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The Spending Problem Nobody Talks About in Retirement

3/26/2026

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​The examples and case studies in this article are hypothetical but represent real situations I have encountered in my practice working with Washington State public employees.

There is a question I hear in almost every initial meeting with a new client.

It is some version of: "How do I know I am not going to run out of money?"

I get it. You’ve spent 25 or 30 years saving, and now someone is telling you to reverse the habit. To start spending.

But here is what caught my attention recently. A Morningstar research report looked at nine different withdrawal strategies for retirees. And buried in the data was a pattern I keep seeing.1

The biggest risk for many retirees is not overspending. It is underspending.

Research has shown that retirees with at least $500,000 in savings had spent less than 12% of their nest egg nearly 20 years into retirement. More than a third had actually grown their wealth.2

People who saved diligently their entire careers are reaching the end of their lives with more money than they started with. They skipped the trips. They said no to helping their kids with a down payment.

For Washington State public employees with a pension, this pattern can be even more pronounced. You already have a guaranteed income floor. And yet the instinct to not spend from the portfolio stays strong.

Why the 4% rule makes it worse


The traditional 4% rule was developed by financial planner Bill Bengen in the early 1990s. Take 4% of your portfolio in year one, adjust for inflation each year, and your money should last 30 years.3

It is a fine starting point. But that is exactly what it is. A starting point.

Even Bengen himself has said he uses closer to 5% for his own portfolio.4

The core problem is that the 4% rule does not adapt. Your portfolio drops 30%? Same withdrawal. Your portfolio doubles? Same withdrawal. It was built for the worst-case scenario, which means in most scenarios you leave a lot of money on the table.

For someone with a Washington State pension providing $3,000 or $4,000 a month in guaranteed income, that rigidity is especially costly. Your pension already covers a significant portion of your basic expenses. Your portfolio does not need to do all the heavy lifting.

What flexibility actually looks like


The Morningstar research tested several flexible withdrawal strategies that outperformed the 4% rule. My personal favorite and the one we use with our clients is called the Guardrails method, originally developed by financial planner Jonathan Guyton and computer scientist William Klinger.5

Here is how it works in plain language.

You start with an initial withdrawal rate. Morningstar's research found the Guardrails approach supports a starting rate of 5.2%, compared to roughly 4% with the traditional fixed method.1

Each year, you check whether your withdrawal rate has drifted too far from that starting point. If your portfolio has done well and the withdrawal rate drops more than 20% below your starting rate, you give yourself a raise. If markets have struggled and the rate climbs more than 20% above, you take a modest temporary pay cut.

That is it. Only one of four things happens each year: you skip the inflation adjustment after a down year, you adjust for inflation normally, you get a raise, or you take a small cut.

The beauty is in the simplicity. You are not guessing. You are not reacting emotionally. You have a set of rules that tell you exactly when to spend more and when to pull back.

How this plays out for a PERS 2 member


Let me walk through a hypothetical example.

Say we have a 58-year-old county employee with 28 years of PERS 2 service. Her pension will pay roughly $4,200 per month. She and her husband have $700,000 in their DCP and IRA accounts combined. They will also have Social Security.

Using the traditional 4% rule, Karen would withdraw $28,000 per year from her portfolio. That is about $2,333 per month on top of her pension.

Using the Guardrails approach at 5.2%, she would start at $36,400 per year, or about $3,033 per month. That is an extra $700 per month in the first year alone.

Over 30 years, the Morningstar data showed the Guardrails method produced roughly 16% more in total lifetime spending compared to the fixed approach, while the median ending portfolio balance was still significant.1

That extra money could bridge health care costs through PEBB retiree coverage until Medicare at 65. Or fund travel in those early, active retirement years. And when markets cooperate, the guardrails tell her it is safe to spend a little more. When they do not, she pulls back modestly. No panic. No guesswork.

The real problem is not math


Here is what gets overlooked in these conversations.

The spending problem in retirement is not really a math problem. It is a psychological one.

