Taking the Leap: Reflections on Water, Dreams, and Adventure

By Mike Singer
It all began with a dream. A dream of wild places, physical hardship, and outdoor adventure. Like many of my liberal-minded classmates at Hampshire College, at some point about half-way to my degree I began getting fed up with the artificial, indoor, technological world I found myself living and studying in. I wanted out.
A class called “Outdoor Leadership” seemed like the perfect springboard to a new way of life. Surrounded by people who shared my longing for authentic experiences, I slowly realized that the dream could be made real.
The class was just the beginning. I soon found myself working for Hampshire’s Outdoors Program, fixing broken backpacks, tents, stoves, skis, and other gear. Over spring break one year, I joined a van full of classmates on a trip to the Smokey Mountains, and learned to whitewater kayak. While more aggressive paddlers capsized all around me, I timidly made my way down the river upright, masking my fears by shouting clever catch phrases like “Eddy-out, man!” and “It’s easy, just rush with the flush!”
I paddled on. Caught up in the present, the future was clear. Upon returning to school, I would buy a kayak, a big leather hat, and some Tevas. I’d spend the summer guiding rafting trips. Come fall, I’d study the psychology of outdoor adventure while learning to climb, dive, ski, and mountain bike. Then, in January, I would graduate into a life of never-ending thrills.
Back at school after the trip, I devoured books by adventure/travel writers like Tim Cahill and Joe Kane, books with titles like Jaguars Ripped My Flesh and Running the Amazon. On nights when I wasn’t reading I watched movies about tough guys like me: Romancing the Stone, High Road to China, Raiders of the Lost Ark. I started doing push-ups, and bought lots of maps.
Then, when summer came, I got a job. As a prep cook in the basement of a restaurant.
“We enjoy and even thrill to the godlike possibilities we see in ourselves in peak moments,” wrote Abraham Maslow, “And yet we simultaneously shiver with weakness, awe, and fear before these same possibilities.”
Maslow was a psychologist. My kayaking instructor Earl was an adventurer, and put the same thing a different way when I embarrassingly returned to school in the fall with nothing to show for the summer except some new vegetable slicing skills: “If you wanna dance, you gotta pay the fiddler.”
Earl was the type of guy you listened to regarding such things. He had a resume as impressive as his forearms. He rock climbed, ice climbed, mountain climbed, cross-country skied, downhill skied, telemark skied, rafted, kayaked, and mountain biked. He had traveled all over the world, had been a raft guide in Costa Rica, and had been on the first descent of a remote river in Siberia.
As the semester wore on, I found myself spending my time reading and writing about adventures instead of having them. I learned a lot about why everyone needs to have dreams, and why some people actually feel compelled to make them real. Yet when friends asked me what my plans were after graduation, I offered a quiet, “I dunno,” because I knew that if I told them the truth, I would have to do it, and my dreams scared the hell out of me. Like many a suburban middle-class product, it was hard for me to imagine a future that didn’t include a house, a car, a nine-to-five world of work. It wasn’t that I particularly wanted all that stuff, it was just all I had ever known.
Not surprisingly, upon graduation in January of 1991, I wimped out. I moved to Los Angeles to live with friends, started temping in banks and insurance companies, and found myself surrounded by people whose idea of adventure was taking the bus. I had big dreams, but the reality was that I was a student loan burdened college graduate without any semblance of a real job in sight. I was depressed, confused, and embarrassed. Maybe it was time to grow up.
Then again, maybe not. The saving grace came from my sister. Younger but infinitely wiser, she screamed at me one night on the phone: “You’re only 23 years old! What the hell are you going to do? Settle down?!”
The next day I bought a book called Jobs in Paradise. It depressed me even more. I quickly realized that seasonal jobs needed to be applied for before the season started, and that I should have gotten my act together while I was still in school and had connections. It was already April, and the chances of my getting a summer job leading trips outdoors were pretty slim.
But fate has a way of helping those who are following their dreams. It seems that once you say yes, and take the leap, the rest is as easy as falling.
It started simply, like this: my sister had a friend in L.A. who was driving up to see her at Evergreen College in Washington State. I took that fact as a hint from the universe, packed my bags, climbed into a pick-up truck with a total stranger, and headed north into a big unknown.
A few days later I was in Olympia, and a day or two after that I was in another pickup truck, on my way to the San Juan Islands. One of my sister’s roommates was heading to Orcas Island to check out a little resort called Doe Bay for summer work possibilities. As the ferry steamed toward Orcas I felt a wave of synchronicity pass through me.
A few hours later we pulled into the parking lot at Doe Bay, and some powerful déjà vu struck again: this was it, the laid-back resort in the middle of nowhere that I had been fantasizing of while reading Jobs in Paradise. We walked down the road toward the water and at the end was a little shack with a sign: “Island Kayak Guides.” Stapled to the side of the shack was a tattered piece of paper: “Wanted: Sea Kayaking Guides.”
“Show me a high brace!” barked the head guide in an intimidating New Zealand drawl. It had been over a year since I had sat in a kayak. So I timidly leaned the boat over the way my grandmother would test the water with her toes at a swimming pool, and promptly capsized into the forty-five degree water. Instant panic. Why, exactly, am I doing this again?! Who the hell am I kidding? Guide people? I can barely keep myself right-side up!
“I’m not impressed,” I heard as I came to the surface.
“Me neither.” I said. “But I’ll try again.” I’ll try again? What was I saying?
