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  • Writer's pictureChris

A Caribbean New Year's Adventure! Part II

This is part two of a three part miniseries about an insane adventure I had at St. John's Virgin Island a few years back. To catch up on the story, read part I here.

Chapter 6

We decide now is as good time as ever to eat that apple, so we both take a few bites and throw the core into the hungry ocean. It wasn’t too comforting seeing the core swirl around and swept out to see in a matter of seconds, but I rather see the ocean eat the apple than us. While resting on a rock I decide to have a back to reality moment with my buddy. Whenever shit hits the fan it is good to take these moments to regain your footing and re-think your situation. I’m responsible for getting myself into this mess, so if something happens, I don’t want him feeling like it’s his fault. I tell my friend that if I don’t make it, don’t worry about it or have some sort of PTSD, my ghost isn’t going to haunt him, it’s my own fault. He says the same back and we decide to scratch our names onto rocks so the search and rescue party at least knows we made it this far.

(Saint John's Virgin Island on our way to Ram Head a couple of days earlier)

Putting that out there is important to me. I’m a believer in Navy Seal Officers and authors of Extreme Ownership Leif Babin and Jocko Willink’s philosophy that leaders must take responsibility for everything in their world. Regardless of what happens in my life, it’s the results of my actions that got me there. One of my favorite quotes is by Bill Gates, “it’s not your fault if you were born into this world poor, but it is your fault if you go out that way.” It’s the same thing only from a different perspective. All three of these people are simply saying, if you got yourself into this mess, either fix it or deal with it. In the classroom, I teach my students the same principle. We live in a world where it is acceptable to place blame on external variables instead of ourselves. This does not teach people the value of taking responsibility for their actions so they can be effective leaders when it is there time. Leadership is the backbone of all the classes I teach and personal accountability as well as trust is the foundation of those lessons.

While searching for a small rock to scratch our names into the bigger rocks, we came across a carbon fiber kayak oar inside its carrying case and we decide to take it with us as a way to increase our reach when attempting to get across small tidal pools of water. The sky is now lit entirely by the moon, the sun set without us knowing as we were searching for carving rocks. so, using this oar allows one of us to stay on the rock while the other hangs on and feels their way through the underwater terrain, praying not to be swept up by a wave and dragged out to sea and bitten by a sea creature.

It wasn’t as frightening during the day, but in the dark, it’s starting to work my nerves a little. As I mentioned earlier, I’m an adrenaline junky with a sore spot for adventure, but I can be better described as an underdog with an addiction to physical challenge and overcoming the odds. Maybe it’s because I grew up as an overweight kid in a low-income family and town that thinks very highly of athletes and I had to deal with a lot of crap as a kid between not being good at sports, or perhaps it was constantly being reminded we couldn’t always afford food when I was in high-school, waiting in line at the cafeteria for my free lunch card, so my mother would often eat cherries so I could have a well-rounded meal and my natural defensive nature is still trying to prove I’m worth a damn. When people challenge my ability to do something I know I can do with practice and effort, it sets my gears into low and drives me deep into the mud. Luckily, as I have gotten older and wiser (hard to believe while reading this, I know), I have learned to tell the difference between people that get me going because they are dealing with their own stuff and people who are simply trying to make me better because they know adversity is the fuel in my arteries. The earlier I have no time for, the later I keep by my side like mentors.

Under the current conditions, I feel myself start getting amped up to cover some ground and enter a flow state. Being very good at convincing people into tackling challenges head first, it’s no problem getting my buddy riled up about how we need to pick up the pace if we are going to get to Ram Head before the late-nighters head home for the evening and we are stuck sleeping on that beach. The sand at the cove where Ram Head begins is filled with little thorns that have fallen off the bushes, so I don’t plan on getting too comfortable if we are stuck there for the night.

We climb, swim, jump, and drag our bodies over rocks and through pools, covering ourselves in small lacerations. It’s important to remember, my friend is just as eagerly pushing the pace. There are moments when I want to push on and moments when he sets the tone. But after about forty minutes of rampaging across the rocks in the dark, I am saying hold on let’s think this through. I gaze up at the moon, it’s almost full and I recall a survival book I read where Navy Seals are dropped out at sea and must swim miles back to shore. Now, this is before I joined the Army and even with that said, we are a land based operating force. I have done minimal water training and when I say minimal I mean negligible. Regardless, I attempt to convince my friend that we need to stop being bashed up against these rocks before we break a leg or get washed out to sea. I try to convince him that we need to put on our snorkeling gear so we can go out about a hundred feet and swim along the coast the mile or so to Ram Head. He quickly and persuasively shuts me down with some vulgar profanity and we decide to stick to climbing the slippery rock. This is why it’s important to understand your limits and take feedback openly, sometimes our judgement can get clouded during stressful situation. In war, you mix your clouded judgement with a dynamic and hectic environment and you get what is known as the fog of war, more on that later.

