· Lathan Lewis
Take This Job and Shove It
Bored at your job? Can’t stand your boss? If you’ve been fantasizing about going out on your own as a gig worker, freelancer, or to start your own small business, there are lots of things to consider: a business plan, name, logo, etc. One area that becomes a roadblock for many, however, is how to get health insurance. And at a rate that won’t break the bank while you’re trying to get your business off the ground. Luckily you have a few options. As I went through the process recently, I’ll walk you through how I went about it.
The Switch
After school, I took the standard career path of working as a full time employee for various companies. Each provided benefits including health insurance. The health insurance was either free (to me) or heavily subsidized and all I had to worry about was what plan to choose. All was good until I received the proverbial ‘too good to turn down’ job offer. The only catch was this new job was a contract position. While the increase in hourly wage was more than enough to compensate for the lack of benefits, it still meant I had to go out and source my own health insurance. I looked at two options at the time: COBRA and private insurance.
COBRA: Your employers plan without your employer
The Consolidated Omnibus Budget Reconciliation Act (COBRA) requires health insurance companies to let you remain on the same employer plan that you were on prior to leaving your job, regardless of whether you were laid off, quit, or were fired. The benefit to you, besides familiarity with the plan, is that you keep the same provider network and therefore doctors as well as any progress you may have made towards your deductible. COBRA allows you to stay on your previous plan for up to 18 months. Your previous employer doesn’t keep paying, of course, so you pay the health insurance company the equivalent of what your company was paying for you and generally a small administrative fee. The bad news is this won’t exactly be cheap but the good news is your employer was getting a group discount so the price will almost certainly be less than if you went out and acquired the same level of coverage via private insurance directly.
COBRA is a good option right out of the gate if you are happy with your existing plan and don’t want to spend a lot of time researching alternatives. Your employer should provide you with information on how to sign up for COBRA but if they don’t, simply reach out to your company’s HR rep.
Private Insurance
Private insurance refers to buying your health insurance directly from the insurance provider (e.g. Blue Cross Blue Shield, Cigna, United, etc.). While you may not have access to all the same plan options as an organization would, you’ll still find plans very similar to what you would get through an employer. The downside is you’ll be paying the full retail rate rather than getting a group discount. Insurance provider options vary by state and even by county in some cases so you will need to research what is available in your area. The Affordable Care Act (ACA), also known as Obamacare, came into effect in 2010 and introduced a Marketplace for buying private insurance. If your situation meets certain income criteria (see below), you may be eligible for subsidies so it is worth investigating. And if you spend time building your business with little to no revenue, the likelihood of subsidy eligibility goes up. Even if you don’t qualify for subsidies, you can still search for and buy insurance plans via the Marketplace but the options will often be more limited than if you go directly to the insurance provider’s website.
Figure 1 - ACA Subsidy Income Limits
| Household Size | Minimum Income | Maximum Income |
|---|---|---|
| 1 | $15,650 | $62,600 |
| 2 | $21,150 | $84,600 |
| 3 | $26,650 | $106,600 |
| 4 | $32,150 | $128,600 |
| 5 | $37,650 | $150,600 |
| 6 | $43,150 | $172,600 |
The Decision
In my case, I liked my previous employer’s plan and the job switch happened suddenly so I went with the COBRA option after a quick search of private plan options didn’t show anything particularly appealing. All was good until the 18 months were almost up and I was forced to start looking at alternatives. There were only two options at that point: private insurance or a health share plan.
Private insurance was a known quantity as I could select a plan similar to the one I was on, albeit for a quite a bit higher price. In a quest to save a few bucks I started looking into health share plans. Health share plans aren’t insurance but they serve the same function: they pay your medical bills once you exceed your deductible. See what is health sharing for more details. I really liked the concept behind health share plans but at that time most health share plans I came across required a religious affiliation and a statement of faith. Claims could be denied if you misrepresented yourself. Further, health sharing organizations were still relatively small and information on their track record for paying claims was limited. I decided the risk wasn’t worth it and found a private insurance plan. It was expensive but I had the peace of mind knowing it would pay if I needed it.
Leveling Up
Fast forward to the end of 2025 when I received notice of open enrollment for the coming 2026 year and the fact that my private insurance provider was increasing my rates from $1610 /mo. for a family of four to $2640, a 64% increase. Oh, and they were also increasing my deductible and out-of-pocket maximums along with it. All this for a high deductible plan (emphasis on the high) that I rarely ever met the deductible for and therefore received very little benefit from. I was therefore motivated to take another look at health share plans. After a lot of research and deep dives into the various health share options, I ended up signing myself and family up for a plan through MPB Health at a cost of $753 /mo. Here was my reasoning:
- I saved $1887 /mo. Cha-ching!
- No religious affiliation or statement of faith required so less risk in a claim being denied
- The health share plan covers the same emergency medical claims as private insurance, but with a lower deductible and no lifetime or yearly maximums
- The plan I chose included Minimum Essential Coverage (MEC) and therefore the same preventive services my private insurance plan covered and was HSA eligible to boot so I could continue taking advantage of the ‘triple play’ tax savings as laid out in our MEC and HSA Eligibility guide.
- MPB Health had plenty of public reviews indicating a consistent track record of paying eligible claims and was willing/able to provide an audited annual report of their operations and current financial position
- Did I mention I saved $1887 /mo.?
That sounds too good to be true so what’s the catch? The reality is health shares aren’t a good fit for everyone. Since they aren’t health insurance, they are not subject to ACA rules and therefore have restrictions on pre-existing conditions. There is generally no coverage in the first year and years 2-4 generally have caps. Coverage for maternity related costs either aren’t covered (religious health share plans) or don’t kick in until 6 months after your start date and only if you conceived after your start date (MPB Health plans). The bottom line is you have to read the health share plan’s guidelines to understand what it does and does not cover. But if you’re willing to do the research, you can expect to save anywhere from 40-60% on average over private insurance.
Bottom Line
Don’t let the cost and complexity of finding health insurance keep you from becoming your own boss. There are options available. You just need to weigh the pros and cons relative to your situation in order to choose the best one.
| COBRA | Private | Health Share | |
|---|---|---|---|
| Traditional Insurance | Yes | Yes | No |
| Keep Existing Plan | Yes | No | No |
| Individual & Family Coverage | Yes | Yes | Yes |
| ACA Regulated | Yes | Yes | No |
| Pre-existing Conditions | Yes | Yes | Yes, but phased in over multiple years |
| Eligible for Subsidies | No | Yes | No |
| Monthly Cost | High | Higher | Low |
| Provider Network | Often | Often | Not generally, plan specific |
| Requires Careful Plan Review | Somewhat | Somewhat | Yes |
| HSA Eligible | Plan specific | Plan Specific | Rarely, MPB Health is only current option |
| MEC Preventive Services | Yes | Yes | Rarely, MPB Health is only current option |
Side Note: I was so excited about the benefits of moving to a health share plan that I wanted to spread the word. I created Smart Share as an advisory firm for MPB Health and am happy to answer any questions you may have on MPB Health plans or health sharing in general via our contact page. Please also see our resources section for guides explaining the ins and outs of health share programs.