Ask me if being a freelancer is awesome and nine times out of ten I will emphatically say, YES! You get to live basically anywhere you want (anywhere with a steady internet connection, that is. ) You get to work in your footie pajamas, take spontaneous naps with pets, and grab lunch with old friends who are only in town for a brief layover (hopefully you change first.) If what I am saying is making you feel even the slightest twinge of jealousy, STOP. Like everything in life, the grass is greener on the other side. 

Anyone who has ever freelanced, been self-employed, or owned a business knows how daunting this time of year can be. Like many others, tax season is the equivalent of getting dragged by your toenails through Dante’s nine circles of hell. Seriously, this stuff sucks. 

Our tax system is flawed (but you already knew that) but luckily there are things out there that can make your life a whole H E L L of a lot easier (pun intended.) Below are there things that have literally kept me from balling up in the fetal position and crying for my mommy:

Receipt Manager 

There is no reason why you should have a folder or envelope stuffed full of crumpled (or worse—fading) receipts. In the era of modern technology, there is most definitely an “app for that.” While there are lots of apps out there that aim to help you keep track of receipts and expenses, I happen to like Foreceipt because it automatically syncs to my Google Drive (which I use daily to manage client proposals and projects.) The best part is that once I’ve taken a picture of the receipt, I can crumple those pesky things and never have to see them again.

Credit Cards

I know what you’re thinking, credit cards are the devil. Debt is bad. Cash is king. Well you know what—I love my plastic! And here’s why, not only is it a great way to keep track of my spending, but many credit cards offer rewards for loyal customers. For example, my Southwest Credit Card (powered by Chase) delivers beautifully organized expense reports going back 2 years. Not only that, but they gave me two roundtrip tickets when I signed up. Now don’t get me wrong, I’m not advocating that you take out a bunch of lines of credit and max them all out. Instead, consider using your credit card for all business-related purchases and then pay your card off monthly (racking up interest defeats the purpose of receiving benefits, after all.) 


As I was getting pulled further and further into a TurboTax vortex I quickly realized I needed some musical motivation to keep me afloat. I could feel my shoulders starting to slump, my mind slowly turning to mush and my eyes growing heavy, or maybe those were tears, either way I was in too deep to turn back. I fought the urge to call my mommy and instead turned this song on. Within a few seconds, I felt motivated to keep going: 

Hustler, Simian Mobile Disco

Needless to say, though these thing above helped, I am still no where near finishing my taxes. I have to wait 14 business days for Healthcare.gov to send me a corrected 1095-A form. Until then, you can find me banging my head against the wall.

Nicole Paulus, Nico New Media

Photo Credit, Flickr

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