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Hi, Friends!
This week's edition covers two topics that don't get talked about enough, one that affects nearly everyone reading this, and one that matters if you or someone in your life runs a small business.
Let's start with Medicare. I've talked to people who assumed they had more time than they did, and it cost them. This week, we walk through exactly when each window opens and closes, what Medicare actually costs in 2026, and the one penalty that doesn't just cost you once, it follows you for as long as you have coverage.
Then we're shifting gears to business owners. If you run a small business or you're helping a family member who does there are a handful of numbers that quietly predict trouble long before it shows up in the bank account. We're talking about a small set of numbers you can check in a few minutes a month that tell you more than most people realize.
Both articles are the kind of thing we'd want someone to hand us before we needed it, not after.
Warmly,
Mike Bridges
You don't have to have it all figured out to make progress. You just have to check one thing you've been avoiding
FEATURED ARTICLE
This week's article breaks down the enrollment calendar in plain terms, along with the costs tied to it and the one penalty that doesn't go away once it starts.
Medicare enrollment doesn't run on one deadline — it runs on several overlapping ones, and missing the wrong window can follow someone for years, not months. The rules changed as recently as 2023, and most people never hear about it until they're already past the date that mattered.
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This week's article walks through the handful of monthly numbers worth a few minutes of attention, and what each one is quietly trying to tell you.
Most small business owners end up wearing every hat — bookkeeper, collections department, and retirement planner, often all in the same afternoon. The numbers that actually predict trouble rarely show up on their own; they have to be checked on purpose.
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