I am not an obsessive compulsive person by nature - I am just low on that spectrum. I'm a bit compulsive about keeping track of my money now though. I keep track of every dime and where it goes. I have a spreadsheet with dozens of 'line items' and I separate paper towels from groceries from cat food even if I have to go down a list for $300 worth of junk at Walmart to do it. I think that simply comes from years of scrambling and trying so hard to keep track of money to pay the bills when someone else was always sabotaging the family budget (but always the first to enthusiastically make a new budget or get excited about a new plan - my god how crazy making - words and follow through actions were so opposite). I had zero ability/success with planning anything for the future (near or far) with our money and felt so insecure because of it.