Five Things: August 27, 2026

NOTE: One week late and my commentary may be more scattered than usual because I’m in the final stages of a big move that’s dominated my summer and I’m exhausted af, so as always, be sure to click the links!

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_ONE

500 applications, 0 callbacks | Melissa & Johnathan Nightingale

But the sell was always that, with enough grit and hustle and getting the details right on your cover letter and your action verbs and your fonts — you could get in the door and then impress them in the interview. As shitty as that experience was, it at least gave a sense of predictable return on effort. Whatever ability you had to swim in it has become almost irrelevant. Overnight.

I had an interesting conversation with an internal recruiter recently about the various challenges job seekers face getting to an actual interview in today’s market, and I mentioned my continued fondness for cover letters — both as an applicant and hiring manager. Even if a position doesn’t require a cover letter, I write one anyway because it helps me decide if I’m really interested in the role (and the company), or I’m just trying to feel productive by applying to as many jobs as possible.

My summer of un(der)employment has pretty much gone as expected, although it’s been a little depressing how few interesting roles have been posted in my primary markets, and how most roles anywhere are made less interesting with prominently vague references to “AI” usage. I’ve been mentally preparing myself to expand my scope, including the possibility of finally stepping away from the book publishing supply chain I’ve spent most of the past fifteen years working in.

The Nightingales are always a good read, and while this one might not hit the inspiring note they were aiming for, that’s probably because the market is arguably even worse than it was back in April when they first published it. Their two main takeaways are important, though: the front door IS absolutely fucked, and IRL networking is still essential.

__TWO

AI Is Undermining Leaders’ Judgment. Here’s What to Do About It. | Leonid Sudakov and Nathan Furr

When the AI tool encouraged human evaluators to reject submissions that the expert panel approved, the humans largely went along with those recommendations, filtering out high-potential innovations. What’s more, they less were likely to override an incorrect recommendation from the AI when offered a narrative explanation. Instead of improving the evaluators’ judgement, the narrative explanation made it worse.

While the Nightingales (above) have become one of my favorite sources for insights on modern leadership, I resubscribed to the Harvard Business Review to expand my professional radar even further. Although a lot of their editorial coverage slants in the “AI is inevitable” direction, it’s usually tempered with solid research and reality checks that are often missing everywhere else.

I’ve always been a fan of organizations that support and nurture “intentional dissent”, which has become even more critical as chatbots deceive people into believing they’re suddenly the smartest person in every room. Ironically, those rooms are often purposefully filled with sycophants whose desire to please rivals the chatbots who could justifiably replace them without missing a beat because neither has a spine.

This year has found me engaging with multiple people who openly outsource “creative” tasks they admittedly have no real experience in to their preferred chatbots, which has meant seeing drafts and entire presentations that make me long for the days when senior executives begrudgingly knew and accepted their limits. Give me an indecisive leader who listens to feedback from multiple perspectives and understands only half of it before acting, over one who believes their AI prompting actually delivered a strong first draft, or worse, a strategy ready to present to key stakeholders.

___THREE

After Editing Two AI-Assisted Manuscripts, I Rewrote My Client Agreement | Mary Kole

In essence, the clients who’d hired me had outsourced their creative expression first to AI, and then to me, the human implicitly tasked with bridging the gap. Instead of simply evaluating execution, I found myself making authorial decisions: reshaping emotional arcs, deepening characterization, stripping back thematic overstatements, and rebuilding character interiority so it sounded like a distinct voice rather than a statistically probable Everyman.

There have been numerous examples of organizations that pivoted to AI and laid off entire teams of humans (mostly in development and customer service roles) being forced to rethink that strategy, but Kole’s ground level examples get to the heart of the problem on the creative side of things.

I’ve had to work with copy and presentations that were “generated” with AI assistance, and the additional effort Kole mentions is absolutely different work that should cost more.

____FOUR

The only reason you’ll ever need not to write with AI | Colin J. Carlson

Using generative AI inherently exposes you to the risk of career-ending accusations of plagiarism… What I’ve come to realize is that, regardless of any true similarity between your words and someone else’s, or your ideas and someone else’s, generative AI exposes you to risk that you, as a writer, cannot mitigate.

AI watermarks and stylistic tells* have been getting a lot of attention recently, but Dr. Carlson gets to the heart of the problem with relying on these new tools to “assist” your writing in any way. You may convince yourself that your clever prompting isn’t the same as plagiarism and the output is uniquely yours, but deep down, most of y’all know that’s a lie.

Why gamble your credibility and reputation just to [theoretically] save a little time that would be better used actually doing the hard work that will steadily improve your own writing instead?

*NOTE: Many AI “tells” are actually solid writing standards in certain types of writing, but in the wrong hands and context, the “assistance” becomes obvious and the writing loses some of its humanity. I’ll always prefer to read someone’s awkwardly written authentic thoughts than a polished version their fingerprints were sanded off of to sound… average.

_____FIVE

Creating media with an uncooperative mind | Baldur Bjarnason

The problem that producers of niche media – such as comics or prose books – face when trying to market their work is that they are guests in a bigger world. We are working in an environment built on dynamics and structures very different from our chosen media. We constantly encounter a mismatch between the venues and skills that are effective for promotion and the skills and capabilities we have developed for our work and craft.

Bjarnason occasionally writes something that makes me jealous for its combination of poignant insights and personal introspection, and this long read is the latest example.

He starts with an important observation about books’ place in the larger media ecosystem (one that I built an entire initiative to help validate), and then goes deep on his current journey of experimentation, which I can also totally relate to — on several levels.

______BONUS