I use YNAB (YouNeedABudget). I am insistent that DH hands me his receipts so that I can break up a convenience store purchase into his cigars vs food for instance. You can link your accounts to the software so most of it is automated like Quicken. I'm with you. If I don't know what I'm spending money on, I feel like I'm lost in the middle of a forest. I need the signposts.