The sea's only gifts are harsh blows, and occasionally the chance to feel strong. Now I don't know much about the sea, but I do know that that's the way it is here. And I also know how important it is in life not necessarily to be strong but to feel strong. To measure yourself at least once. To find yourself at least once in the most ancient of human conditions. Facing the blind death stone alone, with nothing to help you but your hands and your own head.
Primo Levi via Into the Wild
I'm fascinated with the idea of obsession. It seems like every once in a while, you get an idea or thought so unique and absurd that it forms an unrelenting grip on your mind. It's this idea that stirs people to change careers, start companies, and explore distant lands. It's as if we're looking for something — anything — to give meaning to the mundanity of daily life and challenge us.
It was the summer of 2013 and I was 18 years old. I had just graduated from Riverside Military Academy where I spent 3 years fighting the "system" and battling with a degree of intellectual isolation. Preparing for college in the Fall, I was spending my days working at a local web development agency, hacking together dashboards and fixing bugs in Wordpress themes. It wasn't the most exciting work. It was something, but certainly not a challenge.
These two elements combined to form a lens through which I viewed the world, so it's hardly surprising that the story of Christopher McCandless (Into The Wild) resonated so strongly with me. After reading Into the Wild that summer, I found myself obsessed. Like McCandless, I craved this adventure and exploration. The idea of leaving and not telling anyone where I was going, surviving on my own, and abandoning the systems and seeking refuge in the literary classics of Tolstoy, Plato, Witman, and Thoreau had an irresistible pull.
Later that week, I decided to take action — to run a test. As trivial as it sounds, I was going to leave for the weekend, not tell my parents where I was going, and venture up to my grandparents house as resourcefully as I could. It was the rebellious act of leaving home and not telling anyone where I was going, the priming of my parent's reaction, and testing my resourcefulness to get there on my own.
This wasn't the primary adventure, though. While McCandless set his sights on the Alaskan Wilderness, I wanted to explore somewhere a bit more, well, warm. Having recently binge watched LOST, the sunny beaches of Hawaii called my name. On this trip, I'd test my resourcefulness — taking a backpack full of books, $100 cash, and my LG En-V. No iPhone. No credit card. Into The Wild style — measuring myself in the process.
Visions of sweeping floors to get myself a burger, hitchhiking across the island, reading for hours on end, and sleeping on the beach stirred in my head. But the real draw? The Haiku Stairs — an old military installation on the island of Oahu. A magnificent view and "illegal" hike, it called to me and I became obsessed. The minute I laid eyes on them, I was gripped by some supernatural force and my sights were set. Like McCandless and his maniacal pursuit of the Alaskan Wilderness, I couldn't get those stairs out of my mind.
So my mission was set. I would go Hawaii to exploit my resourcefulness, read, explore, and most importantly — climb the Haiku Stairs.
On June 21, 2013, I booked my $183.99 flight on the budget airline, Allegient for a random date in October. Unsure of my schedule, I bought travelers insurance and decided I would rebook once I finished up my summer job, but before I started my freshman year.
This anticipation fueled my daydreams for the next couple months while I wrapped up my job. It was my own little secret that one day, at random, I would just be gone. No one would know where I went and I'd be off to explore.
I should have known that buying travelers insurance — which let me rebook my flight as many times as I wanted — was bound to mess with my plans. I soon realized that carving out the time to go would require making some hard decisions around priorities. Without a forcing function to go and the flexibility of travelers insurance, I had the leeway to defer, defer, defer. Including deferring my flight to sometime during my freshman year of college.
I started college and a whole new world opened up to me. As I got involved in clubs, events, and relationships, it became harder and harder to leave. There was always an exam, a date, an event, a project, a scheme (I was always scheming). So, like clockwork, I would open up my reminders list, hop on a call, and rebook my flight.
I ended up rebooking it 4 times that year.
I guess you could say I was delusional. At this point, I was holding onto the ticket like it was a youthful dream and I was trying to keep the idealism alive. I remained somewhat hopeful though I'd go that summer. That was, until I had landed an irresistible summer internship.
Argh — choices and priorities.
No sweat. I'd make it after the internship and before school started. It wouldn't be as long of a trip, but it would at least give me a taste for adventure and get me up those stairs.
Around July, my quarterly reminder popped up to rebook my flight. Per usual, I hopped on a call, and made the change request, and could go on dreaming for a couple months longer.
Not this time. I couldn't rebook.
Turns out that my unlimited rebooking spree was only good for 12 months and I was snapped back to reality. I couldn't keep chasing the dream and had conflicting priorities (first girlfriend), so I couldn't even take the flight I had set. I had to eat the ticket, slamming the door shut on this adventure.
Irritated, but not hopeless, I noted the lessons and committed to myself that one day I'd hike those stairs.
