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Facing Fears in Big Island

19 min read — #Blog #Travel #Hawaii

Balancing work & vacation, finding strength in the face of limitations, and travel recommendations for a big hunk of volcanic rock in the Pacific.

If you’d like to skip straight to my recommendations, please click here.

A few months ago, I went to Hawaii (again) with Mack during a beautiful interlude in-between jobs. This post is the first in what I hope will become a series of journal entries that dive into my travels. Here are a few goals for this maiden voyage:


Why Hawaii? Ah yes, a question I frequently ask myself. A friend who was living in Oahu at the time came to SF for the weekend. He was the high-achieving consultant type whose ambition had been channeled and refined by the salt and waves of the Pacific Ocean. Mack and I had visited his turf earlier in the year, and spending time with him again began to convert some offhand jokes about “sending it” into a concrete plan. The sun and the sea had yet again enchanted us.

We decided on Big Island since we figured Oahu would be more crowded during the “post-vaxx travel bonanza” but on a deeper level, we both wanted to explore a more raw and unfiltered version of Hawaii. Waikiki is cool and all, but it can’t compare to the volcanoes, caves, and rainforests peppered throughout Big Island.

After a few hours of feverish planning, we had a barebones travel framework with the necessities handled (lodging, car, and flight) and the rest handed off to spontaneity. I like traveling with the big-ticket items & milestones taken care of, with room for flexibility and exploration in between. The visual of a jar that you first fill with rocks, then pebbles, and then sand comes to mind here.

I tried to create some AI Generated Art to describe the visual of “jar filled with rocks, pebbles, and sand in hawaii” and here’s where I got after 400 iterations.

The night before we flew out was a quarterly full send™️ after an amazing birthday weekend — this involved post-vaxx bar-hopping / clubbing in the mission with good friends, tequila shots, and cheesy pupusas. Needless to say, rolling out of bed for the the 11am flight to Kona was a challenge.

Kona’s fancy but impractical outdoor airport

Kona’s fancy but impractical outdoor airport

Work-Vacation Balance

Our first few days in Kona were standard. We got some morning coffee, I rolled into work at 7am, grinded out some code, and clocked out by 3pm. The evenings were filled with walks, historic sites (more on hawaiian history here), and sunsets by the small beach near our Airbnb known as “Keiki Beach Queen’s Bath”.

By merging the energies of work and life in this way, I’ve realized that I genuinely enjoy working on meaningful projects while on vacation. It sounds counterproductive, but I find it difficult to fully disconnect for over 3 days without getting restless. I like being able to choose this lifestyle, and it might be that choice that makes all the difference. Over the course of a week, here’s how I’d like to spend a vacation:

I like to blend my vacations with meaningful work and balance the polarities of being “On and Off”. The conventional notion of a “vacation” in which you work intensely for several months and then chill by a beach resort with cocktails for a week just doesn’t appeal to me. After being “on” for so long, it takes a while to turn “off” if you’re not regularly exercising that skill. I’d much rather shorten the feedback loop by going hard for a few days at a time, fully relaxing for a bit, and then getting back at it. Eventually, I hope to turn this ideal vacation lifestyle into my everyday existence.

Transcending Limitations

A few days into the trip, we biked to Magics Sands beach to splish-splash in one of the island’s only white sand beaches. We rented some biki bikes and rode the windy and precarious route down Ali’i Drive. Along the way, some fellow tourists en route to the airport needed our help — they couldn’t bring their Kona Seltzers on the flight, so we did our duty and took them off their hands and downed them on the side of the perilous road.

We eventually made it to the water. Hailing from Florida, the sand itself was banal, but the waves caught our attention. Some were over 10ft tall and broke dangerously close to shore. It might’ve been the seltzers or the determination I had to overcome my fear of water but I decided to wade in.

Trying to maintain balance in the water and bodysurfing to shore was fun for a bit. At some point, the swells started to expand as if the ocean was inhaling — I knew a huge wave was imminent. I began to get sucked into water and saw a menacing bulb of water heading towards the shore. Before I knew it, I was on the ocean floor, bodies flying everywhere. Luckily, the worst injury I had sustained was a scraped elbow and some waterlogged sinuses. As we attempted to escape, another massive wave came, knocking us over again — this time getting sand everywhere.