Research shows retirees spend about 80% of the income they receive from guaranteed sources like pensions and Social Security. But they spend less than half of what they could from their investment accounts.2

Same dollars. Same purchasing power. But money that arrives as a paycheck gets spent. Money sitting in a brokerage account feels untouchable.

That is why rules-based frameworks matter. When you have clear guardrails telling you when it is safe to spend more and when to pull back, you are essentially turning your portfolio into a paycheck. And for my clients with DRS pensions, that portfolio paycheck is supplementing an already solid foundation.

What to do with this


If you are a Washington State public employee within a few years of retirement, here is what I would think about.

First, know what your pension and Social Security (if you have it) actually covers. Log into your DRS account and look at your estimated benefit.6 That number is the foundation for everything else.

Second, stop thinking of the 4% rule as a ceiling. It was built as a worst-case floor. If you are willing to be flexible with your spending, the research suggests you can start higher.

Third, consider whether a rules-based withdrawal strategy fits your situation. If you need perfectly consistent income with zero variability, a more rigid approach might suit you better. But if you can tolerate modest adjustments, the potential payoff in lifetime spending is meaningful.

Your pension gives you a head start most retirees do not have. The question is whether you are going to use it.

​Sources

1. Arnott, Amy. "The Best Strategies for Boosting Starting Withdrawal Rates in Retirement." Morningstar. https://www.morningstar.com/retirement/best-strategies-boosting-starting-withdrawal-rates-retirement
2. "Retirees can be too frugal with their spending." CBS News. https://www.cbsnews.com/news/retirees-can-be-too-frugal-with-their-spending/
3. "Determining Withdrawal Rates Using Historical Data." RetailInvestor.org. https://retailinvestor.org/determining-withdrawal-rates-using-historical-data/
4. "The inventor of the 4% rule just changed it." MarketWatch. https://www.marketwatch.com/story/the-inventor-of-the-4-rule-just-changed-it-11603380557
5. Guyton, Jonathan. "Decision Rules and Portfolio Management for Retirees: Is the 'Safe' Initial Withdrawal Rate Too Safe?" 2004. https://www.semanticscholar.org/paper/Decision-Rules-and-Portfolio-Management-for-Is-the-Guyton/384c2ebfa36a69f9c346f9456c5cbca63306b4c9
6. Washington State Department of Retirement Systems. "Online Account Access." https://www.drs.wa.gov/
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The Healthcare Gap That Keeps Washington Public Employees Working Too Long

3/19/2026

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Note: The examples and case studies in this article are hypothetical but represent real situations I have encountered in my practice working with Washington State public employees.

I keep a running list of the questions I hear most often in client meetings. And if I had to pick the one that comes up more than any other, it would be some version of this:

"But what do we do about health insurance?"

It usually comes right after we've looked at the pension numbers. Right after we've mapped out Social Security timing and portfolio withdrawals. Right after the whole plan starts to come together and the idea of retiring at 57 or 58 feels real for the first time.

Then healthcare enters the conversation, and everything stalls.

I get it. The gap between early retirement and Medicare at 65 can feel like a giant question mark. And when you start searching for answers online, the numbers you find can be genuinely alarming.

But here's what I've noticed after working with Washington public employees: the healthcare gap is almost never the dealbreaker people think it is. It's a real cost that requires real planning. But it's solvable. And I've watched too many people work years longer than they needed to because they never sat down and put actual numbers to the problem.

The scary headlines (and what they're actually saying)


Let's start with what you'll find if you Google "healthcare costs in retirement."
Fidelity's 2025 Retiree Health Care Cost Estimate found that a 65-year-old retiring today can expect to spend an average of $172,500 on healthcare throughout retirement¹. That number has been climbing steadily since Fidelity started tracking it in 2002.

Meanwhile, a recent survey from the Nationwide Retirement Institute found that 73% of U.S. adults list healthcare expenses going out of control as one of their top retirement fears². And about two-thirds of respondents said they couldn't even estimate what those costs would total².

