Been tossing receipts and invoices into a shoebox for a year, and tax season is creeping up. Last year was chaotic trying to sort it all out last minute.
I tried a basic folder system, but I’m curious if there’s a more effective way to manage this throughout the year.
Digital scanning works better than folders for me. I scan receipts right after getting them and dump everything into one computer folder by month.
Makes searching way easier when tax time comes around. Takes maybe 30 seconds per receipt but saves hours later.
I switched to a three box system after years of trying different methods.
Box 1: Business stuff that makes money (invoices, contracts, payment records)
Box 2: Business stuff that costs money (supplies, equipment, services)
Box 3: Personal tax stuff (W2s, medical bills, donations)
The trick is having a pen tied to each box. Soon as something comes in, I write the date and what it was on the receipt before it goes in. Sounds stupid but you forget what random charges were for.
I also keep a small calendar just for writing down cash expenses. Those $20 parking fees and coffee meetings add up but there’s no receipt trail.
This setup takes maybe 2 minutes when mail comes in, but my tax prep went from a weekend nightmare to a few hours of just sorting the boxes by date.
I just keep everything in one big envelope honestly.
Skip the shoebox completely and get a basic accordion file with monthly dividers. Costs like $5 at any office store.
Here’s what I do:
The key is doing it weekly, not daily or monthly. Weekly feels manageable and you won’t forget what expenses were for.
I also keep a small notebook in my car for writing down business trips right when they happen. Way better than trying to remember in December where I drove in March.
Just use two folders. One for money coming in, one for money going out. Sort by date later.
Get yourself a manila envelope for each month and label them January through December. When you get a receipt, write what it was for on the back and toss it in the right month’s envelope.
I keep mine in a drawer at home and empty my wallet into the current month every few days. Takes two seconds and you’re done.
Here’s a solid breakdown of the whole system:
Been doing this for years and my accountant loves me for it. No fancy systems needed.