Medicare is one of the most consequential — and confusing — decisions you’ll face as you approach 65. In this episode, Greg sits down with Danielle Roberts, co-founder of Boomer Benefits and author of 10 Costly Medicare Mistakes You Can’t Afford to Make, for a clear-eyed breakdown of how Medicare actually works. From the structural difference between Original Medicare and Medicare Advantage, to the one-time Medigap enrollment window most people miss, to the income-based premium surcharges that can blindside high earners — this conversation gives you the roadmap to make smarter decisions, earlier.
About Danielle Roberts
Danielle Roberts is the co-founder of Boomer Benefits, an independent insurance agency helping people in 49 states navigate Medicare. Over two decades and more than 100,000 policyholders, Danielle and her team have built their practice around making a complex federal program simple and accessible. She is the author of the bestselling book 10 Costly Medicare Mistakes You Can’t Afford to Make and hosts free public webinars walking people through enrollment step by step.
Key Takeaways
- Original Medicare and Medicare Advantage are fundamentally different products. Original Medicare (Parts A and B) provides nationwide access to any Medicare provider. Medicare Advantage works like group Health insurance — network-based, usually lower premiums, less flexibility. Today the two options split the market roughly 50/50, with Advantage plans slightly edging ahead.
- Your initial enrollment window is seven months, and the clock is running. It opens three months before your 65th birthday and closes three months after. Missing it triggers permanent late penalties on Parts B and D.
- The Medigap underwriting window is a one-time, six-month opportunity. Starting from your Part B effective date, you have six months to enroll in any Medigap plan with no medical underwriting. After that window closes, insurers can decline you based on health history.
- Plan G is currently the most comprehensive Medigap option. It covers everything except the Part B deductible ($283 in 2026). Once that’s paid for the year, your out-of-pocket costs for covered services are effectively zero — regardless of what medical events occur.
- Skipping Part D drug coverage carries a permanent penalty. Every month without qualifying coverage adds 1% to your Part D premium for life. Even if you take few medications, maintaining a low-cost plan protects you from both penalties and unexpected drug costs.
- The donut hole is gone — but Part D is still worth understanding. Under the Inflation Reduction Act, out-of-pocket drug costs are now capped at $2,100 annually (2026). All plans must cover six mandatory medication classes, including Cancer, anti-depressants, and antiretrovirals.
- High earners pay more for Medicare — and can plan around it. IRMAA (Income-Related Monthly Adjustment Amount) can push Part B premiums to over $600/month per person based on income from two years prior. Financial decisions at 63–64 — IRA distributions, capital gains, severance — can significantly affect what you pay.
- Start your Medicare research at 64½. Give yourself six months to learn before you need to decide. Arriving at enrollment with knowledge under your belt changes the entire conversation with a broker.
Resources & Links
Me? I'm a chill late 60-something, (very late), women's health coach, podcaster, wife, step mother, Gigi to 2 grand baby boys, 3 cats, 2 goats, and many chickens. Former pro chef turned entrepreneur. My current ventures include BeMoreMarketable, copywriting for coaches and Rebellious Wellness Lifestyle, where I host a podcast of the same name and write on healthy aging topics that mainstream media skips. I untangle the confusion around health trends and bust the myths around aging so common today--like "this is what happens at your age." What age is that I want to know!
My side gig is gardener and flower arranger.
