As I am just entering the work force, I'm curious to hear about the financial status of the people replying to this thread. I understand if you're reluctant to share that here, but I think it would make a big difference. For example, if a lot of high-income earners/high wealth-owners in this thread tend to do X, I might be more disciplined to do X.
I would probably be considered high income/moderate wealth. I started tracking everything with Quicken back in the 90's when I realized I was just pissing it all away. I switched to MoneyDance when intuit started screwing with the Mac version of Quicken, and it does what I need. I track and categorize every expenditure and every account: cash, asset, liability, retirement, college, investment. I learned to do this from the book, "The Millionaire Next Door". They had results from a study they did that showed people who spend more time watching their money tend to have more of it over time (i.e. even if they started with little). After a while it becomes routine. I spend collectively 1-2 hours per month working on my finances.
Thanks for the book recommendation! I'll have to take a look at it.