, and every diver who ventures into an underwater cave brings backup gear — tanks, regulators, lights, computers. That way, when a light goes out or a hose pops, the diver still has a very good shot at getting out alive by relying on the backup equipment.

But the one piece of equipment that cannot fail is your brain. “Your mind is your regulator,” says Skiles. “It takes a constant inventory of your body, your gear, and your environment. If all systems are go, your mind controls your pace, your rate of breathing, and the ways that you reevaluate the risks as you go deeper into a system. Cave diving is the ultimate cognitive undertaking. People compare it with an endurance race, but it’s really more of an extreme game of chess.”


The risks increase exponentially as divers push ever farther into a system. On deep dives — and a place like Wakulla Springs is a very deep dive — nitrogen builds up in the body. Unless divers spend time in shallower water letting gas bleed out of their system, they will suffer decompression sickness, more commonly known as “the bends.” So divers must constantly manage their depth. And that can mean keeping track of as many as eight regulators and eight pressure gauges of the gas mixtures that they are dealing with, as well as the guideline — that umbilical cord back to the land of the living.

That’s not all. As they push farther into the deep, divers endure a form of psychological stress called “perceptual narrowing.” Sensory overload begins to take its toll, and they become less and less aware of their surroundings.

“You start to get that ‘way-back-in-the-earth’ feeling,” says Skiles. “You know that you’ve passed the edge of normal human experience, but you don’t know how far you’ve gone. In mountain climbing, you can see the summit, the lofty goal. In underwater-cave exploration, no one knows what’s down there. You can’t quantify whether you’re halfway there or three-quarters of the way there. The weight of the unknown really bears down on you. When you get back into these deep places, you’re so perceptually narrowed that you can’t understand the nuances of what you’re seeing and what you need to do in order to survive.”


To evaluate the risks of underwater-cave exploration, Skiles starts by evaluating himself. He does this by leveraging the “theory of pie.” A pie is a metaphor for a diver’s maximum problem-solving potential. As he preps for a dive and descends into a cave system, the diver loses a slice of pie with each distraction or setback. An O-ring blows while he’s gearing up, and he has to stop and change it: Take away a slice. He accidentally sets his tanks down on a dive light and cracks it: There goes another slice. If he loses too many slices, the diver must quit: He must call the dive. If he doesn’t — if he makes the dive with just half a pie — he won’t have all of the mental resources that he needs to deal with a real underwater emergency.

Skiles first put the pie theory into play when he was 19. He was on a dive with Sheck Exley, a cave-diving pioneer who set numerous world records for deep dives. (Exley died in 1994, while diving below 900 feet in Mexico.) Their plan was to dive into the cave system in Florida’s Blue Springs, swim 3,000 feet back into the network of tunnels, and lay 1,000 feet of line. (That is, push another 1,000 feet into the unexplored system.)

“It was a hot day, and I felt really rushed as we geared up,” Skiles recalls. “When we got into the system, Sheck started swimming really hard, and I had trouble keeping up with him. My pacing wasn’t good that day. Then my regulator started to leak. I could still breathe through it, but it was free-flowing pretty hard. So I flashed Sheck down and showed him that my regulator was bubbling. And he looked at me like, ‘Shit, all of my regulators bubble.’


“If ever there was a guy who I would blindly follow no matter what, especially at that age, it was Sheck Exley,” Skiles continues. “It was a major embarrassment for me to disappoint Sheck. But I knew that I had lost too many slices. I had to call the dive.”

And that’s exactly what he did. In a way, it would have been easier to keep swimming after Exley; Skiles didn’t want his hero to doubt his skill and courage. But looking back on the experience, Skiles realizes that it took even more guts to call the dive. In the long run, quitting gave Skiles the confidence to push on — to take on even bigger challenges — because he knew that he had the mental agility to manage the pie.

Diving Solo: Real Risk Takers Work Alone

Calling that dive was a turning point for Skiles. He knew then that he could never be dependent on another diver. He vowed that from then on, he would take control of his own destiny. He would lead, instead of follow. And he would be relentlessly self-reliant — even if it meant diving alone.


Skiles went on to rack up hundreds of solo dives. Now, flipping randomly through his logbook, he quickly hits on one of them: 125 feet down and more than a mile back into Devil’s Ear. He was underwater for three hours. He used up seven tanks (some of which he had cached on his way in). And he did it all without a dive partner.

For an open-water diver, this is heresy of the highest order. The first commandment of open-water scuba diving is: Thou shalt always dive with a partner. A dive buddy is your backup. Dive buddies remind you to check your depth, time, and air-supply limits. If a regulator blows, they are there for you, and you are there for them. But a buddy can be a liability for a pioneering cave diver.

“A lot of what you learn in cave diving runs completely counter to open-water diving,” says Skiles. “Depend on a buddy in a cave, and you’ll end up with a double drowning, because each guy is relying falsely on the other. Neither one of you is prepared to deal with an emergency on your own terms.

