During the fateful summer when the bottoms of my feet first made contact with a surfboard, the last thing I needed in my life was another time consuming outdoor activity. Especially one that required more bulky and expensive equipment. In my small apartment set amongst the precariously steep streets of San Francisco, it already took effort to find the cream colored walls behind densely packed rows of outdoor sport paraphernalia.

My penchant for adventure combined with a newly acquired engineering salary predictably resulted in a straight-out-of-university lifestyle of trying to squeeze as many outdoor excursions as possible into the couple days a week when I wasn’t required to be sitting in an office. During my play time, you could usually find me somewhere on a rugged mountain; either trying to walk up it or ski down it.

I had recently invested heavily in overly expensive mountaineering gear and guided courses with an ambition to take my high altitude forays to the next level. As if that wasn’t enough to drain my wallet and free time, I had also decided to see what it was like above the mountains themselves, with several days and a significant amount of adrenaline hormones spent training to complete a solo skydive.

Spreading myself too thin has always been a personality trait I’ve had to manage, but things were starting to get a little ridiculous. Which is why, when my good friend Sarah asked me if I wanted to join her for a surf on a sunny afternoon in Santa Cruz, my immediate mental response was “definitely not”.

Growing up on the temperate shores of the Long Island Sound in Connecticut, my opinions on large bodies of salt water didn’t extend much further than thinking they could be nice to look at. While I was well aware of the existence of surfing, it might as well have been a sport practiced on another planet. The biggest waves I’d seen at my home beach were barely large enough for a chipmunk to ride on a wooden ruler. For me, true recreation was found in places where earth and rock thrust their way high into the sky.

Then there was also the fact that when I was younger, my dream states were often invaded by nightmares of large and terrifying walls over water rising up and crashing down on top of me. And it certainly didn’t help that my number one irrational fear in life is sharks.

These factors led me to spend the first year of residency in my new home of California all but ignoring the “official state sport” as well as the watery setting in which it was practiced. A few friendly invitations from wave seeking acquaintances had been extended and rejected without thought.

However, for a long forgotten reason which I can only ascribe to the universe having a plan for me, on this particular weekend, I decided to go against all my instincts and accept Sarah’s offer to “go for a surf”. What was the worst that could happen?

Boards were haphazardly strapped to the car roof, and a brief ride down the road to Capitola ensued. In the charming coastal town modeled after an Italian fishing village, parking was in short supply, and we almost gave up and drove back home. Then, at the last minute, we managed to snag a back alley spot being vacated by a local who was clearly flustered by how quickly we managed to take away his prized resource.

Several minutes later, I was perched on the sidewalk overlooking a small inlet filled with sparkling blue water. While I had seen plenty of waves before, this was the first time I was looking at a bumpy ocean surface with the intention of riding on top of it. Thin shadowy bands started forming a hundred meters out, slowly thickening as they approached the shore. Upon reaching the crowd of two dozen floating people, a section of the leading band would abruptly transition to white, then begin to spread outwards, slowly transforming each dark line into a textured gurgle of foam.

The perfectly positioned riders clad in stretchy black suits seemed to know exactly where the transition from dark to white would occur on each band, and used the opportunity to pop up onto hydrodynamic slabs and let the natural force pushing from behind carry them forward. 

Seemed easy enough. I wasn’t worried about having the strength to paddle, due my near-daily gym routine depositing plenty of muscle onto my upper body. Then the riding part on these small waves would also be a breeze. I had prior experience carving boards through steep snowbanks, plus a large percentage of my childhood was spent developing a keen sense of balance by playing hockey on sheets of ice with blades underneath my feet. Surely these things would translate into a flattened learning curve on the ocean.

Dead wrong.

That first day spent in the water can only be described as an absolute struggle. Having been given no guidance on how to do anything properly, I floundered about on my stomach and spent most of my energy merely trying to keep the board from tipping over. My aesthetically pleasing muscles proved next to useless in helping propel my board across the surface. The first ten minutes of frantic arm splashing produced aches in areas of my back and shoulders which I had never before felt.

