I do it kind of like DollarBill, but I'm not so organized, so I use YNAB to help with this. I have one savings account with Smarty Pig (but separate goals within the one account) to track intermittent things like preschool tuition (paid Aug & Dec), insurance (life, car, and renters, some paid 2x/yr, some annually), vacation, and other planned larger purchases (new mattress.) Smaller things, like the occasional swimming lesson or birthday gift, home maintenance expense, that just sits in the checking account, but is earmarked by YNAB for the specific purpose. We keep a 1K buffer in the checking account, but I'm thinking about moving towards a full month expense buffer. Also, if you are in a joint household, YNAB is great w/ auto syncing. I actually have yet to get DH on board with using YNAB, but he is pretty diligent about reporting all expenditures to me so that I can keep it updated.