Those are real numbers. But context matters.

That $172,500 Fidelity figure? It assumes enrollment in Medicare Parts A, B, and D. It covers premiums, copays, and out-of-pocket costs spread across the entire retirement¹. Nobody writes a check for $172,500 on their first day of retirement. It's an ongoing budget item, not a lump sum.

And here's the part that rarely makes the headlines: according to Fidelity's own breakdown, about 44% of that total goes to Medicare Part B and Part D premiums, which are predictable, fixed monthly costs¹.

What does the gap actually cost in Washington?


For Washington State public employees, the healthcare question from retirement to Medicare at 65 really comes down to two options: PEBB retiree coverage (or some other association coverage such as WSCFF) or the ACA marketplace.

Let's talk about PEBB first, because this is one of the biggest advantages you have as a state employee.

If you're a vested member of a Washington State retirement plan (PERS, TRS, SERS, LEOFF, or others) and you meet certain eligibility requirements, you can continue your PEBB health insurance into retirement³.

That's a significant benefit. You're not shopping for insurance on the open market with no employer backing. You're staying in the same pool you've been in your entire career.

Now, the cost is real. For 2026, the PEBB retiree monthly premium for UMP Classic (subscriber only, non-Medicare) is $970.43 per month⁴. For subscriber and spouse, it's $1,935.11 per month⁴. That's meaningful money.

But compare that to what the broader market looks like. According to recent data, average monthly ACA marketplace premiums for a 55-year-old are around $1,084, and for a 60-year-old, they climb to roughly $1,319 for a mid-tier Silver plan⁵. For a couple in their late 50s or early 60s, the math adds up fast.

And employer-sponsored health benefit costs keep climbing. Mercer's National Survey of Employer-Sponsored Health Plans found that health benefit costs per employee rose 6% in 2025, with an even higher increase of 6.7% projected for 2026, the highest in 15 years⁶.

The point isn't that healthcare is expensive (it is). It's that these are knowable numbers. You can plan for them.

Putting it in your retirement plan


Here's how I think about this with clients.

Let's say you're a hypothetical PERS 2 member, age 56, planning to retire next year. Your spouse is also a public employee. You've got a combined $800,000 in retirement accounts and other savings.

The healthcare gap for both of you is roughly nine years (from age 56 to 65). At current PEBB retiree rates, you're looking at around $1,935 per month for the couple. That's about $23,200 per year, or roughly $209,000 over nine years before Medicare kicks in.

That's a lot of money. But it's a line item in your plan, not a mystery. And when you factor in your pension income, your DCP withdrawals, and eventual Social Security, this becomes a budgeting exercise, not a guessing game.

From a tax perspective, those early retirement years before Social Security and required minimum distributions start can actually be the lowest-income years of your entire retirement. That creates an opportunity. You can do Roth conversions in lower tax brackets, pull from taxable accounts strategically, and potentially qualify for ACA premium tax credits if you go the marketplace route instead of PEBB.

The tax planning and the healthcare planning are connected. You can't do one well without thinking about the other.

What actually works


After working through this with numerous public employee families, here's what I've seen make the biggest difference.

Know your PEBB eligibility before you set a retirement date.
The rules changed for PERS 2 members separating on or after January 1, 2024. Make sure you understand the age and service requirements that apply to your specific plan³.

Budget for healthcare like you budget for other expenses.
It's a large, predictable expense. Build it into your cash flow projections from day one. Don't treat it as an afterthought.

Compare PEBB retiree coverage to the ACA marketplace every year.
Depending on your income in retirement, marketplace subsidies could make a significant difference. This is especially true in those early retirement years when you're controlling your taxable income through strategic withdrawals.

Think about the bridge, not just the gap.
PEBB continuation coverage (COBRA) can serve as a bridge to PEBB retiree coverage if you need it³. Understanding the timeline and enrollment deadlines is critical. You generally have 60 days from when your employer-paid coverage ends to enroll in PEBB retiree coverage³.

