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Week One

I started my cross-country road trip from Oakland, my home. My friend Adam and I shared friend chicken sandwiches, our ennui evaporating under the warming sun. I was ready to start the trip, but sad to say goodbye to my friend (and ten other friends this night before).

I made my way swiftly up to South Tahoe in just over 3 hours on a clear late March afternoon. I listened to the new Beyonce album, and the first song immediately reminded me of the Beatles. I also listened to this lofi jazz album which was playing as I got higher up into the Sierra and it began to snow.

I was hosted in Tahoe by my friends Chelsea and Derek who are also co-authors of an upcoming book that we're writing. We got some work done, and also had some meandering conversations amongst the trees. Derek came out of the closet as a vegan, which we've all known for a long time.

After two nights at altitude, it was time to descend into the dry of Nevada. I called my mom on the east coast as I rolled down the back side of the Sierra. We had been together on the same road a few months earlier, and she cajoled me into driving safely.

Nevada beckoned me down two lanes with a double yellow: Route 50: "The Loneliest Highway." Each arid valley was followed by a set of gorgeous but anonymous mountains. Then another wide valley floor would erase the last, one after the other, all day, like unrelenting waves of earth. Only a few small towns dared to eek out an existence and brave that loneliness.

As the afternoon threatened an end to the day, I pulled over to research a place to camp. If you've never car-camped in the American West, freedom still exists here. There are vast tracts of land owned by you and me, and managed by the Bureau of Land Management. You can camp on your land with no permits for up to two weeks at a time in each spot. I found a spot on a trusty app that was just over the Utah border and had a nice network of dirt trails to find a camp spot. I doubled back toward the main road over a short, well-groomed dirt road, with a destination set for my hopeful camp's Lat/Lon.

I found the turnout and kept my momentum going through soft, sandy conditions. I raised two fingers from my wheel to acknowledge the two smirking old buddies having a beer as I passed their rigs. The sand got even softer as I climbed the hill, and I decided to loop back while I still could. My car barely has AWD, and I respect it's boundaries. I camped in the lee of a big juniper, and made haste to set up as the sun's death threats were now coming to fruition. I looked back west toward California, and felt the distance.

I tried to set up my satellite internet, but hadn't paid for an account yet, so I was relegated to a final bar of 5G E at the top of the hill, which I used to let a few friends know I had made it home. I cheated and made an instant camp dinner, brewed a liter of tea for my thermos, and burrowed into my space-age shelter.

The next morning I packed up camp and was on the road by 9am. As I drove deeper into Utah, the valleys got greener and farmers started to make use of them. The clusters of houses became larger, and slowly I found myself in civilization at the bottom of the Utah Valley. My destination was Spanish Fork, where I would meet with a small business owner who had converted his auto repair company into employee ownership.

I met Kevin in the office above one of the repair shops, and we talked shop about steward-owned holding companies and other topics from the book I'm writing. I booked a cheap hotel room, had a shave and shower and then headed for the edge of town and found a trailhead parking lot where I finally got my satellite internet set up. The next day, Kevin and I met up for lunch and he told me about a program he launched for the blue-collar staff at his company to unpack what they care about and find more purpose. I walked away one friend richer, and made my way southward.

I had researched an open camping spot near a hot spring, but found myself going further up a dirt road, and made Camp # 2 at higher up the mountain. It was cold and windy, and I felt some deep pangs of loneliness as I rushed to make mac and cheese. I went to bed early and woke up late, relishing in my winter-rated down bag. Just as I was putting my shoes on to get up, what seemed like rain drops began gently thwapping the tent. I opened the door to scope, and an inch of dry, fluffy snow had fallen without me realizing.

I managed to get some laptop work done while it continued to snow and the snow stopped around 11am, and the snow started warming up. I checked the weather, and it seemed like it would thaw, and then get cold again. My water jug was partially frozen, and between that and the prospect of the dirt roads getting muddy, I made aggressive moves to decamp for better conditions. I was planning to meet with a friend the next day all the way south in Utah near Zion National Park, so I figured south and lower elevation would be the remedy.

Armed with local intel, I made Camp # 3 on the edge of a mesa with a theatrical view of Zion. Still windy and cold, I felt a bit sad arriving at this miraculous vista without anyone to enjoy it alongside me. I trudged on with setting up my gear, and ate dinner sitting on a big rock and was finally able to enjoy the view, noticing my vision soften and allow more detail to hit me. I remembered a dharma talk I had listened to that morning about how all the feelings that we want can be mustered inside ourselves. This sentiment felt true but out of reach as I sat there hoping that the beauty of the landscape would spark some inspiring feeling. I saw my folly in reaching for it, and also know these things take time. I made a little fire after sunset and the rhythm of the day gave me what I needed.

And so, we keep going. Out of my comfort zone. Into the world. One week in.

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In six days, I'm leaving home for three months. Camping gear lies in semi-organized clusters on the Persian rug in my living room. My girlfriend and I recently broke up, and waves of heartbreak are still coming in sets. But I'm moving forward into the unknown, carrying a lantern.

What's the lantern?

My lantern is a set of questions that are guiding me. Questions I can't shake. A feeling that our society needs us to wake the fuck up and grab the wheel before we careen over a ditch. A feeling that the loneliness in our society can't go on, and a hunch that the way we get our mojo back is waiting for us on the other side of this loneliness. A feeling that we need to change course and try something different, and that those of us who have the ability really need to step up. No one is coming to save us, but us.