Once he is done explaining how dumb of an idea that is with sharks and who knows what else is living in those waters, I imagine us swimming out and getting caught in a rip tide that pulls us south out to sea towards Brazil, only to be eaten for dinner by a shark or washed up on a beach a few days later. That’s not what I had in mind, but that’s also why I never do this stuff alone. It is important to always ask your peers and subordinates for feedback, and I am glad I did that night.

Sometimes I have the good ideas and sometimes my buddy has the good ideas, it depends on the situation. We come from opposite schools of thought and survival training so we always discuss something beforehand. That’s a sound principle behind any partnership, surround yourself with people whose skill set varies from yours and build upon each other’s strengths, creating synergy. It’s gotten us through countless mischief and is how I prefer my business and personal relationships as well. Surrounding yourself with people just like you is boring, you will never grow as a person. Challenge your comfort zone and learn what makes the world different, keep someone very different from you close.

There is a great anecdote I heard once about two young children fighting over an apple in a tree that was slightly out of reach. After arguing for a while, they put their differences aside and one of the children hopped on the other’s shoulder so they could reach the apple. It was only after they put their differences aside and worked together did they get to split the apple rather than having nothing. And man, do I really wish we packed a second apple at this point.

Just as we are discussing hunkering down for the night in a small cave we had passed a few yards back, we decide to see what’s around the next corner (this is about the third time we have done this) to see if we can see Ram Head. Well, this happens to be the most insane part of the entire venture thus far. We are glued to the side of this rock shimmering around a bend like two people standing on a window ledge of a sky scraper. This is no exaggeration, we were dumb. I gaze over my right shoulder and see a peninsula in the distance. It’s not Ram Head, and whatever peninsula it is, is about a mile away.

Screw this, I am heading home. We put so much thought into moving forward to safety thinking civilization would be much closer if we kept going than if we turned back, that we forgot turning back is an option. This is common in the mountaineering world and is known as the Everest effect. It’s when we become so focused on the end, that we begin losing touch with reality in hopes of reaching our goal even if it is deadly.

When faced with a survival situation, you should remember to stop and take your surroundings into account. Laurence Gonzales in his amazing book Deep Survival has a saying, “when in doubt, bail out.” Well, we were defiantly in doubt at this point, and Mr. Gonzales also mentions by realizing where you are now, you are essentially not lost and can make a logical judgment call based upon your new surroundings. We were simply driving forward with our emotions attempting to muscle our way through a tough time. It doesn’t help that my buddy is the type of guy that you can knock down a thousand times and he will always get back up swinging and I’m the type of guy that puts so much effort into not being knocked down that I have a hard time admitting when to quit, which is not always a good thing as I’ll later explain.

There was a news article I read years after this trip involving a family driving to the Grand Canyon during the winter. On their way, their GPS took them down a closed road that needed to be plowed. While attempting to turn around and head back in the direction they came, their vehicle fell into a ditch. The mother having taken survival courses decided to leave the father and son in the vehicle and venture out for help. After a 26-mile hike overnight through the snow, the mother finally found safety from the harsh weather in a closed hut. Meanwhile, back in the vehicle the father was worried because his wife was gone for over a day so he decides to hike to a nearby peak and call for help with his cellphone.

Sometimes we get so caught up in the moment and this idea of disaster that we forget that we can be the ones making the situation worse. If the family went straight to the nearby peak rather than over analyzing the situation and deeming it a life and death scenario, they may have been rescued from the warmth of their vehicle a few hours later. I believe that mother who is a triathlete had to have some toes amputated due to frostbite.

Back in the tropics where there are no signs of snow, but we are still a little chilly as the open ocean wind is slapping us against this cliff we logically assess the situation for our first time and after a quick examination of our wounds we make the decision to drink the last of our water and ditch our rock collection and back track to where we saw that family surfing earlier. Intelligent people make mistakes all the time, we are so used to the mediocrity of everyday life that we assume certain things based upon recurring events that form habits. In our case, we were so used to successfully getting out of tough situations that we forget to realize most of our adventures happen in the mountains of the northern hemisphere in the snow, not on the coast of an island in the tropics. We did not accurately assess our skills and knowledge with that of our situation and that is where we went wrong. We finally opened our eyes to reality and did an about face back home. People often inaccurately apply experiences from one domain to another. Although using past experiences to aid in new areas is a great way to approach challenges from a different angle, make sure they are the right skill set. Just because I had experience in the mountains did not mean it was going to transfer over to the coast.

