Broker Check

Navigating the Complexities of Health Insurance

I'm 40 years old and I'm sick of Corporate politics. I want to start my own business...but I need health insurance.

I'm 50 years old and I want to take a sabbatical. I need some time off to rest and re-evaluate...but I need health insurance.

I'm 60 years old and I want to retire or reduce my work hours...but I need health insurance.

At BridgeQuest, we hear this frequently from our clients. The fear of not having quality healthcare coverage, as evidenced by above scenarios, often keeps people stuck in a bad situation. Add in a global pandemic and high unemployment rate [1], and many furloughed clients are also seeking answers to the health insurance question.

As entrepreneurs ourselves, we feel your pain.

According to the Kaiser Family Foundation, 49% of Americans have health insurance through their employers. Twenty percent are on Medicaid and 14% have Medicare [2]. 

Of course, these are 2018 numbers and 2020 has been quite a year. A quick Google search isn't yielding good 2020 data. However, we suspect there are fewer people covered at work now than in 2018.

Whether planned or unplanned, you need health insurance and you are no longer in the 49%. Where can you get it? Here's some information we have found on how you can navigate the complex world of health insurance.

1. If you have a spouse or significant other who can add you to their workplace plan, this can be ideal. There is no medical underwriting and no spousal surcharge since you have no workplace benefits available. Pre-existing conditions are covered and the employer subsidy helps with affordability.

2. If you have been furloughed, most employers with 20+ employees are required to offer COBRA (Consolidated Omnibus Budget Reconciliation Act) coverage. COBRA allows you to keep your workplace health insurance for up to 18 months. However, you must pay the full premium cost, which can be prohibitive.

3. Some workplace health insurance plans offer a conversion option to an individual policy. While COBRA works for shorter gaps, a conversion option (if available) can cover a longer period of time. Again, this may not be cheap, but it is worth checking into.

4. If neither COBRA nor a policy conversion is a viable option, many seek out an independent health insurance broker to shop private insurance rates. This can also come with significant sticker shock and exclusions for chronic or pre-existing conditions. However, an independent health insurance agent can shop a variety of carriers and price points.

5. State health exchanges are frequently the next stop. However, consumers can't just jump in and out at any time. Open Enrollment periods apply, although Special Enrollment Periods may be available due to certain qualifying life events.

On the State Exchanges, pre-existing conditions are covered. Also, if income guidelines are met, the government subsidies can make coverage much more affordable. However, you could have to pay back the government subsidy if you earn more than their stated income limits in a calendar year. Ouch!

6. Healthcare Sharing programs tend to be faith-based and allow members of similar beliefs to pool their resources and share one another's medical expenses. It may look and feel like insurance, but there is no health insurance provider involved. There may be exclusions for pre-existing conditions in the first year and for certain medical procedures based on the beliefs of the particular group.

As long as you are comfortable with the underlying beliefs and are healthy, healthcare sharing programs can offer coverage for $300-500 per month per family. Over 1,000,000 members now participate in the largest 4 programs and it is a rapidly growing space as a health insurance alternative [3].

7. Another option is to purchase a major medical or catastrophic policy. This is a high deductible plan and it does not cover pre-existing conditions or even routine exams. However, it puts an upper limit on the maximum out of pocket you would have to pay if something major or catastrophic were to happen.

8. Professional trade organizations sometimes offer discounted group insurance rates for their members. Check the websites and call any such organizations where you hold membership. You might be surprised at the member perks you have never utilized!

9. Go back to college. What? Yes, seriously. Check your local colleges and universities. Some offer access to group health insurance for students, even if only one course is taken. This will vary from school to school but can make the price of tuition well worth it. Meanwhile, you can study something you enjoy or learn something new!

The confusion, complexity, and expense of health insurance can feel overwhelming, but at BridgeQuest we will be with you every step of the way!

For more information about health insurance, visit


BridgeQuest Wealth Strategies

BridgeQuest Wealth Strategies

Career changes, retirement, aging parents, liquidity events—navigating life’s big transitions gets much easier with an experienced guide. The BridgeQuest team leads you in the right direction with independent asset management tailored to your goals. Your plan will include objective advice and personal attention every step of the way.