Five Things: October 23, 2026

NOTE: It’s been a hectic few weeks with the new gig, and I attended my first industry conference in Philly earlier this week, so this is a bit more random collection of things than usual. Each one’s worth a click, though, so get to reading!

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_ONE

Before Rolling Out a New Strategy, Assess Your Team’s Readiness | Steven Morris

Skill gaps are not personal failures; they’re structural realities. And when they go unexamined, they produce an execution struggle that’s easy to misread.

Throughout my career, I’ve inherited more direct reports and entire teams than I’ve gotten to hire from scratch, which meant I had to develop a process to objectively evaluate strengths and weaknesses before making any strategic decisions that would affect them. That evaluation process always includes the systems that support their work because, as Morris correctly notes, sometimes the people doing the work aren’t the problem.

I like his “Readiness Triad” (Appetite, Capacity, Skillset) as a framework for determining the viability of a strategic initiative because it puts the focus on evaluating the systems and people you have rather than whether or not the strategy itself seems like a good idea on paper.

I’ve seen several strategic initiatives fail as a direct result of one or more of these areas not being paid attention to, and it was almost always because leadership didn’t attempt to understand (or chose to ignore) where the gaps that could derail execution were hiding — often in plain sight.

__TWO

The Railroad Staggers Built | Steve Blinn and Dan Bostek

Staggers is usually described as deregulation, which is close enough to be useless. It did three specific things, and the third one changed the map… The first two changed how railroads earned money. The third changed how much railroad there was.

I’ve been nerding out on trains so much the past couple of months that I actually understood most of this insightful breakdown of the Staggers Rail Act of 1980‘s impact! The more I learn, the more the Union Pacific / Norfolk Southern merger seems like it’s probably a bad idea, but one that will most likely be allowed to happen by the current administration.

There are similarities to the failed PRH/S&S merger in 2022, too, but the biggest difference (besides administration priorities) is there’s so much more hard data on railroads, perhaps best demonstrated by the extremely limited data set the DOJ built their case against PRH on, and Markus Dohle’s infamously hilarious counter-argument that “everything is random in publishing.”

PS: It’s been interesting learning more about a sector where hard data is robust, practical “artificial intelligence” has been a thing for a couple of decades, and new use cases are focused on improving and scaling those applications rather than promoting tech god AGI and LLM magic bean bullshit.

While publishing has ruined my opinion of most of its big players and industry associations over the years, the Association of American Railroads at least has real data to work with in their reporting. Straddling the two worlds is going to be a fun challenge!

___THREE

AI Defiance | Matt Enis

We’re hearing things from library workers like ‘my boss says I have to use AI.’ No other direction. Or these grand pronouncements that sound like they’re reading from a tech company press release—AI is the future, if you don’t get on board with it, you’re going to get left behind. We’ve heard these kinds of narratives around technology for years…. With AI it’s accelerating, and it’s stifling all other critical conversation.

For every twenty articles we get regurgitating tech company press releases or the latest booster’s unchallenged opinions (“I asked Claude to…” FOH!), we get one article that treats skeptics like critical thinkers rather than as Luddites mischaracterized as an ignorant resistance movement yelling at clouds.

Enis does a solid job presenting the informed skepticism of the many librarians who are pushing back on the “inevitability” narrative, reminding everyone that resistance is never futile.

____FOUR

Pangram is not an oracle | Prof. Emily M. Bender

I keep hearing Pangram described as extremely “accurate”. This tells me that a) the company’s advertising is effective and b) we need some public education on what “accuracy” means with respect to language technology and how such technologies are evaluated.

As an informed AI skeptic myself, I’ve found the rise of Pangram in publishing circles to be interesting and concerning, because it’s an industry that’s notoriously slow to adopt new technology, but also extremely fond of magic beans. Bender is one of several informed people I trust for helpful insights that cut through the noise.

Don’t believe the hype. Always dig deeper.

_____FIVE

How Manchester City Got Away With Historic Fraud | Alex Shephard

Manchester City committed fraud on a massive scale primarily as a soft power project for an authoritarian nation because it was allowed to do so. The Premier League chose to look away.

In 2026, it’s almost impossible to enjoy soccer and not be confronted with the various ills of capitalism and sportswashing, and Manchester City is now officially the poster child of that reality. Part of what eventually turned me off the Premier League was the realization that money made an even bigger difference than in US sports, thanks to the promotion and relegation system.

As a fan of underdogs in general, the idea that your favorite team could be ruined financially with a bad season or two, and potentially end up becoming a semi-professional minor league team was wild. While it made Leicester City’s great escape years ago exciting, and their subsequent worst-to-first Championship even sweeter, it still left a sour taste in my mouth, and I realized the Premier League wasn’t for me.

While La Liga isn’t much better with Barcelona and Real Madrid’s financial dominance, and both teams certainly have their own ties to dirty money, there was absolutely no reason for Real Betis or Racing Santander to catch a stray in Shephard’s otherwise excellent takedown!

______BONUS