Ram Head Saint John's Virgin Island

(Messing around at Ram Head a couple of days prior)

Chapter 7

The return trip mentally goes by much faster than our original direction. Without the sun to light up our surroundings we enter a flow state and go. I studied flow as a means of cultivating creativity in adventure and wilderness sports after this same buddy and I scaled the mountain with the waterfall I mentioned earlier almost effortlessly trying to beat the sunset and I couldn’t even recall the trip. That trip inspired me to study flow, and here I was reliving it again on the southern cliffs of Saint John’s island with the same buddy in a more serious yet similar predicament as last time. This is why my wife doesn’t like us adventuring.

Back on the cliffs, I am starting to get tired. When my buddy gets tired he starts taking control of the situation which is my natural role, when I get tired I get temperamental. Do you remember that apple anecdote from earlier? This is its time to start living that lesson. Well, a short while into our return trip and I planted my chest and abs into a small cactus growing out of the rocks. I gave that cactus a piece of my mind after I climbed up over the ledge. My skin was only pricked, but I was tired enough to share words with the pointy bush. At this point I decided to take a time out and watch the waves wash up on the rocks about a foot below me. I started thinking about home and how much I rather be watching one of my then girlfriend’s (now wife) stupid movies that I always complain about how we should be doing something more exciting. This is when I realized things were bad. Ok, I reminded myself. As much as I adore my wife and my current life, my upbringing has trained me to simply not enjoy home. Everything I have now at home is perfect, purposeful job, amazing friends (except for this jackass that hauled me to Saint John’s), and a promising (although not at the moment) future. My natural default from childhood is when things are bad, don’t go home because they will not get better. It’s the reason why after track practice in high school I would lift strength train for two hours, then do all my homework at the library. This is not a biography of my upbringing, but let’s say home wasn’t where I wanted to be. So, with this being the first time in my adult life I craved going home, I had a coming to Jesus moment and got up and told my friend let’s get the hell out of here!

I stood up to continue, ready to enter another montage moment and cover some ground when about three steps into it I stepped onto another cactus. That high lasted about three seconds before I went Hulk again and started pulling cactus needles out of my foot. I ended up having got ditch the insole in my shoe and continued in my soggy sneakers with a missing insole in one of them that was replaced with tiny incisions for about another hour over rocky terrain until we finally reached a sandy beach. This beach was still way after we saw that family in the afternoon and even further from where we could get up the cliff (they had a fancy escalator to their house remember, who knows if we could climb up it).

But, somehow that afternoon while day dreaming and chatting about who knows what, we missed a trailhead into the woods on this beach that was right in front of us and our current search mode made it clear as day. Thank you very much, I’ll take door number one and we said bye Felicia to the coast and moved to the much safer inland.

Chapter 8

After hiking for a quick quarter mile, we came to the Reef Bay Rum Factory Ruins. During the day, we crossed paths with other ruins like this on the island and they are creepy enough then, but in the middle of the dark when you are thirsty, exhausted, and starving, you say screw the monsters let’s get out of here! We hiked past the ruins seeing bats flutter around the old mill and continue down a trail. It’s pitch black and we have not lights with us so we take our time hiking down what seems like a dried-up river bed. Perhaps it is, I can’t tell if I am on the trail anymore.

While hiking down what is possibly the trail, we start talking about being afraid of the dark when you are a kid. My friend tells a story about how he was afraid of entering his basement in the dark, so he would purposefully go down there to face his fear. His story checks out with me, knowing much hasn’t changed in his adulthood. Fear is an asset essential to keeping us alive, however, growing out of our unrealistic fears and learning to operate in the face of manageable risk is essential to excellence. Gahndi, a strong leader known for extreme civil disobedience, standing against the face of discrimination across the map was known to be afraid of all sorts of unrealistic things including the dark as a child (Sheehan, 2007). Being a leader is being self-reliant, it also involves inspiring people to stand behind you. The key to overcoming fear is knowledge. The more knowledge we have of something, the less fear stems from it. Fear stems from the unknown. Gahndi would never have been able to rally the millions of people behind him as he did if he never outgrew his un-rational childhood fears.