Don't forget about Medicare planning ahead of time.
When you do turn 65, you'll want to enroll in Medicare Parts A and B. If you're on PEBB retiree coverage and become Medicare-eligible, you're required to enroll in Medicare to keep your PEBB benefits³. Start that process a few months early to avoid gaps.

The real cost of waiting


Here's the thing that doesn't show up on any premium schedule.

Every year you work past the point where you could have retired is a year you didn't spend doing the things that matter most to you. For my clients, that's usually more time with grandkids, traveling while they're healthy, or just having a Tuesday morning where nobody needs them to be anywhere.

The healthcare gap is real. But it's not a wall. It's a bridge you have to plan for and pay for. And once you see the actual numbers, most people realize the cost of the bridge is a lot less than the cost of the extra years they were thinking about working.

If you're a Washington State public employee within five years of retirement and you've been putting off the healthcare conversation, now is the time to sit down and put real numbers on it. The answer might surprise you.

​Sources


  1. Fidelity Investments. "Fidelity Investments Releases 2025 Retiree Health Care Cost Estimate." July 30, 2025. https://newsroom.fidelity.com/pressreleases/fidelity-investments--releases-2025-retiree-health-care-cost-estimate--a-timely-reminder-for-all-gen/s/3c62e988-12e2-4dc8-afb4-f44b06c6d52e
  2. Nationwide Retirement Institute. "Rising Health Costs Force Even Insured Americans to Skip Preventive Care." 2025. https://news.nationwide.com/rising-health-costs-force-even-insured-americans-to-skip-preventive-care/
  3. Washington State Health Care Authority. "Retiree Eligibility." https://www.hca.wa.gov/employee-retiree-benefits/retirees/retiree-eligibility
  4. Washington State Health Care Authority. "2026 PEBB Retiree Monthly Premiums." Effective January 1, 2026. https://www.hca.wa.gov/assets/pebb/51-0275-retiree-monthly-premiums-2026.pdf
  5. Kiplinger. "Average Cost of Health Care by Age and US State." December 12, 2025. https://www.kiplinger.com/retirement/average-cost-of-health-care-by-age
  6. Mercer. "National Survey of Employer-Sponsored Health Plans." 2025. https://www.mercer.com/en-us/solutions/health-and-benefits/research/national-survey-of-employer-sponsored-health-plans/
 

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Dividend Investing Feels Safe. Here’s What It’s Actually Costing You.

3/12/2026

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Note: The examples and case studies in this article are hypothetical but represent real situations I have encountered in my practice working with Washington State public employees.

I was reviewing a portfolio for a county employee, 24 years in PERS Plan 2.

Nearly every holding was a high-dividend stock or fund. AT&T. Verizon. A couple of utility companies. And a variety of mutual funds.

Her pension alone will cover most of her essential expenses in retirement. And yet, she had built her entire investment portfolio around generating dividend income.

"I just want my investments to replace my paycheck when I retire."

I hear this all the time. For 25 or 30 years, your paycheck just showed up. Then one day, it stops. According to a recent Schroders survey, 87% of non-retired Americans are concerned about how to generate income once they stop working.⁶ Dividends feel like they solve that problem.

But here's what I've learned working with Washington State public employees: you already have a paycheck replacement. It's called your pension. And that changes everything about how your portfolio should be built.

The birthday cake problem


A dividend isn't extra money being created out of thin air. It's a portion of the company's value being removed and handed to you.

Think of it like slicing a piece of birthday cake and putting it on a separate plate. You didn't create more cake. You just moved it. Research from Dimensional Fund Advisors confirms this. They examined the 10 largest companies in the S&P 500 High Dividend Index over 20 quarterly dividends each. The average dividend was $1.00 per share, and the average price decline on those ex-dates was $1.15.⁷

If you reinvest that dividend, nothing really changes. But most retirees aren't reinvesting. They're spending those dividends. And that's where the tax problem begins.

