Sounds like you just need some cash reserves. Pull out your bank statements for the last 6 months or so and figure out on average when your expenses and desposits take place then just mark out on a 30 day calendar when & how much your inflows and outflows are with a running total of aproximately how much cash you need in the bank to cover the expenses. For example: On day 5 I have to pay insurance of $200, on day 8 & 16 I have to pay employees for X $. These are based on averages so you'll need to add some fudge factor to the numbers. For my one timers, I bill them immediately after service. Unless it's around the 1st of the month, then I just bill them with my other customers to make my life easier. All of my monthly service customers get billed on the 1st of the month for that month's services I am to perform. I switched to this last year and I love it, and my clients don't have a problem with it. I don't give them a due date per se but I do send reminders on the 15th to those who haven't paid yet. Typically almost all of my clients have paid me by the 15th so I have yet to have a need to institute "due dates." I have one 90 year old lady who is slow to pay sometimes but she always pays me so I don't really worry about it. I've been meaning to go pickup a credit card reader to offer credit card billing. I'm almost at the end of the season now so I'll probably just wait til the spring.