153R | Navigating Health Insurance

153R | Navigating Health Insurance

Medical debt is a big financial burden for many people. Brad and Jonathan spoke with Craig and Jerry from RIP Medical Debt to find out more about their solution to this problem.

If we can continue to foster these kinds of conversation, not only we win but also those around us, those in our zone of awareness, those whose lives we have some impact on, they also benefit.

Check out the full episode here to find out more about medical debt collections and forgiveness.

Watch this episode on YouTube. 

Jonathan's Experience

Earlier this year, Jonathan and his wife welcomed a new baby into their family. With that joyous occasion cam an expensive year in terms of healthcare. Jonathan and his family are on a self-employed health insurance plan that comes with a hefty price tag.

He pays $1,000/month for the plan. There is a $13,000/year deductible for the family and $6,500/year deductible for individuals within the family. This structure means that he is basically paying up to $27,000 per year for healthcare. After the $13,000 deductible, he has zero coinsurance so he is not responsible beyond that.

It is important, just like anything, to know the rules of how this works.

Based on the deductibles of the plan, he was expected to get a medical bill for $0 when his wife hit her deductible for the year. However, after the birth of their child, the hospital sent him a bill for $4,000.

He had to do quite a bit of legwork to find out that the OBGYN had not charged the insurance company for their services yet. Instead, they were sitting on $2,700 of Jonathan's payments. He was able to get a refund for the $2,700 from the OBGYN. It took a lot of phone calls but he was able to get it sorted out.

Healthcare After FI

If you leave your W2 job, then you might lose your regular health insurance. Healthshares are a different option than healthcare insurance. Although they can be great for what they are, it comes down to your risk tolerance.

Find out what your risk tolerance is.

If $200,000 of medical expenses would break your financial future, then you might want to insure against that. You just never know what the future can hold.

If you are self-employed, then you might consider writing healthcare off as a tax deduction. If you are FI and have the ability to control your income, the ACA might have affordable options available to you.


Health insurance companies are able to negotiate rates in mass for better prices. The healthcare systems know the game, so they often charge higher than the market price. If you are on a healthshare plan or don't have insurance, you can still negotiate for better prices.

You have the ability to negotiate discounts on your own.

Ask for a discount for paying upfront. If you paying current medical expenses, then you might be able to negotiate a 10% discount. However, if you are paying down medical debt baggage from years ago then you may be able to negotiate 50% off.

If you pay in full, in all likelihood, you can get at minimum at 10% discount I think just by asking the question.

As you go through the process, take notes and write down names. Let them know that you keep track of what is happening. Build a relationship with the person on the other end of the line. Make sure to get any debt resolutions in writing to avoid any problems down the line.

Community Feedback

Let's hear what the community has to say this week.


Clayton wrote in to share their medical debt story. After a period of high medical expenses to battle an autoimmune disease, they had received over $150,000 in medical bills. With a healthshare plan, $5,000 in savings and no debt, they tackled the medical bills head-on.

They successfully negotiated their medical bills down 70% to around $50,000. This was all done without any collection agency interaction. Clayton found ways to avoid fees and avoid snags in the healthshare reimbursement process.

It is possible to negotiate your medical bills on your own without any prior experience. Clayton wishes anyone in this situation the best of luck.

Nadine- Military Credit Card Perks

Nadine wrote in to ask if there were credit cards that waive fees for active-duty military. Luckily, the answer is yes!

  • Chase Sapphire Reserve: Chase waives the $550 annual fee for active duey military members. This card offers significant benefits including a $300 travel credit and more redemption value for your Chase Ultimate Rewards.
  • The Platinum Card From American Express: As Nadine mentioned, the Platinum Card From American Express also waives the annual fee for active-duty military. Definitely take advantage of that!

Find out more about our recommended cards for military members here.


Emily wrote in to let us know she is taking action on the tips she is learning in our new book, Your Blueprint to Financial Independence.

Great job Emily!

Frugal Tip From Jim

Jim wrote in to let everybody know about awesome holiday savings. Kroger is waiving the $4.99 pick up fee for groceries in November and December.

If you haven't given online grocery shopping a try, it is worth an attempt. It might just save you time and money. This is the perfect chance to give it a try.

Making A Difference With RIP Medical Debt

ChooseFI is doing a campaign with RIP Medical Debt to wipe out medical debt. Donations have an incredible ROI, so we are excited to partner together.

Brad is donating $1,000 and Jonathan is donating $500. If you are interested in joining our campaign, then consider donating here. We are looking forward to making a difference together!

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Your Financial Resilience Toolkit

Affiliate Disclaimer

ChooseFI seeks to uncover helpful services that help you be financially resilient. However, we may receive compensation, at no cost to you, from the issuers of some products mentioned in this article, including from CardRatings for our coverage of credit card products. Opinions are the author’s alone, and this content has not been provided by, reviewed, approved or endorsed by any of these entities. See our disclosures for more info.

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