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Stay Wealthy Retirement Podcast

Why 37% of Retirees Have Regrets (And How to Avoid Them)

Stay Wealthy Retirement Podcast

Taylor Schulte, CFP®

Financialplanning, Retirement, Money, Taxplanning, Stocks, Wealth, Business, Investing, Retirementplanning

2.4606 Ratings

🗓️ 13 June 2025

⏱️ 10 minutes

🧾️ Download transcript

Summary

"I planned for 30 years of expenses—but zero years of purpose."

This was a recent client's confession, and she's not alone.

In fact, nearly 40% of retirees say they wish they had waited longer to retire (and it's not about money). 

In this episode, I'm revealing why even the most financially prepared retirees fall into identity crises and regret.

I'm also sharing my 5-step "Bridge Strategy" to help you retire with clarity and purpose, not just a seven-figure portfolio. 

If you're planning FOR retirement but haven't considered what you're retiring TO, this episode is for you.

***

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We help 100+ families across the country navigate retirement, optimize investments, and reduce taxes.

🗓️ Learn more and schedule a Discovery Meeting with us.

***

EPISODE RESOURCES:

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Transcript

Click on a timestamp to play from that location

0:00.0

A client recently told me, I planned for 30 years of expenses, but zero years of purpose.

0:06.8

And she's not alone.

0:08.1

According to the National Bureau of Economic Research, more than one in three retirees say they wish they had waited longer to retire.

0:15.7

But it's not about money.

0:17.3

It's about meaning.

0:18.5

So today, I'm going to break it all down.

0:20.2

First, I'm going to share exactly all down. First, I'm going to share

0:21.3

exactly why the retire as early as possible movement is quietly backfiring for so many people.

0:27.6

And then I'm going to walk you through my five-step bridge framework to help you retire

0:32.1

successfully with purpose, not regret. Welcome to another episode of the Stay Wealthy Retirement Show.

0:39.1

I'm your host Taylor Schulte, and every week I tackle the most important financial topics

0:43.6

to help you stay wealthy in retirement.

0:45.7

And now, on to the episode.

0:52.0

Early retirement sounds like freedom.

0:57.6

No more commutes, no more meetings, no more deadlines. But that freedom often comes with an unexpected price tag, leading many people to wonder if they just made a big mistake.

1:05.7

As I just mentioned, more than one in three retirees wish they had waited longer to retire, 37% to be exact.

1:13.1

And here's the kicker. Early retirement regrets don't typically get better with time. They compound.

1:20.8

It turns out no amount of spreadsheets, simulations, or clever withdrawal strategies can prepare you for the emotional challenges retirement can create.

1:29.1

A family friend recently said something that stuck with me. She said,

1:32.7

retirement gave me everything that I wanted except direction. And she's not the only one faced

1:39.1

with that challenge. In fact, one academic study found that nearly 50% of retirees experienced some form of identity crisis during their transition.

1:50.0

There's also the mental challenge of second guessing the retirement decision itself.

...

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