I generally hate tax season because I don't organize all those receipts during the year for deductions on my income property. I have to sit there sorting out all of them, what I can claim 100% on, 50% on, and if I paid anyone over six hundred bucks a year provide the information of who I paid it to. I just have a tray I stack them all on and sort them out at the beginning of tax season. About the most I manage during the year is a general rule of thumb, no receipts go in the trash until I make sure there's nothing I need to report at the beginning of tax season. The time consuming part is writing them all done in a ledger as receipts have a tendency to fade over time, so I number the receipts to the same number on the ledger and write down everything that was on the receipt. When I had my own business too, it was pretty much the same thing, only a lot more time consuming. Plus I had an apartment above my business that I had to keep track of, so finding a way to get it all organized, set yourself into a pattern, helps a lot.