How do I shop for health insurance?

Premiums are skyrocketing – whether you get insurance through work or from the Obamacare marketplace. Here’s how we approach looking for the least-worst coverage.

Our team navigates 2026 open enrollment. Plus, a listener asks: is health insurance even worth it?

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

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

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

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

Some tips for making sure your insurance plan covers the meds you need.

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

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

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

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

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

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

How to think about traditional Medicare vs. Medicare Advantage, and why you might want to think twice about the latter.

Wading through the “alphabet soup” of Medicare and its supplemental plans.