Reflecting on the year living in my car visiting all the national parks
long overdue!
Context
When I turned 30, I quit my job at Instagram as a software engineer, bought a Tesla, and set out on this journey to explore complete freedom with no job, house, or plan.
Other than this rough idea, I have absolutely no idea what I will do next. The plan is to have no plan. This is the first time in my life where there is so much ambiguity with everything up in the air, yet so much clarity in who I am, what I want, and what drives me — and I think that’s a beautiful dilemma to be in.
more on that here:
Almost 4 years have passed since I originally published that. Since then,
I went to 40 national parks, spent 1.5 years living out of that car I called home.
Started a crypto organization and an International conference in blockchain.
Started a tech start up that got backed by a16z, then started another Taiwan start up and briefly worked with the Taiwan government on pushing new tech.
Sold my apartment in NYC, sold my car. Moved to Taiwan.
Got into education, opened a course for a semester at NTU, and launched a scholarship for students in Taiwan to join international hackathons for free.
Grew my podcast, opened a co-working cafe, and on the brink of opening a new ice bath/sauna business in Taiwan.
It’s been the most unstructured 4 years of my life. Highs and lows, countless learnings and lessons that I will recount after this writing. I’ve never had the chance to meaningfully reflect and publish anything about this trip. There are many reasons for that:
I have this feeling of underachievement in terms of what I wanted to get out of this trip - a book, youtube channel, instagram account…etc. due to:
Pulled away by new ventures and ideas listed above, the ending of the trip felt abrupt, without closure, so it hadn’t felt quite complete, thus didn’t justify a reflection.
Deep down, I might still be in denial with sadness that this trip has been more than over.
Reflecting on this and writing about feels meaningful in many ways to properly share some of the stories, and put a temporary closure(,) to this trip. Though I didn’t end up going to all the national parks. I do fantasize re-living/finishing this experience with a partner or kids in the future. And properly documenting it and enjoying it this time around with more presence and no entrepreneurial bug distracting me. (If you’re my future wife, don’t worry, this is optional)
This writing contains some key themes, best/worst parks, most exciting stories, what I would’ve done differently, top lessons, and many gratitudes along the way
Rough Start
This is me trying to map out a potential route that’s optimized for visiting all the parks. I followed this more or less and started from NY and went south west. Here’s link of all of them on Google Maps
It felt surreal to have had all my belongings packed tight into my car. I no longer have an apartment after the hand-off. I started driving away from NYC, such a strange feeling. I was reminded of all the amazing memories I had here as I slowly navigated through the crazy cars and made it through the tunnel going past Jersey.
Was this decision really the right thing? What the hell am I doing with my life? Self doubt rushes and overwhelms me as I drive alone on the highway in the pouring rain. On my way to my first park after seeing my brother in Philly I was immediately hit with a parking ticket and speeding ticket.
While the idea to have no plan was romantic, in actuality and execution, I realized how many micro-decisions and tasks are to be made at every given moment. From not knowing where I can charge, park, sleep, eat, shower, use the bathroom. Everything was a decision and task to be figured out as I drive. Gone was the stability of owning my own bathroom and bed. The most simple and essential things in life and a routine were greatly greatly missed in contrast
I wondered if “having nothing” gives you the chance to “have everything”. The truth is it’s all a trade off. While I can’t be hyper optimized in productivity and creativity. I am experiencing more uniqueness everyday, which will make for best memories and stories and is the trade off I wanted.
But when the moment comes, decisions still need to be made, I was constantly figuring out how to best balance planning vs spontaneity and overcoming occasional indecisiveness that results in analysis paralysis.
First Parks
The first parks were Shenandoah and New River Gorge, but less known but extremely underrated. I built a decent cadence of driving, working on my podcast, and solo exploring a lot of different sceneries and serendipitously coming up on breath taking sunsets. I remember thinking to be able to see sunrise + sunet everyday is crazy, meanwhile:
We forget there are sunset and sunrises everyday when you sit in front of a computer all day
At first, I would fully take advantage of the long drives, zone out a bit with Tesla’s semi-autopilot, and listening to either podcasts, audiobooks…etc. But I’d often run out of content and just end up driving in silence. At first this felt weird to drive in silence, but eventually became one of my favorite things. Feeling the zen and meditation, looking at the sky, clouds, trees, roads, rocks, grass pass by one at a time, each in their own element and timezone. I’m looking at them, thinking about them, but at the same time, not thinking about anything at all. The world slowed down for me and so did my racing monkey mind that was used to New York City.
Loneliness & Friendship
The lack of human interaction compared to NYC is also apparent so it did make me super excited whenever I have a chance to hangout with people or starting conversations with strangers. Even though I’ve always prided myself in being really good at spending time alone and loved it. I remember 2-3 months into the journey, I had started to feel a bit lonely.
Luckily, I had friends that I could call up and would actually join me in different legs of the trip. I was extremely touched when Jesse flew over, met me in Ohio and went all the way to Chicago with me along with visiting Cuyahoga Vally and Indiana Dunes along the way, while we car-aoke-ed to “Whole New World”.
Jesse insisted on not letting me chip in for the hotel we got when we arrived in Chicago, knowing I was no longer generating any income. I’m not sure if you realized how much this all meant to me, but in case you’re reading this - got so much love for our brotherhood and will forever be grateful.
