The Retirement Readiness Checklist: Ten Questions Worth Answering Before You Retire
By Max Novak, Novak Financial Partners · Updated May 2026
Key takeaways
- Retirement readiness is not a number. It is a set of connected decisions, and the ones that have nothing to do with your account balance often matter most.
- The ten questions below start with what you are retiring to, then cover Social Security timing, turning savings into income, Roth conversions, pension choices, portfolio and withdrawal strategy, Medicare enrollment, housing, and estate documents.
- These decisions all impact each other. A Social Security choice affects taxes; taxes affect Roth conversions; conversions affect Medicare premiums. Handling them in separate pieces tends to leave money on the table.
- If a few questions give you pause, that is the useful part. It turns a vague worry into a clear, finite list of things worth resolving.
- This is a checklist, not a scorecard. There is no test to pass, just a structured way to see where you stand.
Most retirees ask one question: do I have enough to retire? It is a natural place to start, partly because the account balance is the number a statement shows you every month. But the years right before and just after retirement are full of decisions that have nothing to do with that balance, and those decisions often matter more than the balance itself.
Over the past year, a number of our clients have introduced us to their parents and family friends approaching retirement. The conversations tend to cover the same ground every time. So we wrote down the questions worth answering before you retire, the ones that quietly get missed because nothing forces you to address them.
This is a checklist, not a scorecard. It will not tell you whether you are "ready." It shows you which decisions deserve your attention so nothing important slips through the cracks. If a few feel unresolved, that is normal. It just means there is work worth doing, and now you know what it is. Here are the ten questions, starting with the one most people skip.
1. Do you know what you are retiring to?
This is the first question for a reason. Retirement is the end of a working career, but it is also the start of a new chapter, and every decision that follows in this checklist exists to support that chapter. Yet it is the question most often skipped, because it is the only one a spreadsheet cannot answer.
There is a real difference between retiring away from something and retiring toward something. Leaving a job you are tired of is a fine reason to stop working, but it is not, by itself, a plan for the two or three decades that follow. Picture the actual mornings: slow breakfasts with the grandchildren before school, the trip to Italy you have postponed for fifteen years, Tuesday afternoons volunteering at the library or food bank, a part-time role you take because you want to, an extra weekly round of golf with old friends. The picture does not have to be elaborate. It just has to be specific enough that you can see yourself in it, because the financial plan is built to fund that life.
There is also a psychological shift worth naming. For 30 or 40 years you were a saver, and watching the balance grow felt like progress. Retirement reverses that: the balance now goes down by design, and for many people that is genuinely uncomfortable even when the plan is sound. A well-built income plan helps beyond the math. When a reliable monthly paycheck arrives from your own savings, spending feels less like draining an account and more like collecting what you spent decades building. The shift from saver to spender is easier when the income is predictable.
This matters for couples in particular. Two people can save toward the same retirement date while quietly imagining very different versions of the years after it. Surfacing that early, while it is still a conversation rather than a surprise, is one of the most valuable things you can do.
Worth checking: Can you describe, in a few specific sentences, what a good week in retirement looks like? Does your spouse's version match yours?
Where to start: Each of you, separately, write down how you would spend a typical retired Tuesday. Then compare. The gaps and overlaps are the start of the conversation.
2. Do you know when you will claim Social Security, and why?
Claiming early at 62, at full retirement age, or waiting until 70 can change your lifetime benefit by a substantial amount. Between full retirement age and 70, the benefit grows by roughly 8 percent for each year you wait. That is a meaningful, guaranteed increase, and it is rare to find one anywhere else.
But "wait until 70" is not automatically the right answer. The decision depends on your health and family longevity, your spouse's benefit and what they would receive as a survivor, and whether you want low-income years before benefits begin to do other tax planning. The point is not to pick a number off a chart. It is to be able to explain why your number is the right one for your household.
Worth checking: Have you compared at least two claiming ages side by side? Have you coordinated the timing with your spouse, including survivor benefits?
Where to start: Create a free account at SSA.gov and pull your estimated benefit at 62, full retirement age, and 70. Seeing the three numbers side by side makes the trade-off concrete.
3. Do you have a plan for turning savings into a paycheck?
Saving and spending down savings are different skills. For decades the task was simple: contribute, invest, repeat. Retirement reverses it. The question now is how to convert a portfolio into reliable monthly income that lasts as long as you do.