“In fact, by depending on a dive partner, you increase the risk factor,” he continues. “There’s this false sense of security that you can push farther, because you’ve got a comrade right there with you. Well, take your partner away, and judge the dive for yourself. Are all systems go? If your buddy wasn’t there, would you still be okay — or would you call the dive? Even when I dive with other people, I dive self-reliant. We all dive solo — it’s just that there are times when we dive solo together.”

When judging potential cave divers, Skiles looks for two critical qualities: alertness and awareness. The two words sound similar, but they have very different meanings. Alertness applies to minute changes and fluctuations during the dive. If Skiles wiggles a flashlight — the underwater signal for “I want your attention” — alert divers immediately turn their heads to see if there’s a problem. But many times, Skiles violently shakes the light and gets no response. The other divers are so task-loaded — they’re struggling against the current, they’re reading their gauges, they’re worried about losing sight of the guideline — that they’ve lost track of the dive itself.

Awareness applies to one’s ability to holistically take in the entire dive environment. Divers who are acutely aware of their surroundings will walk up to a spring, smell the tannin in the water, and know that on this particular day, the water’s visibility may be lower. As they dive into a tunnel, they observe that the silt has changed from sand to soft mud. Sand is generally indicative of a high flow; soft silt in the same passageway means that the water’s velocity is decreasing, and the cave is getting wider. “You can’t teach alertness and awareness,” says Skiles. “I’ve never seen anyone develop those qualities who didn’t have them [ to some degree ] in the first place.”

When judging a potential partner for exploratory dives, Skiles looks for someone who is, at the least, his equal. “It’s not about who is the best,” he says. “It’s about whom you’re completely comfortable with in terms of this specific system. In these pointy-end situations, the kind of buddy I want to dive with is someone who has the will- power and the confidence to get his experience on his own. And a lot of times, I’m comfortable with no one but myself.”

The Voice Of Ambition, The Voice Of Caution

Even when Skiles dives solo, he’s never completely alone. There are always two voices running through his head: the voice of ambition and the voice of caution. One voice pushes him to make more discoveries. The other prevents him from plunging into the abyss. With every dive that he makes, Skiles faces a critical choice: He must decide which of those voices to heed. The answer isn’t always clear.

“You have to judge the motivations of each voice,” he says. “You have to ask yourself, Why is the ‘don’t go’ voice so loud today? Is it because my problem-solving skills aren’t as sharp as they should be? Or is that voice just a defensive mechanism, and if I ignore it, I’ll have a great dive? When you call a dive, you never know whether you did the right thing. But there’s one thing that I do know: If the safety voice isn’t there, something is wrong. I’ve got to make myself slow down and give the dive proper consideration.”

Skiles once heeded the wrong voice in a place near High Springs called the Azure Cave System, a network of tunnels that he discovered with two other divers. After rappelling by rope down a dry shaft, the trio geared up and plunged into the maw of the cave. They swam into a series of enormous rooms and then separated, each choosing to explore a different tunnel.

Skiles pushed into a chamber that gradually shrank to a height of just 18 inches. He was wearing a pair of side-mounted tanks, which often enabled him to squirm through narrow restrictions. But this was one hell of a chest-cracking squeeze. Even so, the voice of ambition said, Go. The cave’s bottom was made of soft mud, and Skiles found that by bracing his feet against the ceiling, he could push off and inch his way through the muck. He was sure that the passageway would eventually open into a bigger tunnel.

He never found out. He had burrowed himself 50 feet into the chamber when suddenly his air supply began rushing out of his regulator in a torrent of bubbles. That’s not all. He had stirred up so much silt that his visibility was reduced to nil. He was losing air fast, and he couldn’t see a thing. Groping in the darkness, he managed to grab his backup regulator and shove it into his mouth. Horrified, he discovered that this regulator had begun free-flowing air and leaking water. Fear overcame him, but he fought off the impulse to turn and flee. His only hope was to get his priorities straight and to solve each problem.

“I knew that if I tried to run for my life on a free-flowing, flooding regulator, I wouldn’t make it,” Skiles explains. “I’d simply race my breathing. Then I’d choke, my trachea would spasm, and I’d drown. My number-one priority was to get control of my breathing.”

Skiles grabbed the first regulator, took in a few breaths, and then — nothing. The free flow had emptied his tank. His whole world was now reduced to learning how to get a usable breath out of a backup regulator that was force-feeding air and water. He found that by lifting his tongue, he could block the rushing water and still suck in some air. Only then, when he managed to take in a few workable breaths, did he allow himself to turn around and push his way out of the restriction.

But he wasn’t home free yet. He had lost track of the guideline and was swimming blind, when suddenly the silt cleared and he broke into crystalline water — a very bad sign. Clear water meant that he’d taken a wrong turn down a side tunnel. He had wanted to see a wall of silt: The mud that he’d kicked up on the way in marked the way out. He had no choice but to turn around and swim back into the maze. Somehow he managed to backtrack into the maelstrom of silt and retrace his passage from there. By maintaining a shallow, low-demand pattern of breathing, he was able to make it out of the cave with just a wisp of air remaining in his tank.

It wasn’t his lungs that got him out alive — it was his confidence and his experience. He had taken on too much risk, and when the risk went bad, the only way to survive was to prioritize, problem-solve, and tamp down the Big Fear.