In 2016, I had the opportunity to go back to Hawaii with Eli. His mom was working on a project in Oahu and invited us both out to stay with her for Spring Break. Not daring to pass up a chance to get on the same island as those stairs — not to mention a free spot to stay — I was all in.
I figured, if I could get myself to the island, I'd have my chance to climb the damn stairs. Not quite the same as going solo, but I took what I could get. At this point my obsession became less about the solo adventure and more about proving to the universe that my plans to climb those stairs wouldn't be foiled.
We booked our flights and before we knew it, we were being welcomed at the Honolulu Airport with leis and smiles. Over the next several days, we found ourselves in a world of adventure, the kind that you would expect from two 20 year old college guys free from all responsibility.
One such adventure was making our pilgrimage to the Haiku Stairs. Excited to share this experience, but hesitant of getting fined, we saved it for the last day. We'd get up, navigate through the back alleys of the Hawaiian neighborhood required to get to the base of the stairs, make our climb, and then get picked up just in time to head off to the airport.
Back in 2013 when I was first planning planning this trip, I did my homework. I knew there were a handful of paths through this quiet Hawaiian neighborhood that would get us to the base of the stairs and around the guard who was rumored to be posted there to turn away explorers as early as 5am.
We had Eli's mom drop us off at 4:30am. Giving us a half an hour to trek through the jungle and beat the guard. We hopped out of the car, and took the path through the jungle — hopping over barbed fences, tripping over muddy roots, and trying not to get lost.
We got about 30 minutes in and I realized that we were in fact completely fucking lost.
I reluctantly pulled up the guide I had assembled and tried to recreate the steps to get us around the guard and to the stairs. As the first hint of dawn showed through, we found ourselves directly under the freeway overpass and could see the start of the stairs.
As we made our way over to them, I realized I had miscalculated. We were spit out onto a concrete road and followed it about 200 yards. To my dismay, this is where we found the guard, sitting in his car waiting to stop those of us daring enough to show up.
And stop us he did. There was no aggression, just an explanation that the cops would be called if we continued and there could be a $1,000 fine. Feeling my burning disregard for authority and foolish rules bubble up, I was ready to say fuck it all and go for the climb. We were so close!
We looked at the time. We'd burned two hours trekking through the jungle. With the hike round trip being four hours, there was no way we'd make it up and down in time without missing our flights. We missed our time window.
There I was again, plans foiled. The polynesian gods were harassing me in some sort of cosmic joke. They clearly got some sick sense of pleasure out of fucking with my plans.
While deterred, I was not defeated. I had another traveler whose plans were foiled take a photo of Eli and I with the guard; a photo to serve as both evidence of our attempt and as a reminder to myself that I'd be back.
The idea that I'd never make this trip happen started to haunt me. There were always commitments that I had to fulfill while wrapping up school. Then when I started my career at Superhuman while still finishing undergrad, the possibility seemed less and less likely — especially since I feared missing out on some of the compound growth early on in my career.
After a wild ride, a new opportunity presented itself. Rishab had recruited me to work with him on his company. I saw my opening. I agreed to join on the contingency that I'd have a couple of weeks in between things to take my long desired Hawaii trip. Done deal.
I put my two weeks in at Superhuman on November 12, 2018. I had five weeks until starting with Rishab. After wrapping up at Superhuman, I made a quick trip out to New York for my annual HustleCon work and then I was off to Honolulu.
This time I was going to climb those stairs, at all costs.
I arrived in Honolulu. explored around — traveling solo for the first time in my life presented me with a delightful freedom I had never tasted before — and on the second day, I prepared to hike up the stairs.
I wake up at 3:00am, rolling off my squeaky hostel mattress and snatching my Red Bulls from the fridge. While I wait for my Lyft, I slam both Red Bulls. Feeling the sugar and caffeine literally pulse through my veins, I'm feeling alive and amplified (and of course I blast, "Alive and Amplified").
I'm ready to fucking rock.
The come up on these Red Bulls is strong. Absurdly chatty for 3am, I'm pretty sure my driver thinks I'm on drugs. I don't care. I'm zoned in. I'm ready to climb these stairs and catch the sunrise coming up over the crest of the Pacific ocean from the top.
After about 30 minutes, we pull into the neighborhood. Memories of my last attempt flood my brain — the barking dogs, barbed wire scrapes, muddy jungle trails. I close my eyes. This time, I'm not going the roundabout way. I'm going direct. Straight hopping the security gate and making a run up the service road where the guard drives in. Whether he's there or not, I don't care. I can see success. Having visualized my path, I take a deep breath in and open my eyes.
Red & blue lights flash behind us.
Fuck, fuck fuck, fuck. The edginess from the caffeine converts into anxiety as the driver pulled over. Slowly stepping over towards the car, I can see the smug look on the prick's face.
