Hello, my imaginary friends

Title: The Conversation I Need to Have Tomorrow
Duration: 5:49

Simon walks home in the woods in the dark with his head torch on, after a bonus walk to fit in his steps. Clients' Wi-Fi blocks Claude, so he couldn't use his usual tool at the client's office, and they've chosen Copilot instead. He has moved his workflow onto a new agent setup, which has 25 open questions for him. He plans a difficult conversation with his team tomorrow, telling them they can do much better and need guidance. He ends by recommending atmospheric electronic music from a radio show for dark walks.

Title: A Retrospective With a Former Client
Duration: 3:02

Simon finishes a client meeting with an old client, a retrospective on a project he worked on for about a year before a three-month gap. His main learning is that he should call out clients when they look under-resourced, and be more audacious about that. He plans to apply the lesson to his new project straight away.

Title: Lots of New Voices in the Mega Feed
Duration: 1:28

Simon puts the bins out and listens to the NaPodPoMo mega feed, enjoying hearing lots of new voices he hasn't come across before. He notices that some people introduce themselves at the start and end of their episodes, and he recommends doing the same, so new listeners know who's speaking. He ends by saying he'll keep this one short.

Title: Two Years of Audio Diaries, and a Gift to My Future Self
Duration: 4:02

Simon marks the first day of NaPodPoMo on Sunday 1 November 2026 by looking back at two years of his almost-daily audio diary. This is also episode 304 of his Audio365. He started again in November 2024 after being prompted by Bernie (@topgold) and inspired by Paul (@omaniblog) and NaPodPoMo. He has been transcribing old recordings and building a searchable database of them in Claude and Obsidian. Going through them, he found some from March and April 2020, a tough time at work, and found it striking to hear himself six and a half years later. He has long suspected the only person really listening to his diaries is him, and he still appreciates messages from Bernie, Paul, Clay and Joe. He urges others to keep a daily diary as a gift to their future selves.

With about $250 of unspent Anthropic credits on the last day of October, Simon spends part of a Saturday in Claude Code building an agentic system from an empty OneDrive folder. The orchestrator is called Dudley, after Anne Dudley of The Art of Noise. In under an hour, describing what he’s learned over two months, he gets an inbox processor, daily and weekly progress report agents, topic agents, a RAID log manager and a dashboard agent. He also gets a Needs Attention file, so questions come back to him one at a time. Test files from his old system were processed and prompted questions, and the dashboard shows seven items needing attention. He lists what’s still missing, including a vault map, a directory of people and project awareness. His main expected wins are being able to spin off new topic agents easily, and managing everything through one orchestrator and one chat window instead of monitoring many.

(The image attached is the dashboard, but I got Claude to turn it into lorem ipsum to protect client information.)

Title: Feeling Confident in My Setup, and in Myself
Duration: 3:56

From a Friday coffee shop at the end of his working day, Simon notes he's a day behind, having skipped his walk and his recording yesterday, though he did yoga both yesterday and this morning. He prepared this week's weekly report a day early, on Thursday, with the help of his Claude setup, so he could present it at a 9 o'clock check-in with his senior stakeholders. He's feeling more confident about his Claude and Obsidian setup and about his own ability to do the job. He's staying on top of the weekly reporting, and this week the team presented back to client stakeholders on a couple of the major topics, risks and all, and they seemed quite receptive.

Title: Is a Ribbon Worth More Than a Good Night's Sleep?Duration: 9:51

Simon walks in the dark woods after dinner, delighted that the fallen tree that had blocked his path has been cleared. He recounts last night at Toastmasters, where he gave a speech evaluation that focused on celebrating and unpacking a long, excellent speech, delivered it with energy, and won Best Evaluator, his favourite ribbon. Today was exhausting: he didn't want to get up, skipped his yoga mat, and had back-to-back double-booked meetings, including two more hour-long candidate interviews with senior leaders, and a headache all day. He also caught part of a presentation by colleagues of an AI tool that connects knowledge about products and projects, with a graph like his Obsidian one and MCP connectors, built at production scale. That leaves him wondering whether to discard what he's built or build alongside it.

Title: Presenting, Interviewing, Exhausted
Duration: 4:54

For episode 300, Simon walks back through London from the office after a long day. His client presentation went fine, and most of the day went on a long workshop where he met more people and became better known to them. He also sat on a panel interviewing a candidate, in a group-format session. It was a very high-stakes conversation for the interviewee, and it added pressure for him because the person he was interviewing alongside is an important stakeholder. He's exhausted after presenting, a Q&A and the interview, and used Claude very little. He plans to process his interview notes with it later or tomorrow, and still has an evening meet-up ahead, so it will be a long day.

Title: Using the Tool Instead of Building It
Duration: 2:40

Simon walks beside the road with his little flashing light and reports a good work day. It's notable because he spent little time in Claude, and mostly organised information and notes in Obsidian rather than running or training his agents. He got the weekly report done, applied extracts into his PowerPoint slides, changed a Confluence page, and had a one-to-one with his boss. He wonders whether the difference is simply using Claude as a tool rather than developing it. Tomorrow he's in the London office doing a presentation and meeting lots of people for the first time.

Title: A Weekend With My Daughter, and a Laptop Swap
Duration: 4:48

Simon catches up on the weekend. His daughter Emilia came home from university on Friday evening and stayed until Sunday morning, with celebrating, lots of food, cake and a windswept trip to the seaside. He describes her as such a ray of sunshine and a welcome presence in the house, and says they miss her. The visit was the occasion for a laptop swap. She now has his 2020 MacBook Air, which he'd left dormant for two weeks waiting for her, and she loves how fast, thin and light it is, running the latest macOS, Microsoft Office and iPhone mirroring. He takes back her 2015 MacBook Pro, which he once won in a work raffle, and upgrades it with OpenCore Legacy Patcher to macOS 13, the sweet spot since macOS 14 was too big for it. It has twice the memory and CPU speed of the 2013 MacBook Air he'd been using, plus a better display and battery life.