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Expectation vs. Reality: A Graphic Designer’s Tale

Community Manager
Lena E Community Manager Member Since: Apr 7, 2015
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From managing cash flow and planning your personal finances to finding insurance and looking after yourself, growing a business is easier when you have help. Upwork Business Resources makes it easy for you to find service providers and connect with them directly—with special deals for Upwork members. Eagerto is one of the program partners.

This narrative is based on a composite of hypothetical scenarios graphic designers may encounter.

Freedom to follow my passion and work on what I want, with whom I want.

That was my main objective when I left my job at a big Chicago ad agency to launch my own business as a freelance graphic designer. It’s the feel-good story you yourself might relate to in one way or another. But along the way there were some hurdles I hadn’t considered when I left my corporate career.



I consider myself one of the lucky ones. I built a great client portfolio with a lot of repeat customers. Many of these customers also happened to be friends, so our working style always tended to be loose— a quick phone call, short emails, and sometimes even communicating on a project over texts. It worked for me, and my clients always appreciated how quickly I could turn things around. I had been able to develop a system that worked well with my customers and was proud to call myself a “success.” I thought that’s how it would always be. I was wrong.

Because of my “success,” the design director at a huge national food company contacted me on LinkedIn to design a new cereal brand’s logo. It was by far my largest and most lucrative client, but before I knew it I was making revision after tweak after edit and taking numerous calls “after hours.” However, my efforts to make the alterations quickly to try to impress the client, and hopefully create opportunities for additional business, completely backfired – so much so that he threatened to sue me over the logo. He said my “fast-paced,” careless working style and “unprofessional” way of doing business over the phone allowed too much feedback to fall through the cracks. I had no idea this was coming.


Do Your Homework
After a lot of research, I discovered professional liability insurance. After reading more and more about it, I was shocked I hadn’t considered the importance of not only protecting my reputation, but also my livelihood (Oh, I know how: I thought I was invincible and nothing bad would ever happen to me).

Liability insurance is a policy that protects an individual or business that is sued and held responsible for malpractice, injury, and/or negligence. When you’re self-employed, liability insurance provides financial protection if you make a professional mistake and are either 1) sued or 2) asked for monetary compensation.


If you find yourself in a tricky spot like I did, having this insurance policy can help cover—up to your coverage limit—expenses you may incur, like legal fees. Companies like Eagerto have policies ranging from $50,000 to $500,000 in coverage, with plans available at different price points.

Ask Questions and Get Answers
I had to do some digging to find out whether I had any options, but don’t let that deter you because there are resources out there! It’s important to understand more about the companies who offer freelance-specific insurance plans and what they cover, such as:

  • Assess the benefits to your business.
    Do you have a Certificate of Insurance I can share with clients and prospects to demonstrate my financial security?

  • Determine both a policy’s coverage and exclusions.
    How comprehensive is your coverage, and in relation to my particular plan?

  • Understand your deductible.
    What out-of-pocket amount am I responsible for before my coverage kicks in?

  • Vet the claims process.
    If I need to file a claim, 1) how do I do it and 2) who is there if I need help and explanations along the way?

  • Gauge the financial strength of the company underwriting your policy.
    How is your company funded and who writes the policies?

Figure Out the Right Plan for You

Just as every job you work on is unique, your insurance plan should be, too. And it’s easier than you think—you only have to know four pieces of information:

  1. What industry you’re in
  2. How many projects you work on per year
  3. Your earnings per project or by hour
  4. Whether you’ve ever been sued or had a claim filed against you

Get Insured
Based on your responses, you can find a plan that suits your needs. Then you set up a payment with your provider and get a confirmation note about your policy.

Don’t Freak Out, Because You’re Now Protected

I wish I had this peace of mind from the start, and that I had researched my options before being thrown into a challenging situation. Many people don’t think about health insurance until they go to the doctor or fill a prescription, and in the same way you never know when you may need liability insurance…until you find yourself in a tough spot. That’s the beauty of liability insurance—it allows you to focus on your passion, not worry about the tough spots, and if the time comes to file a claim, you’re protected.

To learn more about the insurance options available to you, contact Eagerto—or check out one of the other Upwork Business Resources partners.

This story was submitted by Eagerto and does not constitute the views or opinions of Upwork. Ghost written from a graphic design perspective as a part of Upwork’s partnership with Eagerto.