466583_32876683I find receipts in the craziest places: not only do I find them in wallets and purses but it’s not uncommon to fish them out of the filing cabinet or out from behind the couch. After all, those tiny slips of paper can slide away the moment your back is turned. The only way to keep them in line is to have a simple organizational system. For years, the classic approach has been a shoebox stuffed full of receipts. It’s a great way to ensure that all of our bits of paper are in one place, but it still leaves something to be desired. Come tax season, we get the choice between handing that box to an accountant or sorting through them ourselves.

There are other plans that can make more sense: we can eliminate a lot of the work that goes along with tracking expenses with a little technology. The options below can simplify the situation and make for a smoother tax season.

1. Stick to plastic

If you can make all of your purchases with a credit or debit card, you may be able to eliminate your receipt collection. Most bookkeeping software packages can retrieve your account information for your accounts — and interpret it to a certain extent. There are certain drawbacks to relying entirely on your card statements, though. Most don’t specifically identify just what you’ve purchased and it can be hard to remember whether a particular payment to the bookstore last year was an education expense. Cash payments can also through a big wrench in the system — there are plenty of opportunities for expenses that you need to keep track of that will be cash only (think splitting a meal with a client). There are other specific issues that go along with whether you decide to use a debit card or a credit card.

You can annotate your expenses in most bookkeeping programs, though, so as long as you keep up with your receipts, you can avoid organizing and categorizing your receipts beyond once a month. It’s not a perfect solution, but it won’t make your accountant cringe the way that shoebox of receipts does.

2. Pick a service

For a fee, services like Shoeboxed will take your receipts and scan them in. They use a system that not only recognizes the text and puts it in a format you can use but it can also automatically categorize your receipts. Because Shoeboxed and other services typically operate on a monthly basis, the number of receipts you can get scanned between now and April 15th may come up short. However, you can do a brief triage on your receipts and eliminate all those that don’t actually affect your taxes: groceries, movies and what not may not need to be scanned, unless you’re working on getting all of your expenses and your budget under control.

Pricing can vary on such services. Shoeboxed has plans that go from $9.95 a month up to $49.95 — I consider that a deal. It’s significantly cheaper than paying someone to scan in your receipts for you.

3. Scan in your receipts yourself

At first glance, it might seem that scanning in your own receipts is a step backwards from paying a service to do it for you. But with the right equipment, you can pretty much automate the process at home. In this case, the right equipment is a scanner meant specifically for receipts: I’ve been using the NeatReceipts system and actually find it easier than packaging up my receipts and sending them off. I sit down in front of a television show or movie and feed my receipts into the scanner. Its optical character recognition is very good — for the majority of receipts, the scanner extracts all of the pertinent information and puts it in a format that I can dump it into my bookkeeping software (as well as saving it as a PDF).

Whether the price tag that goes along with purchasing a scanner just for your receipts is worth it can depend on how many receipts you plan to process: depending on where you pick up the scanner, the price can be more than the cost of a year’s basic plan at Shoeboxed — but less than a mid-level plan. Use it for more than a year, or scan more receipts with it than a service allows for, and it’s not actually all that expensive. And, as long as you’ve got the receipt, you may be able to write off the scanner on your taxes.

4. Going Old School

If you’d rather not spend the money on tools or services to take care of your receipts for you, there’s always the old school approach. You can enter your receipts into Excel or another bookkeeping option by hand. But it’s worth noting that such an approach isn’t just expensive in terms of time: it requires more discipline than most people are willing to devote to managing receipts. If you get even a little behind, it can seem absolutely impossible to catch up.

Other Services and Tools

I mentioned tools and services that I’ve actually had the chance to use and found reliable. But I know there are many other options out there — if you’ve used a service or tool to organize your receipts that you’ve particularly liked, please share a link in the comments.

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