Linear Digressions

Still summer break: back next week by Katie Malone

Summer break: back soon by Katie Malone

After a five-year hiatus, the podcast that burned out partly over the tedium of writing episode descriptions is back — and using AI agents to handle exactly that task. The season-11 finale turns the lens on the podcast itself, putting the AI agents built throughout the season to work on real production tasks. It's a fitting, self-referential close to a season spent dissecting how agents actually function — and a honest look at what they can (and can't) take off your plate.

Capabilities get all the attention when it comes to AI agents — but what happens when a highly capable agent makes a bad decision in the real world? Trust, oversight, and control are the unglamorous but critically important flip side of the agentic AI story. This episode digs into the security concerns that emerge when you combine powerful models with real-world tool access, and why judgment (or the lack of it) might matter just as much as raw capability. --- Website: https://lineardigressions.com Apple Podcasts: https://podcasts.apple.com/us/podcast/linear-digressions/id941219323 Spotify: https://open.spotify.com/show/1JdkD0ZoZ52KjwdR0b1WoT Substack: https://substack.com/@lineardigressions

Whether you work best solo or thrive in a team, you know collaboration is complicated — and it turns out AI agents face the same tensions. This episode dives into multi-agent systems, exploring how networks of AI agents can overcome the individual limitations of a single model, and what the research says about when collaboration actually helps versus when it just adds noise. Think scaling laws, but for teamwork. --- Website: https://lineardigressions.com Apple Podcasts: https://podcasts.apple.com/us/podcast/linear-digressions/id941219323 Spotify: https://open.spotify.com/show/1JdkD0ZoZ52KjwdR0b1WoT Substack: https://substack.com/@lineardigressions

Knowing when an AI agent has failed sounds straightforward — until it isn't. Agents have a frustrating habit of finishing confidently while quietly doing the wrong thing, or looping endlessly without ever crashing in an obvious way. This episode tackles one of the thorniest problems in the agentic world: evaluation. If failure is hard to see, how do you measure it systematically? And how do you know when your agent is actually working?

Despite what the marketing hype might suggest, AI agents are far from infallible — and if you've ever actually used one, you already know this. Today's episode dives deep into the many, varied, and sometimes surprising ways AI agents can fail, from subtle reasoning errors to cascading task breakdowns. It's episode six in the show's ongoing season arc on AI agents, and failure modes turn out to be a surprisingly rich topic worth unpacking in detail. --- Website: https://lineardigressions.com Apple Podcasts: https://podcasts.apple.com/us/podcast/linear-digressions/id941219323 Spotify: https://open.spotify.com/show/1JdkD0ZoZ52KjwdR0b1WoT Substack: https://substack.com/@lineardigressions

When tackling a complex, multi-step task, even the smartest AI agent can fail without a solid game plan. This episode dives into the research around agentic planning — how agents move beyond simply reacting to what's in front of them and instead model a path forward, explore different routes, and course-correct when things go sideways. It's a subtler problem than memory, and a fascinating one: can an agent actually *think ahead*? Tune in to find out what the research says.