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Updated: Mar 25

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

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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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In the last hundred years, Western liberal democracies have been very successful at technological advancement and economic growth. But what have we neglected in this race of progress? Where does hope lie for bringing our world back into balance?

Despite the "upgrades" in economics and technology, we're still humans with the same fundamental biology and psychology as our ancestors who wrote Shakespeare, paddled skiffs to Hawaii and survived famines and plagues. Over the last few centuries, we got caught up in insulating ourselves from the discomfort of nature- creating ever better agriculture, creature comforts and infrastructure. We have emancipated ourselves from vulnerability to nature but it's left us physically rich and spiritually bankrupt. In the quest to survive, we have over-succeeded, now threatening our own species with the toxic byproducts of over-consumption.

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As we enter 2024, the zeitgeist suggests that wealth concentration, runaway AI and unaddressed climate change are hurtling us toward a dystopian future. Although probably a bit dramatic, it does like seem as a society we lack a compelling positive vision. Even if we had a vision, we lack the unity to act decisively as a society. If fact, it feels like we aren't really a society at all any more. Algorithms feed two versions of reality, fueling a political divide that stymies productive action from government. The pandemic exacerbated an already crippling loneliness epidemic. Middle class security seems laughably out of reach for Millennials and Gen Z. Climate change is now driving major weather disasters and could be past the point of no return.

Instead of harping on the intractable problems we all know about, let's starting focusing our attention on new angles and root causes.

It seems like we must learn to become a functioning society again. It seems like we have to drop the idle complaints and have some respectful conversations with our neighbors. It seems like we would benefit from redirecting the time we spend scrolling on screens into constructive collaboration on meaningful projects. But how do we actually do it? Let's start by framing up a basic foundation:

  • We have all the technology + resources we need to solve climate change; we just need to implement it.

  • We have all the food we need to feed the hungry.

  • We have all the money we need for everyone to make a dignified living

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The root of our troubles is akin to a global mental health epidemic.

We have the resources we need to solve our problems, the issue is, we can't get our act together as a group of people to mobilize broad-scale action to make the necessary changes. Yes, it's at a large scale with a lot of complexity and nuance. But a political impasse is essentially just two groups with incompatible mindsets. That's a cultural problem. That's an attitude problem. Thats a psychological problem. So let's solve psychological problems.

We are all stuck in a tangled web of unhelpful mindsets, consumerist addiction, financial ambition and social comparison. The more each of us chooses to live for something more meaningful, the easier it becomes for others to quit trying to fill the empty void and instead, stare it down. We need to mature as individuals and as a society, and there comes a time in life when you either choose to align yourself with something real and meaningful or you fritter away your time with comforts, luxuries, status or respect. Luckily, as each of us level up, we set a new precedent, making it more visible, understandable and attainable for our peers to start authoring a better story. Fundamentally, more people simply have to take more responsibility for the world we call home.

In future posts, I'll outline the ways I'm orienting toward these issues:

1) Take Personal Responsibility: How the best thing you can do to change the world is to change yourself

2) Invest in Friendship: Rebooting post-pandemic community

3) Focus Your Impact: How choosing a lane makes deeper, more satisfying impact

4) Get Physical: Engaging with actual people in the real world

Please share your reactions in the comments!

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Collaborative Advantage as Competitive Advantage

Most people associate evolution with "survival of the fittest," but actually symbiosis is the dominant pattern in nature. Collaboration drives more success than hardcore individualistic competition. How can organizations in the economy build collaborative advantage much like how organisms in nature build group resilience?

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Researching Infrastructure for Win-Wins

For the past few months, I've been working on a symbiotic economics research project in conjunction with three groups: Purpose Foundation, OneProject and Common Trust.

The project actually has a broader scope than shared ownership-- we are also interested in ways of doing business that weave multiple firms together toward shared prosperity. In particular, we are interested in a "collaboration infrastructure layer" that sits between business and government.

Business is mostly concerned with starting and operating individual firms, and managing for the financial outcome of that one company. Government is mostly focused on regulating business for safety and fairness, but isn't very good at stewarding the economy to avoid major recessions or ensure most citizens actually get a fair shake. Civil society tries to fill in the gaps that government misses, with private funding.

So our research focuses on an infrastructure layer for managing relationship within the economy; almost like a civil society for the business community.

Infrastructure Layers of Society. Hallucinated by MidJourney.

A quick peek at some of our topics:

  • Continuous Liquidity Mechanisms

  • Balance Sheet Aggregation

  • Stakeholder Holding Companies

  • Financial Products for Employee Buyouts

  • Pooled Credit Networks

  • Deep Trust + Relationship Capital

  • Mutual Exchange Networks

  • Private Collaboration Networks

  • Retail Investment + Secondary Markets

Uhhh, could you give me an example of that?

A great example of Private Collaboration Networks is a shared services cooperative. Instead of hiring a 3rd party vendor to run HR or bookkeeping, multiple small companies pool together and start an HR & bookkeeping service that they time-share, at cost. This ensure the service is totally focused and designed for their exact needs, and they get quality, affordable outcomes.

What's Next?

We're about halfway through our research- we've done the initial legwork, and now we're starting to make sense of what we've found. We'll be sharing more of our learnings soon, both in incremental posts and a final glossy report. We're extra keen on very actionable opportunities that don't require tons of philanthropic capital or major government policy changes.

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