How To: Organize Your Paper Trail STAT!

If you’re a cash-only person and you don’t hang on to old bills, stop it! Ask for receipts to help you track where the money is really going. And don’t crumple them and toss them into your purse, only to find them smooshed up with gum at the bottom of your purse (not that I would know anything about that…). At the very least, keep your receipts in a container or a large envelope. Even better, set up a filing system to separate the different categories of expenses: one folder for food, one for rent—you get the idea. Keep it on your desk or anywhere you can get easy access to it. Once a week, or even once a month, go through the receipts you’ve collected and drop ’em in the folders. This may sound a little old-school, but it works for me. If you want to be more new-school, there are lots of websites and apps that will scan and organize your receipts for you, too, like Shoeboxed and OneReceipt.

And while you’re getting a handle on your expenses, organize your paper trail moving forward, too. You will thank me when your favorite time of year rolls around: tax time! You don’t have to save all of your receipts for deductions and whatnot, but those related to business, charitable donations, mortgage, student loans, and medical are a must. Here are a few scenarios and the types of receipts you should save for each:

• If you work out of your home: utilities, cleaning supplies, office supplies
• Travel expenses for work: hotels, flights, car rentals
• All work-related things: cell phone, internet, trade books and magazines…pretty much anything you purchase for your work (it could be paint if you’re an artist, dog treats if you’re a trainer, wigs and big shoes if you’re a professional clown)
• Business meals/entertainment: meals, games, shows, wherever you take clients to do business (but FYI, there are a lot of restrictions for deducting these, so be sure to document who, where and why for each receipt)
• Anything medical-related: premiums, prescription drugs, contacts, medical tests (not over-the-counter stuff or “preventative” treatments like…spa days)

It’s time to get organized, bitches… and get it all.