THEN, WE WENT ANYWAY: The story of an improbable 8th grade adventure

Jake Aaron Ward
19 min readMay 4, 2018

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Photo by Flo Maderebner on Pexels

I went to a very strange middle school.

For this story, I’ve changed the name of the school to “Steinway Academy”. I’ve also changed the names of some of the people involved. If you continue to read, I’m sure you’ll quickly begin to understand why…

Most people do not remember their middle school experience fondly, and virtually all of us go through the same awkward, hormonally traumatizing transition from child to teenager during these few awful years, coloring the whole experience negatively and temporarily turning us all into defiant little cretins. While I’m not a teacher, it seems widely agreed upon among those who are that middle school students are the least cooperative, least engaged, most rambunctious and frustrating age to teach by far, and it’s very easy to see why. In fact, many of us (myself included) can even recall what little shits we ourselves were at that age. This, when coupled with piles of homework, hours of boring, repetitive classes every day, and an endless list of annoying rules and expectations from our superiors, is enough to drive virtually every 12 and 13 year old to retaliate with at least some level of disruptive, disrespectful actions or outbursts.

Back then, we all simply wanted no rules whatsoever to follow, no schoolwork or homework we were ever held accountable for, and no authority figures that could ever dictate our behavior. We all wished there could be a school where this dream was a reality.

Steinway Academy was just such a place.

Somehow, the stars had perfectly aligned. In a hyper-liberal, forward-thinking small city full of parents who love organic food, still wear Grateful Dead t-shirts, still smoke pot, and still haven’t gotten a haircut since 1969, the ideological soil was, perhaps for the first time in history, miraculously and improbably ripe for the real-life manifestation of the dream of every rebellious adolescent student. It took just the right amount of privilege, just the right amount of new-age bullshit, and a hefty dose of admirably good, yet incredibly misguided intentions on the part of the adults to create such a wonder.

At Steinway Academy, which was located outdoors and in the woods behind the local university, class was held in hand-made little red shacks. Students were meant to be immersed in nature, and put through a supposedly “progressive” style curriculum that mainly involved copying what the teacher wrote on the chalkboard word-for-word, but using colored pencils and crayons to make sure it looked unique and pretty. We were also exposed to frequent and bizarre music classes, where we sang supposedly “traditional” songs from alleged ancient cultures that I am almost certain do not actually exist; at least not outside of the imagination of the school’s administration. We were essentially forced to do manual labor in the form of unbelievably futile woodwork, making strange benches that no human being could ever sit on comfortably. This particular woodworking class was also taught by the grossest and meanest human being I have ever encountered, named Bodo (this name I haven’t changed, cause fuck him). There was also a ludicrous sewing class taught by the runner up for nastiest person I’ve met, a woman who hated me so much that I eventually tried to make her hate me as much as possible, just to see how much hatred she could possess.

But above of all, we were subjected to the strangest mandatory dance class in middle school history, which was also coincidentally supposed to be the most important class in the entire curriculum, somehow. Twice a week, every 6th, 7th and 8th grade class would be led into a special room with no desks or chairs, and we would be instructed to put on ballet slippers. Then, a truly disturbed woman would lead us through a kind of primitive spooky ritual of improvised, slow movement that was supposedly a “language” we were speaking. A friend of mine and I used to actually plan our weekly diets around this particular class to make sure we could both spend the entire time farting and laughing instead of paying any attention to the teacher. Maybe we were hoping she’d turn around and say “watch your language!”

Needless to say, I received no formal education whatsoever during the two years I spent at this school. The people who ran it were generally good, well-intentioned people, but they had no clue how to teach, or even what to teach, and most of the time they couldn’t control us at all. Considering what immature twerps some of us (myself again included) used to be, this was a powerful recipe for total dysfunction. I’m sure the entire school staff was in a living hell, but for us kids, it was like a dream come true. No more were the days of rules and homework and being stuck in class! No longer were the restrictions of adult authority! My friends and I would routinely leave in the middle of class and go play basketball, or go off into the woods, or prank each other. In general, our behavior on the campus was virtually indistinguishable from what it would have been without any adults present at all.

Considering the fact that standard middle school curriculum doesn’t really teach kids anything worth learning anyway, I actually feel that the level of total freedom we received as middle school students was a rare thing of genuine profundity and beauty. I would have come to cherish it as a unique and special experience even if we had never managed to make it out to Kauai, for what could only be described as “the grand finale.”

