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Voice of Experience

Voice of Experience: April 2025

Are You Ready to Retire?

Julie Jason

Summary

  • The transition from one source of income (employment) to a self-directed source (savings) needs to be anticipated and planned in advance of retirement due to a new set of risks that need to be addressed.  
  • Risks include the following: sequence risk when a retiree starts to withdraw funds just as a market turns into bear territory; inflation; taxes; required minimum distributions; longevity; incapacity; legacy.    
  • Eight questions to answer before attempting to create a  “retirement paycheck” that needs to last a lifetime. 
Are You Ready to Retire?
istock.com/MOYO STUDIO PTY LTD

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Retirement Investing Requires a Change in Approach

Not too long ago, a retirement timeline assumed you lived into your seventies, supported by a pension and Social Security retirement benefits. Today, pensions are almost nonexistent, life expectancies are longer. Further, the desire to provide a legacy for heirs and charity can extend the timeline decades beyond our own lifetimes. Effective financial management in retirement is no longer optional: it’s critical.

Retirement investing is very different from investing before retirement. Before retirement, things are easier. Living expenses and taxes are intended to be covered through employment. Investing is focused on capital appreciation.

Financial market declines and loss of purchasing power due to inflation are much more concerning when using savings and investments to pay for living expenses and taxes – and they need to be dealt with, as these concerns are real.

Multiple Risks to Manage

The transition from one source of income (employment) to a self-directed source (savings) is a critical period of time that can define a person’s future financial stability. If unprepared, and worse, if the timing is not right, moving into a self-directed source of funding just as a bull market collapses can decimate retirement savings.

Long-horizon retirement portfolios call for a multi-faceted risk management approach to satisfy conflicting demands: cash flow needs and wealth protection (for the present) plus capital appreciation (for the future) - taking into account the risks imbedded in the markets, cash flow management, consumption (spending), taxes (income taxes and estate taxes), inflation (loss of purchasing power), legacy desires, and incapacity risk. Add to that list the risk of a spouse or partner who has no interest in finances.

That’s a heavy lift for anyone – even the astute investor.

Market Declines

Every calendar year, without exception, the broad stock market experiences declines that occur within the year (“Intra-year declines”). For example, 2024 ended the year with a solid 25 percent gain but experienced an intra-year decline of 8.4 percent. The year 2022 ended down 18.1 percent but fell further (-25.4 percent) during the 2022 calendar year. At this writing, the S&P 500 TR Index is down 4.3 percent for the first quarter of 2025 (through 3/31/2025); we’ll see if the year ends up or down.

Daily declines are also to be expected. The market’s largest one-day decline (-20.5 percent) since the 1920s was recorded on October 19, 1987, a Black Swan event (an outlier not captured by risk measures such as standard deviation). The 1987 year ended up 5.3 percent.

The next four largest one-day declines of the top 25 occurred in the 1920’s and 1930’s. But in sixth position, is the -9.5 percent decline of March 12, 2020, during the one-month long Coronavirus Bear Market (February 19, 2020, to March 23, 2020). In eighth position is the October 15, 2008, decline of 9.0 percent during the Great Financial Crisis (October 9, 2007, to March 9, 2009).

Sequence Risk

Imagine retiring just as a bear market begins its descent. To recover losses an investor needs a strong upward movement, and time.  

Bear markets are measured by a 20 percent drop from the previous peak. “Mega Meltdowns” are bear market drops of more than 40 percent. The most recent occurred during the Great Financial Crisis, when the market fell 57 percent from October 9, 2007, to March 9, 2009.  A drawdown of 57 percent called for a gain of 133 percent to make it back to even, which occurred by March 28, 2013, four years after the March 9, 2009, bottom.  

Earlier, the Internet Bubble burst on March 24, 2000, dropping 49 percent by  October 9, 2002. You needed a gain of 96 percent to recover  from the 49 percent decline, which occurred almost five years later on May 30, 2007.

Declines of between 20 percent and 40 percent are “Garden Variety” bears, the most recent being a decline of 25 percent that lasted from January 3, 2022 through October 12, 2022. Breakeven required a gain of 33 percent, which occurred less than two years later on January 19, 2024.

These bear market returns and recoveries are defined strictly by the up and down movements of the market. When retirement portfolios need to factor in funding retirement expenses, downward market periods are even more important to understand, something you or your professional investment adviser would be expected to calculate, manage, and monitor over time on an after-tax and after-inflation basis. If you add a retiree’s withdrawals into the equation, declines are deeper, and recoveries take longer.

Risk is not limited to stock market volatility. Depletion can occur with safe assets as well as more volatile stock market holdings.

For an example of the stock market outperforming, consider the Great Financial Crisis Mega Meltdown. Withdrawing four percent per year for expenses, increasing annually for actual inflation, T-Bills underperformed the S&P 500 Index by far, by a factor of ten. Over the 18-year time span available to us (through 2024), one million dollars invested in T-Bills ended with about $260,000, while the S&P 500 Index ended with over $2.6 million, before taxes.

However, in the preceding Mega Meltdown (Internet Bubble), T-Bills and the S&P 500 ended an 18-year time span with almost identical ending values (about $400,000 after investing $1 million at the beginning of 2000, before taxes).

Preparation Is Critical

In studying bear market declines it becomes clear that the fate of the person who ignores market volatility is at higher risk of potentially depleting assets – it’s better to be prepared.

Portfolio Approach

In retirement, a list of recommended investments no longer satisfies the larger enterprise of managing retirement needs. Now, a portfolio approach is necessary. The term “portfolio” has a special meaning. In the words of Nobel Prize–winning economist and father of portfolio management Harry M. Markowitz, a portfolio is “more than a long list of good stocks and bonds . . . [it is a] balanced whole [that provides] protections and opportunities with respect to a wide range of contingencies.”

