The pros and cons of freelance accounting

Posted on Wednesday, April 24, 2019 by Abby Draper

laptop open on natural wooden desk with cell phone and desk lamp. Facing window and looking out on snowy landscape.
By Abigail Draper, OSCPA communication and engagement manager

An annual study conducted by the Freelancer’s Union and Upwork found that the freelance workforce has grown by 3.7 million to total nearly 57 million freelancers over the past five years.

If you search websites like Indeed or, there are dozens of freelance accounting jobs up for the taking. So, what is the appeal of freelancing to accountants? And is it right for you?

To get some answers, we spoke with a former freelance accountant, OSCPA’s own Tiffany Crosby, CPA, CGMA, CTP, MBA, the Society’s director of learning.

The pros of working freelance:

- Freelance working often provides you with the flexibility to create your own schedule. The study mentioned above noted that 42% of freelancers say they are able to have the flexibility they need thanks to freelancing. Crosby said that even when she did not have flexibility with her time, she did have the flexibility to say “no.” She was able to go on a mission trip to India because she was able to turn down work during that time.

- No salary cap — with freelance work, you can take on as many jobs as you feel comfortable taking. This means there is no limit to how much money you can make. According to Forbes, “among the 17.2 million [in a 2017 survey] who said they quit a traditional job to freelance, two-thirds said they earn more on their own.”

- Those who are self-employed often have many tax-deductible business expenses. For example, the home office deduction might be applicable for freelancers who work out of their homes.

- Discounts are available through the Freelancer’s Union for things like Moo print products, Geico auto insurance, ASPCA pet insurance and more.

The cons of freelancing:

- No employer-provided medical insurance. There are some options through the Freelancer’s Union, but purchasing your own medical plan might be more expensive than a group plan through an employer.

- The stress of finding new work or having too much. Freelance positions do not last forever, so freelancers are always searching for new positions. This can be stressful if there is a lull in positions that hire you or even if you have taken on too many projects at one time. The Freelancer’s Union Report states that 63% of full-time freelancers feel anxious about the amount of work they have to manage and the unpredictability of their workflow.

- A lot of financial and tax responsibility (though accountants are better equipped to handle this). Crosby said there are a lot of hidden costs to freelancing and running your own business. She said you need to pay for workers comp, employment tax and tax liability — “basically the whole FICA.” She also said another challenge was a lack of resources. When you work for yourself, you have to pay for all memberships, networking and supplies. “You just have to make sure you have a realistic budget.”

- It’s hard to determine whether a business and its leadership team are ethical when you don’t meet them in person. “If they are unethical,” Crosby said, “this can easily affect the accounting.” She said she would always look at what they were paying for the position — if it was too much or too little for the work, then she knew something might be off about the company.

With freelancing, there is an opportunity for more pay and flexibility, but there is also a lot of financial responsibility attached to it.

“I don’t know if I would fully go back that way [to freelancing] again,” Crosby said, because of her experience. However, if you are able to find a position that allows you to afford the additional expenses of working at home while still providing for yourself and your family, freelancing may be a great option for you!

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