Real Talk Health Insurance

By Alison Lobron

“I would love to do what you’re doing,” a 20-something friend said. “But I need benefits.” She went on to tell me about her dream of starting an interior design company, a dream she’s put on hold until — well, until someday.

I heard comments like hers often in the year I spent as a freelance writer, so I said to her what I said to many other friends: You can buy benefits. You just have to factor it into your costs when you consider whether a business idea can work.

“People have this sense that health insurance is somehow special to employers,” says my friend Mike, 33, an unemployment lawyer who has counseled dozens of friends and clients on purchasing their own health insurance. “When I was self-employed for a while, the response would be, ‘What about benefits?’” he remembers. “People don’t seem to realize that there is a dollar value to their health benefit that can be factored into their pay.” 

When I left my job as a high school English teacher (to what felt like an entire Greek chorus of family and friends intoning, “But what will you do about benefits?”), I was surprised at how easy it was to buy my own — and that it was cheaper than staying on my former employer’s group plan via COBRA. I had to rejigger my notions of what I needed in the way of salary, and put up with the mild hassle of determining which plan made the most sense for me. I did, at times, long for the days when I just filled out some forms, got my nice plastic card, and didn’t think about any of it again. I was also aware that if I weren’t fairly young, and blessed with good health, the process would have been much harder. But if you’re in your 20s or 30s, and don’t have a lot of people depending on you for financial support, you can do this, too.

Yet so many people seem to think they can’t. It’s as if health insurance occupies as much emotional space as financial space, and symbolizes more than its dollar value. It’s a kind of protection, a sense that somebody else is taking care of things and you don’t have to. If you’re anything like me, you went directly at age 22 or 23 from a parental plan to an employer’s plan and as a result, that employer — and subsequent ones — came to fill a quasi-parental role. Letting go of an employer’s health plan doesn’t just mean reconnoitering your ideas about income to account for that extra $250 to $350 a month. It means letting go of safety, letting go of someone else being in charge, letting go of Mom and Dad all over again.

“I felt a little bit like an orphan at first,” Mike remembers, but now “health insurance has lost its mystique for me. I view it just as insurance, just like auto or home coverage. It is nice to have your employer pay it, but doing it myself was far easier and less painless than I expected.”

I’m not the first to point out that it makes no sense to tie health insurance to employment. The practice began amid wage controls in the 1940s, when employers who couldn’t compete for workers based on salary began offering benefits to attract talent, and it’s been with us ever since, long after the wage controls ended. For those of us in our 20s and 30s, this way of doing things is so deeply rooted as to be almost unquestionable: A job means insurance, and no job means no insurance. Since Massachusetts instituted tax penalties for the uninsured in 2007, the psychology may have changed slightly, but not very much. If anything, the new law may make letting go of an employer seem even scarier.

Many problems with employer-based health insurance have been well-documented. Still, I wonder about the problems we can’t document, and what this system has cost us in terms of businesses unstarted, innovations unrealized, and dreams unchased, all due to the fear of being without benefits. In a recession like the one we’re facing, the last thing we want is for people to dig in their heels and be afraid of the kind of risk-taking that could lead to economic growth. In a perfect world, we’d all have health insurance, people wouldn’t be penalized for getting sick, and people providing care would be better paid than those who sit around figuring out how to avoid paying for care. But in our current, imperfect system, the cost of buying insurance still shouldn’t be the obstacle to starting that interior design business or web-hosting company — or, to be more accurate, it shouldn’t be any bigger than its actual dollar value.

I found my year of self-employment alternately terrifying and empowering. It required managing things I’d never had to manage (taxes, health insurance) and then discovering, most of the time, that it wasn’t that hard. As one entrepreneur friend in his early 30s puts it, you simply swap one set of challenges for another. You’ve got to visit the state’s health insurance website (, compare deductibles and co-payments and co-insurance, and start wondering when “co-” became a synonym for “patient pays for everything.” You’ve got to get acquainted with new tax forms and do more money management than you probably did before (unless you were in money management).

On the other hand, nobody controls the bulk of your weekday waking hours, tells you what to wear, or sets up a firewall to prevent you from playing solitaire online. Mom and Dad have left the building. As was the case in high school, sometimes you’re glad to see them go, and other times you sort of wish they’d come back.

It is, in some ways, ironic that in an era of layoffs and diminishing employer loyalty, we attach such psychological significance to the benefits we get from our employers. Perhaps it’s the desire to feel rooted and cared for, or just the need to feel part of something. After all, many of my friends don’t belong to any organizations other than their employers (no religious organizations, no Elks clubs). I’ve recently started a new full-time job, and I am conscious of getting a satisfaction from all those lovely benefits that are worth more than their price tag. Much as I’m glad I experimented, and glad to know I could do it again, I’m glad to come back into a fold. It’s belonging. It’s safety. It’s — well, it’s insurance.

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