The portfolio must be organized to both grow and fulfill cash flow needs.

The portfolio must be managed to meet long-horizon goals. A market-weathering portfolio calls for planning, executing, and, equally important, monitoring progress against goals to provide for sufficient cash flow after taxes while adjusting for changing markets, needs, and circumstances over the decades that comprise the investor’s lifetime – or longer when there are legacy interests, whether family or charity. Very simply, the portfolio strategy and methodology need to flow from your unique situation.

Before Starting: Points to Consider

Consider these factors before starting on a course of action.

  1. How a retirement portfolio should be structured; whether the economy and other news events should trigger buy, sell, and hold decisions; and the effect of taxes and inflation. The ability to make these assessments takes knowledge, typically gained over time.
  2. How living expenses are figured. It is important to highlight discretionary expenses so that they can be delayed if necessary.
  3. How living expenses are covered. What are the sources, such as Social Security and pension income, cash produced by investments, or other holdings? When is it time to redirect or reconsider how you are producing and spending cash flow after inflation and taxes? The ability to either prepare or review this information is essential in structuring a proper portfolio.
  4. How to assess conflicts of interest embedded in financial relationships. To understand conflicts takes experience and the ability to scrutinize disclosure documents (think “fiduciary”).
  5. How to interact with financial professionals who may have close, long-standing relationships (should all recommendations be accepted; when and how to say “no”). This takes judgment, wisdom, and a dose of healthy skepticism.
  6. How to calculate your retirement income gap. The gap is the difference between the amount of income you are receiving from Social Security, pensions, and employment and how much you are spending.
  7. If you have a retirement income gap, you will need to turn your savings into a cash flow stream that will not only last a lifetime but also outpace inflation and taxes and prepare you for the unexpected. Having a retirement income gap increases the need for vigilance and planning and calls for organizing multiple accounts into a consolidated portfolio. Someone who does not have a retirement income gap has a significantly simpler investment challenge.
  8. Also consider your family structure. If your spouse or partner is not interested in making investment decisions with you, then managing your own portfolio would create risk for him or her in the event you become incapacitated or predecease him or her.

Experience

Most people retire only once in a lifetime; they have no experience creating a “retirement paycheck.” Even most savvy, self-directed investors and financial industry experts, have not experienced managing long-horizon retirement portfolios.

Given that truth, let me share simple retirement income illustrations that can help frame the expertise needed to succeed in retirement.

Situation 1

There is no retirement income gap. There is no need for regular portfolio withdrawals. Instead, the goal is to grow or preserve capital, potentially leaving a legacy. This type of retirement portfolio is the easiest of all to structure and manage. In fact, this is the best situation to manage on your own if you are a self-directed investor who has a great interest in the financial markets. Be aware that if you are married, and your spouse does not share that interest, consider the risk to your spouse if you become incapacitated or pre-decease him or her.

Situation 2

Retirement income gap without legacy interests. The goal is to use savings to help pay bills for your lifetime (terminal value of zero). The management of this portfolio is more complicated than the first situation but much less complex than the third, which follows. Complexity will depend on the capital involved, family structure, financial knowledge, interest, and horizon. If assets are modest, there may be product solutions that can be appropriate. If assets are significant, there is more to lose if inexperienced.

Situation 3

Retirement income gap with legacy. The goals are twofold:

  1. To create a “paycheck” that lasts a lifetime, increasing over time to offset inflation, taxes, and the unexpected, such as health care costs or long-term care needs.
  2. To grow capital with the potential for a legacy for heirs or charity.

If you have a retirement income gap and a legacy goal, your situation is more complex to conceptualize and manage than others. Your portfolio management methodology needs to be precise in terms of the source of cash flow to fill the gap. Will the portfolio be structured to pay out only dividends and interest? Will holdings be sold when bills need to be paid? Will some other method be used to make sure that the portfolio will not suffer during market declines? Or is the plan to decrease the gap by decreasing withdrawals, which means decreasing spending?

You Control Only Certain Elements, Not All

Your personal situation controls one side of the retirement equation: Your investable assets, tax situation, consumption (spending) and cash flow needs, family, and plans for the future. These factors will be important for determining the proper portfolio strategy and construction.

The other side of the equation you don’t control: The markets, inflation, your life expectancy, your health, and tax rates -- and while you don’t control conflicts of interest embedded in financial services, you can choose to engage a firm that limits conflicts by design. Likewise, you control the choice of retirement experts to work with.

With the help of a trained and skilled investment adviser who follows a historically proven methodology for retirement portfolio management, you can jointly address the predictable and knowable and thereby be better prepared for the unpredictable.

Your Situation Is Unique

Retirees are not all alike. Some have retirement income gaps, and some don’t. Some have legacy goals, and some don’t. Before anyone can offer you advice on how to invest for your retirement, you need to know where you fall. Then, you can determine how to proceed.

As you look to retire, consider these questions:

  • Do I (and my spouse) have the interest, time, and skills to plan and manage retirement finances for a lifetime?
  • If I need help, where can I turn?

In my experience as investment counsel (a type of registered investment adviser focused on tailored portfolios), I have found that lawyers, accountants, business owners, corporate officers, and other successful individuals enter retirement with a number of brokerage accounts, retirement accounts, and even multiple financial representatives that have served them well with accumulating wealth.

Things change  at the precipice of retirement. At that point in time, a fresh outlook is called for, one that allows for the creation of a comprehensive retirement plan that runs smoothly and is easy for you to live with.

Sunny Skies

My big message is this: Retirement is not the time to learn how to manage retirement risks through trial and error. There is too much at stake.

A program needs to be considered, structured, implemented, and monitored over time — all executed, hopefully, within an environment of calm seas, sunny skies, and smooth sailing.

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