The right retirement planning questions, asked early enough, are what turn a savings balance into an actual plan. Yet, confidence is slipping. The 2026 EBRI Retirement Confidence Survey found that only about six in ten workers said they feel confident they’ll have enough money to live comfortably in retirement. Inflation, healthcare costs, and worries about Social Security are all cited as drivers of this uncertainty. The good news is that most of that can be addressed through a manageable set of questions as you approach retirement. Below are the questions worth asking yourself, and asking an advisor, well before you retire to make sure you’re on the right track for the retirement you want.
Retirement planning questions at a glance
- When should I start saving for retirement?
- How much income will I need in retirement?
- How much do I need to retire?
- How do I know if I have enough?
- How will I pay for healthcare and long-term care?
- What percentage can I withdraw from my savings each year?
- What’s my tax and withdrawal strategy in retirement?
- How do I make my money last and plan for inflation?
- What happens to my plan if the market drops early in retirement?
- When should I claim Social Security?
When should I start saving for retirement?
This might be the most commonly asked question and the easiest to answer. Start saving for retirement as soon as possible. We know that paying off student loans, buying a house, and starting a family can impact retirement savings. However, time can be a tremendous asset in retirement planning. The earlier contributions begin, the greater the benefits of compounding investment returns. We recommend people save 10-15% of their pre-tax income. If your employer offers a matching 401(k) contribution, be sure to maximize that benefit through salary deferral.
How much income will I need in retirement?
A widely cited starting point says that retirees need roughly 70% to 80% of their pre-retirement income to maintain their standard of living. The logic is that certain costs typically fall once you stop working:
- You’re no longer saving for retirement
- Payroll taxes drop
- No longer commuting
- Other work-related expenses are reduced
It’s a useful benchmark, but your own figure could be higher if you plan to travel extensively, carry a mortgage into retirement, or face significant healthcare costs. It could also be lower if your home is paid off and your lifestyle is modest. Social Security replaces only about 40% of the average worker’s pre-retirement income, so the rest generally has to come from your savings, any pension, and other sources.
How much do I need to retire?
Like most financial decisions, how much you need to retire is partly dependent on what you want and what your goals are. Do you want to work in retirement? Do you want to travel? Do you want to buy a second home or downsize? Enough” isn’t universal; it’s whatever supports the specific life you intend to live in retirement. Financial planning helps you determine not only what you have invested today, but also projects your investments and the income from those investments throughout your retirement years. We are then able to compare that to your expected lifestyle and needs in retirement.For a closer look at this for couples specifically, see our guide on how much income a couple really needs in retirement.
How do I know if I have enough?
This is one of the hardest questions to answer, because even if you know your goals and current financial situation, you have to estimate many unknowns. How long will you live? Will you be healthy? What will you spend? What will the rate of return be on your investments in the future? Estimating these variables is helpful, but because they are variables that can change often, solid financial planning involves evaluating scenarios and revisiting your goals and investments periodically.
How will I pay for healthcare and long-term care?
Medicare eligibility begins at 65, so if you retire earlier, even by a year or two, you’ll need to bridge the gap in coverage yourself through the individual marketplace, a spouse’s plan, or COBRA, and that coverage can be expensive. Once Medicare begins, it helps, but it doesn’t cover everything. You’ll still have to pay premiums, supplemental coverage, and out-of-pocket costs throughout retirement. The larger unknown is long-term care. Medicare does not cover extended custodial care, and an extended care need can become one of the largest expenses of later life.
What percent can I draw off my assets?
The 4% rule says that you can draw 4% of your total assets in your first year of retirement, adjusted for inflation annually after that, to support a 30-year retirement. However, while this rule is a helpful starting point, it does not take into account every investor’s unique financial situation. The 4% rule assumes a particular time horizon and portfolio mix, and it can’t account for your actual spending, your tax situation, or the market you happen to retire into. Customized planning provides the greatest insight into cash flow analysis for retirement.
What’s my tax and withdrawal strategy in retirement?
