The decisions that follow you from room to room
There are seasons when the hardest part is not the decision itself, but the way it follows you from room to room before you've named it.
Medicare is one of those decisions. It arrives at a specific moment — usually around a birthday, a job change, or a letter in the mail — and it carries more weight than it first appears to. The timing matters. The sequence matters. What you choose in the first year can shape what's available to you in the years that follow.
Most people learn this after the fact.
The information exists, but it's scattered across government websites, insurance company brochures, and well-meaning advice from people who made their own choices under different circumstances. The rules are real, but they're explained in pieces — leaving you to assemble them into a single decision while the clock is running.
That's what I wanted this letter to address. Not a newsletter in the traditional sense — not a stream of updates or a product announcement each week. One useful note, written for the moment you're actually in. A question worth sitting with. A rule worth understanding before it applies to you. A situation someone else navigated that might be yours next.
The Sunday Letter is free. It doesn't sell plans. It doesn't have a sponsor. It arrives once a week and asks nothing of you except a few minutes on a Sunday morning.
If it's useful, keep it. If it's not, one click and it's gone.
— Dan
The next letter arrives Sunday.
One useful note each week. No product updates unless you choose those separately.
Send me The Sunday Letter →