How to Save Money on Health Insurance | Open Enrollment Explained with Eileen Dougherty – EP 254

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Getting ready for Open Enrollment this year? We hear and understand you. Switching or having additional healthcare plans takes thorough decision-making. In this episode, we wanted to create an easier pathway toward understanding how to save money on health insurance. Your Frugal Friends, together with Eileen Dougherty, piece together the whats and hows of saving money during Open Enrollment.

Understanding spending on healthcare insurance could save you tens of thousands of dollars over your lifetime, way more than cutting lattes.


  • Best case scenarios. They’re doing a hard push to remind the general public that they still exist. When we had our intro call with them, we did sense a tinge of bitterness regarding how much attention ‘worst case scenarios’ get. Best case scenarios aren’t promising that it will always pan out that way, BUT they do want us to consider them. Best case scenarios; avoiding catastrophes, de-escalating that situation, and championing that dream job. ALSO best case scenarios are strong supporters of high-yield savings accounts, you can connect the dots as to why that would be. If you’re here for best case scenarios check out CIT banks high-yield savings account at

Eileen is a 25 year veteran of the US Healthcare industry. Today she is the Executive Vice President of growth at Zelis Payments and a nationally recognized expert in many areas of healthcare. She has four children, all boys, and lives in St Petersburg, FL.

The Annual Open Enrollment and Its Exceptions

Open Enrollment is a once a year period wherein people enroll in health insurance plans for the next calendar year. Most plans are based on limits, deductibles, and maximums that ensure less risk for the people they are insuring. However, there are special enrollments that are situational depending on restrictions and all important details about this are relayed in plan documents. 

Switching Healthcare Plans

Eileen emphasizes that when someone wants to change or modify plans, they should ask themselves “has my life changed?”. Switching healthcare plans takes thorough decision making in order to realize key details such as if your life status has changed, will your current plan still cover you efficiently, or if in reality is it still the best plan available to you now.

Preparations for Open Enrollment

Your best option is to read and evaluate plans, and yourself. It is best to look into what is most important to give attention to in the year to come, to find what is the plan that would make most sense for you. Things to consider are what’s best for you personally and your family’s sake, as well as your current financial ability.

Maximizing the Open Enrollment Period

Americans are known to be smart consumers. And as consumers we must learn to dig deeper into educating ourselves on basic terms and knowledge concerning healthcare. This is important for you to clear blind spots before you head into the enrollment period.

An interesting health insurance experience we had and what we learned from it

  • Eileen: Was admitted to ER for appendicitis and surgery was covered 100%!
  • Jill: In collections for bloodwork done between insurance companies
  • Jen: Uses healthcare sharing and pay out of pocket for most doctor’s visits

Bill of The Week

Thank you Eileen for sharing your bill about the explanation of benefits that say ‘THIS IS NOT A BILL’ which comes from health insurance provider!

Thanks so Much for Listening!

Thanks so much for listening. Many of you know we have a private community where we do monthly money challenges and offer accountability groups. We want to congratulate one of our members for a big win.

Just thinking about my values with every purchase was so helpful.

I did the challenge during the last seven days of September, and I didn't actually make very many purchases, but I thought about this every time. This is a very different mindset for me, and a real game changer. One of my values is work. I really love my job, and I've been working a lot of hours the last couple of weeks on a special project. I decided to use a grocery delivery service for my shopping for the week and spend a little extra for that so I could focus on working without needing to go out to the store (which always takes longer than I think it should).

Since I combined that with a strong meal plan for the week, I may even have saved a little in the end by not making any impulse purchases since I wasn't in the store looking at all the things!

Congrats! If you want to check out our monthly challenge community head to to see what challenge we have coming up next.

And keep leaving us reviews on iTunes or Stitcher, and sending the screenshot to And don’t forget to share your favorite quote from the episode by using the hashtag #FrugalFriendsNote. 😉

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