[mdeck_]

Planning to do sentiment analysis in the future on your own writing that you’re also planning to do in the future seems like using a cannon to kill a mosquito—way overA-powered and unlikely to yield nuanced results anyhow. Why not just add to your journal entries a few quantitative (incl. multiple choice) measures of how you felt each day? Then there’s need to deduce anything about how you probably felt—it’s right there in black and white, and with much more nuance.

The rest of your self-tracking sounds like a fun project.