You Only Get One Retirement

Dwight D. Eisenhower once said, “Plans are worthless, but planning is everything.”¹ I think that is especially true when it comes to financial planning and retirement.

Retirement isn't a finish line where you can simply check a box and walk away. It is a transition into a new phase of life—and one that typically only happens once. You have to get it right the first time.

And while retirement planning involves plenty of numbers, it is not just a mathematical exercise. There is a significant psychological component to retirement, too.

For many people, work has provided structure, purpose, identity, social interaction and a sense of accomplishment for decades. Suddenly replacing a paycheck with a portfolio—and asking yourself, “Can I really spend this money?”—can be surprisingly difficult.

That is why good retirement planning is about more than determining whether you have accumulated enough money. It is about helping you understand how your money fits into the life you want to live, and giving confident permission to spend and enjoy your money.

How much can you actually spend?

One of the most important questions in retirement planning is determining how much you can reasonably withdraw from your portfolio without running out of money.

Bill Bengen's groundbreaking research on retirement withdrawals has become the foundation for much of the industry's discussion around sustainable retirement income. His original research found that a retiree could withdraw roughly 4% of a portfolio initially², increase that dollar amount with inflation, and historically have the portfolio survive at least 30 years. His more recent research has refined that analysis³ and emphasizes the importance of the retirement time horizon.

Bengen's updated research shows approximately:

*These figures come from Bengen's updated research and specific historical assumptions. They are not a recommendation for an individual retiree. Actual planning needs to account for taxes, investment allocation, fees, Social Security, pensions, spending changes, market conditions and the possibility of living longer than expected.

The takeaway isn't that everyone should withdraw 4.7%, 5.5%, or 8.9%.

The takeaway is that retirement income is a planning problem—not simply a percentage.

Four things you need

I often think about financial planning in terms of four things:

Time. Interest. Knowledge. Discipline.

If you have all four, you can do a tremendous amount of what a financial planner does yourself.

You have the time to research, organize and monitor your finances.

You have the interest—the desire and willingness to actually engage with your financial life and make thoughtful decisions.

You have the knowledge to understand the decisions you're making and their potential consequences.

And you have the discipline to stick with the plan when markets, taxes, life events and emotions inevitably get in the way.

But the minute you don't have one of those four things, it may make sense to outsource some—or all—of the planning.

That's not because financial planning is complicated for the sake of being complicated. It's because there are a lot of interconnected decisions, and retirement gives you very little room for a major mistake.

And if you're five years away from retirement, there's a good chance you should have started true financial planning five years earlier.

The closer you get to retirement, the more important the decisions become—and the less time you have to correct a mistake.

It's usually not just, "Can I retire?"

For most of my clients, the question eventually becomes less about “Can I retire?” and more about:

How do I retire most effectively?

How do I keep more of my money?

How do I pay less in taxes?

How do I mitigate risk?

How do I make the most of the assets I've accumulated?

And, ultimately, how do I enjoy retirement?

Those questions require more than an investment portfolio. They require coordination and planning across a team of professionals, taxes, investments, insurance, Social Security, estate planning, cash flow and the many personal decisions that come with retirement.

You are going through one of two doors

Ultimately, every retiree is going through one of two doors.

Door #1: You outlive your money.

Door #2: Your money outlives you.

Our job in retirement planning is to help make sure you go through Door #2.

That doesn't necessarily mean dying with the largest portfolio possible. It means having the confidence to spend, give, travel, help your family and enjoy your retirement—without constantly wondering whether you are spending too much.

And that's where planning becomes more important than the plan itself.

This is where tools like Monte Carlo simulations can be helpful. They allow us to stress-test a retirement plan across thousands of different market and economic scenarios. But an 80% or 90% probability of success does not mean you're destined to fail 20% or 10% of the time.

It means the plan may need an adjustment along the way. An 80% probability of success can be thought of as a plan that may require a course correction in roughly 2 out of 10 scenarios—not a prediction that you will run out of money 2 out of 10 times.

The psychology of retirement

One of the hardest parts of retirement can be giving yourself permission to spend the money you've spent decades accumulating.

You spend your entire working career being told to save. Save for retirement. Save more. Invest. Don't spend too much.

Then one day, the advice changes:

Now you need to spend it.

That can be psychologically difficult.

A successful retirement isn't simply about maximizing your portfolio. It is about finding the right balance between security today and security tomorrow.

You don't want to spend so little that you miss the opportunity to enjoy the fruits of your labor. But you also don't want to spend so much that you create unnecessary anxiety about the future.

Good planning helps create a framework for making those decisions with confidence.

A great client once told me:

“I need purpose, family and friends, AND income.”

I completely agreed.

But I would add one more:

Health.

We need our health to travel, spend time with family and friends, pursue our interests and hobbies, and make purposeful decisions.

Ultimately, the goal is not simply financial independence. It is the ability to use your financial independence to live a meaningful life—with purpose, people, income, and health.

Keep both hands on the wheel

There is a story often told about prison escapes: the escapees can spend enormous amounts of time planning how to get out, but once they are outside, they don't necessarily have a plan for what comes next. I’ve read stats as high as 75% are captured in the first 24 hours of getting out.

Whether or not every version of that story—and the statistics sometimes attached to it—is accurate, the lesson is a good one:

Getting out is only part of the plan. Staying on course is what comes next.

Retirement is similar.

You can spend years planning for your retirement date. But the day you retire isn't the end of the planning process. In many ways, it is the beginning. Getting to the top of Mount Everest is not the finish line – it is just the start of the most difficult part of the climb – going down. In financial and retirement planning, this is the distribution and de-cumulation phase.

Markets will change. Inflation will change. Taxes will change. Your spending will change. Your health, family, travel, charitable giving and priorities may change.

That's why you have to keep both hands on the wheel.

A good retirement plan isn't something you put in a drawer and revisit five years later. It is something you monitor, test, and adjust as life unfolds.

Because you typically only retire once.

You have one retirement. You have one opportunity to get it right.

Sources

1, Eisenhower, Dwight D. “Remarks at the National Defense Executive Reserve Conference,” November 14, 1957. The American Presidency Project, University of California, Santa Barbara. https://www.presidency.ucsb.edu/documents/remarks-the-national-defense-executive-reserve-conference
2. Bengen, William P. “Determining Withdrawal Rates Using Historical Data.” Journal of Financial Planning, October 1994.
3. Bengen, William P. A Richer Retirement: Supercharging the 4% Rule to Spend More and Enjoy More. 2025.
4. Lange, Jamie. “Bill Bengen’s New Safe Withdrawal Rate: A 17.5% Raise For Retirees.” Forbes, October 23, 2025. https://www.forbes.com/sites/jlange/2025/10/23/bill-bengens-new-safe-withdrawal-rate-a-175-raise-for-retirees/