A withdrawal plan answers three things: which accounts you draw from, in what order, and how much is sustainable each year. Most people approaching retirement have a clear picture of what they have saved and a fuzzier one of how it becomes a paycheck. Closing that gap is one of the most reassuring things you can do before you retire.
The mortgage decision belongs here too, because it sets the size of the paycheck you need. Whether to pay it off before you retire is a genuine judgment call: doing so lowers the income you must generate each year and can simplify the rest of the plan, but it uses liquidity that might be working elsewhere. There is no universal answer, but it is a decision worth making on purpose rather than by default.
Worth checking: Do you know roughly what your first-year withdrawal will be, and which account it comes from?
Where to start: Write down your estimated annual spending in retirement, then subtract guaranteed income (Social Security, any pension). The gap is what your savings need to cover each year.
4. Have you looked at Roth conversions before age 73?
The years between retirement and when Required Minimum Distributions begin (age 73 or 75, depending on your birth year) are often the lowest-tax window you will ever see. Wages have stopped, Social Security may not have started, and the IRS is not yet forcing taxable withdrawals from your retirement accounts.
Converting some traditional IRA or 401(k) money to a Roth during that window means paying tax at a rate you may never see again, and that money then grows tax-free and never appears on a future tax return. The conversion math is not universally favorable, since it interacts with Medicare premiums, Social Security taxation, and state tax. But the window is finite, and every year that passes without a plan is bracket space that quietly disappears.
Worth checking: Have you mapped your projected tax brackets for the next five years to see whether a conversion window exists for you?
Where to start: Find last year's tax return and note your taxable income and bracket. That is the baseline for judging whether the gap years open up a lower-tax window.
5. If you have a pension, do you understand your options?
If you are fortunate enough to have a pension, you will likely face two choices that are difficult or impossible to reverse. The first is lump sum versus monthly income. The second is single-life versus survivor benefit.
A lump sum gives you control and something to leave to heirs, but it moves investment and longevity risk onto you. Monthly income is steady and predictable but generally stops when you (and any survivor) pass away. The survivor election in particular determines what your spouse lives on after your death. These decisions deserve more than a quick read of the paperwork the week it arrives.
Worth checking: Do you understand exactly what your spouse would receive under each survivor option?
Where to start: Request your pension's benefit-election packet from your plan administrator and read the lump sum and survivor figures before any deadline pressure arrives.
6. Is your portfolio set up for the withdrawal phase?
Two things change once you stop saving and start drawing income. The first is risk. A portfolio that served you well while saving may carry more risk than you want once you depend on it: a steep market decline early in retirement, combined with ongoing withdrawals, can do lasting damage that the same decline would not cause during your working years. Planners call this sequence-of-returns risk. The fix is not to retreat entirely to cash, since most retirements last decades, but to hold enough safer assets to cover near-term withdrawals so you are never forced to sell stocks at a low point.
The second is the order you withdraw in. Most retirees hold money in three kinds of accounts: taxable, tax-deferred (a traditional IRA or 401k), and tax-free Roth. Which you draw from first affects your tax bracket, how much of your Social Security benefit is taxable, and your Medicare premium surcharges. A tax-efficient strategy looks at lifetime taxes, not just this year's bill, and sometimes that means drawing from a tax-deferred account earlier than feels intuitive to keep future Required Minimum Distributions from pushing you into a higher bracket later. Both the allocation and the withdrawal order are worth deciding deliberately rather than leaving on autopilot.
Worth checking: Have you reviewed your asset allocation since you settled on a retirement date, and do you know how your planned withdrawals could affect your Medicare premiums?
Where to start: List your accounts in three buckets (taxable, tax-deferred, and Roth) with a balance for each, and note roughly what share is in stocks versus bonds and cash. That single picture is the starting point for both decisions.
7. Do you have a plan for Medicare and healthcare costs?
Medicare is one of the few retirement decisions with a hard deadline attached. Your Initial Enrollment Period runs for seven months: the three months before the month you turn 65, your birthday month, and the three months after. Miss it without qualifying employer coverage, and the late-enrollment penalties for Part B and Part D can follow you for life.