The tax drag nobody talks about


Here's the part that hits home for me as a CPA.

Every time a dividend shows up in a taxable brokerage account, the IRS sees income. You owe taxes on it that year, whether you need the money or not.¹ Qualified dividends are taxed at capital gains rates (0% to 20%). Ordinary dividends get taxed at your regular income rate.²

You don't control the timing. The company pays the dividend, it hits your tax return, and you pay the bill.

A Cambria Investments study found that a top-100 dividend yield strategy returned roughly 14% annually before taxes from 1974 to 2022. At the highest tax bracket, after-tax returns dropped to about 8.6%.⁸
Tax drag compounds. Every dollar that goes to taxes is a dollar that can't grow for you over the next 20 or 30 years of retirement.

Now, some of you might be thinking: most of my money is in my DCP or an IRA. Dividends aren't taxed inside those accounts, so this doesn't apply to me.

The annual tax drag doesn't hit you the same way inside a tax-deferred account. But if you're selecting funds based primarily on which ones pay the highest dividends, you may be owning slower-growing, lower-quality companies without realizing it. A big dividend doesn't automatically mean it's a strong company. The Cambria study found that a straightforward value approach outperformed the high-dividend strategy even before accounting for taxes.⁸

Why this matters even more for Washington State public employees


As a PERS, TRS, LEOFF, or SERS member, you're going to have multiple income sources on your tax return in retirement: your DRS pension, Social Security, DCP withdrawals, and investment income.³ Add uncontrolled dividend income on top of that.

Those dividends could push you into a higher tax bracket, increase how much of your Social Security becomes taxable, and trigger higher Medicare premiums through IRMAA.⁴

You don't get a say in any of that if your portfolio is generating dividends on its own schedule.

"I just spend whatever my portfolio pays out"


I hear this one a lot too. Some people tell me they just live off whatever dividends and interest their portfolio generates, so they never have to worry about withdrawal strategies or selling anything.

But here's the thing. When your income is determined by what your portfolio happens to distribute rather than what your retirement plan actually calls for, you've handed the controls over to a dividend schedule that knows nothing about your goals, your spending needs, or what's happening in the rest of your financial life.

Maybe you need more income one year because of a big expense. Maybe you need less. Maybe your tax situation changes. The dividend schedule doesn't care. It pays what it pays, the tax bill follows, and you deal with the consequences.

That's not a plan. That's just reacting.

What actually works better


A total return approach puts your retirement plan back in the driver's seat. Instead of relying on whatever income your portfolio happens to generate, you build a diversified portfolio and withdraw strategically based on what your plan actually calls for.

Your pension is your paycheck.
Your DRS pension already provides the stable, predictable income that dividends try to replicate. Your portfolio doesn't need to duplicate what the pension already does.

You decide when to create income.
You choose when to sell, how much to take, and which account to pull from. You can coordinate withdrawals around your tax bracket, Social Security, and Medicare premiums.

Your DCP gives you built-in tax flexibility.
Washington's DCP now offers both pretax and Roth options.⁵ You can pull from either depending on what makes the most tax sense in any given year.

A war chest of bonds handles volatility.
Keep several years of withdrawals in high-quality, short-duration bonds. When stocks drop, spend from bonds. When they recover, replenish.

You can use the tax code to your advantage.
This is the part that gets me excited as a CPA. With a total return approach, you might intentionally realize some capital gains in years where your taxable income is low enough to fall within the 0% long-term capital gains bracket. ²  That means in the right year, you could sell appreciated investments and owe zero federal tax on the gain. You can't do that when dividends are forcing income onto your tax return whether you want it or not.

The piece most people miss


Dividend investing feels safe. It feels like you're not touching your principal. But you are.

The same Cambria study found that a simple value strategy excluding the top 25% of dividend payers outperformed the high-dividend strategy on both a pre-tax and after-tax basis.⁸ The value premium did the heavy lifting. The dividend just came with a tax cost.

