I've been making investment mistakes and trying to learn from them for 15 years now. Recording a couple sentences about your reasons why or why not helps a lot. People aren't naturally good at learning from decisions with long feedback delays -- you have to keep notes.
I wish I had decision notes from earlier life choices, like why I studied EE instead of CS, why I chose my PhD advisor, why I joined companies, got married, etc.
I keep track of investment decisions, but not life decisions...life is too big for me to have it tracked on excel.
But I hear you...sometimes you lose sight of your big goal. It helps to have your goal/vision engraved in your mind, it helps to write and dream about it.
After a year I go back and compare my ratings to how much each startup raised, IRR..etc.
In the first batch I rated one of the startup 1/5, after a year, when the startup raised a lot $$$$ I went back to my comment on why I rated it 1/5
My note said “too niche”
It hit me and I realized it was as if Jeff Bezos was pitching me Amazon and I said e-commerce for books only! This is a niche market.
It’s very helpful to go back and read your comments about these startups. You learn with every startup you mess..