Retirement Planning: The 6 Questions Retirees Ask Most
Introduction
If you’re nearing retirement, it’s normal to ask the big questions—Will I have enough? When should I start Social Security? Should I pay off the mortgage? The challenge is that generic rules of thumb don’t always fit real life—especially when taxes, healthcare costs, and market volatility are part of the picture.
This article walks through six of the most common retirement questions we hear from pre-retirees and retirees—framed in a practical, planning-first way that helps you make confident decisions.
How much money do I need to retire?
This is the most common retirement question—and the most misunderstood. The answer isn’t just a number, because retirement isn’t an “asset game.” It’s a cash-flow game.
Instead of starting with “How big is my portfolio?” start with:
- How much monthly income do I need to live the life I want?
- What income sources will reliably show up each month?
- What gap must my investments fill—and for how long?
Why income sources matter more than a single savings target
Two households can have very different “required” nest eggs even if they live in the same neighborhood:
- One may have strong, steady income from Social Security, a pension, or rental real estate.
- Another may rely heavily on withdrawals from a 401(k) or IRA.
A portfolio doesn’t need to do all the heavy lifting if other income sources are covering a meaningful portion of your lifestyle.
A practical way to think about withdrawals
Many retirees use a “sustainable withdrawal rate” concept—often referenced as the 4% rule—as a starting point for planning. While it’s not a guarantee and should be personalized, it helps translate savings into income.
For example:
- A $1,500,000 portfolio at 4% supports about $60,000/year in withdrawals (before taxes).
- If you also have another income source—like rental income—your portfolio may not need to produce as much.
The key takeaway: retirement readiness is about building dependable cash flow, not just chasing a headline number.
When should I take Social Security?
Social Security timing is one of the most important retirement decisions you’ll make—because it impacts:
- Your lifetime income potential
- Your spouse’s survivor benefits
- Your taxes (especially in years when you also draw from retirement accounts)
The two questions that drive Social Security strategy
A solid Social Security decision usually comes down to:
- What are my income needs right now?
- What are the tax implications of taking—or delaying—benefits?
Delaying benefits can create a planning window where you intentionally draw from retirement accounts earlier (before required distributions begin), potentially reducing future tax pressure.
Factors that commonly affect the decision
There isn’t a one-size-fits-all “best age,” but these variables matter:
- Your health and family longevity
- The income difference between spouses
- The age gap between spouses
- Your ability to fund early retirement years without Social Security
- The value of increased benefits for delaying (often cited as ~7% per year up to full retirement age and ~8% per year up to age 70)
If you’re thinking about healthcare costs, this decision often intersects with Medicare timing, supplemental coverage, and how you plan to handle larger medical expenses later.
Will I run out of money in retirement?
This question is at the heart of retirement planning—and it deserves a thoughtful answer, not a sales pitch.
The reality is: no plan can control everything. Market returns, inflation, and longevity all introduce uncertainty. But a good plan reduces the odds of unpleasant surprises by building in guardrails.
How retirees reduce risk in real life
One practical approach is building “stopgaps” such as:
- A cash reserve for emergencies and near-term spending
- A bucket-style structure for short-, mid-, and long-term needs
- A diversified investment allocation designed to support withdrawals over decades
The biggest variable most plans can’t ignore: longevity
Many people are living longer—and that changes the math. It’s not unusual for retirement to last 25–35 years, especially for those who retire in their late 50s or early 60s.
That’s why planning shouldn’t be built on a single forecast. A strong plan stress-tests assumptions—then adjusts as life changes.
Should I pay off my mortgage before (or in) retirement?
This question can get controversial, but here’s the planning-first lens:
When you’re retired, fixed payments reduce flexibility. And again—retirement is a cash-flow game.
Why being debt-free can strengthen retirement cash flow
A mortgage payment isn’t just a line item—it’s a withdrawal requirement.