Let’s stop for a moment and just imagine this school, with these students and these teachers, going on an 8 day class trip to Hawaii. Granted, our classes were relatively quite small, but still, imagine the level of preparation and planning it would take, or how much money you’d have to raise to take roughly 20 people there for 8 days. Imagine how organized and level headed the adults would have to be, and how focused and disciplined the students would have to be. Think about how vitally important the teachers’ total control over the students would be at every single step of the journey.

To say there were doubts would be a massive understatement. Nobody thought we had the planning skills. Nobody thought we were organized enough, or disciplined enough, or focused enough. Everybody said that we, as a class, had a lot of growing up to do before we could even think of going on a trip like that, and, while nobody said it out loud, everybody also probably thought that our teachers needed to get a far better grip before supervising us on such a serious journey. Our far-fetched dream had all but been completely dismissed by our teachers and administrators.

You might expect me to say that we proved them wrong, got our shit together, and went on a safe trip. But this is important: the key to this story is something completely different. As the months counted down, and the day we would supposedly leave grew closer and closer, nothing changed. If anything, teachers became even less able to control our behavior. We never developed even a vague plan to make sure we stayed safe, stuck together, and all returned home in one piece. Nobody in my class made even the slightest effort to improve our collective inability to stay focused or be responsible, at any time for any reason. Nobody did any growing up; I personally felt that I only become more comfortable and confident in my own immaturity.

The point is: we didn’t get our shit together at all and then… we went anyway!

Here’s how it all went down:

The first and biggest obstacle we needed to overcome was funding the trip. Plane tickets and travel expenses for the entire class were not cheap, and while many of our parents were very supportive and willing to pitch in generously, a sizable chunk was left for us to come up with on our own. As scrappy young kids who couldn’t even drive yet, we had to get highly, highly resourceful in our fundraising efforts. I spent many weekends babysitting. Other friends trimmed lawns, cleaned houses, or washed cars. My friend’s family owned a local restaurant, so we all hosted a dinner party and served as waiters and waitresses, breaking plates, spilling drinks and dumping hot food all over customers.

But the biggest moneymaker, and by far the most brilliant idea, came from a friend and classmate who lived within walking distance of the local university campus. Every year, on April 20th, roughly 100 billion university students would gather ceremoniously on campus and celebrate 4/20 by smoking just about all of the marijuana that existed on Earth at that point in time. Even though recreational marijuana was still (technically) illegal in my state back then, the police would show up every year, get an immediate and powerful contact high from going anywhere near the campus, and end up simply enjoying the sunshine and trying to make sure everybody stayed safe in the festivities. So, year after year, over and over, the same thing would always happen.

My friend’s idea was to celebrate this particular year by having a bake sale. We spent the first half of the day in her kitchen, baking as many fresh cookies as we possibly could, and then in the afternoon, once the party on campus was really roaring and the mass-munchies were starting to kick in, we filled a wagon with cookies and marched up the street towards the giant cloud of smoke that was now looming ominously over the entire university.

Our prices were naively, outrageously steep, but it didn’t matter; our bake sale was a huge success. Stoned college students looked at us as if we were angels who had just descended upon them. They emptied their wallets for us, often buying way more cookies than we expected them to. The highlight of the day (I swear to you, this happened) was when a bus driver literally pulled over in the middle of the road and bought cookies for the entire bus, which was jam-packed full of stoned college students. This utterly depleted our supply and filled our bag of cash to the brim.We walked back to my friend’s house that evening feeling like entrepreneurial geniuses.

To the shock (and perhaps horror) of everyone else, our class somehow eventually managed to scrape together just enough money to fund the bare bones of the trip to Kauai. We were going. The teachers quickly stopped pointing out why we couldn’t go, and began pointing out all the things we really, seriously needed to fix now that we were in fact actually going. But our success as young businessmen and businesswomen had really gone to our heads, and now we were even less interested in our teachers’ advice than we were before.

The next step was planning to ensure that we took a safe, organized trip. Fortunately, the school administration eventually decided that our current supervisors (there were only about 2 or 3 adults from the school who were even going) really couldn’t handle it all on their own, so they decided to enlist the help of an outside professional who had handled many trips like this before.

Unfortunately, the school administration was the Steinway Academy administration, so they picked the most unorthodox and bizarre choice you could possibly imagine.

