Can Millennials Count on Social Security? w/ Mike Piper #1127

About this episode

The episode discusses the future of Social Security and retirement planning for Millennials and Gen Z with expert Mike Piper.

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…

People in this episode

Guest: Mike Piper

Topics covered

• Social Security
• retirement planning
• financial strategies
• generational differences
• claiming strategies
• investment mistakes

Keywords

• Social Security
• retirement
• claiming strategies
• financial planning
• investment mistakes
• trust fund
• early retirement

Mentioned in this episode

Organizations: Oblivious Investor, Open Social Security

More episodes of How to Money

• Friday Flight - Overblown AI, Portfolio-Powered Wealth, & K-Shaped Credit #1152 · June 12, 2026 · 36 min
• The Invisible Economic Forces Shaping Your Life w/ Planet Money's Alex Mayyasi #1151 · June 10, 2026 · 60 min
• Ask HTM – Butting Heads with Investing Gurus, 4% Mortgage Ripoff, & Hoarding Cash at Retirement #1150 · June 8, 2026 · 56 min
• Friday Flight - Space Stocks, Delaying Debt, & Home Insurance Hardships #1149 · June 5, 2026 · 39 min
• Avoiding the 'Middle Class Trap' w/ Scott Trench #1148 · June 3, 2026 · 1h 1m
• Ask HTM – Liquid Cash (How Much is Too Much), AI WW3 Portfolios, & Shopping Local (for a Mortgage) #1147 · June 1, 2026 · 54 min