When doing what you love doesn’t come with health insurance (Part I of IV)

“…if the creativity of any living creature could be seen, what would it look like?“- K. Moyes

This is Part I in a series called Health Insurance for the Self-Employed: When doing what you love doesn’t come with health insurance. The posts in this series focus on the importance of health insurance and finding, evaluating, and enrolling in individual health insurance. I’ll also discuss strategies to save money and different ways to access health insurance or find health care. There is an incredible amount of resources out there on this topic. I digest them in each post.

The energy of musicians is something I love being around. Going to shows, music festivals, and having conversations with local and student musicians is incredibly fun for me. One day, I’d like to host touring bands with home-cooked meals in exchange for living room concerts (there’s no better sound).

In 2012, I started studying for my financial planning license to help public service workers and the economically vulnerable with objective, qualified advice. I also want to be a resource for people who give up the typical 9-5 job for their creative passions.

In the next few years, I plan on transitioning into self-employment as a financial planner. Deciding to go without full-time employment with an institution in order to do what you love can be exhilarating and life changing for the better. It’s easy to focus on the positives of becoming a freelancer. More flexible hours. Better pay. More independence. A greater sense of self-confidence.

Then comes that questionwhether you ask it yourself or someone asks for you — to pop the bubble:

What about health insurance?”

Do I really need it? How will I pay for it? Will I be able to find a new health insurance plan?

Pursuing my new career, much like what artists must go through when they decide to pursue their craft independently full force, has also come with some anxiety and a lot of unknowns. I’m worried that I’m making a financially irresponsible decision. I’m nervous about leaving behind a steady paycheck and a neat employee benefits package. I’m scared of making the changes I’ll need to make when I finally take the plunge.

I was inspired to do more research on these questions after reading this article on Grizzly Bear, a great band that I recently got to see in concert. They have an enviable career that sustains them creatively. And they are respected and celebrated by loyal fans. But even with all their success, some of the four band members are without health insurance.  I’m not sure if this is by choice or necessity. Still, they love what they do and wouldn’t trade it for anything.

Ed Droste, the original member of Grizzly Bear, believes “the biggest thing you can’t do is focus on money.” I agree. But it’s important to distinguish between focusing on making money as the main goal of your work versus focusing on your personal finances to better prepare yourself for the ups and inevitable downs of life.

It’s necessary to make money matters a priority in your planning before they turn into a source of worry, or even worse, a reason to not pursue what you love.


Other posts in this series:

Part I: When doing what you love doesn’t come with health insurance (current post)

Part II: Why enroll in health insurance? (upcoming post)

Part III: How much does health insurance cost? (upcoming post)

Part IV: 8 ways to save on health insurance or health care (upcoming post)



  1. […] Part I: When doing what you love doesn’t come with health insurance […]

  2. […] Part I: When doing what you love doesn’t come with health insurance  […]

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