I Asked AI What to Do With the Next 5 Years of My Life
In a Nutshell
AI retrospective analysis of personal decisions reveals memory is consistently 20% inaccurate and startup stories become heavily sanitized over time, while AI tools now enable 20-year decision audits in hours rather than years. AI excels at refining existing ideas and cross-referencing health data but struggles generating original concepts, and its productivity gains mainly accelerate low-value work. The most valuable application is asking AI open-ended questions about five-year career and life directions with full conversation history, producing high-quality suggestions that match friend-level insights.
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Using Claude code with Ferris APIs to conduct a 20-year retrospective analysis of angel investing. The analysis examines who made what introductions, which companies were not replied to that ended up being successes, and which companies were turned down that ended up being really important. The goal is to test personal stories against actual data rather than relying on remembered narratives about why certain decisions were made.
A wearable device categorizes AI and listens 24/7, revealing that people typically know about 70% of what they think they know. The device demonstrates memory discrepancies, such as when someone requests a dark chocolate bar at 7:00 p.m. but the recording shows it was requested at 5:00 p.m. and specified as milk chocolate. This reveals that memory is consistently about 20% off from actual events.
Startup genesis stories undergo significant sanitizing and editing over time. Founders work on material for so long that they come to believe their edited version is the actual truth. This applies to both public storytelling and private self-narration, where individuals are not exempt from this memory editing process.
LLMs provide significant value in holistic health management by synthesizing data across medications, supplements, predispositions, side effects, and historical health events. The speed and depth of analysis allows for interrogation of complex health questions. The primary benefit has been avoiding potential disasters by checking contraindications between substances and determining whether symptoms A, B, or C could explain symptom D.
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