I found quicken to be enlightening. It took me two months to master my family’s finances and budgeting and I’ve never looked back. Learning it’s ins and outs and why it is what it is and provides some features but not others was a wonderful learning experience.
I worked with John Wiegley for a couple of years and discovered one of his projects, Ledger (https://ledger-cli.org/), during our conversations. This tool taught me double-entry accounting and helped me understand finance and blockchains on a deeper level.
Unfortunately, I’m too lazy to use the tool on a daily basis, so it’s the second most insightful piece of software I’ve never used :D
