×
×
homepage logo

Layin’ It on the Line: Why the same average return can fund one retirement and ruin another

By LYLE BOSS - Special to the Standard-Examiner | Sep 28, 2026

Photo supplied

Lyle Boss

October is nearly here, and October has a reputation. The 1929 crash. Black Monday in 1987, when the market lost 22% in a single day. The worst of 2008. If the stock market has a haunted month, this is it.

I’m not going to predict a crash. Nobody can, and the people who claim to are selling something. But every fall, as the canyons turn and the market gets jumpy, I have a version of the same conversation, and it’s about something more dangerous than any single bad month.

It’s about the order your returns arrive in. Because here’s the uncomfortable truth: Two retirees can earn the exact same average return over 20 years, and one runs out of money while the other leaves an inheritance.

Same math, opposite endings

Picture two neighbors in Kaysville, both retiring with $800,000, both withdrawing $40,000 a year, both averaging 6% over two decades.

The first one catches good markets early and the bad years come late, after two decades of growth have built a cushion. He’s fine. Better than fine.

The second one retires into a downturn. The portfolio drops 30% in the first two years while he’s pulling out $40,000 each year to live on. Now every withdrawal comes out of a shrunken pot, and the shares he sells at the bottom are gone. They aren’t there to recover when the market does. By the time the good years arrive, they’re compounding on a fraction of what he started with. Same average return on paper. He runs dry in his early 80s.

Economists call it sequence-of-returns risk. I call it the reason your retirement date matters more than your average return, and it’s the risk almost nobody prices in, because for your entire working life it didn’t exist. When you’re adding money every payday, a crash is a sale. The day you start withdrawing, the arithmetic reverses on you.

The first five years carry the weight

The research on this is consistent: The five years before and after your retirement date do more to determine whether your money lasts than any other stretch. A brutal market at 45 is a story you tell later. The same market at 66 can quietly decide what your life looks like at 85.

And you don’t get to choose. The class of 2000 retired into a three-year slide. The class of 2008 watched half their account vanish before their first full year was out. The class of 2026 will retire into whatever comes, and no amount of watching the news changes that.

You can’t control the sequence. You can control the exposure

Since you can’t pick your decade, the job is to build a retirement where the early years can’t sink you. That means one thing above all: The money that pays your bills must never depend on selling something during a bad market.

Social Security is the first layer, which is one more reason maximizing it matters. A pension, for the lucky few, is the second. For most Utahns, the gap between those checks and the grocery bill has to come from somewhere, and this is the job Fixed Index Annuities were built for. Principal isn’t exposed to market losses, growth is linked to an index rather than invested in it, and a lifetime income rider turns a slice of savings into a monthly check that arrives whether the market is up 20 or down 30.

The trade, stated plainly: Caps and participation rates mean you won’t capture all of a roaring year, and surrender periods make this long-term money. What you’re buying is the removal of the one risk you cannot diversify away, the risk of being forced to sell low to buy dinner.

With the bills covered by guaranteed income, the rest of your portfolio can stay invested and ride out a 2008 without you touching it. Bad sequences only ruin people who are forced to sell into them.

A word to the people five years out

If you’re 60 to 65 and still working, this column is aimed at you more than anyone. Sequence risk is best handled before you retire, not after the damage. The years right now, while the paycheck still covers the mortgage and the market is still near highs, are when you carve out the income layer, on your terms, at today’s values.

Waiting to see how things go is a strategy, if we’re being generous. It’s just a strategy that hands the decision to whatever the market does the year you turn in your badge.

October will do what October does

Maybe this October is quiet. I hope it is. The deer hunt will come and go, the first snow will dust the Wellsvilles, and the market will do something nobody predicted.

But if the headlines do get ugly, I want you to be the retiree who reads them with a cup of coffee and no dog in that day’s fight, because your income was never up for a vote on the trading floor in the first place.

You can’t control the sequence. You can absolutely control whether it matters.

Lyle Boss, The REAL BOSS Financial, a native Utahn and retirement specialist who has spent decades helping families across Utah and the Mountain West build secure, income-focused retirement plans. Boss Financial, 955 Chambers St. Suite 250, Ogden, UT 84403. Telephone: 801-475-9400. https://www.safemoneylyleboss.com

Newsletter

Today's breaking news and more in your inbox
I'm interested in (please check all that apply)(Required)
Are you a paying subscriber to the newspaper?(Required)

Starting at $4.32/week.

Subscribe Today