When you woke up this morning, your first thought (after thinking “Nice. The world didn’t end.”) was probably something like “Dang. The world didn’t end. Now I have to deal with my self employed tax deductions.”

Whether it’s deductions, taxes in general, or scrambling to gather slips of paper and receipts that have been collecting dust for 12 months, the end of the year can be a seriously stressful time for small business owners, freelancers and the self-employed.

With a mere 10 days left in the calendar year, and a quarterly tax due date just around the corner (that’d be January 15, 2013, in case you’re interested), even the most diehard procrastinators are beginning to admit that the time has come. Though shalt do thy taxes.

If a post-apocalyptic countdown isn’t enough to get you geared up, check out our completely non-businessy list of ways to motivate yourself to move those self employed tax deductions from the to-do list to the DONE list!


Finishing your taxes can be a massive task, especially if you’re a solopreneur running a one-woman or one-man show when it comes to your business. If no one is going to do your taxes but you, and you’ve waited until now to start getting organized, you may be facing a project as big as those stones the Mayans used to predict our December 21st expiration date.

In order to get motivated to dive in to your taxes, bribe yourself with a treat that is more enticing than the dread surrounding your deductions. This is not the time to splurge on a chocolate bar or a new iTunes download. We’re talking about some serious carrot dangling here. Spoil yourself with something along the lines of:

  • A massage. A 90-minute massage.
  • A long weekend at the most exotic location you can reach by car in 5 hours or less.
  • An entire day (24 full hours!) with the phone and computer turned off, the guilty pleasure marathon of your choice on TV, and a tube of cookie dough for dinner.


After reading the Shoeboxed blog all year, you’re obviously armed with a crazy amount knowledge as to what qualifies as self employed tax deductions. After all that learning, it’s time to cash in! Grab your virtual assistant, your significant other or your best friend, and place bets as to the grand total of qualified write-offs you have for 2012. You can even get fancy and bet on specific categories: travel, office supplies, health insurance premium payments, the sky’s the limit!

The winner of the bet gets the prize of their choice from the “Bribe yourself” section above!


If you use FreshBooks for your accounting, a lot of your procrastination pain will be relieved come tax time. Besides providing you with year-end invoicing totals and helping you calculate expenses, FreshBooks creates nifty graphs and charts that let you see how much you’ve earned and spent throughout the year.

These charts are seriously motivating! Set goals and see if you can beat your own best record. The faster you get your taxes done, the faster you’ll be able to hang up your graph on the fridge!

FreshBooks Chart


You, your other self employed buddies, and a pitcher or two of margaritas. Oh, and you’re doing your taxes. What could be more fun than that? Host an end-of-the-year tax party with all the fixings. You’ll be able to swap war stories, share tips and tricks, help each other with accounting, and answer each others’ questions about whether or not that trip to Cabo counts as a write-off.

How do you get motivated to do your taxes?

photo credits: valleydalemassage.com, freshbooks.com