Through sheer willpower, I finally reached the place in the water where everyone else was lining up to step onto the waves. After multiple failed attempts to furiously paddle into the breaking section, it dawned on me that the thousands of hours I’d accumulated in other athletic endeavors might be wholly unapplicable in this strange, wet world. All around me, cackling children continuously caught every wave in their vicinity with dumbfounding ease, adding to my frustration.

Needless to say, I didn’t even come close to riding a wave during that session. After two hours of fighting a losing battle with the mellow, waist-high swell, I accepted defeat and sloshed my way back to shore with a large bundle of stray kelp wrapped around my leash. But as soon as I stepped exhaustedly onto the sand, something remarkable happened. My body began to tingle. It took my mind a few seconds to register what I was feeling. Pure exhilaration. 

How was this possible? Everything about the ordeal I had just endured from an objective standpoint was miserable and demoralizing. And yet, I felt incredible. Little did I know I was experiencing my first “surf high”. A feeling familiar to anyone who’s spent more than a handful of sessions amongst waves, it has a consciousness consuming quality to it which places a golden hue on everything else that happens to you while you’re embraced by its alluring grip. In all my years of seeking, I have yet to find another activity or ingested substance that produces quite the same effect.

Here I was, staring out at the glistening expanse of water which had just handed me a thorough ass-kicking, and smiling like a circus clown. First contact had been established with the teacher, mentor, enemy, and friend I would come to know well in the following years, and the first lesson had been hinted at. 

—

Humbled by the struggles and made deeply curious by the resulting mental state, I decided to spend the very next day going for a second attempt. Except this time, I made myself a deal. If I caught and rode three or more waves that day, I would buy myself a cheap second-hand board and start my career as a surfer.

Somehow, the previous day’s shenanigans had affected me on such a level that I was willing to throw away all of the clear and logical reasons why buying a board and committing myself to yet another outdoor activity would be a terrible idea. Most of the voices in my head were screaming in protest at the nonsensical deal, but one mysterious and deep part of me (which I would later come to call my intuition) was unphased and offered silent encouragement.

This time, before entering the water, I spent the better part of a half hour sitting on a bench marinating in the smells of the nearby local fish market, and watching the figures below me cavorting amongst the azure waters. This became the primary way in which I would teach myself to surf. While I was well aware of the existence of surf schools and instructional videos on the internet, for some reason, I felt that the most pure way to learn would be through direct experience and observation. Every surfer appeared to have their own unique style, and I wanted mine to grow completely organically.

Once the anticipation got to the point where I couldn’t resist it anymore, I grabbed my soft-topped board and launched into the shallows. What proceeded was the experience which would truly snare me; hook, line and sinker. While the difficulties of the previous day were still present in full form, something clicked. I began paddling out ahead of gentle waves the height of my belly button, and awkwardly fumbling my way into a standing position on the board.

There was a distinct rush every time I felt my board lift up and forward, and elation as I realized I no longer needed to paddle and could rely on the kinetic energy of the wave to move me towards the beach. I’ve never quite gotten used to how surreal that feeling can be, and to this day experience it with regularity while taking off on waves.

The total count of waves ridden that day is something I still debate with myself, but it was at least five and no more than eight. I would come to understand later that the number of waves caught is a poor metric for measuring how successful a surf session is, but for now, all I could think about was the fact that I had crushed the official three wave goal. The surfing high kicked in once again, and my mind was no longer my own.

Heading straight to a used board shop while still under the influence, I briefly negotiated with the overly relaxed, sun-baked salesman before being convinced to fork over a few hundred dollars for an ancient monolith of a custom shaped fiberglass longboard. Blazing red with royal blue accents on top and a slightly psychedelic pattern on the bottom, he was promptly named Clark Kent, after the super man he clearly resembled. His age was estimated around fifteen years, with multiple repair jobs adding considerable weight to his already hefty figure. His 9 foot 6 inch length meant he would occupy the longest possible diagonal space in my Subaru Forester for the ride home.

