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The Perennial Horizon

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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