Recalls Skiles: “Can I say that I wasn’t afraid — that I kept endorphins and adrenaline from dumping into my blood stream? No, I can’t tell you that. Did I squelch them so that they didn’t control my mental process? Yes, absolutely. If you let that alarm go off, it will absorb your ability to work the problem.

“I knew as clearly as a human being can know that I was facing the ultimate challenge of my life,” he continues. “I had dug myself into a mud tomb, I had zero visibility, and I was losing air — but I had to cancel out those problems. If I had let anything distract me from getting control of my breathing, I would have died.”

“We’re Freaking Out Of Our Minds”

Before I made the trip to Florida, I had asked Skiles’s partner, Peter Butt, a naive question: “Will you guys be going on a ‘dangerous dive’ while I’m down there?” The question had unnerved him.

Cave diving is their work. Nothing more, nothing less. After logging hundreds of hours each in underwater caves, they have learned how to prepare for every kind of risk and have dealt with just about every type of emergency. They possess the most advanced equipment. So for them, cave diving is one of the safest forms of diving. It is almost a routine part of their day. Butt thought that I’d be disappointed. Skiles had to remind him just how dangerous cave diving can be for others. Now Skiles put the question to me — and came up with his own answer.

“Danger is inherent to cave diving, but we’ve learned to harness the danger and to manage it,” he said. “We’re comfortable living inside of a bubble that would scare the hell out of most people. So when you ask, ‘Are you going to do anything dangerous?’ what do you want to hear? From us, the answer is no. We’re not doing anything dangerous. But evaluated by you, we’re freaking out of our minds.”

And with that, Skiles said good-bye and headed for his truck. He had heard about a new hole, some-where back in the woods. He wanted to dive.

Bill Breen ( is a Fast Company senior editor. contact Wes Skiles ( by email, or visit him on the Web (

Sidebar: Risk for Beginners

“A lot of us in business throw around the word ‘risk,’ without really knowing what it means,” says Michael Bane, 50, a frequent speaker on risk taking in the new economy. “The definition that I use comes from white-water rafting: The level of risk corresponds directly to the increased consequence of failure. Fall out of a raft in a class I river, and you get wet. Fall out of a raft in class V water, and you die.”

In his book Over the Edge: A Regular Guy’s Odyssey in Extreme Sports (Indigo, 1997), Bane gives a firsthand account of learning how to cave-dive. He describes two critical lessons for up-and-coming risk takers in any field.

First, know the difference between perceived risk and actual risk. “I’ve seen companies spend millions of dollars on mitigating risks that are beyond their control,” Bane says. “In fact, this may be the single biggest mistake that companies make — wasting critical resources on perceived risks. Cave divers have a saying: ‘Control what you can control.’ They identify the actual risks, and they figure out what they need to do 100% right, 100% of the time, in order to survive.”

The second lesson, says Bane, is to understand that risk takers can’t always depend on the certainty of cause and effect. In business or in cave diving, cause and effect break down when people push into the unknown. “Cave divers are arguably the most superstitious people I’ve ever met,” says Bane. “I have seen major cave dives canceled in the parking lot of the dive site, simply because someone had a hunch that something wasn’t right. When you journey to the edge of human experience, you don’t know what keeps you alive. So, as a corollary, you can’t rule anything out.”

Contact Michael Bane ( by email.

Sidebar: My Deep Dive

The water at Florida’s Ginnie Springs is so clear that the dozen or so people swimming in it appear to be floating on air. But my eyes are drawn to the floor of the springs. Twenty feet down is the oyster-shaped maw of a cave. Accompanied by master diver Peter Butt, I’ve agreed to dive into that black hole. Since the early ’60s, some 25 divers have perished here.

We descend and hover 10 feet above the cave’s entrance. My adrenaline kicks in. A voice in my head says, “Don’t go in.” Peter fins into the cave and beckons for me to follow. I take a last look up at the sun-splashed surface, click on my dive light, and go in. The sunlight quickly ebbs and gives way to utter darkness. But the beams of our high-powered lights cut through the black, spotlighting the sides of the cavern.

Peter unspools a line of nylon rope and ties one end to a rock. Then he swims to the edge of a drop-off and dives headfirst into the dark. I push off to catch up. No go. The valve on my tank is tangled in the guideline. My instinct is to pull hard against it; I need to catch up with Peter. But I make myself calm down, back up, and free myself from the snag.

We swim up to a metal grate that has been welded across the tunnel, preventing us from continuing deeper into the cave. The grate was put there to stop the loss of life. Peter and I had prearranged to cut off our lights for 30 seconds, which we now do. The blackness is tomblike, all-enveloping. There are absolutely no distractions. What a contrast when, several minutes later, we return to the mouth of the cave. We swim out and arc up toward blurred, watery images of oak trees and blue sky. And then we break the surface — into the world of light and sound and the living.

Learn more about the Ginnie Springs Camping and Diving Resort on the Web (

Update: Ginnie Springs Outdoors’ Web site has moved.