The man they picked was an extremely rugged, sixty-something guy with a scruffy mountain-man beard who we shall call “Bill.” Bill is easily one of the most fascinating characters I’ve ever encountered. If you look up “mixed bag” in the dictionary, there might be a picture of him. He dressed, groomed and smelled in such a way that he genuinely appeared to be a homeless man. The first time we met him to talk about his plans for our trip, I was sure some kind of cruel mistake had been made. But very quickly, I began to like him.

To our surprise, he came into class one day without warning and announced that he would be the leader of our trip. He told us his philosophy about why we were going, and what we would be doing.

At 13, I thought it was just about the sickest shit I had ever heard in my entire life.

He told us we would be deliberately avoiding any and all tourist locations. He told us we would essentially be living like Tarzan: outdoors,, in tents on his own, wide-open, enormous private natural reserve he owned deep in the jungles of the island. He looked us very sternly in the eyes, held up a firm hand, and told us it was completely against the rules to not jump off of waterfalls, try surfing, or go on dangerous hikes. I’ll never forget the part where he actually shook his fist triumphantly and, as if we were in an action-adventure movie, he exclaimed “we’re going to capture the heart of the island!”

I am certain that our teachers, and anyone else from the school administration who was in the room at the time, shit themselves immediately. What had they done? How did they even find this guy? The man they chose to hold the whole trip together and keep the kids safe sounded even crazier than the kids themselves. At one point he actually said to us “I don’t care if you’re scared, I’LL PUSH YOU IN THAT WATER MYSELF!”

However, to the students, it was music to our ears. After hearing that, I reached a point where I absolutely could not function I was so excited. I wasn’t sleeping at all. What little schoolwork I may have feigned the possibility of trying to do vanished entirely. I was counting down the days. 2 months…..1 month….3 weeks…..2 weeks….a week…..3 days…..tomorrow….

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We had to get up at around 4 AM to go to the airport, so I remember absolutely nothing until we had already boarded the plane and taken off. Of course, all 20-something of us couldn’t sit together, but the seating appeared to have been strategically arranged to maximize the disruption and chaos we were going to cause onboard. All of my male friends were in the same group of 9 or 10 seats. Best friends were consistently seated next to each other. The same was true for the girls, who were in a different area a few aisles over, but whose attention could easily be attained at any time, simply by yelling loudly or throwing something in their direction. All of the adults, on the other hand, were seated very far away on the other end of the plane, completely oblivious to hour after hour of total mayhem that was unfolding behind them. Freely ordering as much sugary junk food and caffeinated soda as our excited hearts desired (which of course the adults had to pay for), we were absolutely awful flyers. The noise was incredible. The mess was probably unprecedented in the history of aviation. I sincerely hope that everyone else on the flight ended up having a good vacation afterwards, because we certainly ruined the plane ride for them.

We landed on a warm summer morning at the Lihue airport. At the time, it felt completely surreal to be walking around an airport on Kauai with all the kids and teachers from school. It seemed like some kind of weird dream I was having. We managed to rent two vans, which we squeezed all our bodies and all our luggage into, and we drove off to meet Bill at his mysterious jungle paradise.

Something you may have noticed if you’ve ever been to a Hawaiian island is that there is generally one main road that seems to go around the perimeter of the island. On one side, you have all the spectacular beaches, and on the other side, you have all the resorts that people stay in, as well as most of the restaurants and shops that tourists flock to. Everything that 99.9% of the people who visit Hawaii ever bother to see or do is accessible via that main road, so basically everybody, in a continuous stream of similar looking rental cars, just drives on that road the whole time.

I distinctly remember the feeling of suddenly turning off that road in the van with my classmates. It was kind of like one little fish breaking out of an entire school of other fish and swimming off in a completely different direction. It felt so unusual I almost thought we would get pulled over for it if a cop happened to see us. We then proceeded to drive for quite some time down a windy, pothole-filled dirt road that led us deep into the wild. Immediately, our surroundings changed. The commercial, modern vibe on the coastline disappeared within a few hundred feet, and instead of shiny hotel buildings, crowded picturesque beaches and rows of attractive storefronts, we were presented with mostly forest. Occasionally, one might see a rundown-looking barn or another road leading elsewhere, but the sudden lack of metropolis was very striking. It occurred to me that, once we’d gone inland just a little bit, the island probably looked the same as it did 50 years ago.

