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Ready For Retirement

The Real Reason Most People Struggle in Retirement (It’s Not Money)

Ready For Retirement

James Conole, CFP®

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

5706 Ratings

🗓️ 15 September 2025

⏱️ 7 minutes

🧾️ Download transcript

Summary

Retirement planning is often framed as a numbers game where you can get lost in focusing on maximizing your 401(k), minimizing taxes, and chasing investment returns. But financial security alone doesn’t guarantee fulfillment. The bigger challenge many retirees face is psychological, not financial. The transition from decades of work into retirement often sparks an identity crisis. A career provides structure, purpose, and community—when it’s gone, retirees can feel adrift. Without clarity on ...

Transcript

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0:00.0

Most people watching this video think retirement is all about the numbers. How much have you saved?

0:04.7

Can your portfolio withstand the next downturn? Do you have the right tax strategy in place? And while all

0:09.5

those things are important, if that's all you're focused on, you're really going to struggle when it

0:13.7

actually comes time to retire. But here's the truth that no one actually talks about. The number one

0:18.2

reason people struggle in retirement actually has nothing to do

0:21.2

with money. And while money can be a supporting factor here, the number one reason people struggle

0:26.2

is they don't actually know what they want their life to look like. And if you don't actually

0:30.2

know what you want your life to look like, then no amount of money. Doesn't matter what your financial

0:34.3

strategy is, nothing can replace that in terms of giving you the type of retirement that you're looking to live. In one of his blog posts, Morgan Housel had this to say. He said, if you have no strong views on what kind of life you want to live, who you are, what you desire, what makes you happy and what doesn't, you're likely to want to mimic the most visually appealing person you come across, which is often the person with the biggest house, fastest car, or nicest clothes. That may work. It may not. We see this all the time.

1:01.1

We have goals for retirement. We know that by a certain age, we should retire. We know we should

1:04.9

max out of 401k. We know what to do to optimize Social Security. And then we get there and we freeze.

1:09.8

And we freeze because we think, what am I actually going to do? The past 30 years, the past 40 years, all I've been doing is working and grinding and raising a family and doing all these things that matter. But I've lost this sense of who I am and what I want to do. So when I set goals for my retirement, it's not actually my goals. I don't even know what my goals are. I'm just going to mimic what I see other people doing. They must be happy, right? They have the nice cars. They take the nice trips. They do the things that seem to make them happy. Maybe that's what I want for my retirement. But if that's the way that you're approaching it, you're going to be let down. You're going to retire. You might enjoy it for a short

1:44.4

brief period of time, but then you're going to feel this sense of loss. Why? Because your job was

1:48.9

your identity. Your job was your structure. Your job was your social connection. Your job was this thing

1:53.7

that even if you didn't absolutely love it, provided these things that all of us need, provided

1:57.9

this purpose that gave you this sense of identity. And then one day,

2:02.0

just like that, all that changes. You now have the money. You know, have the time. You've retired

2:07.3

from that, but what have you retired into? And that's what I want to address today? How do you

2:12.1

avoid that scenario where even if you have the best financial strategy in the world, you may have

2:16.3

a very tough retirement

2:17.6

if you don't address these questions first. So what do you do? Well, if it's not about looking

2:22.3

at other people's homes, other people's golf trips, other people's idea of what a good retirement

...

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