When I'm lost, even when I can't see very far at all, my job is to stay calm and focus on what the lantern allows me to see.

I can see far enough to take a step.

I can probably even see two or three steps ahead of that. So would I rather stay put and make no decision, and guarantee I get no where? Or would I rather be willing to take a random step, and risk that it could be in the "wrong direction." At this point, I'd rather know that at least I tried.

We have to find the courage, or the stupidity, or the bravado, or be so fed-up with ourselves that we just get started. We foolishly act - before we have the security of a fully-fledged plan. Because the plan is a mirage. It stays on the horizon, and you become a hamster on a wheel.

That's what it looks like to start before you're ready. Some things can't come about from thinking and planning. Some things take action for the wheel to start spinning. Some things are about movement, and only make sense when they are in motion. Do you master bicycles by reading a book about them? Or do you go out, find a bike, throw your foot over the saddle and try to ride it?

So I'm hitting the road, armed with a vague but passionate inquiry about wisdom and community. I'm fueled by a desire to get out- out of my house, out of my city, and out of the comfortable habits that are getting me nowhere.

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Updated: Mar 25

Scouting for the building blocks of pragmatic wisdom on a 3-month road trip.

Image created with Midjourney AI

I'm getting my long-term road kit together. SUV, check. Solar power, check. Satellite internet, check. I have all the gear for extended off-grid wilderness living in the vast expanse of the American frontier. I’m taking a month to drive from Oakland to Vermont, then meditating at a monastery for a month, and taking another month to meander home.

I want to tell you why I’m doing this.

As we ponder the exponential impact of what AI might bring, we could be standing at the precipice of a turning point. If technical work becomes increasingly automated, our focus shifts to cultivating the fundamentally human qualities that computers cannot replicate. In fact, we need to invest in our humanity more anyway. Even without AI, our world is top-heavy with advanced technology and global industrial prowess, but our ability to solve social problems is profoundly weak. 

There are core issues in human life that all people have grappled with across human history. Academics call these the “perennial problems” of the human condition, because they have been with us so long. Some examples:

From philosopher Kyle Takaki essay on perennial problems:

  • The Problem of Evil (why are there bad people? (atheist) if God is good why is there evil? (theist)

  • The Problem of Suffering / Ignorance ("worldly" suffering like being cold)

  • The Problem of Affliction ("spiritual" suffering like feeling shame, regret, guilt)

From John Kekes book on Wisdom:

  • The Problem of External Goods (availability of resources is not fully in our control; we must strive to get them, issues of unfairness in their access)

  • The Problem of Internal Conflicts (we have to make decisions in life that have tradeoffs, and we feel conflicted about what to choose)

  • The Problem of Evaluative Contingencies (we have difficulty honoring all our commitments)

My thesis is that the cultivation of true wisdom, and its stewardship across generations, is one of humanity’s strongest assets in addressing the perennial problems of the human predicament. This matters because we are causing more problems for ourselves with our current attempts to solve the perennial problems of life. We have been trying to address these core human problems by insulating ourselves from discomfort, which has resulted in apocalyptic consumerism. In our mad dash for creature comforts, we are threatening our planet’s ability to sustain human civilization.

“Wisdom is expertise in the fundamental pragmatics of life.”

- Paul Baltes, creator of the Berlin Wisdom Project

A wise and mature society is one that can make progress on these issues - not through attempts to permanently eradicate them, but by building beautiful, imperfect, dynamic scaffolding that helps us live well despite them. We need make more serious efforts to build a society that can address perennial problems without destroying the planet, or taking huge risks tinkering with our DNA or embedding computers even deeper into our lives.

My goal is to go out and listen to the hard-earned insights of those who have dedicated themselves to understanding how to live well and build a society that is fair and decent to all its citizens. I plan to meet with everyone from main street business owners to monks, from philosophers to fellow community leaders. By shining a light on what is already working, I hope to help re-discover a non-delusional attitude that works better than the “the world is fucked” narrative that has become the status quo across our political and cultural spectrum.

Images created with Midjourney AI

This trip builds upon a decade of experience creating co-living communities, where I saw firsthand both the power and pitfalls of a microcosm of society. We built 19 communities with 400 residents, some had healthy cultures, while others struggled with conflict. Community doesn’t always work out, and I’d like to dive deeper into how perennial problems play into the formation and evolution of strong communities. 

I’m also diving deep into philosophy, cognitive science, and practical techniques to study and cultivate wisdom. Although I’m physically embarking on this journey alone, it’s really about trading notes and learning from other people. Some friends are invited to join for segments of the journey, and I’m hosting a group of “fellow travelers” – folks who are passionate about these questions and want to learn together. We’ll read the same books and watch talks on the same cadence, and have an ongoing discourse about what we’re discovering. 

My hope is that this journey contributes in some small way to the larger task of our time – to rediscover a sense of meaning that serves to embolden us to action. I look forward to seeing what we can learn and build together!

The best way to follow the journey is Instagram: @yodelheck

If you’d like to join for the philosophical journey, join the discourse group, or you have ideas of places to visit or want to caravan through the desert together, shoot me an email:

Images created with Midjourney AI

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