The Tale of Two Self-Employed Freelancers and Obamacare

Self employed and Obamacare

First it was the website troubles. has crashed repeatedly — or perhaps “continuously” is a better word. The site seems to be unavailable more often than it is available to Americans trying to research coverage options, let alone sign up.  According to a government report dated November 13, 2013, just 26, 794 individuals had selected a plan through the Federal website as of last week.  Another 79,000 had selected plans via state healthcare exchange websites.

Then other news rocked the American public:  nearly 5 million Americans have had their healthcare coverage cancelled, by one estimate. Millions more are expected to get cancellation notices over the coming year.

Policies are being cancelled because plans don’t meet requirements for certain mandated coverage.  Let’s say you’re past childbearing age – you may still be required to have a policy with maternity benefits.  Or you have a high deductible policy, and you’re OK with it because you’re relatively healthy.  It doesn’t matter.  Insurance companies are required to cancel policies that don’t meet certain requirements.

The cancellation news started as a trickle and soon became a flash flood. There’s at least one site set up where Americans are sharing their health insurance cancellation notices at

Self-Employed Business Owners are Impacted

Despite the delay in the employer mandate until 2015, small businesses are being impacted by Obamacare right now. The individual mandate is still in place.  Self-employed business owners and freelancers are among the very people likely to have health coverage under individual plans — or no coverage.

Two examples from the ranks of the self-employed demonstrate the situation some small business owners now find themselves in.

Bruce Barcott, a freelance writer, was notified that his insurance premium would go up by 94%.  Even though he and his wife would have preferred to stay with their high-deductible plan, they couldn’t.  But when he went to his state’s healthcare exchange website, he was met with few good options and many unanswered questions.  The result:  frustration.  He writes that he found himself, “seething at a President I helped elect.”

He’s still an Obamacare supporter.  His point is that he expected clarity and competence.

And remember Jessica Sanford, the self-employed court reporter touted by President Obama as being an Obamacare success story?  Turns out she isn’t.  If you recall, she was the woman who penned a thank-you letter to President Obama when she thought she would be qualifying for a healthcare credit and inexpensive insurance.  In October, she was present standing behind President Obama during a Rose Garden speech (she’s in red, in the above image).

After that she was notified that the Washington state exchange she used made a series of complex errors.  Now she says she won’t be getting low-cost health insurance coverage after all.  She will instead pay the $95 penalty, she is quoted in a CNN story as saying:

“I had a good cry,” Sanford said about her reaction to the latest news from the state.

As a self-employed court reporter, the new quote was simply out of her range.

“This is it. I’m not getting insurance,” Sanford told CNN. “That’s where it stands right now unless they fix it.”

She says she’s still an Obama fan, though.

No Easy Fix

Meanwhile, President Obama has proposed a fix for the cancellations, involving allowing people to opt to keep their cancelled policies for one year.  However, the situation is not going to be easy or quick to fix because it involves state insurance regulators and the entire health insurance industry — not just politicians in Washington.

Some self-employed business owners are asking the question:  will my family and I be better off under the Affordable Care Act in 2014?  The answer as of this moment for some seems to be either “no” or “I just don’t know.”


Anita Campbell Anita Campbell is the Founder, CEO and Publisher of Small Business Trends and has been following trends in small businesses since 2003. She is the owner of BizSugar, a social media site for small businesses.

10 Reactions
  1. I am amazed at the hubris surrounding this program. Applying for insurance is a very complex process and their stated goal was to get MILLIONS of people into the system. To think they could put up a site that would handle this in such a short time was foolish.

    I feel like it’s a classic situation of a politician’s promise meeting reality and falling short.

  2. The working man gets caught in the crossfire again.. the govt cant get anything right. How are people supposed to live and care for their family when the insurance is cut off and Obamacare is too f****** expensive??

  3. Anita,

    I’m not into politics and I’m not good at macro-economy… but I do have a fear that Obamacare will “kill” small businesses. We do know that small businesses drive a nation’s economy. Will U.S. economy collapse – and take other countries, as well? To be honest with you, I’m terrified of that thought.

    But small business owners are known as being resilient. I truly hope we can find a way to respond to the changes.

    • Hi Ivan,

      There are some who believe the U.S. economy is close to collapse. I am not one of them. I have a more positive sense about the resiliency of this great nation.

      We do our best here to sidestep politicking as much as possible — while still addressing important issues. When we cover Obamacare, we try to cover it from a practical element: what you need to know about it for your business and yourself/family as a business owner. We avoid the strident arguments either for or against, because most business owners are heads down focusing on what they can control around them, not what’s out of their control with politicians in Washington.

      The entire healthcare situation has been difficult for many, because in the U.S., unlike many other countries, healthcare insurance is usually provided by the workplace. That often puts small businesses at a disadvantage. Small businesses don’t have a large enough pool of employees to negotiate for “cadillac” plans like many large corporations and large unions can negotiate. And the smallest small businesses often can’t afford healthcare insurance for employees (because employers subsidize the policy payments).

      Many thought we needed change in how healthcare is dealt with – there are some aspects of the health system that were deeply unpopular across the board, such as exclusions for “pre-existing conditions.” But how to change the system is the question. That’s where there was and is a lot of disagreement.

      Unfortunately, at least in the near term, many people seem to be in worse shape. We’ll see how it shakes out. 🙂