Self Employed Tax Deductions: How to Turn Procrastination into Motivation!

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?

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Small Business Lifehacks: Making Your Software Work for You

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When it comes to small business lifehacks, finding bomb accounting or management software is at the top of the list. But once you’ve weighed the pros and cons of QuickBooks vs. Wave and software vs. the Cloud, where do you go from there?

Purchasing and implementing software and online applications that truly meet your needs is super important. But so is what happens next. Once you’ve decided on a product, here are some simple lifehacks that will show you how to get the most out of it.

1. Play Around

Many small business entrepreneurs are so stoked to begin using their new software, they dive right in without having a clue as to what the program or app can actually do. Before you log any expenses or start linking bank accounts, spend at least an hour just playing around. Think of it as if it’s your first time surfing the web – you don’t know what’s out there, and you’re not sure how to get there, but you’re sure if you keep searching you’re going to find something great.

Playing around allows you to explore your new tool without the pressure of trying to make it perform. By scheduling some get-to-know-you time with your new software, you’re sure to stumble upon some twists and turns within the application that will turn out to be vital to your new organizational paradigm.

2. What’s it For?

Many accounting and management software programs offer multiple functionalities. Is your new software going to serve as your accounting platform and your Customer Relationship Management software? Will it be used to create expense reports, process payments, or both?

By deciding beforehand how you’re going to use the software, you’ll be able to plan how to transition between the old and the new (even if the old was pretty much you writing down what you spent on a coffee-stained napkin).

3. Who’s it For?

Who is going to have access to and be using the software on a regular basis? How many people does the software affect? For example, if you’re using new accounting software, is it compatible with what your accountant uses?

If you’ve chosen new CRM software, how many of your employees need to be trained to use it? Don’t just think in terms of who will be using it on a daily basis; what happens if someone is out sick, or away on business? It’s a great idea to cross train as many of your employees as possible on multiple platforms, so everyone is speaking the same language. Consider bringing a company representative in to do an employee-wide training so everyone has a chance to ask questions and practice. Which leads us to…

4. Read the Manual

Ok, so maybe we don’t mean this literally. But most web-based software comes with tons of online video tutorials, customer support via webchat or phone, testimonials and forums, and troubleshooting tips and lifehacks. Take advantage of it! You may even want to make sure the Help section of your software’s website is navigable and thorough before making a purchase.

Tutorials and FAQs aren’t just for troubleshooting, though. They can be a great way to learn the application, and discover shortcuts you never would have found on your own. If your software program offers any kind of live assistance – whether that’s an in-store class like those available at Apple, or a live webinar with the company’s tech support experts – take advantage! Many common frustrations and baffled expressions can be easily resolved by simply using what’s been put there to help you.

Accounting and managerial software can be an enormous help to any small business, but it’s not a magical elixir that eliminates all effort on your part (If only, right?) Make your software work for you by putting in some extra effort in the beginning to learn the program inside and out. Doing so save you time and money (and headaches!) in the long run.

5 Creative Home Lifehacks for the Holidays

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The holiday season has officially begun, and there’s no better time of year to incorporate some fresh new lifehacks into your organizational life.

“But it’s only the first week of November!”

Yes, that’s true, but on November 1st Starbucks switched to those red holiday cups. There’s no going back now.

Whether you’re self-employed, a small business owner, or an employee at a small business or startup, the level of organization in your home has a direct impact on your work habits and productivity. This is the case regardless of whether or not you actually work from home.

Leaving an organized home, and coming back to one at the end of a long day or night, refreshes both body and mind. It does something to you, psychologically. It provides an overall feeling that you’ve got it together, you’re in control, and you’re brimming with power and creativity. It’s that kind of attitude – in addition to the home lifehacks you can apply at the office – that will grow your business, gain clients’ trust, and make you seriously think about throwing the office holiday party at your place this year.

Here are a few of our favorite organizational lifehacks for home (and office!):

1. DVD/CD cases for creative storage

We’re not talking about old CD cases that used to contain music CDs, oh no. Collect the blank CD and DVD cases that come with 50 to 100 blank, recordable discs. These have cool plastic tops and enough room to serve as mini storage containers. You can wrap coiled ribbon around the center, or use them to store men’s ties.

2. The Old Entertainment Center

With the advent of flatscreen TVs, gigantic television entertainment centers are becoming big heavy eye sores in many people’s homes. But don’t list it on Craig’s List just yet! You old entertainment center could function as a:

  • Craft Cupboard – add some smaller shelving and store art supplies, tools, paints, and ribbon
  • Display case – open up the doors of the center to showcase framed photographs, collectibles,  and unique trinkets
  • Dresser – move the center into the bedroom to create tons of storage space for sweaters and other foldable clothing items

3. Lazy Susan

These aren’t just for the kitchen anymore!  A swirling Susan can be placed inside your closet as a makeshift shoe rack, on a dresser as a movable jewelry box, or in the bathroom to give you easy access to toiletries.

4. Organize your Cords

Smartphone, laptop, tablet, eReader…nowadays, each one of use comes with 4 to 5 devices in tow, and darn it, we need to charge them! Until everything is wireless all the time, finding a way to organize all of those cords is essential to creating an organized home or office. Nothing looks worse than a tangled mess of dusty electronic tails!

Create a cord “docking station” with binder clips. Secure each binder clip to the edge of a table or desk. The metal portion of the clip holds the plug-in part of the cord, and the rest of the cord will remain untangled. You can also label each cord with bread bag clips. Write on each clip with permanent marker and slip into onto the appropriate cord – they fit perfectly!

5. Egg Cartons

Save old egg cartons to you as mini-storage spaces. Think about it – each carton has 12 built-in compartments that can separate jewelry, flash drives, beads, paper clips, or whatever is most difficult for you to keep track of. You can have fun painting and labeling the cartons too. Try these categories on for size:

  • Earrings
  • Rings
  • Office supplies
  • Spices
  • Ornaments
  • Paints (use each carton as a painter’s palette!)
  • Seeds – plant a flower or herb in each individual compartment

You can also use ice cube trays for the same things.

This is the perfect time of year to get organized for the holidays – it’s not too late to incorporate some fun organizational tricks into the home, and we still have two more months of Candy Cane Lattes.