Starter Packs are our best answers to some big questions, and collections of favorite podcast episodes. See them all here.

Starter Pack

How do I shop for health insurance?

Picking a health insurance plan can be overwhelming. Here’s our best advice.
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Choosing insurance: the basics

Shopping for health insurance: it’s not exactly retail therapy. We put together some strategies for making the process as painless as possible.



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How to shop for insurance, 2023 edition

A couple things have changed since we published this in 2023. But most of these five quick tips are as relevant as ever.



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Avoiding crappy health insurance

Pro-tip: Don’t just pick the plan with the lowest monthly charge. It could really, really cost you more.



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WTF even *is* this health insurance I’m picking?

Are the terms HMO, PPO, POS, EPO, HDHP, and HSA blending into one big bowl of alphabet soup? We’ve got you covered.



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Buying your own health insurance? Healthcare.gov. Full stop.

It still sucks—but at least it’s legit.



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The Medicare Episode

Your choices when you first sign up for Medicare are more consequential than you may realize.

Our war stories and some tips

This entire process can be super stressful — but you aren’t alone.



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Fight! My family tries to pick health insurance for next year. COVID makes it harder.

Go behind the scenes with Dan and his family as they select a new insurance plan.



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Why you (and I) will likely pick the wrong health-insurance plan

We spoke to some super-smart economists who proved that buying insurance is confusing. And it’s not our fault.



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This is Water, and it sucks. Let’s talk.

Is finding health insurance that’ll work for us even possible?



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Will we be able to afford insurance in 2026?

Insurance premiums are set to skyrocket in 2026 — especially in Obamacare plans. Our team tries to get a handle on it.

Health insurance "alternatives"

If it sounds too good to be true, it probably is.



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A "deal" on health insurance comes with troubling strings

We spoke with a financial therapist who tells us why she chose to use a Christian “health share” instead of regular insurance.



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A wild health insurance hustle

They thought they were buying insurance. Instead, they got fake “jobs.”

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