The Biggest Retirement Mistakes People Make (Avoid These!) Jesse Cramer

The Personal Finance Podcast

Andrew Giancola

Business, Investing, Entrepreneurship

4.7 • 1.4K Ratings

🗓️ 28 March 2026

⏱️ 68 minutes

🔗️ Recording | iTunes | RSS

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Summary

Join the community built to help you master your money, stay accountable, and reach financial freedom. 👉 Try Master Money Academy free for 7 days today! In this episode of The Personal Finance Podcast, Andrew sits down with Jesse to explore critical retirement planning decisions—why Social Security isn't just a math problem and the biggest mistakes people make when claiming, when delaying benefits makes sense versus when claiming earlier is smarter, how married couples should think differently than singles, why Roth conversions are both overused and underused, the danger of overly optimistic return assumptions like 12% or 10%, the number one thing retirees get wrong about their own spending, and the most important actions to take 5-10 years before retirement. Listen to The Business Show here. Join The Master Money Newsletter where you will become smarter with your money in 5 minutes or less per week Here! Partner Deals Join the loyalty program for renters at joinbilt.com/PFP Indeed: Start hiring NOW with a SEVENTY-FIVE DOLLAR SPONSORED JOB CREDIT to upgrade your job post at http://Indeed.com/personalfinance Go to http://policygenius.com to get your free life insurance quote. Thanks to Fundrise for Sponsoring the show! Invest in real estate going to http://fundrise.com/pfp Go to Acorns.com/pfp and start automating your investments and get a $5 bonus today! Get 50% Off Monarch, the all-in-one financial tool at http://www.monarch.com/PFP DeleteMe: Go to https://joindeleteme.com/PFP20/ and Use Promo Code PFP for 20% off! Connect with Jesse Cramer: Personal Finance For Long-Term Investors Podcast The Best Interest Website X Instagram Linkedin Connect With Andrew on Social Media: Instagram TikTok Twitter Master Money Website Master Money Youtube Channel Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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1:26.4	copilot. The biggest retirement mistakes don't come from bad math.
1:30.3	They come from fear, they come from assumptions,
1:32.3	and they come from decisions that look right on paper,
1:35.3	but feel wrong in real life.
1:37.3	Being overly conservative, it might make you feel safe,
1:40.3	but it's creating risks that you might not even be aware of.
	...

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