"Why did he have to ruin my morning? This asshole..I'm going to pull this off anyway." I think to myself.
The driver rolls the windows down. The officer barely addresses her. Instead, he looks right at me with his piercingly dark eyes. There was no denying my athletic gear and hiking backpack. He knows exactly what I'm here to do. He wastes no time.
"Son, you know that what your here to do is illegal and you'd be trespassing. It's also be a shame if your driver here were to get a ticket for…"
I stop listening. He's bluffing. There's no crime committed — yet, my smugness evaporates. I'm helpless. I cave and anxiously tell my driver that we'll be heading back to Honolulu. I can't let my own selfish desire put this poor woman's finances at risk — even if the implied threat was groundless. I'd extend the burden of responsibility for this adventure onto someone else and I can't bring myself to do it.
In a stark contrast to the ride there, the ride back is completely silent. With my forehead pressing against the window staring up at the pitch black sky, I hear the gods laughing once again. Feeling the surge of adrenaline stacked on top of the Red Bulls, I simply breath as we make the 45 minute trip back.
We get back. I thank the driver for her flexibility (I'm sure she's happy about the $100 trip) and I lay back down in that squeaky hostel bed. Still full of energy I stare blankly at the top bunk and realize that sleep is not in the cards. My mind wanders. Tomorrow, I have an Airbnb set on the North Shore, so I'll have to catch the hike on the way back.
Two days later, I venture back down the coast.
I realize that the only surefire way to get to the top is by taking a different trail and climbing up the back ridge. I don't dare risk not making it to the top, so I compromise. When I get back to Oahu, I gear up and set out again.
Off I go. Following the path outlined by some lovely people online, I slowly climb my way up the ridge. I'm prepared physically, but not quite mentally for how close to the edge I come when climbing up this thing. One gust of wind, one slip, and I'll tumble far and fast. Since know one knew where I am, a fate similar to that of McCandless flashes in my mind.
I brush it off and keep moving, slowly climbing into the heavens as my view of the island steadily expands. After about three hours, I make it to the top.
As soon I'm up there, I'm completely overwhelmed with this weird emotional unbundling that takes place. I have the adrenaline, the gratitude, the caffeine (because, always more Red Bull), the satisfaction, the fresh air, the scenery, the warmth of the sun — all of these things combine into a concoction of complete bliss.
It's great, but as a man of principle, I have to ask myself — have I technically climbed the stairs? Have I achieved what I set out to do?
No. I have not — climbing the ridge to the top of the stairs is not the same as "climbing the stairs".
So, off I go, climbing all the way down the stairs all the way until I can see the guard sitting there. I smile, smugly and nostalgically remember when I met one of his kind almost three years ago. Okay, enough. Back up I go. Step by step.
I hang out at the top for a couple hours. The whole time, I revel and reflect in this state of appreciation. An appreciation for an accomplishment that took 4 attempts and 6 years to achieve. While the specifics are a bit personal, I take the time to retrace my experiences from 2013 when I booked that first ticket all the way up to today, December 18, 2018. I can't help but feel closure.
On what? I'm not sure. There are lots of adventures ahead. But for whatever reason, this moment feels extremely cathartic — peaceful yet motivating. As I basque in this state, I wait for the sun to slowly set and just as slowly work my way back down the mountain.
This isn't some wild narrative arc where I circle back with some takeaway or conclusion.
Instead, I simply want to comment on the nature of this obsession. Once locked in, I couldn't let it go. Despite the absurdity of the quest, I always had a voice in the back of my head telling me to go — to explore and discover — and not let the weight and expectations of the world win. This gave me hope amidst some of the personal challenges I worked through over the years. This youthful hope that things can be as simple or as complicated as you make them. Furthermore, it's this voice & obsession that I (and we all) have to fight to keep alive.
It's through these adventures, obsessions, ambitions — of any type — that you feel alive. However, they can be easily beaten out of you. The world wants you to play it's game: some rules, some status quo, some track. It really doesn't want you to win, as conformity is how the system keeps churning.
I'm reminded of this essay — the Bliss of Distant Shores:
But what he seeks, perhaps even more than his family, is a life of adventure. A life of inspiration. He longs to feel that light-headed euphoria of being lost in a cause. He deathly craves the intoxication of forgetting himself.
For some time, the Haiku Stairs served as a simple calling for me in one dimension of my life — an intoxicating adventure to pursue. Perhaps the closure I felt is a chance to pick up a new, more ambitious adventure – one more grounded in the needs of myself and others. As I navigate this crazy thing called life, I'm actively searching for this adventure, this obsession, this intoxication. This thing, whatever it may be, that I can pursue irrationally and wholeheartedly — the Haiku Stairs of my own mind and ambition.