I have to agree with garli above, in that YNAB is not for everybody. I am a super duper on-top-of it budgeter and I get tremendous joy out of beating my budget (as in, underspending my allotments every month) and I’m definitely a Genie and not a Kate, but I cannot stand YNAB’s interfaces. I tried it for a whole month (or however long their free trial is) and I just could not like it, even though I know a lot of people raved about it over Mint (I prefer Mint and use it every day). So I’d encourage Genie to maybe relax your stance on YNAB as the solution here, because maybe Kate could benefit from a slightly less rigid budgeting system. I wonder if Kate may have better success if she didn’t feel like failing at YNAB was failing at budgeting.