There is also a gap worth planning around: standard Medicare does not cover extended long-term care, the ongoing assisted living or nursing home costs that are among the largest risks a retirement plan faces. How you would cover that, whether through insurance, set-aside assets, or another approach, is a decision better made early than late. Two genuinely free, unbiased starting points are Medicare.gov and your State Health Insurance Assistance Program (SHIP), which offers free, unbiased one-on-one Medicare counseling.
Worth checking: Do you know the exact dates of your Initial Enrollment Period, and do you have a plan for potential long-term care costs?
Where to start: Mark your seven-month enrollment window on a calendar now. It opens three months before the month you turn 65. A free SHIP counselor can walk you through options.
8. Have you thought through where you will live?
For many retirees the home is the largest asset they hold outside their investment accounts, and even when the mortgage is paid off it still carries real ongoing costs: property taxes, insurance, maintenance, and utilities do not stop. That makes the decision to age in place, downsize, or relocate a financial one as much as a personal one. Downsizing can release home equity and lower those ongoing costs. Relocating can change your cost of living, your proximity to family and healthcare, and, less obviously, your tax picture.
That last point catches people off guard. Some states tax retirement income and IRA or 401(k) withdrawals; others tax neither, so a move across a state line can change the after-tax value of the same savings. This is not a reason to choose a home for tax reasons, only a reason to keep the housing decision and the financial plan in the same conversation.
Worth checking: If you are considering a move, have you factored in the state tax treatment of your retirement income, plus moving costs and any change in home equity?
Where to start: Have a frank conversation with your spouse about staying, downsizing, or relocating, before running any numbers. The financial analysis is easier once the preference is clear.
9. Are your estate documents current?
Estate planning is not only for the very wealthy, and it is not only about who inherits money. It is also about who makes decisions for you if you cannot, and about sparing the people you love from confusion during a hard time.
Most people should have a current will, a durable power of attorney for finances, a healthcare power of attorney, and an advance directive. Just as important, and frequently overlooked, are beneficiary designations on retirement accounts and life insurance. Those designations override whatever your will says, and they are often years out of date, still naming a former spouse or a now-grown child. Reviewing them takes an afternoon and prevents real problems.
There is one gap we see often: the house. If you do not have a trust in place, the home can end up passing through probate even when every other account has a named beneficiary. In many states a beneficiary deed (sometimes called a transfer-on-death deed) lets the home pass directly to the people you choose, outside probate, without the cost or complexity of a trust. If there is no trust, it is worth confirming the house is covered by something, rather than assuming the will handles it cleanly.
Worth checking: Have you reviewed every beneficiary designation in the last three years, and do your documents reflect your life as it is now?
Where to start: Log in to each retirement account and life insurance policy and read the named beneficiary. This takes one afternoon and catches the most common, most costly oversight.
10. Do you know who is coordinating all of this?
Notice how often the questions above referenced one another. The Social Security decision changes your tax picture. Your tax picture determines whether Roth conversions make sense. Conversions affect your Medicare premiums. Your withdrawal strategy depends on all of it.
These decisions are not really separate. Handled in isolation, each one can look fine on its own while the combination quietly costs you. The most valuable thing in retirement planning is often not any single decision but the coordination between them, one person looking at the whole picture and making sure the pieces fit.
Worth checking: Is there one person looking at the whole picture, or are these decisions being handled in separate pieces by separate people?
Where to start: Go back through questions 1 to 9 and circle the three that feel least settled. Those three are your agenda, whether for your own planning or for a conversation with an advisor.
Common mistakes we see
After enough of these conversations, the same handful of avoidable mistakes come up again and again. None of them happen because someone was careless. They happen because nothing forces the decision, so a busy life simply lets it slide. Here are the five worth guarding against.
Leaving beneficiary forms and deeds out of date. Beneficiary designations override your will, and they are routinely years behind real life. The fix is an afternoon of logging in and reading each one, plus confirming the house is covered by a trust or a beneficiary deed rather than left to drift into probate.
Claiming Social Security too early, without running the numbers. Claiming at 62 is often a default rather than a decision. For some households it is the right call, but it should follow a comparison of claiming ages and a look at survivor benefits, not precede one.
Missing the Roth conversion window. The low-tax years between retirement and Required Minimum Distributions pass quietly, and the bracket space they offer cannot be reclaimed later. Many retirees only learn the window existed once RMDs arrive and the tax bill is larger than it had to be.
