In October I argued that the federal election security network had come apart, and that whatever broke on November 3 would look like a local failure with a cause several layers down. The morning of November 3, 2026, Westchester County's ballot scanners started rejecting ballots across the county. It'll be remembered as a Westchester problem, not a national one. This time I'm writing about what the administration did to the parts of government that make rules matter.

Two big companies announced job cuts within three days of each other this month. Both came with the same backdrop: large companies trimming staff while they pour money into AI. From the outside, they look like the same move. I'm covering them together because they put weight on different parts of each company. If you lead a team, that matters. It means the repair has to be different too.

Founders discover how much of the place was them at the exact moment they can no longer do anything about it. Ted is unusual because he spent three years handing pieces away while he still had the power to keep them. He gave the goldfish to the players. He gave Roy the freedom to find his (f***ing) humanity. He gave Nate a second chance. By the time he got on the plane there wasn’t much more of him that he could’ve given. A year after you go, what would still be running in th

It’s not that hard to find your opposite. Telling that person the things they’re supposed to stop you from doing is, though. Writing down that list means admitting that there’s a chance we’re wrong. Which, I think, is why we generally don’t go through the painful process of doing it. We find our counterweights, and then we don’t give them permission to sit opposite us on the seesaw. We’ll listen to their opinions, but nothing they do can move us until they’re on the same bar

We’re stuck with two options. Keep the decision open and pay for it with bursts of energy, or plan ahead and pay for it in missed predictions and wasted effort. Most leaders and orgs pick a lane, and the failure they can't manage is the one that hides in their strength.

What most organizations do under pressure is fix things near the surface. The urgency is real, and fixes at the execution and systems level produce visible results fast. The problem is that a fix at the wrong level doesn't just fail to solve the problem. It spends capital, creates change fatigue, and gives the skeptics more evidence that nothing ever really changes. The willingness to attempt the harder fix, the one at the right level, gets weaker every time the wrong one is