Let's talk about Social Security. More than music, clothing, or even political views, Social Security might be the single biggest generational fault line in America right now. Boomers are thrilled to finally be collecting on a promise decades in the making while Millennials and Gen Z are quietly wondering if there'll be anything left by the time we get there. And honestly? That concern isn't crazy! Social Security almost certainly isn't going away entirely, but it's probably not going to look exactly the same as it does today either. Mike Piper, CPA and Social Security expert, joins the show today to explore the future of Social Security, optimal claiming strategies, and how to plan for retirement amid uncertain benefits. Specifically covered: What happens when the trust fund is gone?! Downsides of overly conservative financial plans Claiming strategies when we’re living longer Adjusting plans after a health diagnosis The Open Social Security strategy calculator Taking opportunity cost into account Early retirement considerations Common mistakes with DIY investors... and plenty more! Can’t get enough How To Money? Here are some additional ways to get ahead with your personal finances: Mike Piper: Head over to Mike’s site, Oblivious Investor for his latest writings and Open Social Security for his free open-source strategy calculator. Credit card perks: Check out our favorite credit cards that we use to maximize rewards and optimize our spending. Money Gears: Knowing what to do with your money is crucial to your personal finance journey. Newsletter: Sign up for the weekly HTM newsletter. It’s fun, free, & practical. Other money nerds: Find a thriving community of fellow money nerds by joining the HTM Facebook group! And please help us to spread the word by letting friends and family know about How to Money! Help us to change the conversation around personal finance and get more people doing smart things with their money! Best friends out!