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Ready For Retirement

The BEST Retirement Advice (From 909 Real Retirees)

Ready For Retirement

James Conole, CFP®

Investment Planning, Bonds, Education, Stocks, Cash, Business, Dividend Investing, Retirement Planning, Retirement, Investing, Tax Planning

5706 Ratings

🗓️ 4 October 2025

⏱️ 12 minutes

🧾️ Download transcript

Summary

What if the riskiest move isn’t retiring too early, but waiting so long your best years pass by? This episode unpacks the real regrets of 909 retirees and the practical steps they wish they’d taken sooner. Design purpose. Spend on what matters. Do it while health and energy are on your side. Beat the “one more year” trap. Working longer can look safer on a spreadsheet, but life isn’t a spreadsheet. Learn how to prototype purpose before day one, shift your identity from saver to spender withou...

Transcript

Click on a timestamp to play from that location

0:00.0

If you think your biggest regret in retirement is going to be spending too much, then I have news

0:04.3

for you in today's video. We reached out to thousands of people to collect their responses about their

0:09.1

biggest retirement regrets, and we heard back with wonderful feedback from 909 people. Some of the

0:14.3

regrets that these people share have to do with finances, but many of them did not. It has to do with

0:19.9

purpose, how you spend your time, unexpected costs, things of that nature.

0:23.9

And in today's video, I'm going to share with you the real feedback we heard from 909 people,

0:28.0

the regrets they have, and the advice they would have given to their younger selves,

0:31.2

so that you can take this and apply it as you prepare for your retirement.

0:34.8

So here's the advice we received from people who have actually done it, who have actually retired. The first piece is that working longer is not necessarily

0:42.3

safer. How many of us have been caught up in that? We run projections. We see here's the impact

0:47.4

of one more year of work, max out my 401k, one more year, paying into Social Security one more year,

0:52.5

and on paper it has tremendous benefits.

0:54.6

We see what that does to our long-term financial projections. But here's the thing. That money is

0:59.9

pointless if it's not helping us fund the type of life we want to fund. In that life that we want to

1:04.7

fund, so much of it has the potential to pass us by if we're not able to appreciate the opportunity

1:09.7

in front of us. In other words,

1:11.7

I've seen far too many people work too long trying to maximize the financial side of things

1:15.9

that life has passed them by. This was a common regret people shared and therefore a common

1:21.2

piece of advice is working longer isn't necessarily safer. Sure, there's positive financial

1:26.1

benefits to it, but are you missing out

1:28.3

on life by doing so? Are you missing out on your youth, your health, your vigor, your ability

1:33.3

to do the things you actually want to do in retirement because you keep pushing retirement off?

...

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