Six Months of Turning Diaries, Sleep and Finances Into AI Podcasts With Claude

Jaan Altosaar (thejaan) published a long post recounting six months of "lifelogging + LLM": he fed hundreds of Obsidian notes—journal entries, todos, doctor's notes, financial and sleep data—to Claude to produce weekly 15-minute personal podcasts. He says he was first moved to tears by AI while listening to one episode on a bike ride, then wrote a full guide so others can try it.

Confirmed

Episodes weave together journals, sleep and financial data, 15 minutes each; he used the setup for six months and published a complete guide including guardrails.
Hallucination rate: roughly 10% of model-generated sentences are fabricated, e.g., one claiming his father was recovering from surgery in Estonia.
Guardrails: no memory retained between sessions; no follow-up questions to avoid seeking comfort from the model; a fresh session every 5–10 weeks.
Context engineering: instead of dumping all notes, feed only "what changed" (a track-changes-style diff), leveraging Obsidian's built-in version snapshots for high-quality output.

Why it matters

This is a rare long-term personal LLM practice record with a quantified hallucination rate and explicit safeguards. It shows both the emotional impact of models connecting personal data and the 10% fabrication rate and dependency risks, offering readers building life-review apps a reusable method (data sources, diff-feeding strategy, guardrails) rather than a mere experience share.

2026-09-24 ~ 2026-09-24 · 5 related posts

Primary sources

Claude-Generated 15-Min Podcast Linking Journals, Sleep and Finances Made Him Tear Up — thejaan · 2026-09-24 01:10 (UTC+08:00)
Context engineering trick: feed LLMs only what changed, via Obsidian edit snapshots — thejaan · 2026-09-24 01:10 (UTC+08:00)
~10% hallucinated sentences: guardrails for lifelogging with LLMs — thejaan · 2026-09-24 01:10 (UTC+08:00)

Lifelogging with LLMs: weekly Claude podcasts from journals, sleep and finance data — thejaan · 2026-09-24
[source] Claude-Generated 15-Min Podcast Linking Journals, Sleep and Finances Made Him Tear Up — thejaan · 2026-09-24
[source] Context engineering trick: feed LLMs only what changed, via Obsidian edit snapshots — thejaan · 2026-09-24
[source] ~10% hallucinated sentences: guardrails for lifelogging with LLMs — thejaan · 2026-09-24
Six months of Claude-generated personal podcasts linking journals, sleep and finances — mrdrozdov · 2026-09-24