The Retirement Wisdom Podcast

The Retirement Wisdom Podcast

Medicare for You – Diane Omdahl

May 28, 2023

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Some things are not as easy as you may think. And discerning the right Medicare choices for you is one of those things. When preparing to enroll in Medicare, or evaluating your coverage, it pays to look past the commercials, do your homework – and to read the fine print. When I researched Medicare in 2022, I engaged Diane Omdahl and her service 65 Incorporated. She’s written a new book Medicare for You: A Smart Person’s Guide and joins us today to discuss some key things you need to know.

Diane Omdahl joins us from Wisconsin



The author of Medicare for You: A Smart Person’s Guide, Diane Omdahl, RN, MS., is a nationally recognized Medicare expert and the author of Medicare and You: A Smart Person’s Guide.

In 2012, she co-founded 65 Incorporated, a company that provides one-on-one consultations to individuals dealing with Medicare. Her first company, Beacon Health, provided homecare agencies with Medicare compliance guidance from 1987 until she sold it in 2008. Diane has served as a technical expert for the Centers for Medicare and Medicaid Services (the organization that runs the Medicare program) and is a frequent speaker on Medicare-related issues. In addition to being a registered nurse, Diane holds a Master’s degree in Health Services Administration. Diane is a contributor on the topic of Medicare and has been featured in many national publications including the Washington Post, CBS MoneyWatch, Forbes, The Wall Street Journal Market Watch, Kiplinger, and many others. You can learn more about Diane at and


For More on Diane Omdahl

Medicare for You: A Smart Person’s Guide

65 Incorporated

i65 (Fiduciary Medicare Software & Consulting)


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Wise Quotes

On Setting Up Your My Social Security Account

“.. a very important step that they can do at any time in their life is to set up a My Social Security Account. That is the way that they will enroll in Medicare when it’s time. And we have run into people trying to enroll in Medicare who did not have an account. And it’s not always easy to set up. And people who have an account haven’t kept it up to date, they haven’t informed Social Security of their address change. And after a divorce, women with a name change, that’s quite involved. And with the Social Security offices just coming back out from Covid, many of them are still not open completely. If you have to submit documents, you don’t want to send originals in the mail. And so that’s what we say, keep it up to date. Then when you’re actually approaching 65, you can’t do anything until your initial enrollment period, which is three months before your birthday, unless it’s on the first of the month and it’s four months. But people like to start about six months in advance. Given they’re getting all of the advertising even earlier than that, we tell them that’s when you should start thinking about it. And one of our best pieces of advice is that they can  toss out that stuff they get prior to age 65 because as they get closer and know what they need, then they can look for the specific information that will work for them.”

On The Two Medicare Paths

“The two Medicare paths is how Medicare is structured for most people over 65. It is probably the most important decision people will make going forward, yet people give it the short shrift. I read that on average people spend 14 hours shopping for a new car. What do they do when it comes to Medicare? They go with what their spouse has, or what works for a friend, or what’s in the commercials. With a car there are lemon laws, and in the worst case scenario, you’d lose your money and start over. With Medicare, in most states, you won’t be able to start over. So this decision is very important.”


On Researching Medicare Advantage 

“…Don’t call the number on the screen. Again, when you read the fine print, it will say that this will connect you to an agent who may or may not be in your area, who may or may not be selling your plan, or may or may not be selling Medicare Advantage. I actually saw that on one of the commercials. So I tell people, if something interests you in the commercial, go to the Medicare Plan Finder, find that plan in your area, then actually go and look at the evidence of coverage. This is painful for many people trying to find the Evidence of Coverage, which is in the rules. It’s amazing what they say in the commercial and what the actual rules are. Two different stories. Then when you think you like the plan, contact a local agent or you can enroll directly with the plan. But never call that number because there’s been all kinds of reports about people who called the number, thought they were getting this and they thought their meds were covered, but then they weren’t.”


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About Your Podcast Host

Joe Casey is an executive coach who also helps people design their next life after their primary career. He created his own next chapter after a twenty-six-year career at Merrill Lynch, where he was Senior Vice President and Head of HR for Global Markets & Investment Banking. Today, in addition to his work with clients, Joe hosts The Retirement Wisdom Podcast, which thanks to his guests and loyal listeners, ranks in the top 1.5 % globally in popularity by Listen Notes. Business Insider has recognized him as one of 23 innovative coaches who are making a difference. He’s the author of Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy.

The views and opinions expressed by guests on The Retirement Wisdom Podcast are solely those of the guests and do not reflect the opinion of the host or Retirement Wisdom, LLC. The Retirement Wisdom Podcast primarily covers the non-financial aspects of retirement. From time to time we may invite guests who discuss other aspects of retirement planning, solely for educational purposes. Listeners are advised to consult qualified financial and/or medical professionals on those matters.