Knowledge Base


Friday COACHWORX Business Tip: Getting organized for tax season

Although you swore it wouldn’t happen again, we’re guessing that there’s a table in your house somewhere that’s completely covered in receipts and bank/credit card statements from the past year that you now have to go through piece by piece to prepare your tax return…

Somehow you’ll get through it – you always do – but the really important thing to consider is how you’re actually going to do something about it next year. What system are you going to use from now on to stay on top of things – if you actually have the discipline to use it?

No one filing system will work for everyone, but whether you’re a paper person or a digital hack, one of these optins might work for you:

There’s an app for that…

If you do everything on your phone, you might want to consider downloading an app to track your receipts.

Expensify lets you scan and file your paper receipts by category, and will even help you track things like mileage. However, while Expensify can be used to track receipts it was designed to help users create expense reports rather than track an owner’s operating costs. It’s a small difference, however, and you can still use this app effectively.

Receiptmate, available for Android and iOS, does the same thing while using Evernote to store images of your receipts as well as your data.

There are other options to consider as well like Receipts by Wave and SmartReceipt that do roughly the same thing. You can also download Microsoft’s OneNote and use a notebook and the image features.

Advantages – The advantage of going digital is that it automatically saves a digital version of your receipts so you don’t have to worry as much about losing the paper version. It also organizes the data by category (e.g. travel, car, food, office supplies, etc.) so you don’t have to do that again when putting your taxes together.

Disadvantages – Using an app takes a lot of discipline. If you can get into the habit of using it every day, or even every time you get a receipt, then you’ll be laughing at tax time. However, if you’re still stuffing receipts into your wallet with a vague plan to scan them at a later date then you’re going to get into trouble.

Pushing paper … into all the right places


A lot of people still cram their receipts into briefcases, wallets and shoeboxes at the end of the day. If they are really organized they’ll collect those receipts at the end of every month and stuff them into a labelled envelope.

Paper systems can work, however, if you take an extra moment to file things properly.

For example, you can get an accordion folder at any office store that will let you organize your receipts by month or by category.

The problem with paper systems is that you can’t file them both ways unless you take the time to organize category receipts by the date they were received, or by writing the category on the top of receipts you’re filing by date. It’s not impossible, but it requires an extra step to be effective.

Your monthly credit card statement also complicates things – it’s hard matching up January receipts to a statement that runs from Dec. 15 to Jan. 15. Some people have decided not to fight it and now file their receipts according to their printed statement dates.

One of the best systems for tracking numbers requires a bit of redundancy, filing paper receipts while also logging those receipts in a daily business journal.

Advantages – You need to keep the paper anyway and it’s sometimes easier to stuff receipts into envelopes or folders than get your phone out and enter a bunch of data.

Disadvantages – Receipts can get lost or destroyed, and unless you take the time to file them correctly you’re going to be in the same situation where you’re dumping receipts on the table with one hand while popping antacids with the other.

Make filing a habit

The bottom line is that no matter what system you decide to use it’s not going to be successful until you’re disciplined. Discipline is all about making good practices a habit.

For the first few months try adding a reminder to your phone to file your daily receipts. Or put your receipts somewhere that you have to walk by them multiple times every day – like a bright red box with the words “FILE ME!” written on the side. Maybe add a photo of your dining room table at tax time for emphasis.

You also need to set aside a little bit of time every day if you want to avoid the hours-long slog through boxes of receipts. Maybe it’s the first thing you do in the morning after you get up, or the last thing you do before you leave work for the day. Maybe you shouldn’t pay yourself or allow yourself to cash your cheque until the job is done. Or maybe you can find a way to reward yourself for staying on track – like buying a case beer you like at the end of the month or treating yourself to lunch at your favourite restaurant. Any incentive will help to build better filing habits.

Lastly, you need to be consistent – pick a system and stick with it. The last thing you need next year is to create even more work for yourself by digging through apps, envelopes, accordion folders and shoeboxes to find everything you need to file your taxes.

Filed Under: Overview.

We'd love to know what you think.