The Edge of Chaos & Not Waiting for Things to Settle

Borrowed

"DYNAMIC INCOMPLETENESS adheres to the truth that too much form causes resistance and too much void causes chaos. The leader's job is to bring just enough form to inspire the people and frame what needs to be articulated. In a nutshell, that is the art of visioning."

From "The Primes: How Any Group Can Solve Any Problem" by Chris McGoff [Book]

Learned

Last Tuesday, the theme for our weekly team meetup was Barrel 20. To mark the occasion, I built a trivia game with Claude. It's times like these when I wonder if I'll ever not be in awe of AI. I sifted through years of our newsletters, internal and external, in minutes to brainstorm questions, then built the kind of game that would have taken weeks to make even six months ago. What once would have been a project minimized to a simple task. Most importantly, though, the session was a lot of fun.

I'd planned to say a few words before the trivia. I figured I'd keep it casual and make it more of a thank you to the team. But that morning, I listened to Reed Hastings, Co-Founder & Former CEO of Netflix, on the podcast Invest Like the Best, and I couldn't get a couple of the concepts he discussed out of my head (still can't). They put words to what's been on my mind as we navigate a real season of change at Barrel.

The first is the edge of chaos. It inspired Hastings' leadership at Netflix but the concept goes back to the 1980s and was popularized by the Santa Fe Institute. They used it to describe a narrow zone between total order and complete randomness, the threshold where complex systems are able to adapt and evolve. Too rigid, nothing changes. Too random, nothing holds. The best outcomes live on the line between them.

The way I framed it to the team was the space between total flexibility and rigid systems. You want enough structure to keep things together, and enough room for people to stay creative, change, and evolve. Hastings' point is that when you over-manage, when you punish failure and write a policy for every situation, you get order, but you also limit creativity and filter out your high performers. So you run as loosely as you can stand. He calls it managing on the edge of chaos, and I couldn't think of a better way to describe how I see Barrel.

In many ways, the edge of chaos has been my personal default for most of my career. Sometimes I'd question myself, wondering if I was too loosey-goosey, not documenting enough, or creating guidelines. But often the rules were outdated the moment I wrote them, more work to maintain than they were ever worth. As CEO, it's a question that lands harder, because how you operate sets the tone for everyone.

Nothing about where we are today feels like business as usual. We've been reshaping how we work, our processes, and how we serve our clients, while the whole industry shifts beneath us. Heated debates, project hiccups, and difficult conversations are par for the course, but in a stretch like this, it's easy to read them as signs that something's wrong. As a leader, I feel the pull to show everyone there's a light at the end of the tunnel, that once we get through XYZ changes, things will settle. Aspects of that are true, but listening to the podcast energized me in the opposite direction. The settling isn't coming, and that's the point.

That's what I wanted the team to hear. A lot is in motion, and it's a good thing. It's uncomfortable at times, but there's a vision for what we want to create together, and the motion is the signal that we're growing and pushing toward it. Living on the brink of chaos is where we'll do our best work.

The second idea is called talent density, a concept that's become synonymous with Netflix. It's what makes the edge of chaos possible.

If you've ever seen Netflix's culture handbook, you know the bar there is high. Hastings talks about how the draw was never the perks; it was the people, the chance to work alongside genuinely great ones. And the kind of people who make the edge of chaos work are specific. They respect structure, communicate, are candid, give each other feedback, and push each other forward. The looseness is what lets them take ownership and lead. Without the right people, the edge of chaos is just chaos, everyone looking around for rules and guidelines that don’t exist.

Hastings learned this at the company he ran before Netflix. They grew fast, and the average level of talent slipped. His instinct was to add rules to guard against the mistakes. As he put it, "with declining talent density you need a bunch of rules." And that's the downward spiral: the rules push out your strongest people, the ones who never needed them, which thins the talent further, which makes you reach for even more rules.

On the podcast, he offers a gut-check for this, which he calls the keeper test: if someone told you they were leaving, would you fight to keep them? I don't take it as a rule to act on, more a question worth sitting with.

It's interesting, I've seen this tension play out over the years, especially when hiring for new roles or bringing on a freelancer. There's this feeling that for someone to succeed, you have to set them up perfectly: tight onboarding, clear documentation, specific goals, and so on. "Rules." But the people I've seen do the best are the ones who come in, get why they're there, ask questions when they need context, and aren't afraid to make mistakes. You get the best of what drew you to them. The ones who struggle are constantly looking for answers, requesting more documentation, asking to take courses, and ultimately floundering.

Even knowing all of that, when I'm navigating a setback or thinking about how we scale, rules and guidelines can feel like a good idea. Trust me, I just had a meeting last week with our People Ops Manager, Allison, about revisiting our Barrel Handbook. The pull is real, you tell yourself a rule will take a decision off everyone's plate, and it will. But it can also creates a world that looks black-and-white. Do this, don't do that. You lose the nuance, and your best people may start to feel constrained. The work is narrowing in on the few areas that actually need definition. It's a fine line.

Where I'm landing is that these two ideas are best looked at as one. The edge of chaos is a productive place to live, and talent density is what makes living there possible. All of this has been a welcome reminder of why getting the right people in the right seats is one of the most important things we can do.

& Thought

What would I do differently if I accepted the unsettledness as the plan, not the problem?