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Layin’ It on the Line: The paycheck that never stops — Building retirement income you can’t outlive

By Lyle Boss - Special to the Standard-Examiner | Oct 17, 2025

Courtesy photo

Lyle Boss

Imagine your mailbox delivering a check every month for life — no matter how long you live. Rain or shine, bull market or bear, that income never skips a beat. That kind of peace of mind may sound too good to be true, but it’s exactly what more and more retirees are searching for today: a paycheck that never stops.

The retirement fear few talk about

If you ask pre-retirees what they worry about most, the answer might surprise you. It isn’t death. It’s running out of money. Surveys consistently show that retirees fear outliving their savings more than their own mortality. Why? Because living longer — something worth celebrating — comes with a challenge: stretching your nest egg to cover 20, 30, even 40 years of retirement.

Think about it. You’ve worked your whole life, saved diligently and now face decades of expenses without a traditional paycheck. Social Security helps, but for many, it only covers a fraction of living costs. Pensions — the reliable income streams our parents counted on — have all but disappeared in the private sector. That leaves retirees staring at their 401(k)s and IRAs, wondering: How do I turn this pile of money into a dependable monthly check that lasts as long as I do?

The risk of going it alone

Without a plan, many retirees fall into one of two traps.

  1. Spending too fast. You enjoy the early years of retirement — travel, hobbies, grandkids — only to realize your savings are shrinking faster than expected. Market downturns or unexpected medical bills make the situation worse.
  2. Spending too little. Fear of running out leads you to pinch pennies, skip trips and say “no” when you’d rather say “yes.” Ironically, you sacrifice joy in retirement, even though you may never actually run out of money.

Neither scenario is the retirement dream you worked for. You deserve better.

The personal pension solution

This is where annuities and structured income strategies come in. Think of an annuity as your personal pension. Instead of leaving your financial future at the mercy of the stock market or your withdrawal math, you can convert a portion of your retirement savings into a guaranteed lifetime income stream.

Here’s how it works:

  • You take some of your retirement savings and place it into an annuity contract.
  • In exchange, the insurance company guarantees to pay you a monthly check for life — just like an employer pension used to.
  • Depending on the product, that check can also grow with inflation, cover a spouse’s lifetime or even provide long-term care benefits.

The result? No matter how long you live, whether you reach 85, 95 or even 105, the income doesn’t stop.

Why guarantees matter

We live in a world where very few things are certain. Markets rise and fall. Interest rates shift. Even real estate cycles boom and bust. But guaranteed income provides a stabilizing anchor. Knowing you’ll have a check coming in every month — covering essentials like housing, food and health care — creates freedom.

When your basics are covered, you gain confidence to spend more freely on the things that make retirement meaningful: travel, family gatherings, volunteering, hobbies or simply spoiling the grandkids. You stop worrying about whether you’ll outlive your money and start focusing on enjoying life.

The math of longevity

Let’s run a simple scenario. Suppose you retire at 65 with $750,000 saved. Without any structure, you might think, “I can withdraw 4% per year — that’s $30,000 annually.” But what happens if markets stumble early in retirement? Or if you live to 95? The 4% rule, once considered “safe,” has been widely challenged in today’s low-interest, volatile market environment.

Now imagine allocating a portion of that $750,000 — say $300,000 — into an annuity that guarantees $18,000 per year for life. That’s a personal pension layered on top of Social Security. The rest of your savings can remain invested for growth or be used for emergencies and discretionary spending.

Suddenly, the pressure shifts. You no longer need your portfolio to do all the heavy lifting. You’ve secured a base of guaranteed income you can’t outlive.

Addressing the skeptics

Of course, annuities aren’t magic. Some people hear the word and think “high fees” or “lack of access.” But today’s annuity landscape is far more flexible than many realize. Products can be tailored — some allow partial withdrawals, others link income growth to market indexes, and many provide options for spouses.

The key is education and fit. Just as no two retirees are alike, no single income product is right for everyone. The goal isn’t to lock up all your money — it’s to strategically protect enough of it to guarantee the essentials.

From worry to peace of mind

Here’s the bigger picture: Retirement isn’t just a math problem. It’s emotional. When you’re lying awake at 2 a.m. wondering if your money will last, numbers on a spreadsheet don’t bring comfort. A guaranteed paycheck does.

That’s why annuities and structured income strategies are less about “products” and more about peace of mind. They help retirees move from a scarcity mindset — afraid to spend — to a freedom mindset — confident to live fully.

Taking the next step

So, how do you know if building your own personal pension makes sense? Start by asking:

  • How much of my essential expenses are already covered by guaranteed sources like Social Security?
  • Do I want more peace of mind knowing that no matter how long I live, my paycheck won’t run out?
  • Would securing guaranteed income allow me to invest the rest of my portfolio with more confidence?

If those questions resonate, it may be time to explore annuities and structured income planning. The goal isn’t to chase returns; it’s to create a retirement that feels safe, steady and secure.

Final thought

Retirement should be about freedom, not fear. You worked too hard to spend your golden years pinching pennies or second-guessing every withdrawal. With the right income strategy, you can build the paycheck that never stops — the one that keeps showing up month after month, year after year, no matter how long you live.

Because the ultimate goal isn’t just making your money last. It’s making sure your lifestyle, your joy and your peace of mind last right along with it.

Lyle Boss, The REAL BOSS Financial, endorsed by Glenn Beck as the premier retirement advisor for Utah and the Mountain West States. Boss Financial, 955 Chambers St. Suite 250, Ogden, UT 84403. Telephone: 801-475-9400.

Starting at $4.32/week.

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