Hello, my imaginary friends

After a busy work day juggling multiple urgent tasks, Simon describes using Obsidian to capture everything as a to-do list so he can focus on one item at a time rather than holding it all in his head — an upgrade on his old notebook approach, though he's wary of falling into analysis paralysis by over-managing the list itself. He's musing about eventually improving his Claude to-do-list sk...

Simon recounts a hectic day as contest chair for his Toastmasters Table Topics contest — a last-minute entrant signed up mid-day, forcing him to reprint a certificate and redesign the programme for a fifth contestant, who then went on to win. Despite the curveballs, the evening ran smoothly with no mistakes, a strong new chief judge, and high-quality speeches throughout. He reflects on handing ove...

After a couple of minutes of silence by his favourite tree, Simon reflects on stumbling across a shared meeting transcript at work showing colleagues casually discussing their own AI experiments in their spare time — reassuring, since he's not the only one doing this, though he also feels behind. He watched another internal AI-initiatives video on installing Git and the GitHub CLI to work with...

A short one: Simon fits in a quick after-work walk in the woods since dinner's nearly ready, spots a couple of muntjac deer and manages to snap a rough iPhone photo as proof, then pays a brief visit to his favorite tree before signing off.

Episode 247/365 of *Hello, My Imaginary Friends*, recorded Friday 4 September 2026. Sm2n reflects on the number 247/365 falling on this episode number, then covers: cashing in health-insurance activity rewards for a free coffee and — after a month of hitting step goals — a free lunch in London (which still cost £40 in parking and train fares). Also: leftover cauliflower-and-potato curry with a boi...

A short one: Simon went into the London office for the first time in a couple of months, prompted by his newer client being on-site. The main person he'd hoped to meet had to cancel due to personal circumstances, but he met several other colleagues face-to-face for the first time. He's weighing an in-person visit to the client site as an alternative next step.

Sm2n 2026-09-02 #audio365 (245/365) A quieter day: a stakeholder meeting got postponed, but Simon still sent the slide deck so the update counts as delivered. He experimented with a local transcription tool ("hear") on his Mac to batch-transcribe four months of backlog voice memos. He used Claude/Obsidian to build an ad-hoc topic-summary lookup and is considering turning it into a skill that scans...

Simon debates the "refresh task" skill's checkbox-scanning logic with Claude: Claude wanted to re-scan every file for thoroughness, Simon argued for just scanning the open tasks list for efficiency. Simon's approach won, with an accepted blind spot (tasks checked off before their first scan get missed). He reflects on how natural it felt to hash this out like he would with a human developer.

A productive day with Claude: built a title-generator skill for his audio diary, migrated his to-do-list skill to his work computer (Claude self-diagnosed and fixed a memory error), and built a new RAID (Risks, Assumptions, Issues, Decisions) log skill in Obsidian through conversation with Claude, including a review pass that caught missing assumptions. Also turned his transcript-formatting workfl...

Sm2n 2026-08-31 #audio365 (242/365) tea and Todoist

Sm2n 2026-08-29 #audio365 (241/365) I created my first Skill.md !

Sm2n 2026-08-28 #audio365 (240/365) I was missing mcpServers {}

Sm2n 2026-08-27 #audio365 (239/365) that’s why you’re supposed to put the milk in first?

Sm2n 2026-08-26 #audio365 (238/365) enjoying a silent walk, imagining my perfect AI operating system

Sm2n 2026-08-25 #audio365 (237/365) why must the show go on?

Sm2n 2026-08-24 #audio365 (236/365) emergency speech prep

Sm2n 2026-08-24 #audio365 (235/365) hitting token and context limits

Sm2n 2026-08-22 #audio365 (234/365) I've now got Claude integrated to my Obsidian by following the instructions in this video: https://www.youtube.com/watch?v=_PiRCPnQmgk using MCP… so still using the free version of both Claude and Obsidian, and keeping my files off the cloud

Sm2n 2026-08-21 #audio365 (233/365) the best time of day to learn AI

Sm2n 2026-08-20 #audio365 (232/365) checkbox thoughts @topgold

Sm2n 2026-08-19 #audio365 (231/365) work was OK, though

Sm2n 2026-08-19 #audio365 (230/365) it was the wrong kind of speech for at least one person

Sm2n 2026-08-18 #audio365 (229/365) Claude and Obsidian in action, inspired by @topgold

Sm2n 2026-08-17 #audio365 (228/365) I’ve waited a year for this tea

Sm2n 2026-08-17 #audio365 (227/365) speech prep for tomorrow