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.

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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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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The Medicare Episode

Your choices when you first sign up for Medicare are more consequential than many realize. Here are our best tips to avoid buyer’s remorse.



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A wild health insurance hustle

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

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