Are You Planning For Health Costs Or Guessing

Money Matters with Greg · May 26, 2026 · 28m · transcript

Medicare is one of those milestones that sounds scary until you see the rules laid out clearly and realize you actually have more control than you think. We sit down with Paul Jankowski from Shepherd Insurance, a Medicare specialist who has helped people navigate Medicare since 2005, to walk through what happens as you approach age 65 and how to avoid the most common (and costly) mistakes.

We start with the basics that trip people up: Medicare vs Medicaid, when your Medicare effective date begins, and how enrollment works if you are or are not already taking Social Security. Then we zoom out…