I now had everything I needed to begin the journey. A journey which would cause me to go places and do things I could have never begun to predict as I handed a thick wad of cash to the board salesman, my hair still wet from my second ever session on the water.

—

At the same time all of this was happening, a seemingly different type of journey was also taking place in my life. Away from beautiful views and thrilling adrenaline rushes, I was starting to spend a lot of time sitting by myself and attempting to learn the mysterious art of observing the mind.

While I wish there was a compelling rapid conversion story about my immersion into the practice of meditation, the truth is it was a much slower process. However, that it happened at all would appear to be just as unlikely as the fact that my ocean fearing, mountain loving psyche became a wave hunter.

My fraternity brothers who knew me as the gregarious Social Chair – whose primary responsibility was calculating how many thousands of dollars of alcohol would be needed to satisfy all the thirsty college students streaming through our door every Saturday night – would certainly be surprised to find out that just a few short years later I’d be spending my Saturday nights sitting cross legged in silence.

Then there were my fellow computer science engineering students, who spent many a long night with me staring at colorful lines of code in a fortress-like engineering library. It’s doubtful they would have guessed I would put aside the prestigious tech job earned from those efforts to place myself on uncomfortable floors for days on end doing nothing but attempting to look at my own mind.

And of course, there were my outdoor adventure buddies, who knew me as the hyperactive weekend warrior, constantly seeking colder climates with softer snow and steeper inclines, and always planning the second or third trip before the first one had finished. They likely would have been shocked to know I would willingly spend months meditating in painfully humid jungles with no snow or significantly sized mountains for a thousand miles in any direction. All the while experimenting with “living in the present moment” by making no plans more than a few hours in advance.

Underneath the hood of my never-stop-moving lifestyle always lay a deep curiosity about how to live a good life. While growing up, I was a sucker for philosophical quotes, and would spend heaps of time and mental energy internally debating the unanswerable questions of the universe. This engrained attitude of seeking truth likely played a major role in my willingness to enter the world of contemplative practice. 

The seemingly dramatic shifts in my life path that followed my entry may be less surprising to those out there who have committed to a consistent meditation practice long enough to understand the potential. For those who have had the fortune to guide others down a path of meditation, these results may even be predictable.

A curious thing happened to me when I began to turn my attention inwards for the first time. The bright light of awareness started to reveal cracks in the many assumptions I’d made about myself and the components of my life. Initially, it created painful cycles of doubt and confusion. Eventually, it led to a healthy re-ordering of life priorities which continues to evolve today.

The external world surrounding my mind also began to take on new meaning. Or in some cases, new lack of meaning. My heightened awareness extended beyond the bounds of inner self and started to alter my perception of the outside world, breaking down preconceived notions of the way I thought things were “supposed to” work.

There are many types of meditation out there, and they all have their uses. But the techniques I have spent the most time immersing myself in are commonly referred to as “mindful meditation” or “insight meditation”. I personally like to call my practice “awareness training”. What it asks you to do is extremely simple: notice everything occurring in your present moment experience, and observe it passively without reacting to it.

Just as it is absurdly difficult to catch a wave while surfing without your full optical vision, I’ve learned it is challenging to navigate life without a clear lens through which to see the way you’re internally reacting to your external surroundings. Training your mental awareness on a regular basis is akin to periodically wiping the surface of your mental lens clean of the inevitable grime that accumulates from being alive in a messy world.

The cleaner this lens becomes, the more clearly you can see, and the more you can enjoy watching the waves of life as they approach from the horizon, lift you up, and send you on a ride. Whether you soar smoothly across the face of the wave or crash headlong into a shallow reef, at least you’ll be able to see what happened, and paddle out for the next wave a tiny bit wiser.

—

The following pages contain a series of stories.

Stories about how I learned to patiently sit still and keep my balance on the constantly shifting ocean surface in order to greet the next set of waves.

Stories about how I learned to calmly sit still and find balance on a cushion amongst a consistent barrage of mental chatter in order to observe my thoughts without judgement.

And stories about the life enhancing insights that are capable of revealing themselves when these two powerful activities are combined into one.