In this first post of (likely) a multi-part series I’m going to discuss how I am using machine learning, AI, and good old-fashioned elbow grease to make sense of the 3000 files in my ~/Documents/Unfiled directory. The Problem Statement There are several contributing factors to the problem. Let’s start with the obvious ones: I’m a digital packrat I’m a single parent of 3 (and therefore busy) I can be lazy sometimes I have ADHD, and get easily sidetracked from things I intended to do When my dad passed away last year, it got even worse.

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