Claude and Obsidian Turned Her Inbox Into a Daily Brief | Natasha Lee, AI Consultant

Nat Lee has a lot going on at once. She’s running projects, teaching, making content, managing partnerships, and dealing with the hundreds of small things that come with all of that. And email was becoming the place where all of it got messy.So she built a second brain using Claude and Obsidian.In this episode, Nat opens up the whole system and shows how she uses it day to day. Emails get pulled into Obsidian, deadlines and commitments get tracked, and a daily brief tells her what needs attention and what’s overdue.She also shows what went wrong along the way. Dates were one of the first problems. If an email said “tomorrow,” Claude couldn’t just guess what that meant. So she started giving every email its actual sent date and made Claude calculate the date from there. Then there’s her knowledge wiki, which helps Claude find the right information without having to read hundreds of documents every time.In this episode:* Why Nat chose Claude + Obsidian for her second brain* How an incoming email becomes a task and appears in her daily brief* How she manages context across multiple projects* Why giving AI access to everything can actually make it worse* How she wants to move from multiple agents toward an AI chief of staff* The biggest mistake people make when building their first second brain* How to start building your own system without making it an emotional hurdleTimestamps:(00:00) Introduction(00:37) Why Nat built a second brain(01:45) Inside her Claude + Obsidian setup(02:44) Why Claude + Obsidian?(04:36) The problem with AI getting dates wrong(04:57) How she makes Claude calculate dates correctly(07:27) How much iteration did this take?(08:38) Why not just use a calendar?(09:17) Live demo: email to Obsidian(10:39) How the daily brief works(11:45) Turning email into task management(13:30) The biggest challenge: managing context(15:57) Building toward an AI chief of staff(17:06) Where the human stays in the loop(19:24) How she manages context with Claude + Obsidian(19:42) Building a knowledge wiki(21:35) How she organizes documents inside the wiki(23:36) Live demo: Claude builds a knowledge wiki(28:18) How to improve the wiki with your own context(29:13) How to build your first knowledge wiki(31:32) Start small and keep it manageableResources & Links:* Claude Code: https://claude.com/product/claude-code* Obsidian: https://obsidian.md* Token Thoughts: https://www.linkedin.com/newsletters/token-thoughts-7460866816886824961/Connect with Natasha Lee:* LinkedIn This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit shippingwithai.substack.com