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Bookkeeping and Tax Challenges That Have Come With Freelancing

5 May 2023 16:00:00 Marshie

More folks are turning to side hustles and freelancing to earning extra money and full-time money.  Along with this earned income comes along the responsibility to keep up with your taxes. According to Daniel Ruby with DemandSage, there are 73.3 million freelancers in the U.S.A. alone not to mention the millions in other countries fighting for the freelance space with Fivver and Upwork. In 2017 we had 57.3 million freelancers; they are projected to grow up to 90 million by year 2028. (source Statista)

Bookkeeping Challenges


People love having the control of running their own business and calling the shots.  However, many of these folks fall victim to the “tax man” because they were caught up in the excitement of running a business, they failed to learn the tax implications of their businesses.  They were used to their previous employer or current employer handling their taxes for them.  Suddenly when it comes tax time, they are not sure what estimate taxes are, sales tax or the other taxes that come along with being a freelancer they feel like they are sinking in quicksand.  It is slow at first and quickly catches up with them when penalties and interest start engulfing them. Once this happens it is hard for them to stay afloat in their business because they don’t have the cash flow necessary to stay open for much longer.

Bookkeepers play a major part in a freelancer’s business fiscal health.  What do bookkeepers do and why are they so important?

  1. They keep up with the deadlines.
  2. They pay and prepare your taxes such as, estimated, sales tax and liability taxes.
  3. They advise you on what deductions you can take.
  4. They help prepare your yearly taxes and books for your CPA.
  5. They take care of the books so you can focus on making money.

Freelancers need to enlist the help of an experienced bookkeeper and financial professional to combat challenges to bookkeeping and save money on taxes.  Freelancers have the entrepreneur instinct to “do it all themselves”, yet they may lack the skill set to handle the back-end of their business. When things suddenly spiral out of control, from the IRS, Social Security and State organizations who are all asking and demanding money ultimately, it is the freelancer who has to deal with burden.

Taxes for freelancers


Often times freelancers are not aware they need to pay taxes throughout the year.  Some don’t even realize if you don’t earn a profit, you still have to file taxes.  There is a difference between paying and filing taxes and a bookkeeper can help you keep them on track.


Marshie Morgan is an Author - Bookkeeper - Financial Representative with M & M Biz Solutions.

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