Then, we crossed a bridge that went over a shallow river and pulled onto Bill’s property, where he stood waiting eagerly to greet us.

You wouldn’t believe Bill’s property even if I could show you a picture of it, so I fear the description I’m about to give will be a wasted effort. However, I still feel compelled to give it my best shot. The land he owned had to be worth millions and millions of dollars. It looked like the lair of an Indiana Jones villain. Located right next to a beautiful winding river and tucked in a small, secluded valley shaded by exotic foliage and towering palm trees, Bill’s property was an endless expanse of luscious green grass and strange, untamed plants. There was a small little building that housed a modest bathroom, and a patio with tables, chairs, and a small outdoor kitchen. There was a spot at the edge of the field where the ground was lifted, and it made for a perfect stage. According to Bill, The Grateful Dead have actually performed on that stage in the past. This still strikes me as entirely possible.

Of course, the most exciting part of this property was the fact that there were no boundaries anywhere in sight. In every direction was straight up jungle. Back the way we came was the winding river. On either side were steep hills, covered in bushes and rocks but easily scalable. Best of all, straight ahead, past the end of the field, was a wide open, golden plane, and, Disneyland-style, there was an apparently wild horse that seemed to be prancing in that area for the entire time we were there. It was clear that we were going to be able to go wherever we wanted, whenever we wanted, and chances were good that our severely under-equipped, already worn out school supervisors would probably not even know it, let alone be able to stop it.

What followed over the next 8 days were some of the most magical experiences I may ever have. I truly believe that the stage was set perfectly, through a vast string of unlikely circumstances, to create a very unusual situation and a very, very unique opportunity for us kids. Here we are all were; brats and punks who had spent day after day stuck at school together, and now, we were just on this island. That’s it. A dozen or more adventurous young kids, and a wide open, mysterious paradise. It was as if we were playing a video game and we selected Kauai as the starting place. We stayed up late every night and explored wherever captured our interest. We befriended some locals who were our age and they showed us this crazy place only they knew about: a giant hole in the earth, which had a ring of different waterfalls you could jump off of and into a big pool they all shared way, way down below. We went on a massive hike to the location where it rains more than any other place on the planet, and it was raining! We went to the place where they supposedly first invented hula dancing, on a bizarrely flat square of grass and rock that overlooked the ocean which could only be described as a “natural dance floor,” and we danced the hula…badly. We found the biggest, oldest tree in Hawaii, and we were instructed to literally hug it by Bill (after he was finished, which took some time). We hiked to a monstrous hidden cave that went sharply downhill into a pool of water, where the ceiling was glow-in-the-dark blue for no possible reason. While there, we also ran into some people working on a Pirates of the Caribbean movie, and at some point after we left, Jack Sparrow discovered the same cave on one of his own adventures...but we found it first! We tried surfing, making sure to avoid any kind of lessons or proper instruction, and we were blissfully awful at it. Last, but not least, at Bill’s adamant insistence, we all spent the last night out in the wilderness by ourselves. Everyone went off in different directions. I hiked out over the river, climbed over several sets of hills, and eventually found a cave just big enough for one person to hang out in. I had no blankets or pillows, but in the tropical summer climate it never got that cold. I spent the evening of June 6, 2010 as a kind of coming-of-age moment in that cave, completely alone and immersed in the wild. It was my 14th birthday.

But it wasn’t all wonderful. Nobody, and I mean nobody, showered the entire time we were there. Also, we all got extremely dehydrated and food poisoning seemed to be a popular trend the entire time. Most of us got sunburned. Two of my friends actually challenged each other to a contest where the first person to put on any sunscreen lost (a good illustration of the adult supervision that was taking place). They both got roasted immediately. One of them complained that his nipples were sunburnt, and he seemed to be searching the sky for an explanation as to how that was even possible. He walked around like C-3PO from Star Wars for the rest of the trip.

