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The Boring Newsletter, 7/20/2025

When you ask Cigna if your dentist is in-network and discover they hired George Orwell as a consultant Hi Friendos, As you know from prior newsletters, I’ve been learning a lot about health insurance this summer. Today I am writing about something that I’ve learned is not at all a new topic, but was new-to-me: […]

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The Boring Newsletter, 9/22/2024

Hi Friendos, A recent episode of Gabe Dunn’s excellent Bad with Money podcast discussed money questions that people don’t even know they can ask, like: I wanted to share an example from my own life when asking a question paid off. So far this has saved us at least $920. If you have examples of […]

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The Boring Newsletter, 10/29/2023 🩺

Hi Friendos, Today is our fourth installment discussing tax-advantaged medical accounts (HSAs and FSAs) where we’ll look at how these fit into the overall selection of a health insurance plan. I am always grateful to have insurance (really grateful) but I *hate* that choosing a plan is so complicated. My approach is to consider the […]

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The Boring Newsletter, 10/8/2023

Hi Friendos, Health insurance open enrollment is coming up in a few weeks so this month I’ll write about some related topics. This week is about explaining the financial benefit from FSAs and HSAs (“flexible spending account,” “health savings account”), specifically, how they save you money. Next week I’ll talk about how much. This helps […]