I've been using YNAB for two weeks now and I love it. I've done quicken and spreadsheets. They are backward looking historical records of where you spent your money. With YNAB, it is forward looking in that you set a budget each month in your own categories. Instead of thinking "I have $1,500 in checking, I can buy that pair of shoes", you look at your clothing budget to see what's available to spend. $50 a month for me. Since I won't be buying anything in May, in June it will show a $50 budget plus a $50 carryover giving me $100 available for clothing. If I overspend in clothing, it's rule 3, roll with the punches. I can just tell it to subtract from next month's budget amount, or just transfer some money from some budget category that I am underspent for the month, like golf and hobbies, or gas, or groceries. I have sinking funds set up for everything, car insurance, home insurance, lawncare, homeowners association, property taxes etc. I have one budget category called Buffer that is $100 a month for stuff I haven't budgeted for. When income comes in, you give every dollar a job - maybe you put some in your fun money budget, increase your groceries budget, or add it to your investments budget. Again, you change your mindset to check your budget, not your checking account balance.