From Sleepaway Camp to Retirement: Planning for the Long Haul

Living Longer, Planning Smarter

If you’re approaching retirement, you’ve probably asked yourself the big questions: Will my money last? Have I saved enough? What if I live longer than I expect?

In this episode of The Own Your Retirement Show, hosts Josh Bretl and Mark Elliott dig deep into the topic of longevity—and why planning for a longer, healthier retirement is more essential than ever.

A Campfire Story With a Point

Josh opens the episode with a personal story: sending his daughter Maggie off to YMCA sleepaway camp. It’s a sweet, relatable tale about watching your child grow, trusting that they’ll be okay on their own, and resisting the urge to panic when you don’t see a smiling photo right away.

But there’s a bigger message here.

“Each kid’s different,” Josh says, “and so is every retiree.” Just like Maggie and her brothers had very different camp experiences, retirees have unique visions for their golden years. The takeaway? Your retirement plan should fit you, not some one-size-fits-all mold.

Why Longevity Changes Everything

If you’re 65 today, odds are good you’ll live another 20 to 30 years. That’s not just a statistic—it’s a fundamental shift in how we should think about retirement.

• The average 65-year-old male today lives to 84; females to 86.
• 50% of retirees will live even longer than those averages.
• Americans age 90+ tripled from 1980 to 2010—and are expected to triple again by 2040.

Josh calls it “the longevity revolution,” and it’s reshaping retirement planning. Longer lifespans mean:

• More years of spending.
• Higher likelihood of medical expenses.
• More emphasis on guaranteed income.
• Greater tax exposure.

The Hidden Risk You Probably Haven’t Planned For

Josh shares that the biggest retirement planning risk isn’t market volatility or inflation—it’s taxes.

Too often, retirees assume their tax burden will shrink. But with Required Minimum Distributions (RMDs), taxable Social Security, and limited income flexibility, taxes can take a huge bite out of your savings—especially if you haven’t planned for them.

Josh says it plainly: “Taxes have become the single greatest variable that will impact how much money you have when you leave this earth.”

Income: The #1 Happiness Factor

Josh references several studies showing that retirees with guaranteed income streams—like Social Security, pensions, or certain annuities—report the highest levels of financial confidence and life satisfaction.

Why? Because they’re not worried about running out of money. They can spend more freely, travel, give to grandkids, or support charities—all without stressing over market returns or the latest economic forecast.

And don’t overlook the non-financial side: strong social connections and a sense of purpose. As Mark jokes, even just having golf buddies can boost your happiness and longevity.

Are You Spending Too Much… or Too Little?

Josh shares that many of his clients are actually too frugal in retirement. After years of saving, they struggle to shift to “spending mode.” The result? They may shortchange themselves on travel, fun, and family generosity—despite having more than enough saved.

“We want clients to dream big,” Josh says. “You don’t have to wait until you’re gone to help your family. You might be able to do it now and live a little.”

What About Withdrawal Strategies?

The show also dives into withdrawal strategies—where to pull money from, when, and how to do it in a tax-smart way.

Josh cautions against cookie-cutter rules like the 4% rule. Instead, he emphasizes:

• Understanding your tax buckets (pre-tax, Roth, brokerage).
• How unexpected life changes (like selling a home or downsizing) can alter your plan.
• Revisiting your strategy regularly to reflect your real-time situation.

Part-Time Retirement? Yes, Please.

Josh and Mark discuss the growing trend of phased retirements—working part-time or shifting to “fun” jobs that provide both purpose and a paycheck.

Josh shares stories of clients working at Home Depot, umpiring baseball, or gradually reducing hours at a job they still enjoy. The result? They delay big IRA withdrawals, extend their Social Security growth, and stay socially and mentally engaged.

Taxes, Again… Because They Matter That Much

Josh circles back to taxes multiple times. Why? Because your retirement income may look great on paper—until taxes eat away at it.

He challenges traditional tax planning (which aims to minimize taxes this year) and instead promotes lifetime tax planning.

Sometimes paying a little more now—like doing Roth conversions—can save you tens of thousands later. That’s why working with a team that understands both retirement and tax planning is crucial.

Takeaways: What You Should Be Thinking About

If you’re within five years of retirement, Josh encourages:

• Estimating your spending now and in retirement.
• Identifying key concerns (healthcare, kids, housing).
• Working with an advisor who specializes in retirement—not just investing.

And most of all? Start the conversation early. It’s way easier to smooth out the bumps before you hit the road.

📞 Ready to talk? Call (630) 478-9599 to schedule your private 15-minute call with an FSR advisor.