Navigating the Healthcare Maze: One Solopreneur’s Journey

March 20, 2014

Editor’s note: the following is a personal story about one entrepreneur’s experience with Obamacare. FreshBooks is not promoting or endorsing Obamacare. We understand that everyone will have their own experience. Healthy dialogue is invited below. 

When I was 19 years old, I was struck with a rare spinal cord tumor. It enveloped my nerves. I nearly lost function of my legs, went through extensive surgery, completed 33 rounds of radiation, and pushed myself through physical therapy. I fought hard to never let the illness stop me from living life – to never lose hope that I would recover.

Hope and perseverance carried me far. I taught myself how to walk—and eventually even run—again. By the time I turned 24, I had co-founded a health center in New Delhi, graduated in the top-third of my college class, earned a graduate degree debt-free, and started a company as a side-business.

I am the happiest person on earth and grateful for every moment that my ‘second chance’ has given me. I’m empathetic, treat others with respect, and strive to empower the people around me. It’s human interest—not money—that inspired me to become an entrepreneur. I wanted a chance to improve lives and add value to the world around me. To be a leader for good.

A statistical liability

Until 2014, that chance came at a price. Health insurance companies could discriminate against me—even though I’m healthy, walking, and tumor free. No matter how hard I worked or how much I grew my side business, I was—in the eyes of corporate America—a statistical liability and nothing more.

Words cannot describe how angry, hopeless, and powerless I felt. I hated the health insurance companies for punishing me—for something entirely outside of my control. It made me sick to my stomach that a health insurance company could, with one mouse click, destroy my biggest life passion. I felt that I was being punished for something completely outside of my control—something that I had worked so hard to overcome.

And then, the Affordable Care Act passed.


In January 2014, the U.S. government launched state and federal health insurance marketplaces where the public can purchase their own health insurance plans. The American public was in an uproar—complaining about costs, uncertainty, and website blackouts.

The marketplace was in chaos, and I couldn’t get clear answers from anywhere—medical providers, health insurance companies, and even the State of California were all ill-equipped to answer basic questions. Instead of throwing my hands in the air, complaining, and giving up, I self-directed my research. I spent hours sifting through information to figure out:

  1. Whether I could still see my doctors
  2. Whether health insurance marketplace plans were in any way ‘inferior’
  3. Whether I could find a plan that was as good as my employer’s

Peeling away the rumors

I was skeptical of whether the health insurance marketplace was something worthwhile. I’d been hearing complaints of plans being ‘low quality’ or unreliable.

But these were just what I suspected—rumors. Here was my experience:

I’ll admit that the process has been clunky. There was a period of time when I thought my health insurance was dropped due to a technical error. I get confusing letters describing ‘updates to my plan’ on an almost weekly basis. I spent an hour and a half on the phone trying to make sure that my first payment went through.

But you know what? I’m okay with it. All of these scenarios are minor inconveniences—and far from doomsday.

Scaling up

Even though I am a solopreneur, I am optimistic that I will one day hire employees. What I’ve learned is that Employer Mandates—which require employers to offer adequate coverage to their employees or be liable for tax penalties—apply to businesses with 50 and 100 employees.

The Affordable Care Act does, however, place obligations on all employers (including businesses with fewer than 50 employees):

1. Employers were required to notify employees by October 1, 2013 of the following:

2. Employers are required to educate employees with a summary of benefits of company plans.

3. Employers have a withholding obligation for potential increases in Medicare Part A Hospital Insurance (HI) taxes.

4. Group health plans may not implement a waiting period longer than 90 days.

What’s important to notice is that the costs associated with these ‘obligations’ are inconsequential—they will place zero restrictions on my business’s ability to scale.

Deadline looming

March 31st marks the open enrollment deadline for signing up on the state health insurance marketplaces. After, you’ll need to wait for a ‘qualifying event’ such as a loss in coverage, marriage, moving to a new state, or the addition of a new family member—the process is exactly the same as signing up for health insurance from an employer. The open enrollment period opens from November 15, 2014 to February 15, 2014 for coverage beginning in 2015.

Yes, there will be road bumps. Yes, the process will be frustrating. The biggest lesson I’ve learned, however, is to not let media pessimism or logistical headaches stand in my way.

More ideas to help your business

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FreshBooks Tip

Discover how to charge a flat-rate on your side-gig project.

about the author

FreshBooks is the #1 accounting software in the cloud designed to make billing painless for small businesses and their teams. Today, over 10 million small businesses use FreshBooks to effortlessly send professional looking invoices, organize expenses and track their billable time.

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