Retiring without a real withdrawal plan. It is common to reach the retirement date with a clear savings total and no clear answer to which accounts the monthly paycheck comes from, in what order, and at what sustainable rate. The savings are there; the plan to spend them is not.
Carrying an allocation that no longer fits. A portfolio built to grow is often left untouched into the withdrawal phase, with no deliberate adjustment for the new job it has to do. The allocation that served you while saving is rarely the one you want while drawing income.
What to do with this list
If you read through all ten questions and felt confident about every one, you are in good shape. Keep doing what you are doing.
If a few gave you pause, that is the useful part. A vague sense that "I should probably look into retirement stuff" is stressful precisely because it is vague. A specific list of three or four unresolved questions is not stressful. It is just a to-do list, and a finite one.
The bottom line
Retirement readiness is not a number. It is about making sure the connected decisions around that number have each been thought through. The questions above are the ones that tend to get missed. If a second set of eyes would help, that is what a conversation is for.
A few free, unbiased resources
You do not need to pay anyone to start gathering the basics. A handful of government and nonprofit resources are genuinely free and independent:
- SSA.gov: create an account to see your estimated Social Security benefit at different claiming ages and to check your earnings history for errors.
- Medicare.gov and 1-800-MEDICARE: the official source for enrollment timing, plan comparison, and what each part of Medicare covers.
- State Health Insurance Assistance Program (SHIP): free, unbiased one-on-one Medicare counseling, funded by the federal government.
- Eldercare Locator: a free federal service that connects you with local support for long-term care, in-home help, and other aging-related services.
- HealthCare.gov: the place to compare ACA marketplace coverage if you retire before you are eligible for Medicare at 65.
These will get you the raw numbers. Turning those numbers into a coordinated plan is the harder part, and it is the part we are happy to help with.
Want a second set of eyes on your retirement plan?
Here is a simple next step: work through the ten questions, circle the three that feel least settled, and bring just those to a free 30-minute call. No preparation beyond that, and no obligation. You will leave with a clearer sense of where you stand.
See if flat-fee planning is right for youFrequently asked questions
How do I know if I am ready to retire?
Retirement readiness is not a single number or a yes/no answer. It is a series of decisions: what you are retiring to, when to claim Social Security, how to turn savings into income, whether to do Roth conversions, what to do with a pension, how to position investments, and whether your estate documents are current. A useful way to assess readiness is to walk through each of these decisions and identify which ones are still unresolved. If a few feel unsettled, that is normal. It simply means there is a clear, finite list of things worth sorting out before you retire.
How do I decide what to do in retirement?
Before the financial decisions, it helps to picture what you are retiring to rather than only what you are retiring from. Leaving a job is not by itself a plan for the two or three decades that follow. People tend to navigate retirement better when they have a concrete sense of how the time gets filled, whether that is family, travel, volunteering, part-time work, or a hobby taken seriously. It does not need to be elaborate, but it should exist, because the financial plan is built to fund that life. For couples, it is especially worth checking early that both people are imagining a similar version of the years after the retirement date.
When should I claim Social Security?
There is no universal answer. Claiming early (as soon as age 62), at full retirement age (66 to 67 depending on birth year), or at 70 each changes your lifetime benefit substantially. The right choice depends on your health and life expectancy, your spouse's benefit and survivor needs, your other sources of income, and whether you want to do Roth conversions in the years before benefits begin. Many high earners benefit from delaying, since the benefit increases roughly 8 percent for each year of delay between full retirement age and 70, but the decision should be coordinated with your overall tax and income plan rather than made in isolation.
What is a retirement withdrawal strategy?
A withdrawal strategy is the plan for converting your savings into a reliable paycheck once you stop working. It decides which accounts you draw from (taxable, tax-deferred, or Roth), in what order, and how much you can sustainably withdraw each year. A good withdrawal strategy coordinates with Social Security timing, tax brackets, and Medicare premiums. Saving for retirement and spending down those savings are genuinely different skills, and the second one rarely gets the planning attention it deserves.
What is a tax-efficient withdrawal strategy?
