I try everything that looks low commitment with low expectations. Whatever works, I do it again, repeatedly until it stops working. Then I stop doing it promptly. The key is freedom: no commitment, no trust, always ready to move on at the drop of a hat. A sort of hobo ethic.

It’s nearly the opposite of the way I was raised. I was born high IQ but raised stupid. In retrospect, my parents’ and teachers’ lack of success ought to have been a warning to me.

The problem with middle management is that its purpose is to buffer the children (employees) from the adults (executives).

These are very different problems.

It does sort of seem like webshit (or dumb generic whatever) is, with maximal irony, the least crummy field, for the rationally self-interested individual.

What does your funnel look like? Mostly word of mouth?

I had to make a major upheaval of my approach to life to escape the straitjacket. I was so reluctant to make that scary leap that it took a disaster to push me to it.

I never loved the system. I wasn’t quite as stupid as that. It’s just that I didn’t hate it as much as I should have. I thought I could make an arrangement with the powers that be. I wanted peace in my time – as do most people – but then I had my Hitler-in-Poland moment.

It seems to me that the best structure is a small structure. Peter Gabriel has a song about that.

It’s not always true, though–I’ve known a couple of them who somehow slipped through the cracks, and to this day, all it would take to get me on a plane, no questions asked, would be a phone call from either of them. The funny thing is, though, they were entirely unaware of their own charisma. The “bad charismatics” I’ve experienced, though? All too aware.

I don’t think that it’s necessarily that people are bad at identifying who shouldn’t have power, but that the system prevents us from doing anything at all effective about it. In the military, we always knew who the bad commanders were, and you’d be astonished at how quickly and how decisively people will take action to avoid working for them. I remember being in a unit that got word a specific senior leader was slated for command over us, and within a week, the senior NCO cadre had put in retirement paperwork, called in favors for transfer, or dropped extension requests that were contingent on new assignments in theater. Before that guy ever stepped foot on the Kaserne, two-thirds of the NCO cadre had taken steps to ensure they wouldn’t be working for him, and the remaining third was drinking heavily.

Root problem isn’t that we can’t identify these assholes, it’s that we set up systems that straight-jacket us into having to work for them. Which goes right to my long-held contention that we’re really, really bad at organization, and need to back off from creating these inevitably-captured-by-idiots-and-scum social structures.

People are very bad at identifying who is worthy of power.

The problem with all too many of our organizations and institutions is that the tendency is for the stupid and energetic to rise to the top and accumulate others of their type. You let one idiot into the upper ranks, and before you can say “WTF?”, they’ve proliferated and taken over the place.

The really astonishing thing I’ve noted, too, is how little real education about management and leadership a lot of these sorts of guys get. You almost never see them reading, and if you ever try to engage with them about things like the Peter Principle, you get stares of bewilderment.

But, boy howdy… Can they set themselves up for the multitudinous seminar circuit, following the latest management fad of the day.

The only thing that’s predictable is that management will screw up and then blame the engineers.

In business and (I presume) the military, those in charge read Sun Tzu and Clausewitz. The only thing analogous to that for software is a collection of essays (somewhat outdated now) by Donald Knuth plus a blog by Eric Raymond. I’ve yet to meet a manager who had heard of either of these.

I fear you missed the point of that truism my old boss subscribed to: It’s not that he meant to shortchange the planning in lieu of abusing the troops, but that he wanted men on the ground who could make things work in the absence of plan, knowing only intent.

Military planning is a lot less predictable than it is in other spheres–You go in with a set of assumptions and intents, not knowing what the enemy is going to do, not knowing what’s going to happen. In business or government conditions, it is much more predictable and you generally don’t have your competitors out laying landmines along your trucking routes. So, the planning environment is inherently chaotic in the military. There was one commander who made the point during the delivery of his oral Operations Order that the plan was going to be the first casualty; he had a copy of the main body of the OPORD ceremonially dropped into the shredder they wheeled into the conference room where he was giving it, which I suppose he meant to represent it being “killed in action”. I’m not sure everyone got that point out of it all, but he still made it.

It also illustrates the fact that if you don’t pay attention to fundamentals, it doesn’t matter how good everything else might be. Dyson, British Leyland, and Mabey-Johnson are representatives of British industry that I’ve personally experienced dropping the ball between product design, and the minutia of getting that superior product out the door and supporting it. From what I’ve been able to discover, most of that stems from a break between mid-level management and the people working the shipping docks and factory lines–The Brits have issues at that point, across a lot of their industrial core. It’s notable that the same bunch of workers who couldn’t keep British Leyland solvent are churning out much higher quality product under Japanese management, and sometimes out of the same plant.

There’s a lot to be said for good planning, but when the plan is going to be administered and performed by the sub-par? It doesn’t matter how good it might be. With good people executing it, you can occasionally get away with a bad plan; however, absent those good people at the execution level, ain’t no amount of “quality planning” going to help you pull it off.

Nowadays I make a lot less money doing random freelance jobs over the Internet, and I’m much happier and less stressed. This social distancing B.S. barely affects me. There are a lot of horrible clients out there, but it doesn’t matter is long as you keep everything small and short term. No big commitments, ever. One night stands are the only safe sex, so to speak.