There are simpler, more tax-efficient ways to get that same exposure without generating unnecessary taxable income.

So if the math is this clear, why do so many retirees still build their portfolios around dividends?

The Cambria researchers use a great analogy. Back in 1975, Pepsi ran blind taste tests. Over and over, people chose Pepsi. But Coke kept outselling Pepsi by a wide margin. When researchers showed the labels before the taste test, preferences flipped. Most people chose Coke. The brand overpowered their own taste buds.⁸
Dividend investing works the same way. The brand of dividends (passive income, steady checks, never touching principal) creates such a powerful emotional pull that it often overrides what the data actually shows. Investors fall in love with the story, even when the math tells a different one.

I'm not saying this to be harsh. I'm saying it because once you recognize that your instinct might be protecting a belief instead of evaluating evidence, you can step back and look at the numbers objectively.

If you don't believe me, maybe you'll believe Warren Buffett


Warren Buffett's Berkshire Hathaway has almost never paid a dividend. In fact, the company paid a single 10-cent dividend back in 1967. Buffett later joked that he must have been in the bathroom when that decision was made.⁸

Think about that. One of the greatest investors of all time runs an enormously profitable company and chooses not to distribute those profits through dividends. Why?

Because Buffett has long believed that reinvesting earnings back into the business creates more value and higher after-tax returns for his shareholders than sending that money out as a taxable dividend. He'd rather keep the capital working inside the company, compounding for decades, than hand it to shareholders and let the IRS take a cut along the way.

And the results speak for themselves. Berkshire's track record is so strong that even if the stock dropped 99% from its current price, it would still be ahead of the S&P 500 over its lifetime.9

That's the power of keeping capital invested and letting it compound, rather than pulling it out as dividends. And it's the same principle that applies when you're building your own retirement portfolio. Total return, not yield, is what determines how much wealth you actually build and sustain.

What to do with this


If you're a Washington State public employee approaching retirement, a few things worth considering.

Look at your taxable brokerage account. Is it full of high-dividend funds chosen for yield? A total-return approach might serve you better from a tax standpoint.

Think about what your pension already provides. If your DRS benefit covers core expenses, your portfolio has a different job.

If you're still years from retirement, contribute to both pretax and Roth options in your DCP for more control later.⁵

And talk to someone who understands how the pieces fit together. Your pension, DCP, Social Security, and Medicare premiums are all connected. A portfolio built around dividends doesn't account for that coordination.

The goal isn't to avoid every company that pays a dividend. It's to stop chasing yield and start focusing on what actually drives long-term retirement success: total return, tax efficiency, and a plan that puts you in control.

​Sources
  1. Internal Revenue Service. "Topic No. 404, Dividends." https://www.irs.gov/taxtopics/tc404
  2. Internal Revenue Service. "Topic No. 409, Capital Gains and Losses." https://www.irs.gov/taxtopics/tc409
  3. Washington State Department of Retirement Systems. "Deferred Compensation Program (DCP)." https://www.drs.wa.gov/plan/dcp/
  4. Social Security Administration. "IRMAA Sliding Scale Tables." https://secure.ssa.gov/poms.nsf/lnx/0601101020
  5. Washington State Department of Retirement Systems. "Adding Roth to DCP." https://www.drs.wa.gov/wp-content/uploads/2023/02/Roth-Employer-FAQ.pdf
  6. Schroders. "Schroders 2025 US Retirement Survey." October 21, 2025. https://www.schroders.com/en-us/us/institutional/media-center/schroders-study-reveals-americans-not-willing-to-delay-social-security-benefits-for-higher-payments/
  7. Crill, Wes. "A Slice of Dividend Accounting." Dimensional Fund Advisors. January 3, 2024. https://www.dimensional.com/us-en/insights/a-slice-of-dividend-accounting
  8. Faber, Meb. "Is the Best Dividend Strategy to Avoid Them?" Cambria Investments. November 2024. https://www.cambriainvestments.com/wp-content/uploads/2024/11/Cambria-DTAX-11.13.24.pdf
  9. Di Pizio, Anthony. "If This Warren Buffett Stock Plunged by 99% Today, It Would Still Have Outperformed the S&P 500 Since 1965." The Motley Fool via Yahoo Finance. January 9, 2026. https://finance.yahoo.com/news/warren-buffett-stock-plunged-99-103700019.html