Most people hold their retirement balances in three types of accounts:
- Taxable brokerage accounts
- Tax-deferred accounts like a traditional 401(k) or IRA
- Tax-free Roth accounts
Each is taxed differently when you draw from it, and the order in which you withdraw can meaningfully affect your tax bill over the course of retirement. A common approach is to draw from taxable accounts first, then tax-deferred, then Roth, but the right sequence depends on your tax bracket, your other income, and your goals.
The years between when you stop working and when required minimum distributions begin at age 75 can be a valuable window for tax planning. For some people, converting a portion of a traditional IRA to a Roth IRA during those lower-income years may help manage taxes later, depending on your situation. Because the right withdrawal order and any Roth conversion decision depend on your specific tax situation, it’s worth reviewing the details with a qualified tax professional before acting.
How do I make my money last and plan for inflation?
Inflation erodes what a fixed dollar buys, so income that feels comfortable at 65 can feel tight by 85 if it hasn’t kept pace with rising costs. This is why most long-term plans keep a portion of the portfolio invested for growth in retirement rather than shifting entirely to conservative holdings. Longevity is the other factor. A couple retiring in their early 60s should reasonably plan for one spouse to live into their 90s, which means the plan may need to fund 30 years or more.
What happens to my plan if the market drops early in retirement?
The timing of a market downturn matters, and the years immediately before and after your retirement date are the most sensitive of all. This is sequence-of-returns risk. The reason it’s so consequential is that a downturn early in retirement hits while you’re withdrawing income, so you’re selling more shares to fund the same spending, leaving less in the portfolio to recover when markets rebound. Many plans manage this risk by holding a cushion of more stable assets in the early retirement years, so a bad market doesn’t force selling investments at a loss to cover spending.
When should I claim Social Security?
Benefit eligibility for Social Security begins at 62, the earliest retirement age. However, this isn’t always the best time to begin claiming benefits, since benefits are reduced permanently when you claim early. For anyone born in 1960 or later, full retirement age (FRA) is now 67, the age at which you receive 100% of your earned benefit.
Claiming benefits before your FRA when you still have earned income may lead to a loss of part or all of your Social Security benefits. Waiting until after your FRA eliminates any reduction in benefits due to continued earnings and also provides for an increase in your monthly benefit. If you can defer beginning benefits even longer you’ll increase the monthly income you receive for the rest of your life. For some, deferring to age 70 will provide the largest amount of overall lifetime benefits from Social Security.
Talk through your retirement questions
If working through these questions surfaced a few you can’t answer with confidence, that’s exactly what a conversation with an advisor is for. Schedule a consultation to talk through your situation with an advisor. If you’d prefer to start on your own, our Financial Health Self-Assessment can give you a quick look at where you stand today.
Frequently asked questions
What are good retirement questions to ask?
Good retirement questions address income, taxes, and timing. How much income will I need? How much do I have and will it last? When should I claim Social Security? What’s my withdrawal and tax strategy? And what happens if the market drops early in retirement?
What is the $1,000-a-month rule for retirees?
The $1,000-a-month rule is a rough guideline suggesting that for every $1,000 of monthly income you want in retirement, you may need about $240,000 saved, based on a 5% annual withdrawal rate. The right withdrawal rate for you depends on your timeline, your investments, and market conditions.
What are the three Cs of retirement?
The three Cs are often described as clarity, confidence, and control: clarity about what you want retirement to look like, confidence that your income can support it, and control over the decisions that keep the plan on track.
What are common retirement planning mistakes?
Common mistakes include underestimating healthcare and long-term care costs, claiming Social Security without weighing the timing, ignoring the tax impact of withdrawal order, failing to plan for inflation and a long retirement, and having no strategy for a market downturn early in retirement.
What questions should I ask a financial advisor about retirement?
Ask whether they’re a fiduciary and how they’re paid, whether your income will cover how you plan to live, in what order you should draw from your accounts and the tax impact, when to claim Social Security, and how your plan is protected against a poorly timed market drop.
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