When most people hear “$10 million retirement,” they picture yachts, first-class flights, and never having to think about money again.
That’s not reality.
In practice, retirement with an eight-figure portfolio often looks far more ordinary than people expect. The real difference isn’t unlimited spending. The real difference is flexibility—and the responsibility that comes with it.
Let’s walk through what actually changes, what doesn’t, and how people with $10 million or more truly approach retirement.
How People Typically Reach an Eight-Figure Portfolio
Before we talk about retirement itself, it’s important to understand how people usually get here.
Most individuals with $10 million or more did not save their way there by maxing out retirement accounts alone. In most cases, that level of wealth comes from owning equity. That might be equity in a business they built and eventually sold, or equity compensation at a company that performed exceptionally well over time.
Sometimes inheritance plays a role, but more often than not, the common thread is ownership. Years of work, reinvestment, and patience eventually result in a large, concentrated pool of assets that can dramatically change what retirement looks like.
A Case Study: Roger and Katherine
To make this concrete, let’s look at a hypothetical example.
Roger and Katherine are both 62 years old. They have accumulated a little over $10 million in total net worth, with nearly $7 million in a taxable brokerage account. The majority of that came from equity compensation in a publicly traded company that did very well over the course of their careers.
They also have traditional retirement accounts, a primary residence with a modest remaining mortgage, and strong earned income that will continue until age 65. They plan to retire at 65 and delay Social Security until age 70.
At first glance, their financial picture looks incredibly strong. But the most difficult part of the planning process wasn’t investments, taxes, or estate strategy.
It was answering a much simpler question.
The Hardest Question for High-Net-Worth Retirees
Many people assume that once you reach this level of wealth, spending decisions become easy.
In reality, the opposite is often true.
Most people who retire with significant wealth did not live extravagantly while they were building it. They were focused on growing businesses, reinvesting profits, or holding equity that wasn’t spendable cash. When they finally reach retirement, they’re left asking how much they can actually spend without making a mistake.
So instead of starting with aggressive assumptions, we started conservatively.
Roger and Katherine suggested a comfortable lifestyle of about $10,000 per month in after-tax living expenses, plus $25,000 per year for travel. Healthcare costs were estimated based on retiring at 65 and transitioning to Medicare.
The initial goal wasn’t to optimize or push the numbers. The goal was simply to determine whether this lifestyle was clearly sustainable.
Retirement Always Starts with Cash Flow
No matter how much money you have, retirement planning always follows the same framework.
Before retirement, your salary covers your lifestyle. Once you retire, that paycheck disappears, and income must come from other sources. The question becomes where that income will come from and when it will begin.
In Roger and Katherine’s case, their salaries cover everything until age 65. From age 65 to 70, they have no earned income and no Social Security, which means their lifestyle must be funded entirely from their portfolio. At age 70, both Social Security benefits begin, reducing the amount their portfolio needs to support each year.
This income gap is not a problem, but it must be planned for intentionally.
Understanding What Life Actually Costs
From there, we built a year-by-year picture of expenses, all expressed in today’s dollars and adjusted for inflation over time.
Their core living expenses came out to $120,000 per year. Housing costs included a remaining mortgage that is projected to be paid off in their early seventies, after which only property taxes and insurance remain. Healthcare expenses were estimated based on Medicare premiums and reasonable out-of-pocket costs.
Travel was budgeted more heavily in the earlier retirement years, recognizing that spending often declines later in life. Taxes were also included, because while payroll taxes disappear in retirement, income taxes, capital gains taxes, and taxes on Social Security often do not. Later in retirement, required minimum distributions increase taxable income, which is an important planning consideration.
Looking at expenses this way allows us to see how costs change over time, rather than assuming retirement spending is flat and static.
The Key Question: Is This Sustainable?
Once total spending is clear, the most important question becomes how that spending relates to the portfolio.
For Roger and Katherine, the highest withdrawal rate occurs in the early years of retirement, when they are fully relying on their portfolio and Social Security has not yet started. Even then, withdrawals are roughly 2 percent of the portfolio.