For example, a $3,000/month principal-and-interest payment is $36,000/year that must come from:
- Your portfolio withdrawals, or
- Pension income, or
- Social Security, or
- A combination of all three
If you’re using a 4% withdrawal framework, generating $36,000/year from investments alone can require close to $900,000 in portfolio value (before taxes and volatility considerations).
The bottom line
While every situation is different, many retirees benefit from entering retirement as close to debt-free as possible—because it improves cash-flow stability, reduces stress, and increases your ability to adapt when markets (or expenses) don’t cooperate.
For households, this can be especially relevant when planning for:
- Property taxes and insurance changes
- Home maintenance on aging properties
- Potential future healthcare or assisted living costs in Olmsted County and surrounding communities
How do I know if I’m invested correctly?
A strong retirement portfolio isn’t designed to “win” a bragging contest. It’s designed to support your lifestyle through good markets and bad ones.
Step one: confirm your strategic allocation
The first question is whether your overall mix matches your risk tolerance and income needs—typically broken into:
- Stocks
- Bonds
- Cash
A common (very broad) rule of thumb some people reference is: your age may approximate the percentage in more conservative holdings (bonds/cash). Example: a 60-year-old might consider something like 60% conservative / 40% growth.
That said, this is not a prescription. Your income needs, pensions, Social Security timing, and taxes can change what’s appropriate.
Step two: evaluate diversification and “tactical” mix
Within stocks and bonds, there are many categories (large vs. small, growth vs. value, domestic vs. international; treasuries vs. corporates vs. municipals, and more). This is where thoughtful diversification and disciplined rebalancing tend to matter more than market predictions.
A key principle: avoid building a portfolio that forces you to guess the market.
What should I do when the market drops?
Market drops feel personal—especially when you’re close to retirement. But a well-built plan anticipates downturns.
In many cases, the right move is not a dramatic move. If your portfolio is properly allocated and your cash-flow plan includes reserves for near-term spending, you can often avoid selling long-term investments at the wrong time.
A steady approach during volatility usually includes:
- Reviewing your allocation and rebalancing if needed (rather than panic-selling)
- Confirming near-term cash needs are covered
- Revisiting withdrawal strategy and tax implications
- Staying disciplined with a long-term plan
The goal is not to eliminate volatility. The goal is to make sure volatility doesn’t derail your lifestyle.
How often should I review my financial plan?
At a minimum, most retirees and near-retirees should review:
- Their financial plan
- Their investment portfolio
At least annually, even if nothing seems to have changed.
Review sooner if there’s a major life change
It’s wise to schedule a check-in when something material happens, such as:
- A change in income (retirement date moves, job change, part-time work starts/ends)
- A major purchase (vehicle, home renovation, second home)
- A decision about Social Security timing
- A health event that may impact long-term care planning
- Tax law changes that affect distribution strategy
Retirement planning isn’t “set it and forget it.” It’s closer to routine preventative care—small, consistent check-ins that help you stay healthy over the long run.
Conclusion: Focus on cash flow, clarity, and confident decisions
If you remember only a few things, remember these:
- Retirement success is driven by cash flow, not just a single savings number.
- Social Security timing is strategic—especially when taxes and spousal planning are involved.
- The risk of running out of money is best managed with guardrails: reserves, diversification, and realistic assumptions.
- Debt-free retirement often improves flexibility and peace of mind.
- Being “invested correctly” means your allocation matches your goals—not the latest market headlines.
- Plans should be reviewed annually, and whenever life changes.
Call to Action (CTA)
If you want help turning these concepts into a clear retirement strategy, we invite you to schedule a 15-minute introductory call. We’ll discuss your goals, your biggest questions, and what a practical next step could look like—without pressure.
Important Disclosure
Fortress Financial Group, LLC is a registered investment advisor. Advisory services are offered only to clients or prospective clients where Fortress and its representatives are properly licensed or exempt from licensure. This material is for general information only and is not intended to provide specific advice or recommendations for any individual. Investing involves risk, including possible loss of principal. Indexes are unmanaged and cannot be invested into directly.