“Yeah, sure, go ahead.”
I tried, and capsized, again.
After an hour or so of this, we paddled in, put the boats away, and rinsed our gear. Incredibly, I was offered a job. Other prospective guides had been scared away. But not me. That fact, apparently, bought me some respect.
There at last was the dream made real, somehow materialized. A few weeks after leaving L.A. I could be living in a tent in the woods, spending my days learning how to kayak in the ocean, and getting paid to do it. It scared the hell out of me and like an idiot, I said I’d think about it.
I went back to my sister’s place in Olympia and thought about it. For three weeks. I thought about how cold the water was. I thought about how deep the water was. I thought about how poorly I kayaked. Then, I thought about the alternatives. Finally, more terrified of office work and prep cooking than of drowning or getting my hair slimed, I took a deep breath, picked up the phone, and said, “Yes.”
I‘ve read somewhere that while we can fear the past (as guilt or resentment), and we can fear the future, it’s impossible to fear the present, since it’s happening right now. As I settled into life as a sea kayaking guide on Orcas Island, I realized that I had wasted unthinkable amounts of time and mental energy worrying about a future that had become a rather amusing present.
I found myself in one of the most beautiful places I had even been. Surrounded by snow-capped mountains, glorious islands, otters, seals, eagles, and herons, I learned to paddle a sea kayak. I learned to brace against the frigid water, and I learned to remain calm when I found myself in it, legs dangling into the dark below. I learned to stay upright, and to rescue myself and others when the challenges exceeded our skills. I learned to “Eskimo roll,” to read nautical charts, to navigate in fog, to use a marine radio, and to move among yachts, fishing boats, tankers, and an occasional submarine. I learned to read currents, and to respect them when they funneled through the likes of Deception Pass, racing past razor-sharp barnacles like a raging river.
A funny thing happened. As I acquired more knowledge and skill, I lost my fear of things that go chomp in the water. I learned what these creatures were, and how they lived. By mid-summer, I was one of them. I spent my days off swimming in Cascade Lake, working on my roll. Being upside down in the water wasn’t particularly comfortable. But it was fun.
My fellow guides had considerably more experience adventuring outdoors. They had collectively paddled and played all over the world. They had mountaineered, backcountry skied, worked for a barge company in Alaska, the Forestry Service in northern Canada, and run guided kayaking trips in Central America. One of them had a business building authentic wood and skin boats. They gave me a sense of what was possible. And in time, I came to feel I was one of them.
From time to time, I could see in my clients’ eyes a certain look of frustrated envy mixed with a self-congratulatory pat on the back, a look that said, “Yeah, he has a pretty cool job, but I have responsibilities.”
It was an admittedly cushy job. I paid no rent on my tent-site, ate free food, enjoyed hot tubs, a sauna, and a weekly massage. With very little effort I managed to stay fit, tan, and rather content. The view from my office couldn’t be better. But this cushy job was not without a price.
Isolated in a world of outdoor adventure professionals, that is to say, in a world composed solely of fit, tan, and rather content people, I suppose I would have had no dilemma. But for better or for worse, a job such as that one only existed because of the interaction I had with more responsible folk-those who had “real” jobs in which they could earn enough money to afford the recreational experience I provided them with. Their looks of envy wouldn’t have bothered me except perhaps for the fact that I grew up thinking work was something you did with a hammer or a necktie, not a paddle.
In strong contrast to the work ethic, the “worth ethic” of outdoor adventure turns work into an unusually pleasurable experience. For me, the price of such pleasure was an equally strong feeling of guilt. Making salads and temping in banks may have been boring, even agonizingly un-pleasurable, but I never felt guilty doing it.
The pleasure of guiding came, I think, from taking responsibility for my own happiness, from doing the things I wanted to do, not the things my friends, my family, or society had mapped out for me. The guilt came, I think, from the knowledge that so many people don’t take responsibility for their own happiness, don’t follow their dreams. It’s much easier to be lazy, to let dreams remain dreams. It takes much more energy, and is far scarier, to follow those dreams and see where they lead, to use their power to overcome the fears and frustrations that can easily prevent them from coming true.
My fears and frustrations that first summer as a sea kayaking guide were many. The waters of Puget Sound were cold and dark. My learning was hampered by unpleasant memories of learning how to swim. My tent leaked, and was shared with spiders, mosquitoes, bees, and caterpillars. My air mattress had a hole. My cheap sleeping bag was always too cold or too hot. My muscles ached, and my knee was bruised from smashing into rocks during an unexpected capsize in huge breaking surf. I grew tired of the same small-talk, the same eagles, the same seals. I missed my favorite TV shows, and only saw a few movies.
With fall came a seemingly perpetual overcast and a drippy, depressing sort of rain. The company ran trips year-round, but I was getting lonely. Most of my friends had left, and most of the tourists were staying home.
I remembered Earl back at school telling me that in his adult life he’d spent more nights sleeping outdoors in a tent then he had inside in a bed. At the time, I thought that was pretty exciting. But after a summer of living outdoors, a tent was just a tent. A very wet tent covered with leaves, and bugs, and mold. Eventually, I packed everything up and headed south to Seattle.
If I learned anything that summer it was this, and its obviousness is precisely what made it so hard for me to see at the time: There are certain experiences that are only available to those who are willing to have them.
In going to Orcas, I took a leap of faith. That was not easy. In leaving, what was even harder was taking the big leap, the one that would let me continue taking the little ones.