How to Know if You Have Enough Money to Retire

For many affluent professionals, retirement is less about stepping away from work altogether and more about achieving the freedom to choose how to spend your time. Yet even with impressive portfolios and years of disciplined saving, one question lingers for even high-net-worth individuals: Do I truly have enough to retire comfortably?

The answer isn’t as simple as looking at a balance sheet. Financial advisors like me use a suite of sophisticated tools and analysis to determine if a client is truly “retirement ready.” Here's a look inside that process.

Defining Your Retirement Lifestyle

One of the first questions I will usually ask is, what does retirement look like for you? Will it include global travel, a second home, charitable ventures or extended family support?

High-net-worth individuals often have unique lifestyle expectations. A typical 4% withdrawal rule may not apply if your spending patterns far exceed the national average. Advisors will model a custom cash flow projection based on your desired lifestyle, often over 30 or more years of retirement. It’s not just about how much you have—it’s about how much you’ll spend and for how long. A good financial advisor will build projections that include inflation, longevity risk, market volatility, and even unexpected medical expenses.

Analyzing Portfolio Sustainability

A key part of retirement planning is stress-testing your portfolio under various market conditions. Good advisors evaluate asset allocation, expected return and risk exposure using Monte Carlo simulations—a method that runs thousands of market scenarios to gauge the probability of your assets lasting through retirement.

This approach helps answer questions like: Can my portfolio weather another 2008-style crash? Would an early downturn derail my plans? Most investors only look at average returns projected during retirement, but the sequencing of when those above average and below average returns happen can make a very big difference.

Accounting for Tax Efficiency

Affluent retirees often have assets spread across taxable accounts, tax-deferred IRA and sometimes, tax-free vehicles like Roth IRAs or life insurance. A good advisor doesn’t just ask “How much do you have?” but also “Where is it located?”

Tax-aware withdrawal strategies can extend the life of a portfolio significantly. This includes:

• Strategic Roth conversions before RMDs kick in

• Harvesting capital gains during lower-income years

• Smart timing of Social Security benefits and pension withdrawals

Incorporating Health Care and Long-Term Care Planning

Even affluent retirees can face unexpected shocks from long-term care costs. Advisors estimate future healthcare expenses, including Medicare premiums, supplemental insurance and possible out-of-pocket costs—when evaluating retirement readiness. Some also recommend long-term care insurance, hybrid policies or simply earmarking a separate pool of assets to ensure health needs don’t derail your legacy plans.

Evaluating Legacy and Philanthropic Goals

Many affluent families have goals that extend beyond their lifetime—charitable giving, leaving a financial legacy or funding education for grandchildren. These goals require proactive estate and trust planning, as well as coordination with legal and tax professionals. An advisor will weigh how these aspirations affect your retirement runway. For example, do you want to spend down to a “minimum” or leave behind a specific estate target?

Conducting a Gap Analysis and Contingency Planning

A thorough advisor will outline your retirement “number”—the amount you need to support your desired lifestyle—and compare it to your current resources. If there’s a shortfall, they’ll suggest potential ways to adjust such as retiring later, reducing expenses or reallocating assets for greater growth. They’ll also build contingency plans for curveballs like economic downturns, family emergencies or early retirement due to burnout or illness.

Having counseled clients who are a few years ahead of where you are currently allows me to offer insight and share stories of how different families have navigated the decisions that you will soon be facing. That’s important because knowing whether you can retire isn’t about hitting a magic number; it’s about clarity, confidence and flexibility. A seasoned financial advisor brings more than math to the table; they offer perspective, strategy, and peace of mind. If you’ve built substantial wealth, now is the time to let that wealth work for you—with purpose, precision and professional insight.

Retirement isn’t an exit—it’s an evolution. By working with a financial planner, you can make sure you’re ready for the next chapter.