Our man Bill was not entirely wonderful either. Despite having an infectious passion for adventure and forever winning our hearts by endorsing and supporting all the dangerous and irresponsible things we were doing, he also seemed to have an anger problem (which, respectably, he was very open and honest about). He also demonstrated a fascinating propensity to sometimes go against his own philosophies in striking ways. One time, he told us a story (perhaps true, perhaps not) of a man who risked his own life just to rescue a group of small, unassuming frogs from getting crushed by the ocean waves on a rocky shore, touting the man’s bravery and his indiscriminate respect for all living creatures. Then, on the same day, we were driving back over the bridge to his property and stopped because there were little frogs jumping around all over it. Suddenly, Bill came zooming by in the other van, barreling straight over the bridge and probably crushing dozens of these little frogs. When we asked him about it afterwards, he said “those frogs fuck up the plants in my field!”

And of course, there was still lots of middle school drama. I found myself in the midst of a lot of it, and looking back I only wish I had allowed myself to enjoy that special experience even more than I did at times. But even then, out of this drama came my favorite experience from the whole trip.

On my 14th birthday (the same day where I later trekked out to spend the night in that cave) I wasn’t in a great mood. That day, Bill took our class to a faraway beach where there were no other people. The sun was shining and the water looked like Gatorade. Perhaps because I simply didn’t know who else to turn to, I actually told Bill what I was feeling and asked him for advice. What he told me was not even remotely what I was expecting.

“Go in the water. It has healing properties.”

I hate that shit. Why don’t you actually answer me instead of dishing me that hippie horse shit, old man? But he said it with so much conviction that I knew he really believed it. So I gave it chance and dove in.

The best explanation I’ve been able to come up with is that there must be something about the whole process. Enthusiastically jumping headfirst into a cold, oncoming wave that you know will shock you. Being physically immersed in water that is constantly shifting, and rhythmically pulsing at the same, slow pace, no matter what you do or how you feel about it. Being unable to avoid having a blast in the waves. Maybe there is something to the idea that the ocean has healing powers. Or maybe Bill just knew that I needed a distraction from my own thoughts. The only thing I know for sure is that I felt very different after I got out. I walked back to shore with a big grin and he looked me in the eye and said “see?” And I said “yeah.” I think that might be the most interesting thing that has ever happened to me.

Ultimately, the reason this trip holds such a special place in my heart is because it showed me something very deep and very important that has shaped my values, my aspirations, and my humanity ever since. The lack of supervision, the lack of organization, the lack of safety…these are all very important ingredients to the story. We didn’t have an amazing trip despite these things; we had an amazing trip because of them. Without a lack of supervision, we wouldn’t have had nearly as many unique adventures, and we wouldn’t have grown as much as young adults. Without a lack of organization, we may have been bogged down by some schedule all the adults had planned for us, and we’d have probably ended up on a very different trip on a different part of the island in the first place. And without a distinct (sometimes incredible) lack of safety, I sure as fuck would have never jumped off of waterfalls with the locals (I actually found out later on that the location they showed us is generally ranked as one of the top 10 deadliest swimming holes in the entire world). I would have never tried surfing without any prior experience. I would have never done even half the hikes that we got to do. All the precautions we always assume are necessary, especially for something like this, would have made the whole trip a shallower, poorer experience compared to the deep, nourishing, moving, formative, soulful, and challenging adventure we had instead.

This is a lesson I really cherish. We dedicate so much of our lives and so much energy to making things run as smoothly as possible. We plan, we prepare, we think ahead, we make sure we’re ready for whatever is coming our way. We avoid challenges, we fear setbacks. We think of a “good” day as a day where nothing went wrong, and everything was easy. As long we’re happy, then that’s good enough.

I’m not so sure about this. While it’s understandable, there are times where I suspect the “pursuit of happiness” is actually quite overrated. When I look back on my insane 8th grade voyage, I don’t necessarily think of it as a “happy” memory. A happy memory is a picnic with your family on a Sunday, or throwing the ball for your dog. It’s too simple a word to describe what happened on Kauai. On Kauai, I grew as a human being. When I stepped off the plane after returning home, I wasn’t just hungrier and smellier than when I left. I was a stronger, wiser person. My perspective on the world and what was possible had changed. I had been exposed to so much that was new, unfamiliar, frightening, and difficult. It was so much more than just a “good” trip, and it certainly didn’t run “smoothly” in any way.

But in the wonderful words of the band Neck Deep: “Smooth seas don’t make good sailors. Jump ship and head for failure.” Looking back, I believe that’s exactly what we did, and I hope I continue to do it for the rest of my life.

Thanks for reading!

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Jake Aaron Ward

Lead Singer for Watch Me Breathe. Songwriter, Record Producer, Magician, Traveler, Questioner