It’s that time again…open enrollment season. And while we know this topic doesn’t get anyone out of bed in the morning, it SHOULD. Because buried in that HR email you ignored is a decision that could cost or save you thousands.

This week, we’re breaking down why so many people just auto-renew last year’s health plan, what rising premiums in 2026 actually mean for your wallet, and how AI can help you stop making five-figure decisions based on casual conversations with your coworkers.

We talk about:

Why health insurance is quietly eating your raise
How to sniff out hidden changes in your 2026 plan
Using AI to compare plans without becoming an expert
The power of a good prompt and what to include in yours
Why planning for next year’s pregnancy, braces, or mental health care needs to happen right now

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