Hello, my imaginary friends

Mistakenly said it's episode 266, but it's actually 265. A second episode from Simon today, recorded walking home rather than to his usual Toastmasters club (he skipped it for a night off after attending a different club earlier). He drifts into a long nostalgic tangent about old chip speeds and 1990s workstations, triggered by the episode number. The real thread: he's sketched a rough voice-memo...

Mistakenly said it's episode 265, but it's actually 264. Simon spent a walk-and-talk episode reviewing three different ways he used Claude while building a presentation. He dictated a rambling problem statement via voice mode (and wasn't a fan of it talking over him), then had Claude tighten it into a punchy line for his slide. He fed Claude his colleague's two-option write-up (dra...

Sm2n 2026-09-21 #audio365 (263/365) A Good Deed for a neighbouring Toastmasters club

I learned today that apparently I’m boiling my eggs the wrong way, and I wanted to cross-check this with @omaniblog and @topgold and anyone else who might be listening

On day 261 (18 September), SM2N talks through his pipeline for turning old Audio 365 recordings into Obsidian notes — transcribing on his Mac, then having Claude summarise, title, and clean each one up before deleting the original from the inbox. He's found a mystery duplicate "episode 190" to sort out later, and is still trying to train Claude to recognise "thanks for listening to... Toodle-boo"...

Simon adds a postscript to yesterday's entry: on his evening woodland walk around 7pm, he noticed an unusual stillness in the air and a group of deer that let him get much closer than usual, seemingly unbothered by his presence. He reflects on the calm, atmospheric feel of the walk without settling on a cause — season, weather, time of day. He's now walking to work in London, heading into...

On his evening walk, mostly in reflective silence, Simon reports that his Miro-based roadmap plan is going down well at work — colleagues want to steal the format, and he's pleased with how collaborative it's become. He puzzles through a comment from @soulcruzer about running Claude, Codex, and a Kimi model inside Obsidian, then describes watching a colleague run Claude via a community plu...

A short extra walk to top up his step count while tea brews, but the real story is a lovely evening: a spontaneous Signal video call with Bernie from his favourite tree, who gave him a tour of his garden and talked through some of his own challenges and solutions — genuinely valuable, despite Simon's phone repeatedly crashing the call with storage issues. He also had a properly mind-bending moment...

A calm post-work walk under some genuinely lovely low, cloud-broken light, worth considering for the episode's cover art. Work-wise, Simon spent most of his day building a Miro-based programme roadmap rather than using AI, and reflects with some scepticism on AI industry leaders (OpenAI, Anthropic, xAI) publicly warning about the dangers of their own technology while pushing for regulation — r...

A meta episode: Simon walks through how his own transcript-cleanup pipeline works — a Mac script transcribes his archived audio into text, then Claude cleans it up into proper sentences, fixes recurring mishearings (Miro board, Emilia, Bernie/@topgold, @omaniblog), writes a short summary, and offers three title choices. He's now processed almost two months of episodes and is brainstorming what...

Sm2n 2026-09-11 #audio365 (255/365) 25 years since The Twin Towers attack

Sm2n 2026-09-10 #audio365 (254/365) Worried about German politics

Episode 253 of Hello, My Imaginary Friends , recorded Thursday 10 September 2026. Simon makes headway on his prioritised to-do list at work, then works through duplicate-task handling with Claude. Claude proposed merging duplicates into a single row with links to both source notes, a combined description, and inherited owner/priority/creation date — but Simon preferred clustering the two duplicate...

Episode 252 of Hello, My Imaginary Friends , recorded Thursday 10 September 2026. Sm2n takes a longer-than-usual evening walk in the woods to make up for missing his step goal by 800 steps the day before — spent almost entirely on a work call, so no podcast or quiet processing time. As the walk went on he needed his head torch to navigate an unfamiliar route, and the bright light caught the eyeshi...

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 !