(2026-08-19) Hon S21e23 The OODA Loop

Dan Hon s21e23: The OODA loop. I’m doing a sort of virtual summer catchup tour and going on a walkabout: I made a list of interesting people I wanted to talk to just hear about what they’re working on

On walkabouts like this you’re supposed to listen and soak everything up. And then do what can be terrifying, which is to ask people how they’d describe you, or even more scarily, ask them what superpowers they would say you have.

Today, I caught up with Isaac Hepworth. Every single one of these calls has been fun and brain-sparking (and, I’m pleased to accept, brain-sparking on the other end, too), but I’m writing this straight after the call.
First, Isaac reminded me that at the end of this exercise I should just write it all up as a sort of zeitgeist piece of what I figured out after talking to 50-odd people. Which I have to admit, and told him, is a stupendous barn-stormer of an idea

Here’s some of the stuff we talked about:

I posted a throwaway comment a while back that I think you could understand what humans would do in a post-scarcity environment by just looking around at what’s happening right now.

• despite the creative industries being completely Capital D Disrupted (and acknowledging that a lot of disruption is also destruction at the behest of the other Capital), people are still creating music and art and film and writing
• sure, why not, make those amazing TikToks or write that fic as the world burns. What else are you going to do? Which is just like the post-scarcity state: what else are you going to do?

The thing that I’ve heard consistently on this walkabout is that if there’s one superpower I’ve got, it’s an ability to create clarity from complexity, to distill it down into what is important for a particular person or audience, SO THAT that person or audience can then do what they need to do.
Isaac reminded me that this is sensemaking: that I’ve got the ability (unparalleled? No, I wouldn’t go that far, but I would accept “unique” and “individual”) to understand how organizations work, how people work in those organizations, the relationships between people and whether they are taut or sproingy, whether they are malleable, the kind of tensile or ductile strength they have. Where something can break. And from a systems thinking point of view

One thing Isaac pointed out is that at some point organizations get too complex that you can be an exec and you don’t know what sort of machine you’re operating. Or you don’t know how it works. I’d go so far as saying that you reach that threshold at around 30 people, and that it’s really a people problem.

did you know there is a part here doing this? Again, the answer can invariably be no. There are a bunch of assumptions being operated upon and honestly and candidly: who has the fucking time? There is a machine to run, and it does things! Just make sure it doesn’t seize up and stop! What happens if I push here? What happens if I put something in there? Which part is critical?
But the thing is, it does seize up and stop.

the mismatch is in finding the people for whom this work or the outcome and understanding and ability to act (and to discover the axes of agency where they may not have been understood to exist) would be intensely valuable, but they just don’t know it yet or don’t know how to ask for it.

At which point several of you I think are waiting for me to autocomplete this line of thinking with Upton Sinclair’s observation:
It is difficult to get a man to understand something, when his salary depends on his not understanding of it.

What to do about people, leaders, say, who don’t yet realize that they don’t understand the machine they’re operating or in charge of operating?

This connected in my head almost like a jigsaw puzzle piece with Boyd’s OODA loop.

the kind of people who’re aware of the OODA loop also tend to be aware that it’s especially useful in rapidly evolving and changing environments. (VUCA)

pitch for what it is that I do for an exec leader is: I am the pilot and navigator for your OODA loop. I am an expert at observing and orienting. I synthesize and create clarity from those observations and orientations to give you the decisions that matter that you and only you can make at that level for which you’re responsible. Then you can act on them. Then we do it again. And hopefully you don’t have me around forever.

What about the people who don’t know? Well! I think I have an answer.
I create the order and direction you need to function when you are surrounded by uncertainty and/or chaos, and outline what you can do to decisively act.

You’re in an environment that’s changing, probably rapidly.
What, exactly, is going on? And you need an answer to that quickly. Worse, because you’re in a leadership position, you need options for what to do about it.

When you are trapped and need clarity in direction, then I am who you get to create clarity and direction where it before it was hidden, non-obvious, or obscure precisely because of the way your organization works.

Why should someone talk to me? Because I create the order and direction you need to function when you are surrounded by uncertainty and/or chaos, and outline what you can do to decisively act.