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The Personal Finance Podcast

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

The Personal Finance Podcast

Andrew Giancola

Business, Investing, Entrepreneurship

4.71.4K Ratings

🗓️ 23 February 2026

⏱️ 68 minutes

🧾️ Download transcript

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 Indeed: Start hiring NOW with a SEVENTY-FIVE DOLLAR SPONSORED JOB CREDIT to upgrade your job post at http://Indeed.com/personalfinance Join the loyalty program for renters at joinbilt.com/PFP  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   Get 50% Off Monarch, the all-in-one financial tool at http://www.monarch.com/PFP  Find your next dream home, start searching now. Download the http://Realtor.com app today 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 Twitter 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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0:00.0

The biggest retirement mistakes don't come from bad math.

0:03.0

They come from fear, they come from assumptions, and they come from decisions that look right on paper but feel wrong in real life.

0:10.0

Being overly conservative, it might make you feel safe, but it's creating risks that you might not even be aware of.

0:16.0

Don't you want to avoid working five extra years that you never would have had to? Don't you want to avoid this fact where you basically scrimped and saved and you didn't live the life you wanted to live? Year after a year, they have been saying they want to retire. Five years ago, they could have retired. More than enough money, more than enough assets, more than enough cash flow coming in to be able to retire. And a lot of it came down to one word, which is fear.

0:41.1

You will convince yourself, oh my God, Andrew, I can't retire until I'm 68.

0:42.6

That's what the spreadsheet says.

0:47.2

Or I would look at it and say, like, well, no, you've been way too conservative every single place you could be, and I think you could retire at 55.

1:02.6

Oh. What's up, everybody, and welcome to the Personal Finance Podcast.

1:05.6

I'm your host, Andrew, founder of MasterMoney.com.

1:11.9

And today on the Personal Finance Podcast, we're going to be diving into retirement with Jesse Kramer.

1:15.8

If you guys have any questions, make sure you join the Master Money newsletter by going to mastermoney.com slash newsletter. And don't forget to follow us on Apple Podcasts, Spotify,

1:21.1

YouTube, or whatever podcast player, you love listening to this podcast on it. If you want to

1:25.6

help out the show, consider leaving a five-star rating and review on Apple Podcasts, Spotify, or your favorite podcast player.

1:32.3

Now, today we're going to be diving into retirement with Jesse Kramer.

1:35.6

And now most people think retirement planning is about the math.

1:39.1

They want to pick the right withdrawal rate.

1:41.4

They want to think about Social Security and make sure they're picking the right timeline. They want to pick the right assumption when they're thinking about

1:47.3

rate of return. But after talking to thousands of different people about money, I've realized something.

1:53.4

The biggest retirement mistakes don't come from bad math. They come from fear. They come from

1:58.2

assumptions. And they come from decisions that look right on paper, but feel wrong in real life.

2:03.8

Today's conversation is about the difference and the gap between spreadsheets in life.

2:07.8

But it also is looking at when you need to make sure you trust the math, but also when you need to make sure you're making the right decisions.

...

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