0.0 Context Setting

Wednesday, August 19 2026 in Portland, Oregon. I am sitting in my study and still, inexplicably, have Def Leppard’s Hysteria on single track repeat. I have nothing to say in my defense and don’t frankly care, either.

0.1 Events

Simple and quick this time:

• How People Work, Live! ... with Marcin Wichary this Friday 21 August at 9am Pacific, where we’ll be talking about design.

Yesterday was the first Happy Hour clinic and I thought we had a bunch of fun. What was slightly less fun was the awkward moment where I realized I had told people the session was going to be recorded, but not told people my intent was to put it online afterwards. So I didn’t do that! I have to admit this time I’m rethinking the whole “and then put it online”. Probably not. Anyway, here’s where you sign up for the next one.

• The How People Work... Does Happy Hour! clinic, every Tuesday at 1pm Pacific.

1.0 Some Things That Caught My Attention

1.1 The OODA loop

I may have written about this before that 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, what’s difficult, and how things are going. The goal was to talk with 40 people inside of 4 weeks -- two a day, every working day. At this point I think I’ve already talked to 20 people, and am on track to hit 50, which seems good!

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 and one that I apparently do have the mental energy to even contemplate. In this case it helps that I’ve got notes of all the calls.

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.

It was a reaction to an observation I saw: that 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 and just being people, which is to say: creating and then creating connection through creation. Even though you won’t get paid, or the prospect of getting paid for creative work is completely up in the air, even though people will say what’s the point of making music if it can just be generated on the fly and it’s easier to do that... people are still making music.

The tie to post-scarcity was this: I mean sure I get people in the Culture or in Star Trek going around having string quartets and writing poetry and creating holonovels or inventing new sports because they have nary a care, etc etc. But it strikes me that there is a depressing similarity/symmetry in “I have all the healthcare I need” and “I have absolutely no healthcare”. Because if you don’t have the healthcare, sure, absolutely, the capacity is diminished and the respect for humanity is eviscerated, AND yet if you can, you still create because at this point, do you really have the agency to get the healthcare you need? So 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, put together an understanding of what it is that the machine is doing and how it works. What information is being created, how it’s being synthesized, what meaning it has, and perhaps crucially, how that information spreads and what happens with it -- how it’s acted upon.

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. The one constant around diagnosing organizations is that every single one of them is populated by people.

BUT! That’s not true anymore, or won’t be, soon! It’s not just people and processes and products that make up organizations, now it’s autonomous agents too, and they can be doing everything from a pig’s ear job of it to, well, hopefully better than that.

So this is sensemaking. It is taking a look at the entire thing, top-to-bottom, and being able to point at it and say: this is what the machine does. Did you know that? Invariably, the answer can be no. Or: 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 problem I’ve always had has been sure, great, people pay me to do this, in part because what makes it successful is that I accidentally do end up, persuasively, in front of leadership and leadership is either willing (great) or I can help reach the willingness activation energy (good to show how I’m valuable and worth money), but that this requires people who want to know about the machine and want that understanding. (Part of that is fine: you don’t want to work with people who don’t want the work and don’t value it in the first place.) And yet 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

So what to do about 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? How do you get through to them or discover them?

This connected in my head almost like a jigsaw puzzle piece with Boyd’s OODA loop.¹ What’s the OODA loop? It’s a way of figuring out what to do that fell out of the brain of John Boyd, a U.S. Air Force Colonel from the 1970s, who Wikipedia says “applied the concept to the combat operations process.”

Look, it’s this: it’s a loop where first you observe, then you orient, then you decide, then you act.

It was, I remembered, a handy way, a model (in the way that all models are useful, etc etc) to describe how I work, what I do, and also implicitly, why it’s valuable, and how it applies across different domains. In particular, 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.

So the simple description and 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.

That’s fine for someone who knows what an OODA loop is, which for my purposes is also great because it’s a filter. If you know what an OODA loop is then chances are you know why it’s valuable, so you’re already partway there on being persuaded. 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.

(Sure, I can do better than that, but I’m thinking out loud. Remember the premise of the newsletter, yeah?)

You’re in an environment that’s changing, probably rapidly. You are under pressure to act -- your boss needs you to come up with a plan, hell, the stock market needs you to come up with a plan, or you’re getting hammered because it doesn’t look like you have one. Sure, that’s the business version. You’re an NGO and you’re in, uh, a “highly volatile sociopolitical environment”. You’re an arts organization and you’re being disrupted from the left and right by, what, vertical video this week and Tilly Norwood the not-actually-an-actress who appears to be instead a well-executed marketing campaign. You are a media organization that is trying to figure out what to do because suddenly it looks like people are playing videogames. You are a news organization who just looked around and suddenly somehow your peers are investing in daily play games. What the hell? 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. Which isn’t to say that’s necessarily a failing of your organization, but that your organization is doing what it’s supposed to be doing.

So. This has tied together so much of what I’ve been hearing from the twenty-odd people I’ve talked to so far.

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.

I don’t know about you, but it feels a bit chaotic and volatile out there. There’s this AI thing happening, for starters.

So, again: I know there are people out there who need my help. You probably know someone who does, or maybe this has finally explained or done a better job of explaining what I do and why it’s valuable. You know how to get in touch with me.

Oh, right. And I can teach your teams to do it, too. Essentially, that’s what I’ve figured out the workshops do, in a sense.

Well that was a weird one to write, but also a simple one that felt like it flowed easily.

How are you doing? Send me a note, remember I love to get notes, even when they’re just a hello.

Best,

Dan