As we recovered by the shore with the remaining seltzer, I heard a man yelling to his blissfully unaware son:


The majority of the folks then got out of the water, save for a few mad-lads on their surfboards. It then hit me. I had just been overwhelmed by the limitless power of the ocean. My worst fear had happened, and it wasn’t so bad. My bigger worry was that my fear would’ve prevented me from helping Mack if things got worse. She’s a natural sea duck, but needs some support getting in and out of the water, due to her foot (more on that later).

We sat sandy and exhausted in the Magic Sands Grill (which had surprisingly good food) and nursed some Kona beers, chicken wings, and kimchi burgers. We made it home thanks to a friendly transplant from San Diego and attempted to get the sand out of our hairs over the course of a few showers. By then, we were too tired to do anything except fall into a deep slumber to rest up for the next few days on the island.

The following morning, I woke up early and made my way to the Airport to pick up a car. After rebuffing the Hertz lady’s pitch to try and upsell me into getting a 4WD car, I left the rental spot with a shiny jet-black Mustang. We drove all around in a whirlwind tour of Big Island. Here are a few highlights:

a young wim

a young wim

On the final full day, I faced my limitations yet again, this time with Mack also being pushed to the brink. We drove a few hours to the Southernmost Point of the US so that we could hike along the coast to Green Sand Beach. As alluded to earlier, she’s had some foot issues for a while due to a fractured sesamoid bone, and a 6 mile round-trip hike is no walk in the park for anyone.

Regardless, she didn’t want to let this limit her so we started on the trek to the beach after slathering on sunscreen to protect us against the UV index, which had reached a sweltering 11. We had been listening to the Acquired podcast’s series on Chinese tech companies and had just a few minutes of Alibaba to wrap up, so we tried listening on the walk. Unfortunately, the wind and sand whipping us in the face made it difficult to hear our own voices, let alone focus on Ben and David’s carve-outs.

Instead, we chatted about the many things we wanted to learn (we are nerds) and things that’ve held us back in life. Trucks filled to the brim with tourists passed by and we scoffed at their unwillingness to just walk a couple of miles to the beach. We would soon regret our arrogance — but I’m getting ahead of myself.

Around the half-way mark, I Mack started to get quiet, so I knew something was afoot. Her sesamoid had started aching, and we still had almost 4 miles left to do (assuming we hiked back). I distracted her with whatever goofiness and support I could muster, and we eventually made it to the cliff face that overlooked the beach.

I suppose that’s green…

I suppose that’s green…

For whatever reason, we both have these limitations that should make use reconsider certain decisions, but we tent to always ignore them. My fear of water and Mack’s sesamoid injury would deter any other couple from hiking all the way to a beach with the hopes of swimming in it. Neither of us wants to let the other down and it turns into a game of wholesome chicken in which we push ourselves for the sake of making the experience enjoyable for each other.

We climbed down the cliff face and made it onto the beach, feeling the green sand clump between our toes. It wasn’t the bright emerald green we’d expected — rather a dark army green that looked as if some trees had accidentally dropped some chlorophyll on the shore. The memory of Magic Sands began to reverberate in my mind and the fear that I’d felt there began to resurface, wave by wave.

I looked over at Mack and she seemed eager to get in the water so I let her and the sunk cost of a 3 mile hike make the decision for me, and waded in. I couldn’t make it past knee-length water. Eventually, we had the brilliant thought to sit in the water to acclimate ourselves.

Bad idea.

Yet again, we got sand everywhere which dampened our experience of the beach and the water.

Defeated, we sat on some rocks by the shore. I vigorously dusted my shorts off to remove some sand, and we thought about our next move. The hike back was arduous and we were dangerously low on vibes and energy. Instead, we chatted with one of the locals who had converted his old Ford F150 into a cash machine by driving tourists to and from the parking lot for $10 a pop. Luckily he took Venmo, so we boarded like sardines in a can on the back of his pickup truck with 30 other passengers.

At some point, there was a bump in the road and a man barreled into me and almost knocked me off onto rocky trail moving below us at a breakneck 10 miles per hour.

We eventually made it back to our car and ate some snacks and even indulged on a diet coke. As we drove back north, there was some tension so we tried to “debug” the experience by narrating the day from both of our perspectives. It turns out that we both felt as though we’d let the other down (me by not being able to go in the water and Mack by not being able to hike back).