-Seth Deal

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The Risk That Actually Ruins Retirement Plans (And It’s Not What You Think)

3/5/2026

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​Note: The examples and case studies in this article are hypothetical but represent real situations I have encountered in my practice working with Washington State public employees.

I was re-reading one of my favorite pieces of financial writing last week.

It’s an essay by Morgan Housel called “The Three Sides of Risk.” Housel is a bestselling financial author, and the piece tells a deeply personal story about a ski trip that ended in tragedy. Two of his closest friends were killed in an avalanche when they were seventeen years old. He survived only because he declined, on a whim, to join them on a second run.

He uses that story to make a point about investing. Not about volatility. Not about routine market corrections. About something far more serious.

About the kind of risk that can end everything.

The three sides you need to know

Housel argues that most people think about risk in two ways.1

First, the odds of something going wrong. Second, the average consequences if it does.

Those two feel manageable. You can wrap your head around them. A 10% chance of losing 15% of your portfolio in a bad year is uncomfortable, but it’s survivable. You run the math. You plan around it. You move on.

But there’s a third side of risk most people never think about until it’s too late.

The tail end consequences.

The low-probability, high-impact events that don’t make daily financial headlines but make the pages of history books.1 Pandemics. Depressions. A market crash that wipes out half your portfolio the year you planned to retire.

These are called “tail risks.” And in my experience working with Washington State public employees planning for retirement, this is the risk that almost nobody has a real plan for.

Why this matters more if you’re retiring early

Consider a hypothetical situation I encounter often in my work.

A PERS 2 member, let’s call her Karen, a budget analyst with 28 years of service, is planning to retire at 57. She’s done everything right. She has her DRS pension lined up, a healthy DCP account, and a solid portfolio of personal savings. She’s run the numbers. She feels confident.

But here’s the problem.

Karen is looking at the average risk. The likely scenarios. A normal market correction she could ride out. A healthcare expense she could absorb. Average consequences. Survivable ones.

What she hasn’t thought through are the tail end consequences.

What happens if she retires in 2008, and her portfolio drops by half in the first eighteen months? She’s 57. Medicare is still eight years away.5 The sequence of withdrawals during a crash that early in retirement can permanently damage a portfolio in ways that average market returns alone cannot fix.

This is sometimes called “sequence of returns risk.” But it’s really just tail risk wearing a different hat.

Your pension helps, but it doesn’t solve everything

Here’s something I genuinely appreciate about working with Washington State employees.

Your DRS pension is a real buffer against tail risk in ways that most retirees don’t have.6 A guaranteed monthly benefit that doesn’t depend on market performance means you aren’t starting from zero during a crash. That matters enormously.

But the pension doesn’t cover everything. Most of my clients rely on a combination of their DRS pension, Social Security, and a portfolio of personal savings. The pension handles the floor. The portfolio is supposed to handle the rest.

And it’s the portfolio that’s exposed to tail risk.

What actually works

The good news is there are practical, proven ways to reduce the damage a tail event can do to your retirement.

Keep a war chest


I build every retirement income plan around what I call a “war chest.” This is typically four to five years of expected withdrawals held in high-quality, short-duration bonds. When a market crash hits, you pull from the war chest instead of selling equities at the bottom. This gives your portfolio time to recover without forcing you to crystallize losses at the worst possible moment.

It sounds simple. It is simple. But simple works.

Own the whole market


We use broadly diversified, low-cost investments for client portfolios. The reason comes back to tail risk, but actually the positive side of it.

