No More Shoeboxes: Steal My Expense Tracking Workflow

No more Shoe Boxes! Paper Receipts are the worst- here's how to tame them

It appears in many of my clients’ homes. In certain seasons I’ve seen it growing in corners of my own home. It’s not mold, but it can be almost as upsetting: an unruly pile of paper receipts.

Okay, I’m a paperless advocate and professional organizer, but there’s still a lot of paper love in my life, sketchnoting at the top. However, when the 21st century revolution finally takes away the inefficient and maddening items that are paper receipts yours truly will be at the front of the crowd cheering and high-fiving babies.

Paper receipts can be a bottomless source of clutter, but today I’m going to teach you how to get a handle on them. That way come tax time next year you’ll click your track pad a few times to create a sharp looking expense report for your tax person, and be free to continue doing the real work of your life. Without any Target receipts from June 2002 standing in your way.

Obligatory disclaimer: I’m not a tax professional, so your mileage may vary. Bounce these ideas off your own tax professional.

Be aware at moment of impact

You’re out in the world, running your errands as a productive citizen of the world and suddenly a cashier hands you a receipt. Or the slightly more progressive version of the scene: the cashier says, “Would you like your receipt?”

This is the moment of impact and without some simple planning that receipt has the potential to be the cherry on top of the 10-year-pile-of-paper-receipts-sundae oozing all over your dresser.

A lot of times you keep receipts because of the false importance computer formatted paper conveys: “Ah look at this nice summary of everything I’ve purchased in this legible font, surely this is important and I need to keep it.” However, that’s rarely true – but here’s the main reasons you might want to keep the receipt:

  1. Tax deductible expense: If you file as a business then you’ll want to keep certain receipts as proof for the IRS and to track your yearly expenses.
    Tip: take some time to know exactly what categories you can and can’t expense for your business. That way you can make a decision right then and there at the moment of impact: is this something to track or is just recycling fodder?
  2. Specific purchase: A big screen TV, an iPad, something of a significant price and value. Even if it’s not deductible you want proof that you bought it on that date for warranty related issues.
  3. Is it all here?: The super diligent might want to check off their grocery receipt once they get home to make sure everything made it in their bags. That’s fine, but then trash or shred the receipt unless either of the two reasons above apply. (Although if you’re buying an iPad at your grocery store, let’s talk.)

Do You Want A Receipt? Flowchart

Repeat this over and over: a paper receipt is a hot potato, a paper receipt is a hot potato, a paper receipt is a hot potato…

Okay, say you accepted a paper receipt because you clearly recognized it as a tax deductible receipt due to a few minutes of studying your deductible expenses from last year’s return. But that receipt is a hot potato, my friend! We need to capture it quickly in digital form and get rid of it before it makes it to the dresser or even the bulging shoebox.

In my last post I explained why I believe Expensify is a more suitable option for this capturing than Evernote and my hot potato elimination routine is taken directly from Brooks Duncan’s post and video: “Paperless Mobile Receipt Workflow With Expensify And Genius Scan.”

Brooks writes:

“I try to capture the receipts as soon as possible – sometimes even right there at the table.”

This is the hot potato mentality in action and if you’re consistent you’ll find the sweet relief that comes from emptying your pockets at the end of the day and finding no crumpled paper.

A lean, mean set of reports in Expensify

When you export receipts from Genius Scan to Expensify they go into a section appropriately titled “Receipts.” (Go figure.) From there you can fill in and correct data like: merchant, cost, and what report you want the receipt you want attached to.

Here’s the reports I’ve created for 2015:

  1. Bos Organization: all my business expenses.
  2. Medical: in my experience you need to spend quite a bit on medical in a year for it to count as tax deductible. Luckily at this point in our life these expenses are at minimum, but I still want to track them…just in case.
  3. Donations: it could be an emailed monetary donation to a non-profit (more on email receipts, next) or a scanned Goodwill donation.
  4. Childcare: here’s an instance where looking at my return for last year helped set me up to track the right things this year. We get reimbursed for a decent chunk of our childcare expenses through my wife’s work,but it certainly doesn’t cover all of it,  so by tracking all the after-school programs and summer camps here, it’ll make totaling all of this next year a snap.

What about emailed receipts?

Glad you asked, as this is one of the features that sold me on Expensify. Any receipt you receive in any of your inboxes can be forwarded to and poof! it’ll show up in your “Receipts” pool just like the scanned receipts. You can also upload PDFs and other files on your desktop from its web app.

Paper is great, but paper receipts that build up in mountains of undefined stress stink. Try this workflow out and make it your own, you’ll no longer feel the tiny tyranny of little slips of paper in your house.

What’s your biggest obstacle in keeping paper receipts organized? Let me know in the comments below.

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  • Anna Hayman

    Unfortunately most receipts are coated in BPA and are not recyclable! Only recycle matte receipts.

    • Ah, didn’t know that, but it makes sense! Another reason for me to look forward to the extinction of “paper” receipts.