Stranger Danger Wedding Crasher
Perhaps one of the most epic memories of this trip, getting invited to a stranger’s wedding I had just met 20 mins ago.
Josiah: “I’m getting married on Sunday, you should come!”
Jacky: “You’re joking! That would be crazy!”
I met Josiah, Tim and Zac on a solo short hike that led to nowhere when we were all looking for our way at Mammoth Cave national park in Kentucky. Wasn’t sure if he was serious until I got the details of the wedding in a text the next day.
Josiah: “Jacky! Nice to meet you yesterday! I’m serious you can come to the wedding in KC if you want and if it doesn’t mess with your plans. We all loved hanging with you!”
That’s when I realized, holy shit, this guy was not kidding about the invitation! After wrapping up Chicago with my brother Jesse,
Jesse: “You’re not actually gonna go to that right?” “People you don’t really know, 10 hours away”
Jacky: “You make a good point, but no way in hell I’m missing this wedding!!”
Jesse: “You’re crazy!”
Jacky: “Thank you!”
Five days and tons of driving later, I attended Josiah & Alexa’s beautiful wedding in Kansas City. I was shy and timid at first, turns out both sides’ family had heard about me and expected to welcome me.
Had the time of our lives, met some of the kindest people. Great music, dancing and dinner - A night of love and new friendships not to be forgotten! I was somehow invited to another wedding from one of the boys there too!
This reinforced one of my core decision making framework of
Always choose the most interest path
This framework has never failed me to maximize life.
Best Parks
(I’ll skip the already popular ones like Grand Canyon/Zion…etc)
White Sands: the most simple, unassuming, yet is the entire point
Dry Tortugas: most unique: 2 hour boat ride out of the tip of key west. It was an old war fortress, yellow fever quarantine site, and jail cell.
Congaree: best kayaking spot!
Redwoods National park: specifically Gold Bluff Beach
Crater Lake/Grand Teton/Big Bend/Acadia/Saguaro
Worst Parks
These parks had no businesses being national parks, merely for economical reasons (I confirmed with the rangers)
Gateway Arch National Park
Hot Springs National Park
Life Hacks
Range anxiety was the biggest theme of the trip, until I figured out how to use a converter and charge at RV parks that are cheap, give me a full charge overnight while bathrooms and showers readily available. One time driving down to big bend, I was 1% away from not making it to the next charge spot…
Planet Fitness across American allowed a place to shower and not be terribly out of shape. Not gonna lie thought, I’ve slept in more gym parking lots, supercharging stations than I’d like to admit to save money and convenience.
Some nights when I really needed it, I would book a cheap hotel to crash at - then I’d realize I sleep better in my car than hotel. My car became this safety symbol to me that had everything I needed, like a giant iPhone that just took care of most of my needs.
Foldable Kayak was so the coolest thing I’ve ever owned in my life. It made me feel like adventure was possible everywhere.
I’d also realize the dirtier the exterior of my car was, usually the happier I was.
Family Time
My family would sometimes visit me, and we’d plan some time to stay at a cabin together and give them a sneak peak of my unapproved life.
Winding Down
Towards the end of the trip, some of the new initiatives, such as the crypto community, conference, and start up I started were picking up a lot of momentum. That’s when I decided to stay in LA with my brother Mike, helping him move in, while also enjoyed a few month of rent free, and brotherhood bonding time living. I would work 16 hours a day, shoot hoops in the complex - and really enjoy each others’ company while chasing new dreams.
Taiwan
When the conference we started was getting closer, I decided to put everything aside, park my car somewhere and come back to Taiwan to host and support. Little did I know.. that would’ve been the end of my trip as one thing let to another.
What would I have done differently?
Content: better plan so I could capture the content I wanted and enjoy the rest of time being present. I packed goPros, a drone, cameras…etc and didn’t really have a cohesive and consistent content production. I focused on being present and didn’t end up sharing a lot of content
Budgeting: financial anxiety was no doubt a factor, not being used to not having a paycheck. They say the most addicting thing in life is heroin and a paycheck. I would have better budgeted allowance so I didn’t feel like saving for the sake of saving when I was actually doing okay.
Pacing: I would’ve slowed down, ensuring I had time after each park to work on projects, digest the experience and share meaningfully rather than scattered.
Ending: while I couldn’t have better predicted, I still wish the ending was more ceremonious rather than abrupt - not even realizing it was the end.
Top Lessons
Life is like lego blocks, you build your life according to the manual, until one day you realized you don’t actually need to. You can destroy every building and take your favorite pieces and build the something you actually love piecing it together where every piece means something. Giving myself a blank canvas inspired many ideas I couldn’t had predicted staying at a corporate job.
You must experience extremity to find your perfect balance. Extreme freedom and independence gave me a good idea of what my ideal life looks like balancing structure and spontaneity. You can also be both extremes of a lost soul with a peaceful mind. Another interesting extreme is the most racist towns usually had also the nicest people. Everything is 2 sides of the same coin.
Seneca used to “practices poverty” so he can be more grateful of his riches and understands how he doesn’t need them to survive. I felt like the richest man in the world knowing that even though I didn’t have income or a home. Only had a car with a mattress, clothes, a foldable kayak and a bike - I had more than enough, I had everything.