Though these things are true, it doesn’t change the fact that we made it out there and tried our best. Transcending limitations isn’t binary — rather, it’s a long journey in which small wins add up to meaningful change in the longer-term. We’ll be back Big Island.

On our final day, I had an overwhelming desire to swim in the ocean. A few minutes from our hideaway bungalow was a path that led to a secluded beach, known as The Queen’s Bath. What struck me first was the serene natural pool formed by volcanic rock and sheltered from the waves of the Pacific. In and around the pool were schools of tropical fish and little crabs scuttling about. I played in the ocean with my goggles and earplugs, swimming laps from rock to rock.

As I splashed around and lay on my back, I felt the comforting presence of Mauna Kea in the distance. The entire archipelago was created by violent geothermal explosions from this and other volcanoes. This transference of matter and energy from deep within the earth to the surface helped imbue Hawaii with it spiritual energy, known to the locals as Mana.

I then realized that something was different. It was subtle, but I felt lighter. I was swimming in this beautiful slice of ocean without fear. I was even enjoying it, and didn’t want to leave after reality started to beckon an hour later. The water at Magic Sands and Green Sands had been harrowing, but I’d made it out with the realization that the water could be scary but that doesn’t mean it has to stop me from enjoying it. Hawaii’s Mana had begun to heal me.

Kenshō is a Japanese term used in Zen Buddhism to describe the “small awakening” that one experiences on the road to enlightenment. My entire life, I’ve been afraid of water. My parents never learned to swim and inadvertently passed their trauma and fear of the water onto me. Countless experiences have gone unlived, and countless attempts to overcome this fear have ended in vain. I tried to discipline myself to learn how to swim since that seemed to be the antidote to all other ailments in life. The difference is that raw discipline doesn’t work in the face of deep-seated fears.

I think I’ve had my first taste of Kenshō with regards to the water. I have a deep respect for the power of the ocean, but at the same time acknowledge the joy that one can feel when connected to it. The way forward now is not through regimented training and YouTube videos, but rather through delightful experiences with those you love. I still have a long way to go to before I would consider myself truly comfortable in the water, but I am deeply grateful to Hawaii for showing me the right path.

Queen Keiki’s Baths

Queen Keiki’s Baths

Travel Guide

One of my favorite things to do before traveling is to create a map using Google’s “My Maps” feature. I don’t even think it’s actively supported anymore, but it still gets the job done. Below you’ll find a map I made with every recommendation I’ve gotten about Big Island.

The best things to do on the island (according to me) have a ⭐️ star next to the name. I don’t think the purpose of a travel guide is to do everything on the list. In fact, we ended up doing < 20% of the items listed on this map. Rather, I think creating & viewing a map like this serves a few purposes:

In terms of advice & data-points for planning your own trip to Big Island, here are some learnings that I think will be useful:

Finally, a major decision that one must make when visiting Hawaii is the island that they will visit. You can “island hop” and see them all in one trip, but depending on the length of your trip 2-3 days isn’t enough to truly enjoy your time — I would recommend at least a week per island. I can only speak for Oahu and Big Island, but here’s what I’ve noticed as to the difference & similarities between the two:

Oahu is far more developed by American standards. It contains the state capital (Honolulu) and thus has more infrastructure and is more catered towards tourism. There are plenty of activities ranging from historical sights (pearl harbor, ancient temples, etc.), to excellent food, to more fancy experiences on the beach-side resorts. Oahu is also home to Waikiki which is tailor-made for tourists, though you can get a taste of a more natural Hawaii by driving 15 minutes north.

Big Island on the other hand feels much more authentic, in terms of what a local would actually experience. The bigger cities (Kona and Hilo) have airports and there is a reliable highway system to get anywhere on the island, but the rest is quite barebones. Ubers / Lyfts are hard to come by, and getting around the island is nearly impossible without a rental car (public transportation also isn’t the best). There are eight different microclimates on the island and you’ll see everything ranging from torrential downpour rainforests to dry deserts to tundra as you ascend the volcanoes. Big Island can truly “do anything”.


This was my first foray into structured travel writing, so shoutout to Linus Lee and Roy Lotz for inspiration on how to frame it. Also thanks to Mack for being a great travel buddy / limitation transcender. 🐈

My times in Hawaii have always been stellar, so I have no doubt that I’ll be back soon. 🌺