Over time, as Social Security begins and the portfolio grows under long-term assumptions, withdrawals represent a smaller percentage of assets. Later in retirement, the withdrawal rate increases again due to required distributions from retirement accounts, not because their lifestyle has changed.
There are no guarantees here. Markets fluctuate, and real life never follows a straight line. But from a planning perspective, this level of spending relative to the portfolio is very different from the risk profile faced by someone withdrawing a much higher percentage from a smaller pool of assets.
What the Long-Term Projection Reveals
When all of these pieces are put together, the portfolio continues to grow over time under reasonable assumptions. Even well into their nineties, Roger and Katherine are projected to have significant remaining liquid assets, not including the value of their home.
At that point, the conversation naturally shifts.
The question is no longer how to maximize the ending balance. The question becomes how to use this money intentionally while they are alive.
Retirement Planning Isn’t About the Final Number
One of the biggest mindset shifts for high-net-worth retirees is realizing that planning is not about dying with the largest possible portfolio.
The real objective is to live well, without unnecessary fear, while structuring assets in a way that supports that life. Taxes and estate planning matter, but they come after lifestyle clarity, not before it.
For Roger and Katherine, that meant asking a different kind of question.
What If You Spent More—On Purpose?
Once it was clear that their baseline lifestyle was easily supported, we explored what spending more might look like if it were done intentionally.
Instead of thinking in terms of arbitrary monthly numbers, the focus shifted to experiences. More meaningful travel. More time with family. More generosity during life, not just at death.
When those changes were modeled, the portfolio still showed a high probability of long-term success. The ending balance was lower, but that tradeoff was intentional and aligned with how they wanted to live.
That’s often the right outcome.
Where Advanced Planning Adds the Most Value
Only after lifestyle decisions are clear does advanced planning really begin.
This is where portfolio structure, tax strategy, and estate planning work together. Thoughtful asset allocation helps balance growth and stability. Tax planning strategies can reduce the long-term impact of required distributions. Charitable strategies, such as gifting appreciated assets or using donor-advised funds, can align generosity with tax efficiency and family values.
At this level of wealth, small planning mistakes can have large consequences, which is why coordination matters.
The Reality of a $10 Million Retirement
A $10 million portfolio dramatically reduces the risk of running out of money. But it does not eliminate anxiety.
In many cases, it creates a different kind of stress: the fear of making a costly mistake and the pressure to use the money well.
That’s why the planning process matters just as much as the numbers themselves.
If you’re approaching retirement with significant wealth, the most important step is clarity. Understand what you want life to look like, understand what that costs, and build a plan that supports living fully rather than simply preserving assets.
The information presented is for educational and informational purposes only and should not be construed as personalized investment or financial advice. The content discusses general retirement planning strategies and is not intended to recommend any specific course of action for any individual.
Social Security claiming strategies involve a number of variables, including life expectancy, portfolio returns, tax considerations, and personal circumstances. Decisions regarding Social Security benefits should be made in consultation with your financial advisor, taking into account your full financial picture.
Examples provided are hypothetical and for illustrative purposes only. They do not reflect any specific client situation and should not be relied upon for investment decision-making. Past performance of investments is not indicative of future results. All investing involves risk, including the potential loss of principal.
Root Financial Partners, LLC provides tax planning as part of its financial planning services. However, we do not provide tax preparation services, represent clients before the IRS, or offer legal advice.
Clients should consult their CPA or attorney before implementing any tax or legal strategies discussed. Nothing in this video should be interpreted as a recommendation to take a specific tax position or legal action.
This content may include discussions around advanced financial planning strategies such as Roth conversions, backdoor Roth IRAs, tax loss harvesting, charitable giving, estate planning tactics, or Social Security claiming strategies. These concepts are general in nature and are not personalized advice. Actions related to these strategies may trigger tax consequences or legal implications. Always consult with your CPA or attorney to assess suitability based on your personal financial circumstances.
Suitability for these strategies depends on your individual tax situation, income, age, investment profile, estate plan, and other factors. Actions related to these strategies may trigger tax consequences or legal implications. Always consult with your CPA or attorney to assess suitability based on your personal financial circumstances.