23 Tools To Make Tax Season Less Horrible For Freelancers

Newfangled ways to capture, collect, and process your financial documents.

23 Tools To Make Tax Season Less Horrible For Freelancers
[Image: Flickr user jeff_golden]

In the U.S., the first few months of a new year are fraught with anticipation over the tax deadline. It’s not that filing taxes is hard, it’s the time involved that prompts procrastination. Thankfully, there’s a host of new digital tools that can make the process much less of a nightmare.


The whole ordeal is best broken down into three phases: Capturing financial information, organizing it, and processing everything. Each stage has its share of apps and online tools designed to lend a hand.


Scanner Pro is a fully featured scanning app which might be a little overkill for basic needs, but it’s perfect for freelancers or independent developers. Beyond the standard auto-detect objects, it also will let you fax directly from the app for an additional fee. [iOS]

Scantastic is a newer app that puts a little extra focus on style and design. Scantastic performs all the basics flawlessly and can auto-upload to multiple cloud services. Its one-tap scanning and uploading makes for some impressive UX design. [iOS]

Receiptmate is a slightly different take on the scanning app. It scans to Evernote and auto-detects amounts, keeping a running total with very little manual work on the part of the user. [iOS]

Doo Document Scanner is very similar to Evernote, but has a little more emphasis on scanning and getting existing documents into the app and keeping them synced across devices. [Android, iOS]

Quick PDF scanner is a free, easy-to-use app with plenty of features for power users. It also also imports from local and cloud locations and multiple file formats. [Android]



Evernote – The do-everything notebook app can be set up to keep track of expenses, income, and other random job-related tasks. It also works with a lot of third-party apps as a repository including things like FileThis Fetch, which will log in and retrieve all your online statements and documents.

OneNote – Microsoft’s all-in-one notebook app has been around a while, but still seems to elude a lot of its average office customers just looking for Word and Excel. If you’ve checked out One Note before but not been interested, the app has been updated recently across most platforms including Android, iOS, and the web. It might fit your work flow a little better with the new version.

Doo Document App – An alternative to Evernote, Doo can be hooked up to email accounts and other cloud services and used for every part of the document collection process. Scanning is also built directly into its desktop apps for Mac and Windows.

Dashlane – In addition to being a password manager, Dashlane also is able to keep track of online purchase recipes asking to keep a copy in its wallet feature at checkout. The most appealing aspect is that it extracts the data and numbers automatically, leaving room for manual corrections if need be.

Then there’s always the obvious choice of using cloud storage services like Dropbox, SkyDrive, soon-to-be-launched OneDrive, Google Drive, and Box.

Beyond just having a central location to collect tax-related documents throughout the year, all or most of the services allow documents to be tagged for quicker search later on.



IFTTT – Everything automated. From sending reminder emails to tying Evernote and Google Drive together. There’s a thousand different uses for finances and tax season. For example, you can have a recipe set up to track miles in Google Drive via text message.

Mint – Linking your bank account and credit cards is a good way to automatically tag your spending and track budgets. Mint will also alert you to high spending at different thresholds so you always know where your money went.

Google Drive/Docs – If nothing else, Google Drive provides a free and simple spreadsheet that can easily be accessed on your mobile device.

Wappwolf – Similar to IFTTT, but run out of your Dropbox. Adding files to different folders can trigger actions to online services.

Zapier – Again, similar to IFTTT, but with over 250 different services it can connect to including Stripe, FreshBooks, QuickBooks, and PayPal.

Expensify – The service works best when used within an office environment, but of course can be tweaked to work for the solo freelancer as well. Keep track of mileage, business trips, expenses, and export them in a way that isn’t ugly.


DocTrackr – The service allows you to send documents privately and securely with features like remote destroy, permissions, and even offers analytics. Best of all, it can be used within Gmail.

Square – If you’re accepting payments with the Square app, you have a simple collection of receipts verses having handwritten ones, or worse, no receipts.

Wave – An all-in-one accounting service that will let anyone keep tabs on their business expenses as well as accept and send payments. If you’re looking for an invoicing system, this might be the place to start.

FreshBooks – Another online accounting service that offers a free version. Users might have more name recognition with FreshBooks, but design wise, people might prefer Wave.

And last but not least, the IRS’s list of tools available, including its free federal income tax preparing and filing option.