I recently listened to a podcast with Casey Neistat, he of YouTube and vlog fame. He talked about being 5 months into working for someone else (Palmer Luckey and ModRetro) for the first time in his entire career. I can relate because I’m in the same position. But he talked about it in such a refreshing and honest way, something I’m just now getting around to. In my scenario, I am wired to be in the lead, but in this portion of my career, I am actually observing from a lower-agency chair on purpose, practicing contentment in a season I did not necessarily choose. As my friend Brent put it well, at the top (read: CEO) you never get the whole truth, because no one in the org can be fully honest with someone who holds that much power. So the middle, where I am currently, is a rare window into what is actually happening under the surface. I have started treating the season as fieldwork instead of a self-perceived “demotion”, and I am fairly sure that is the Lord teaching me something about mattering when no one is watching. The uncomfortable part came when I caught myself, more than once this month, reaching for a decision that was not mine to hold, because holding it felt safer than handing it over. More below.
What I Read
Firepower - Paul Lockhart. Lockhart traces how the relentless pursuit of ever more lethal weapons drove science, industry, and the modern state from the late medieval period through the twentieth century. His central argument is that firepower is not a byproduct of history but actually one of its engines. The demand for better guns and munitions pulled forward metallurgy, chemistry, precision manufacturing, and eventually the assembly line. Meanwhile, the cost and complexity of arming ever larger forces, and moving from feudal, personal forces to standing, conscripted armies catalyzed the concentration of power in centralized, bureaucratic nation-states.
Hardcore History - Dan Carlin. If you are a history buff, they you probably know who this podcaster is. He always goes long, but he ties together so many strings of history together that it is worth it to me. I crushed this 4 hour episode on the way home from Colorado. This latest one is part 4 of the story of Alexander The Great, and it gave me a view inside the Battle of Issus, and the eventual fall of the great king Darius of Persia. Actually pairs well with Firepower, because that book picks up where this one ends, in terms of weapons (the glory days of the pikemen were subsumed by gunpowder).
“Why Companies Are Cutting Middle Managers in the AI Era” (Bloomberg) The coverage frames the flattening as a cost story: fewer managers, leaner org charts, AI absorbing coordination work. I think the cost story hides the real one. The layer being removed is the layer where tasks used to get parceled out and graded, which means the only thing left to delegate is judgment. Most orgs never learned to transfer that. They learned to assign work and called it delegation. I read it as an org-design warning, not necessarily as an efficiency headline.
“The 7 Hires a Hardware Startup Needs To Get Right” (a16z) · I’ve shared this one with a bunch of friends. The value here is the sequencing logic: which authority you need to give away first when you are building something physical and cannot personally be in every room. Pairs with the delegation thread below, and with the “right people, right seats” work I did in a Culture Index workshop this month.
“The Meaning of Your Life” - Arthur Brooks (Triggernometry). Brooks runs an idol-elimination exercise from Aquinas: money, power, pleasure, and honor/fame, the four substitutes we reach for in place of the thing that would actually satisfy. I ran it on myself and the honor/fame one landed hardest. His line for the academic version stuck: honor is walking into a room and having people turn and say “oh, he wrote those papers.” I think imposter syndrome and the hunger for honor/fame are the same coin. That is a very uncomfortable thing to see in myself, and subsequently, it is the most useful thing I read this month. I dug deeper into it it last week. Article is below.
The idol that never says enough
I’ve been talking about idols lately, roughly a dozen times this summer. Some of it in interview rooms, because I’m hiring. Some of it over coffees and calls, because a couple of friends I mentor are both mid-pivot right now, one of them 3 jobs into a single quarter, the other a founder trying to decide how big to swing.
What I’m Thinking About
My natural instinct is to be the person in the room who has already thought it through. When a decision surfaces, I can usually see the answer faster than anyone else at the table, and for years I read that speed as leadership. When I am at my worst, it is armor. Indispensability and insecurity turn out to be the same coin, the same way intellectual superiority and imposter syndrome are. If the company cannot run a hard decision without me, then I certainly cannot be dispensable, right? But the bottleneck is a defense, and the better the company runs on my judgment, the more convincingly the bottleneck passes for value.
The part I got wrong for a long time? I thought I was delegating because I was handing off work. I was handing off tasks and keeping the judgment, which is just running my own decisions through other people’s hands. Delegating a task is easy. Delegating authority means someone else gets to make the call, gets to be wrong, and I live with it. That second act is the one I kept refusing, and I can definitely tend to dress the refusal up as “maintaining my standards”. The counter-move is the same embarrassingly small thing it always is: hand someone the decision before I am sure they will get it right, stand close while they make it, and do the debrief I would rather skip. I’ll be honest: it sucks, it’s slow, and it’s against my nature. But that is how judgment forms in another person, and it is the only way I know to make more of myself than myself. The output of someone scaling a company is other people who can make the calls.
The Sub-Plot
For thirty years, management has mostly meant delegating tasks: break the work down, hand the pieces out, grade the output. AI is now absorbing that entire layer, and fast. The tasks we used to parcel out to junior people are going to agents. What that removes is the thing task-delegation was hiding all along. When the tasks leave, the only thing left to delegate is judgment, the authority to decide and to be wrong, and most leaders never actually learned to transfer it. They/we learned to assign work and call it delegation. The org chart of the next few years has fewer people doing tasks and one enormous unanswered question sitting on top of it: who has the authority to decide, and how did they come to be trusted with it. That capacity transfers through a person standing close to where the judgment happens, and then the debrief. Basically, it transfers through personal mentorship and apprenticeship, not through a rote system. It is a different facet of the same “vault” I mentioned last month: the value was never in holding the decision. It is always in handing it over.
-eddy-
Delegating tasks without delegating judgment creates capacity but not succession. The harder test of leadership is whether someone else can make a consequential call, absorb the feedback, and improve. That is how authority becomes transferable rather than remaining trapped in the founder.