After hiking for a little way, we come across a fork in the trail. Having no clue which direction to head, we decide to go right. About twenty yards after the fork we hear movement in the woods. I am carrying the kayak paddle we found earlier so I hold it like a baseball bat as I stare into the darkness. My friend yells, “let’s get out of here!” So, we creep down the trail only to discover that right we took, was a dead end, or at least we lost the trail. So, we start creeping back towards the fork keeping our eyes on the nothingness before us. I can’t see well, but I see leaves shifting back and forth as something scurries left and right through the bushes. Suddenly, I see something charge at us, so I wind up ready to hit one out of the park, when for whatever reason I decide to yell “Aaahhhh!” and right before I have to knock the small animals head off, it stops in its tracks and about faces its way out of there at Mach-one. It was a warthog. Yep, I saw it about two feet in front of me, short pig like animal with teeth sticking out like little horns coming out of the side. It was either a warthog or the devil’s child. With our luck that day, it could have been Cain we saw that night, but it was most likely a pig protecting its young. I’m lucky I yelled, I later learned that these wild pigs are conditioned to run away from barking dogs, my bark must have been convincing.

Regardless, we make it back to the fork in the road where the moon is peaking through the tress allowing us to somewhat read the sign and my friend claims the direction we were heading in is the way back to the center of the island and home. With that said, we head back into the darkness and once again come face to face with Cain. Well, not quite. This time I am banging the paddle on trees as we go down the trail screaming “Aaahhhh” as we tip toe over the loose rock. After a few yards, we get to where we lost the trail the first time and realize we are stuck and must go back once again to the fork in the road. After a couple of minutes of screaming, tip-toeing, and banging my paddle on trees we make it back to the fork in the road for our third visit. Only this time we decide to head back to the ruins in hopes of finding another trail along the way.

Chapter 8

Once at the ruins we quickly realize there is no other trail and we regretfully have to head back to the ocean. As we approach the coast, I can hear the waves crash up against the rocks and as someone who grew up about 200 yards from the ocean as a child, it has always been a pleasant sound to my ears. When I was little, my dad would take me for walks before bed either to the beach at the end of our street where we could hear the waves crashing up against the rocks and see the infamous Gloucester Greasy Pole bobble up and down in the waves or he would take me down to the boat pier across the street where I would run from side to side as the docks wobbled back and forth. These were peaceful moments in my life, when childhood was ignorance and ignorance as we know is bliss. The sound of the ocean was always a sound of safe heaven. Tonight, it sounds like nails on a chalkboard only the nails belonged to Freddy Krueger and he was laughing in my face as I was entering my nightmare. For a sound that has brought me serenity for so long, including this morning and the past few days I have spent snorkeling in paradise, it was amazing how waves slamming against the rocks was sending chills up my spine.

Fortunately, there were only a couple of tricky areas left to hike over between our current beach and the next one, but if you remember that cactus in my foot from earlier. Yeah, it must have realized I was starting to cheer up because it began reminding me there were about ten small holes in my feet and I was wearing soggy shoes with no insole in one of them. At this point, it didn’t really matter. All I had to do was get to a road and hitch a ride back to town. How hard could it be.

Chapter 9

After a short walk down the beach we eventually made it to houses and found a long winding staircase up the cliffs to an empty estate. We walk down the driveway and onto the main street searching for a house with lights on and someone moving around. Seeing how these are all vacation homes and it’s the middle of the night, the chances of this happening are slim to none. They all appear empty with no cars in the driveway. Until, luck would have it we eventually stumble across a yard with a dog in the front. The dog barks at us as we walk down the street, but not because it is viscous like the two dogs from this morning but simply because that’s what dogs do. Regardless, my buddy in his tired and hungry state tells it to “shut up” as the owner is walking through their door to let him in. Talk about poor timing.

The owner doesn’t like this very much as we plea with him for a ride into town explaining our story he says “sorry”. Fortunately, his wife is much kinder and convinces him to get us a glass of water before we head out. Thank god for angels, we share our one glass of tap water and get on our way.

If you are not familiar with Saint John’s Island, it is composed of many small mountains that are more like hills if you have ever seen the rocky or white mountains. Since we don’t have a map or GPS, we get to know quite a few of them that night as we go up and down looking for a road to the center of the island which we are assuming will be higher than the coast, only to reach dead ends on the tops of about half a dozen small hills. Apparently, there is no such thing as a dead-end sign on the island.

Eventually I decide to lay down in the middle of the road and rest my eyes for a minute. We haven’t seen a car during this entire trip so I am not too worried about being run over. That’s when I see a gallon of water behind a rock next to a house under construction. Well, I am not one for sharing drinks (although I already shared one earlier that night), but I paint this picture in my head of a construction worker bringing this full gallon of water to the site that afternoon, placing it down to take a phone call, and leaving it there untouched. The story sounds good enough for me, so down the hatch it goes. My friend decides against the water. Oh well, someone will find his dried-up body on the road.

Check-in next week to read the final part of this Caribbean tale and see how it all ends.

Always improve,


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