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Ready For Retirement

This Is What a $10M Retirement Actually Looks Like

Ready For Retirement

James Conole, CFP®

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

4.8793 Ratings

🗓️ 4 January 2026

⏱️ 15 minutes

🧾️ Download transcript

Summary

A $10 million retirement is often imagined as the finish line — complete freedom, unlimited spending, and no financial stress. The reality is more complex. James walks through what an eight-figure retirement actually looks like by examining a real planning scenario for a couple entering retirement with roughly $10 million in assets. Rather than focusing on luxury or excess, the conversation centers on how income, taxes, investment structure, and lifestyle decisions evolve once work stops and ...

Transcript

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0:00.0

Most people think a $10 million retirement means yachts, first class travel, never having to think about money again. But the reality is, that's not what a $10 million retirement looks like at all. So let me show you what actually changes and what doesn't going into retirement with an eight-figure portfolio. Here's a case study that we're going to look at. This is Roger, this is Catherine. And Roger and Catherine, you can see right off the bat with their investments here. They have almost $7 million in a stock portfolio.

0:22.3

Now, the way they accumulated that was they had equity compensation in a publicly traded company that did quite well.

0:27.5

Here's the thing about people $10 million plus portfolios.

0:30.0

Usually it's either the result of selling a business or multiple businesses or you had some type of an equity compensation plan where the company that you

0:37.8

worked at performed quite well. Now, for you watch, and if you have that level portfolio,

0:41.9

chances are very high. You either also had some type of an equity compensation plan or you sold

0:47.3

a business or even multiple businesses. Sometimes there's inheritance, sometimes there's other

0:51.1

details, but typically it's owning equity, either in a company that you started or a company that you joined that's going to get you to this position where you have $10 million or more. That's the case with them, but they also have their 401ks and IRAs. You can see their home here and they do have a bit of a mortgage, and Roger and Catherine are 62 years old. The goals that they shared, this is one the hardest

1:11.0

thing for most people. They've saved this money, but believe they're not, a lot of people that have this level of wealth going into retirement, they haven't been living an incredibly lavished lifestyle to get there. They got there, like I said, because they grinded, they started a business, they ran a business, they sold a business, and all of a sudden there's this windfall that they know can radically transform what life looks like, or they had an equity

1:30.1

compensation plan,

1:31.3

where the stock that they were invested in, their employer stock, performed incredibly well to the

1:35.0

point that they look at their potential retirement and it has potential to be significantly more

1:39.1

comfortable than their working years or their years leading up to retirement. So in a lot of cases, people at this level of wealth, they look at retirement and their first question is, I have no idea how much I can even think about spending in these years. So we said, let's start with something. Let's start with $10,000 per month, which would be a comfortable lifestyle and see, can you do it? If you can do that, then we can start working backwards to understand what's actually

2:01.4

doable, given your level of wealth here. They also wanted to budget an extra $25,000 per year for

2:06.4

travel, and then they have annual healthcare costs. If they were to retire before Medicare age,

2:11.2

that would be $9,600 per year. If they retire at age 65 or later, they would have their

2:15.9

Medicare Part B and D premiums, and they would also have an additional $4,000 per year of out-of-pocket expenses. They have their salaries today. They're not planning to retire until 65, so that's the cash though coming in, and they're planning to collect their Social Security benefits at age 70. So this is where we want to start. The same, whether you have $10 million whether you have 10,000, this is the general framework. What's going to be different is what you then do with some of this information. So let's first start with this retirement overview. Let's start by understanding cash flows and see what all goes in to their ability to retire. So if we start here, and by the way, as I'm going through this, if you want access to this software, link is in the show notes below. It's in the Retirement Planning Academy. You can get this and do this on your own, regardless of how much you have in your portfolio. So what we can see here is their cash flows. And their cash flows help us to understand big picture. We have been living our lives leading up to retirement. We have

3:09.0

our salary. And that salary covers all of our needs. But when we retire, that salary, of course, goes

3:13.8

away. So where the heck is income going to come from? Is it going to come from Social Security? Is it going to

3:18.6

come from my IRA, from my Roth IRA, for my brokerage account, these are the questions

3:24.4

top of mind, and this is helping us to answer it. So what we can see here is the next three years,

3:29.8

they have salary coming in. They don't need to worry about living off their portfolio income.

...

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