A New Kind of Leader

People expect leaders to have certain traits. Or at least to pretend to have them. But each age expects a different set of traits: In the 18ᵗʰ Century, being laissez-faire got really hip. Later on, being aligned with the oppressed became important. That one is still important—even Donald Trump must pretend to be aligned with oppressed.

When these traits-of-a-good-leader change, new people come to power. New social visions emerge , and new principles are used to judge everything from businesses to schools to clubs.

In this series, I want to get at all of that. I want to get into new principles, new visions. But I’ll start practical—with five things that we might want leaders to be good at, in the next age of politics and society.

Idea #1. Leaders should be immune to bullshit wisdom.

The 19ᵗʰ and 20ᵗʰ Centuries saw the rise of Science. We built engines to collect, distribute, and certify scientific knowledge — e.g., textbooks, laboratories, and universities. We have also developed methods to verify this knowledge: scholarly debates, laboratory replications, the proofs of mathematics, and so on.

But these developments ignored a kind of knowledge that’s more important to human beings: knowledge of how to live well.

With no good methods to check or organize this knowledge (no wikipedias, scientific archives, citation indexes, etc), it has become a kind of ubiquitous BS. Nonsense authorities—like Gwyneth Paltrow and Deepak Chopra or Sheryl Sandberg—tell us how our lives, relationships, and careers should go. The elderly couple down the street have probably learned more.

What does organized and vetted wisdom look like? How can the people with hard-earned wisdom—rather than a book to sell—be recognized? What would the engines of wisdom look like?

Idea #2. Leaders should put people in moral quandaries.

A century ago, moral decisions were more often made by individuals. Decisions like who to hire and fire, to whom to give a loan, or which customers to serve, were made based on some human person’s sense of right and wrong.

In the 21st century, such decisions are more often made by a committee, a rulebook, an off-site consultant, or an algorithm. This procedural approach was adopted in the name of fairness, justice, efficiency, and scale. But it has also created a gap between individuals and the moral consequences of their actions.

In the future, this gap must collapse. Bankers must walk with families through their foreclosed homes; technologists must spend time amongst the users whose lives they structure. A just society requires everyone to develop themselves morally. This means everyone must be given power, allowed to make mistakes, and then be exposed to the human consequences of their actions.

Idea #3. Leaders should build environments around meaning, not incentives or norms.

Picture two people, Larry and Sarah:

  • Larry lives in luxury and has every imaginable comfort, with a bank account he will never exhaust. But Larry’s affluence has become an insulator, an isolator. He doesn’t see his true friends often, and he doesn’t have projects that are meaningful to him.
  • Sarah, on the other hand, may not be materially wealthy. But she has a freedom many wealthy people seek: She fills her days with the most meaningful work that she can dream up. Her workplace, while simple, gives her space to focus and colleagues to brainstorm with. She confronts life, accompanied by close friends and lovers.

It is Larry’s life that is held up as the American (and European) dream. And modern socioeconomic policies aim for more lives like Larry’s. These policies have focused on the wrong kind of living. We have relatively little understanding of how to spread Sarah’s kind of wealth. We’ll need to figure it out.

Idea #4. Leaders should know the difference between integrity and reliability.

One lesson gets drilled into us—first as children, then as adults—by every system we encounter: “Fulfill your contracts and obligations!”

But integrity is rarely encouraged in us: we aren’t taught to take on just the obligations we believe in, or to break contracts when it’s the right thing to do. We aren’t taught how to discover our values and to live by them—something which can only happen improvisationally.

This elevation of reliability above integrity carries huge costs. Love becomes a matter of setting and meeting expectations. Work becomes about punching the clock. Ethics, beauty, and courage get pushed out of our lives when they don’t fit into our contractual obligations.

By putting integrity back in its rightful place, we can bring back ethics, beauty, courage, love, and autonomous work. So, ask yourself: what systems would put integrity first?

Idea #5. Leaders should build up a dynamic freedom within groups.

Imagine a young bitcoin millionaire named Edward, who bought land and food to live alone in the mountains. He wanted to be free. But here’s what he found:

  • Being on his own limited him (naturally) to one-person projects;
  • Without exchanges and external inputs, his thoughts and explorations had a limited range;
  • Any dreams which would require forming a new community (as most dreams do) were off the table;
  • And most importantly, Edward found himself avoiding paths that would lead him through difficult times. Such paths are hard to manage alone.

What kind of freedom does Edward have? It’s a small, static freedom. And all of us are somewhat limited like Edward. We may have friends and community, but if our friends are overworked, otherwise preoccupied, or just fixed in their routines, they’ll have limited capacity to join us. It is only as we become available to one another, and capable of taking on things together, that we experience a dynamic freedom. Oddly, many of the building blocks of modern Western civilization — cars, single family homes, gym routines, smartphones, television, full time work, even psychotherapy — serve to isolate us. They have negative impacts on our availability, and thus our freedom. A society arranged for dynamic freedom would look different.

The Big Picture

There’s a certain idea of human beings that excited the philosophers and political theorists of the Enlightenment (like Locke and Rousseau). The idea was that people had individual and social goals, and could form agreements (contracts) to work towards their goals together.

This goal/contract-focus infected the guiding principles they gave us. Such principles include giving people the freedom to pursue individual goals, the wealth to fund them, and the knowledge to execute them. In this framework, responsibility means fulfilling contracts, and justice means intervening when goals conflict.

But these principles ignore our non-goal drives (values), our non-contractual relationships (explorations and practices), and our non-technical knowledge (wisdom).

This turns out to be unworkable. Even the parts of society which generate technical knowledge (like science and entrepreneurship) require an underlying social fabric of values, practices, and explorations. And it’s similar with the parts of society which facilitate individual and group goals (including the market and democracy)—they too require this social fabric of values, practices, and explorations.

So the principles aren’t serving us: our static freedom isn’t enough for us; the wrong kind of wealth has been created, and we’ve gathered up an inadequate and drab sort of knowledge. Our notions of responsibility and justice are causing more problems than they solve.

As will become clear in the following posts, we can address these problems by re-emphasizing the neglected parts of ourselves: our non-goal drives, our non-contractual relationships, and our non-technical knowledge. This leads to a new political vision and new social principles.


This post is first in a series. Read the next post: How I Wasted My 20s (Pursuing Goals)

This short series, titled “The Next Enlightenment”, presents new social principles, developed within a small community of technologists, game designers, sociologists, and spacemakers. Thanks to Sam Hammond, Albert Kong, Nathan Vanderpool, David Chapman, Kevin Simler, Andy Matuschak, Kathryn Hume, and Boris Smus for reviewing drafts.