Why Financial Planning for Retirement Matters More in Your 50s and 60s
The retirement confidence gap for today’s workers
National surveys keep finding the same thing: a lot of people are unsure if they’re on track for retirement. In recent Federal Reserve reports on household well‑being, only about one‑third of non‑retirees say their retirement savings are on track, even though most retirees say they’re doing at least “okay” financially. That gap between “I hope we’ll be okay” and “I know the numbers” is where a simple retirement plan can make a big difference.
At the same time, many older adults still rely heavily on Social Security. According to the Social Security Administration, benefits make up around 31% of the income of people over age 65, and for roughly 4 in 10 older beneficiaries, Social Security provides at least half of their income. That’s a good reminder that Social Security matters, but it also shows why building additional retirement income streams is so important.
What this looks like for real families
Picture a couple—let’s call them Mike and Janet—both in their early 60s. Mike works for a manufacturing company, Janet is in health care. They’ve both saved “some” in their retirement plans, they have a mortgage that’s almost paid off, and they keep meaning to “look into Social Security.” They’re not in crisis, but they’re not exactly confident either.
What changed for them wasn’t some magic investment. It was sitting down, listing their real‑life expenses, mapping out when each paycheck stops, and seeing how Social Security, savings, and part‑time work might fill in the gaps. That’s the heart of financial planning for retirement: taking the puzzle pieces you already have and arranging them so the picture makes sense for your life.
The Core Pieces of a Simple Retirement Plan
Knowing what you’ll spend (and where it goes)
Start with your lifestyle, not a random “you’ll need 80% of your income” rule. Think about:
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Housing: mortgage or property taxes, insurance, utilities, maintenance.
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Everyday living: groceries, gas, internet, phone, giving, hobbies.
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Fun stuff: travel, grandkids, games, fishing trips, hobbies.
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Big one‑offs: roof replacements, new vehicles, weddings or big family events.
Many people are surprised when they actually see their monthly number. It’s not about judging; it’s about making sure your retirement plan is based on reality, not guesses.
Turning savings into monthly retirement income
Next comes the big question: How do you turn your 401(k)s, IRAs, or other savings into a retirement paycheck that lasts? There isn’t one perfect answer, but a plan should address:
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How much you can reasonably withdraw from savings each year without trying to “hit it out of the park.”
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Which accounts you spend from first (taxable, tax‑deferred, Roth).
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How to keep some money growing while also building a cash buffer for market ups and downs.
Research on financial well‑being shows that people with a written plan are more likely to feel on track and to follow through on saving and investing behaviors. The point isn’t perfection; it’s having a playbook rather than winging it.
Social Security planning for your retirement paycheck
For many people 65+, Social Security is the backbone of their retirement income. The Social Security Administration reports that for a significant share of older Americans, Social Security provides at least half of their total income. So deciding when and how to claim is a big deal.
A good Social Security strategy considers:
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Your health and family longevity.
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Whether you plan to keep working for a few years.
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The difference in benefits between taking them early, at full retirement age, or later.
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Spousal and survivor benefits for married couples.
This is where financial planning for retirement gets very personal. The “right” answer for a healthy couple with similar earnings may be very different from the answer for someone widowed early or someone with health concerns.
Don’t forget health care, Medicare, and long‑term care
Health care is one of the biggest unknowns in retirement. Medicare helps a lot, but it doesn’t cover everything, and you still need to plan for premiums, out‑of‑pocket costs, and maybe some form of long‑term care. Data on older adults show that many live on modest incomes, which makes unexpected medical costs more stressful.
Your plan doesn’t need to predict every doctor visit, but it should at least:
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Estimate Medicare premiums and supplemental coverage.
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Include a line item for ongoing medical costs and prescriptions.
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Consider how you’d pay for extended care if one spouse needs help down the road.
Common Midwestern Money Myths That Can Derail Your Plan
We Midwesterners are good at working hard and not making a fuss. Sometimes that works against us when it comes to money.
“I’ll just work forever”
Plenty of people plan to “keep working as long as they can,” and there’s nothing wrong with working longer if you enjoy it. But retirement surveys show that many people end up retiring earlier than they expected because of health issues, layoffs, or caregiving responsibilities. In other words, “I’ll work forever” isn’t really a plan—it’s a hope.
A better approach is to build a retirement plan that works even if you have to stop working earlier, and treat any extra working years as a bonus, not the foundation.
“Social Security will be enough for us”
For some households with very modest expenses, Social Security may indeed cover the basics. But many people underestimate how much they’ll want to spend in retirement and overestimate how far Social Security will stretch. Social Security’s own data show that benefits replace only a portion of pre‑retirement earnings for the average worker, before we even talk about inflation and health costs.
Rather than assuming “it’ll be enough,” it’s smarter to see how Social Security fits alongside your savings, pensions (if any), and other income in a full income plan.
“It’s too late to make a difference”
If you’re 58 or 62 and feeling behind, it’s easy to slip into defeat mode. But research on financial capability highlights that even later‑in‑life planning—things like paying down debt, trimming unnecessary spending, or working a couple extra years—can meaningfully improve retirement readiness. You don’t have to go from zero to perfect; you just have to start making deliberate moves.
The truth is, some of the biggest levers in your 50s and 60s aren’t flashy investments; they’re decisions about spending, housing, debt, and timing.
How a Local Financial Planner Can Help
Getting everything in one clear picture
Most people don’t talk to a financial planner because they love spreadsheets. They come because they’re tired of wondering: “Are we going to be okay?” For pre‑retirees, a good planning conversation usually pulls together:
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All your accounts (401(k)s, IRAs, savings, pensions).
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Your Social Security options.
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Your expected expenses, including health care.
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Your goals: staying in your home, helping kids, traveling, giving.
Instead of ten statements in a drawer, you end up with one coordinated view of what retirement could look like.
A down‑to‑earth process for couples 50+
A planning process designed for real families is less about jargon and more about plain talk. That might look like:
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Step 1: A simple “get to know you” visit where you talk through your situation and questions.
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Step 2: A clear, written retirement plan that shows your income sources, timing, and key decisions.
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Step 3: Ongoing check‑ins to adjust when life, markets, or laws change.
People who feel supported and informed about their finances tend to be less anxious and more confident in their retirement decisions. That’s the goal—not perfection, just clarity and confidence.
Your Next Step: Talk Through Your Own Retirement Picture
If you’re 50+ and starting to think seriously about financial planning for retirement, you don’t have to have everything “figured out” before you talk to someone. You just need the willingness to look at where you are today and where you want to go.
At Oswald Financial Group, we sit down with folks like you every week—people who have worked hard, saved what they could, and just want to know if it’s going to be enough. If you’re ready for a plain‑English conversation about your Social Security options, your savings, and what retirement could look like for your family, we’d be glad to walk through it with you.
Schedule a On-Course Retirement Review visit and let’s start putting your retirement picture together—one clear, doable step at a time.
Sources
Federal Reserve – Report on the Economic Well‑Being of U.S. Households
https://www.federalreserve.gov/publications
Social Security Administration – Fact Sheets and Statistics
https://www.ssa.gov
National Council on Aging – Economic Security for Older Adults
https://www.ncoa.org
FINRA Foundation – National Financial Capability Study
https://www.finrafoundation.org
Employee Benefit Research Institute – Retirement Confidence Survey
https://www.ebri.org