3 Spooky Retirement Stories: Financial Mistakes That Can Haunt Your Retirement

Halloween is almost here. The decorations are going up. The pumpkins are glowing. And everyone seems to have a favorite scary story. But some of the scariest retirement stories don’t involve ghosts. They involve money.

Over more than two decades in financial planning, I’ve seen how seemingly small decisions can create significant consequences for people approaching or living in retirement. My experiences helping families navigate financial uncertainty are part of what shaped my Safety First approach to retirement planning.

So this week, let’s look at three retirement stories that may sound spooky—but each comes with a lesson.

Spooky Story #1: The Portfolio That Looked Fine…Until the Withdrawals Started

Imagine a couple who has spent decades saving.

Their retirement account looks healthy.

They retire.

Then the market drops.

They still need money to pay the mortgage, buy groceries and enjoy their retirement, so they continue withdrawing from their investments.

The problem isn’t simply that the market went down. It’s that they’re selling investments while taking income from a declining portfolio.

This is one reason sequence-of-returns risk matters in retirement planning. Morningstar’s 2026 research examines market and spending shocks and how they can affect sustainable retirement income strategies.

The Lesson

Don’t build a retirement income strategy that assumes the market will cooperate every year.

A good plan should consider how income will be generated during different market environments.

SF Financial Services’ approach emphasizes creating a personalized plan around the client’s financial situation and future needs.

Spooky Story #2: The Retirement Plan That Forgot About Taxes

Here’s another frightening scenario. A retiree has saved diligently in a traditional IRA or 401(k). They feel comfortable because the account balance looks substantial. Then retirement arrives, money comes out, and taxes follow.

The surprise isn’t necessarily that withdrawals may be taxable. The surprise is how much taxes can affect the amount of retirement income available to spend. That’s why I encourage people to look at their retirement plan through more than one lens.

It’s not just about how much you have. It’s about how much you can actually use.

The Lesson

A retirement income plan should consider taxes before you need the money—not after.

And if you’re still working, don’t overlook opportunities to review your retirement contributions.

For 2026, the IRS says the employee contribution limit for many 401(k), 403(b) and governmental 457 plans is $24,500. The standard catch-up contribution for eligible participants age 50 and older is $8,000, with a higher $11,250 catch-up limit for eligible participants ages 60 through 63.

Those limits are one reason an annual retirement-plan review can be worthwhile.

Spooky Story #3: The Retiree Who Thought Social Security Was Automatic

A couple reaches retirement age. They’ve saved. They’ve planned their lifestyle.

Then they make a quick Social Security decision because they assume, “I’ll just start taking it.”

But Social Security isn’t simply an on/off switch.

Claiming before full retirement age can reduce monthly benefits. Waiting beyond full retirement age can increase benefits through delayed retirement credits until age 70. For people born in 1960 or later, the Social Security Administration says full retirement age is 67. Claiming at age 70 produces a benefit equal to 124% of the full-retirement-age benefit under current rules. That doesn’t mean waiting until 70 is always the right answer. It means the decision deserves to be part of a broader retirement income strategy.

The Lesson

Don’t make major retirement decisions simply because you’ve reached a certain birthday. Consider how Social Security fits with your other income, investments, spending needs, taxes, health and longevity.

The Scariest Retirement Mistake Is Assuming Everything Will Go According to Plan

Markets don’t always cooperate.

Taxes can change.

Healthcare expenses can surprise us.

We may live longer than expected.

Our priorities can change.

That’s why I believe retirement planning should be less about predicting the future and more about preparing for different versions of it.

On Retire Financially Fit, I regularly share retirement strategies designed to help people think more strategically about their financial future. SF Financial Services describes the show as a resource for tips and strategies intended to help keep retirement assets on track.

And that’s really the lesson behind these three spooky stories.

You don’t have to be afraid of retirement.

You just need to respect the risks that come with it.

A thoughtful plan can help you prepare for the unexpected while keeping your attention on what retirement is really about: living your life with greater confidence.

So, this Halloween, enjoy the candy. Enjoy the costumes. Enjoy the jack-o’-lanterns.

But don’t let avoidable retirement mistakes become the financial ghosts that follow you into the future.

This article is for educational purposes only and does not constitute individualized investment, tax, Social Security or legal advice.

“Investment advisory services offered through Brookstone Wealth Advisors, LLC (BWA), a registered investment advisor and an affiliate of Brookstone Capital Management, LLC. BWA and SF Financial Services are independent of each other. Insurance products and services are not offered through BWA but are offered and sold through individually licensed and appointed agents.”