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

Connect with Julien and Kiersten on our website, Instagram, Twitter, and YouTube.

Join our email list to get updates from us, opportunities for discounts, freebies and a quick rundown on the relevant financial and career news impacting your life.

Get our book Cashing Out: Win the Wealth Game by Walking Away, named 2023 best overall book about investing by Business Insider and one of the best personal finance books by Forbes
If you would like to learn more about investing, check out our newest class, Making Money Grow