Infinite Regress and Turtles — Bob’s Theory of Everything

There’s an old joke where an elderly sage tells a young person that the world is sitting on the back of a turtle. When the young person asks what the turtle is sitting on, the sage thinks for a moment and says it’s another turtle. The young person then sensibly, or precociously, asks what that turtle is sitting on and the sage replies “it’s turtles all the way down.”

This joke is an example of the philosophical problem of infinite regress — essentially trying to determine the root cause of everything — a question that’s occupied folks like Aristotle, William James, and string theorists.

I’m not a philosopher, sage, or theoretical physicist, but I am a writer who is concerned with the improvement of the world.

I believe we are capable of building a society that is more equitable and sustainable — a world where resources, dignity, and power are more evenly distributed, and where the systems we create to feed and power the world are regenerative and cyclical, like natural systems.

My studies and my writing are focused on paths toward building this kind of world. Since determining the root cause of an issue is helpful if you want to fix it, this work quickly bumps into the problem of infinite regress, and over the years my work has come to focus on the single “turtle” of organizational development.

I focus on how organizations work because groups are a kind of superpower for humans. Not only are they essential to our individual survival and happiness, but collective behavior is responsible for our greatest achievements and most of the damage we cause.

Without groups, we would not have rocket ships, art, or philosophy — specialists need a support system around themselves, after all — but we also would not have global warming or genocide.

My work, therefore, is concerned with improving our ability to work together as teams, as nations, and as a species, for common cause and mutual benefit. It’s “organizations all the way down.”

Improving organizational behavior is itself a complex problem; like a spider’s web or an ecosystem, if you tug on one small piece, you end up impacting another part in unforeseeable ways. So I focus on developing an ever more clear understanding of where we are and what we can do to make our organizations better.

Because of its complexity, the study of organizational behavior leads me to study a number of different topics. Over the years, my work has coalesced on a few core areas that feed into my main goal of improving equity and sustainability at the organizational level.

Here are the topics you can expect to learn more about if you follow my writing or what I share on LinkedIn or in my newsletter:

Team Dynamics

I see the team, not the individual, as the atomic unit of organizations. If we focus on the individual, we end up either worshiping the heroic leader giving orders to their pawns or trying to figure out how to create more conformity at the lower rungs.

Either focus reinforces a top-down, hierarchical approach to organizations — an archetype that’s outgrown its usefulness.

So I’m curious about how to create better teams. By better, I mean teams that are able to diverge (disagree) in healthy ways to maximize creativity. The best teams, in my experience, are able to have intense disagreements, but also able to align and take action together. Good teaming begins with welcoming and including a diverse set of skills and perspectives, since this generates more divergence and forces teams to examine more ideas and data points.

In my experience, healthy organizations are collections of healthy teams and are led by healthy leadership teams. For this reason, my consulting work centers on improving leadership team dynamics.

My new book Radical Alignment: How to Have Game-Changing Conversations That Will Transform Your Business and Your Life (co-authored with my wife Alex Jamieson) is about having productive difficult conversations — an essential skill for any modern leader. You can pre-order the book here and get a free chapter here.

Group Psychology (Especially Cults)

Groups can bring out the best and the worst in us as individuals. They can lift us up and tear us down. They can help us do great things and they can exploit us. Due to personal experience, and a general fascination, I’m interested in cults and cult psychology.

I use Janja Lalich’s definition of cults as groups led by charismatic individuals that “espouse an all-encompassing belief system, exhibit excessive devotion to the leader, avoid criticism of the group and its leader, and feel disdain for non-members.”

There’s also a broader way to think about cults as organizations where an individual or group at the top reaps rewards but keeps others involved to their personal detriment. People join these groups voluntarily but stay based on psychological control and manipulation.

Many corporations and political groups exhibit these characteristics, as do multi-level marketing organizations and abusive intimate relationships.

My view is that cults usually arise as the result of predatory behavior on the part of the leaders but are maintained due to what the writer Neal Stephenson calls a mind virus that spreads through the organization. Cults often prey on people’s sense of purpose and desire to do good. I’m particularly disturbed by the cult-like tactics many purpose-driven social ventures use.

Cults, therefore, are not just the story of the strong preying on the weak; they are also the story of bugs in the wiring of human psychology and a testament to how important groups are to our individual thriving and survival.

My intent is to understand the underlying dynamics so we can avoid pitfalls and create better outcomes for the people who work in organizations.

Social Justice

In the long history of human organizations, there has often been a pull toward domination. Those in power routinely seek to secure their access to resources through cultural norms and political and religious laws that exclude and even exploit others.

Systems theorist Donella Meadows called this tendency the competitive exclusion principle, which she describes like this: “if a reinforcing feedback loop rewards the winner of a competition with the means to win further competitions, the result will be the elimination of all but a few competitors.

The work of social justice, therefore, is about equity. It is work focused on creating and maintaining a more fair distribution of power and resources, with dignity and opportunity for all.

While equal treatment may be a worthy goal in many cases, it also has a way of reinforcing existing inequities. So the work of social justice is the work of righting historical wrongs and creating inclusive and fair systems moving forward.

I look at this work as a person who experiences privilege — I’m white, male, cis, middle-class, middle-aged, and straight — who wants to use his power for good and to help liberate others. I also look at this work as someone who believes that equality, inclusion, and equity benefit us all. Diverse teams are more creative and resilient, and a diverse society will be, as well.

A good deal of my attention is spent on anti-racism, feminism, LGBTQ+ rights, as well as issues to do with class, age, and neurological and physical differences. However, I am not an expert or educator on any of these topics and do my best to learn from and share the work of people who are, especially people who wear identities different from my own.

I tend to keep my curiosity focused on underlying issues and dynamics that help understand, create, and sustain organizations that are more equitable and inclusive. I’m specifically interested in inclusiveness as it relates to organization change, team dynamics, and organizational design.

Systems Dynamics

I find it impossible to examine human organizations without learning about how systems operate. A human is a complex system — biological, psychological, and behavioral — nested within organizations, which are also complex.

Systems theory and complexity science are interdisciplinary studies that attempt to understand how systems work, develop, fail, and thrive.

This work connects disciplines as diverse as evolutionary biology, neuroscience, economics, and physics. The goal is to understand and work with systems that are deterministic, meaning what happens now influences what happens later, but so complex we can’t predict the impact of any single action.

Topics of interest to people who work in this space include nonlinearity, emergence, spontaneous order, adaptation, and feedback loops. A classic description of a complex system would be global weather (climate, too) and is captured in the idea of the butterfly effect where the flapping of a butterfly’s wings can create a chain reaction that causes a hurricane on the other side of the world.

My work in organization development as well as my intellectual curiosity keeps me reading widely in this area and attempting to understand which butterfly flaps are significant.

Personal Effectiveness and Creativity

At the end of the day, I’m just a human trying to live the life of an artist and be healthy, happy, and productive. So I read and think quite a bit about how to be more effective (productivity hacks and such), how to be more bold and creative (art and risk-taking), and also how to be a happier and healthier human (meditation, relationships, health, and habit change).

I’m no expert on any of this. I almost always feel I’m failing or flailing in some way, but I do occasionally have flashes of insight or find tools I like to share.


So that’s it; that’s what you can count on me for. If that sounds of interest, please sign up for my newsletter or follow me on LinkedIn. If you want to see a bunch of pictures of my food, cats, and interesting things I encounter on my travels, you can also follow me on Instagram.

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