A tax-efficient withdrawal strategy sequences withdrawals from taxable, tax-deferred, and Roth accounts to minimize lifetime taxes rather than just the current year's tax bill. The order matters because it affects your tax bracket each year, how much of your Social Security benefit is taxable, and your Medicare premium surcharges (IRMAA), which are based on income from two years prior. Coordinating these moving parts can meaningfully extend how long a portfolio lasts.
Should I take a pension as a lump sum or monthly payments?
This is usually a permanent decision, so it deserves careful analysis. A lump sum gives you control and the ability to leave remaining assets to heirs, but it shifts investment and longevity risk onto you. Monthly payments provide guaranteed income for life but typically end (or are reduced) when you and any survivor pass away. The single-life versus survivor-benefit choice is especially important because it determines what your spouse receives after your death. The right answer depends on the size of the lump sum relative to the income offered, your health, your spouse's needs, and your other guaranteed income.
Should I change my investments when I retire?
Often, yes, at least to some degree. A portfolio built to grow during your working years may carry more risk than you want once you begin drawing income from it. In retirement, the goal shifts toward stability and predictability, because a steep market decline early in retirement combined with ongoing withdrawals can do lasting damage (a risk known as sequence-of-returns risk). This does not mean abandoning growth entirely, since most retirements last decades. It means reviewing your allocation in light of your retirement date and withdrawal plan rather than leaving it on autopilot.
What estate planning documents do I need before retirement?
At a minimum, most people should have a current will, a durable power of attorney for finances, a healthcare power of attorney, and an advance healthcare directive. Beneficiary designations on retirement accounts and life insurance also need review, because those designations override whatever your will says and are frequently outdated. Depending on your situation, a revocable living trust may also be worth considering. The key is that these documents reflect your life as it is now, not as it was when the documents were first drafted.
When do I need to enroll in Medicare?
Your Initial Enrollment Period is a seven-month window that begins three months before the month you turn 65, includes your birthday month, and ends three months after. Missing it can cause lifelong late-enrollment penalties for Part B and Part D, unless you have qualifying coverage through an employer. It is also important to know that standard Medicare does not cover extended long-term care such as an ongoing nursing home or assisted living stay, so a separate plan for those costs is worth considering. The official starting points are Medicare.gov and the federally funded State Health Insurance Assistance Program (SHIP), which provides free, unbiased one-on-one Medicare counseling.
Should I downsize or relocate when I retire?
Housing is usually the largest item in a retirement budget, so whether you age in place, downsize, or relocate has a real financial effect. Downsizing can free up home equity and lower ongoing costs, while relocating may change your cost of living and your tax picture. State income tax matters here: some states tax retirement income and IRA or 401(k) withdrawals while others do not, so a move can change the after-tax value of your savings. Moving costs, the emotional side of leaving a long-time home, and proximity to family and healthcare all belong in the decision alongside the math.
Should I pay off my mortgage before I retire?
There is no single right answer, but it is worth a deliberate decision rather than drift. Eliminating high-interest debt before retirement is almost always sensible because it removes a fixed cost from a fixed income. A mortgage is more nuanced: paying it off lowers your required monthly spending and the income you need to generate, but using a large share of savings to do so reduces liquidity and may have tax consequences if the money comes from a tax-deferred account. The choice depends on your interest rate, your other assets, and how much predictable spending matters to your peace of mind.
Do I need a financial advisor to retire?
Not necessarily, but the value of coordination rises sharply at retirement. Retirement decisions are interconnected: a Social Security choice affects your taxes, your taxes affect whether Roth conversions make sense, conversions affect your Medicare premiums, and so on. Handling each piece separately often leaves money on the table. If you choose to work with an advisor, a flat-fee fiduciary arrangement avoids the conflicts of interest that come with commissions and asset-based fees, so the advice you receive is built around your situation rather than a product sale.
This article is for educational and informational purposes only and does not constitute personalized investment, tax, legal, or financial planning advice. Tax rules, retirement account rules, and thresholds are based on current IRS, CMS, and Social Security Administration guidance for 2026 and are subject to change. Every individual situation is different; the right decisions depend on your income, health, family circumstances, state of residence, and other factors. Consult a qualified financial, tax, or legal professional before acting on any strategy discussed here. Advisory services are offered through Core Planning LLC, a Registered Investment Advisor. For additional disclosures please visit corepln.com/disclosures.