In any given year, market returns are not evenly distributed. Morgan Housel’s colleague at Collaborative Fund documented this pattern clearly: in 2017, a handful of companies accounted for half of the S&P 500’s total return. Apple alone contributed more to the index than the bottom 321 companies combined.2 Recent data confirms the pattern continues: in 2023 and 2024, only about 27–28% of S&P 500 stocks outperformed the index itself, the narrowest market concentration in nearly three decades.3

If you’re picking individual stocks, you have to be right about which companies will be the outliers. Almost nobody is consistently right.

If you own the whole market, you automatically own the outperformers without having to predict them. Broad diversification is how ordinary investors capture extraordinary results over time, including the tail events with positive outcomes.

Don’t try to hedge your way out of it.


Every few years, a new financial product gets marketed as a way to have all the upside of the market with protection from the downside. Usually it involves options strategies or complex insurance-wrapped products.

I’ll be direct: the research on these tail-hedging strategies is not encouraging.

AQR Capital Management published a paper on this topic that makes the point plainly: the long-term cost of explicit tail-risk insurance strategies tends to exceed the payouts.4 You pay premiums continuously for protection that pays off rarely. Most of the time, an investor purchasing put options to hedge against tail events ends up with options that simply expire worthless, representing a total loss on that investment. Even when they’re rolled over time, they become a constant drag on portfolio performance.7

The expected return for perpetual insurance buyers is negative. The sellers of that insurance are counting on it.4

The better path is owning the right portfolio structure in the first place: broad diversification, a war chest, and the discipline to leave it alone when things get scary.

Have a written plan for the bad scenario.


One insight from the research is this: the investors who get hurt the worst aren’t the ones who experience the crash. It’s the ones who experience the crash without a plan, panic at the bottom, sell everything, and then miss the recovery.4

Before you retire, write down what you will do if your portfolio drops 30% in the first year. Not what you might do. What you will do. Having a predetermined response to a crisis is the difference between riding it out and making a permanent mistake.

The question to sit with

Most retirement planning conversations focus on the average outcome. Will you have enough? At what rate can you withdraw? What’s the right pension option?

Those questions matter. But they’re not the only ones.

The question that often goes unasked is: what happens in the worst case? Have you accounted for a tail event hitting in your first year of retirement? Is there a plan that holds together even then?

As Housel wrote, tail-end events are all that matter. Once you experience one, you’ll never think otherwise.1

If you’re a Washington State public employee within five years of retirement, now is the time to think through these scenarios carefully. Not because disaster is likely. But because the consequences of being unprepared for it are permanent.

​Sources
  1. Housel, Morgan. “The Three Sides of Risk.” Collaborative Fund Blog. August 8, 2020. https://collabfund.com/blog/the-three-sides-of-risk/
  2. Housel, Morgan. “Tails, You Win.” Collaborative Fund Blog. July 26, 2022. https://collabfund.com/blog/tails-you-win/
  3. First Trust Advisors. “Three on Thursday: The S&P 500 Index in 2024: A Market Driven Once Again by the Mag 7.” January 8, 2025.
  4. Nielsen, Lars, Daniel Villalon, and Adam Berger. “Chasing Your Own Tail (Risk).” AQR Capital Management. Summer 2011.
  5. U.S. Department of Health and Human Services. “Medicare Eligibility and Enrollment.” Medicare.gov. https://www.medicare.gov/basics/get-started-with-medicare
  6. Washington State Department of Retirement Systems. “PERS Plan 2 Member Handbook.” https://www.drs.wa.gov/plan/pers2/
  7. Ordonez, Jose. “Tail Hedging Is Not As Easy As You Think.” Alpha Architect. April 3, 2024. https://alphaarchitect.com/tail-hedging-is-not-as-easy-as-you-think/
 

-Seth Deal

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      Authors

      Bob Deal is a CPA with over 30 years of experience and been a financial planner for  25 years.

      Seth Deal is a CPA and financial advisor.

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