The Retirement Readiness Checklist: 10 Questions to Answer Before You Stop Working
- Erik James Roberts, Founder & Chief Investment Officer | Infinitus Wealth Management
- 1 day ago
- 10 min read
Erik James Roberts, MBA
Founder & Chief Investment Officer
Infinitus Wealth Management
The day you collect your final paycheck is one of the most consequential financial transitions of your life. A well-built retirement readiness checklist is the difference between confidence and quiet anxiety in the years that follow — between a retirement that compounds your life's work and one that slowly erodes it. Too many pre-retirees rely on vague confidence (“we have enough”) instead of a disciplined, numbers-driven framework. The ten questions below are designed to expose the gaps before they become losses. Answer each one with clarity and evidence, and you are genuinely retirement-ready.
Why a Retirement Readiness Checklist Matters More Than You Think
Most people enter retirement on momentum, not strategy. They accumulated for thirty or forty years, watched their balances grow, and assumed the transition to drawdown would take care of itself. It doesn't. The mathematics of distribution are fundamentally different from the mathematics of accumulation, and the portfolio that built your wealth is rarely the one that will protect it.
A serious retirement readiness checklist forces you to confront the questions most pre-retirees prefer to avoid: longevity, sequence risk, tax drag, healthcare inflation, advisor incentives. These are not topics for a single annual review. They form the structural foundation of every successful retirement we have ever seen — and the absence of any one of them is usually what derails the unsuccessful ones.
Work through every question below before you give notice.
Question 1: Do You Actually Know Your Retirement Number?
Not a feeling. A number. Most pre-retirees can estimate their portfolio balance to the dollar but cannot articulate the annual spending it must support — or the withdrawal rate that gets them there.
The classic 4% rule was a useful starting point when it was first published, but modern research has refined it considerably. Sustainable withdrawal rates depend on starting valuations, time horizon, asset allocation, willingness to adjust spending in down markets, and whether you have guaranteed income sources covering essential expenses. A single static percentage is a poor substitute for a stress-tested cash-flow model.
Before you retire, you should know your annual after-tax spending need, your portfolio's expected sustainable distribution at your specific allocation and horizon, and the cushion (or gap) between the two. And the portfolio underneath those numbers should be engineered around them — not pulled from a one-size-fits-all model that assumes your situation matches everyone else's. The first item on any honest retirement readiness checklist is putting real numbers to all three.
Question 2: Where Will Your Retirement Income Actually Come From?
A paycheck is one source. Retirement income is rarely fewer than four. A durable income plan typically blends Social Security, any pension or deferred compensation, portfolio withdrawals across taxable, tax-deferred, and Roth accounts, and sometimes rental income, royalties, or part-time consulting.
The order in which you tap each source matters enormously. Drawing from a taxable brokerage account in the early years while letting tax-deferred accounts continue compounding — and converting strategically along the way — can extend portfolio longevity by years versus a naive proportional drawdown.
This is where a clear retirement readiness checklist separates wishful thinkers from prepared retirees: have you mapped the actual sequencing, year by year, or are you planning to figure it out once you're in? The portfolio architecture should be designed around that sequencing from day one, with each holding positioned in the account type where it can do the most work.
Question 3: Is Your Portfolio Built for Withdrawals, Not Just Accumulation?
The portfolio that got you here will not get you there. Accumulation rewards aggressiveness, dollar-cost averaging, and time. Distribution penalizes volatility, demands liquidity, and exposes you to risks that simply do not exist while you are still saving.
A well-constructed retirement portfolio is generally diversified across asset classes that behave differently in different market environments, includes a reserve sufficient to avoid forced selling during downturns, and is positioned to deliver income with discipline rather than reaction. The shift from accumulation thinking to distribution thinking is one of the most underestimated transitions in personal finance — and it almost always requires rebuilding the portfolio, not just rebalancing it.
This is one reason custom-built portfolios — constructed for the specific client, their specific withdrawal pattern, and their specific risk capacity — tend to hold up better through retirement than off-the-shelf models or generic target-date allocations. A disciplined, research-driven investment process applied consistently across full market cycles weathers drawdowns better than reactive, headline-driven decision-making.
Question 4: Have You Stress-Tested for Sequence-of-Returns Risk?
This is the question that quietly destroys more retirements than any other. Sequence-of-returns risk is the danger that poor market returns in the first five to ten years of retirement, combined with withdrawals, do permanent damage that even a subsequent recovery cannot repair.
Two retirees can experience the exact same average annual return over thirty years and arrive at radically different outcomes — one with millions remaining, the other broke — based purely on the order in which those returns arrived. The retiree who sees bad years early, while making withdrawals, sells more shares at lower prices and never recovers the lost compounding.
Mitigation strategies include holding a meaningful cash and short-duration reserve, using a dynamic withdrawal policy that flexes with market conditions, and maintaining a portfolio that does not require selling depressed equities to fund living expenses. Active portfolio management can also tilt defensively when valuations and macro conditions warrant it — something fixed model allocations cannot do by design. Every retirement readiness checklist worth following stress-tests for this risk explicitly.
Question 5: What's Your Social Security Claiming Strategy?
For most retirees, Social Security is the single most valuable inflation-adjusted lifetime income stream they will ever own. Yet the majority of Americans claim it the moment they become eligible at 62, often leaving substantial lifetime benefits on the table.
Each year you delay claiming past your full retirement age — up to age 70 — adds roughly 8% to your monthly benefit, guaranteed and inflation-adjusted. For married couples, coordination between spouses creates additional optimization opportunities, particularly around survivor benefits, which lock in the higher of the two earnings records for the surviving spouse's lifetime.
The right claiming age depends on your health, your spouse's earnings record, your other income sources, and your tax picture. There is no universal answer. There is, however, a wrong way: claiming reflexively without running the numbers. Every retirement readiness checklist should pressure-test the claiming decision against actual health, longevity, and spousal-coordination assumptions before the irreversible election is made. The portfolio side of the equation gets calibrated around whichever claiming decision you make — a delayed claim raises the portfolio bridge from retirement to age 70, which changes how the early-retirement allocation should be built.
Question 6: How Will You Handle Healthcare and Long-Term Care?
Healthcare is the single largest underestimated expense category in retirement. Medicare does not cover everything. Medigap or Medicare Advantage premiums, Part D drug costs, dental, vision, hearing, and IRMAA surcharges for higher-income retirees can collectively run well into five figures annually per couple. Long-term care, if needed, is dramatically more.
A serious retirement readiness checklist examines what your projected healthcare costs look like from your retirement age through your late eighties, how you intend to bridge the gap if you retire before Medicare eligibility at 65, and whether you have a funding strategy for potential long-term care needs — whether through dedicated insurance, hybrid life-and-LTC products, self-funding from a designated portion of your portfolio, or some combination.
Within a custom-built portfolio, healthcare and long-term care funding can be segmented into a dedicated lower-volatility component without disrupting the growth engine that has to support the next thirty years of living expenses. Hoping you stay healthy is not a plan. Building the portfolio so it can absorb the possibility you don't is.
Question 7: Is Your Tax Strategy Built for the Distribution Decades?
The tax decisions you make between ages 60 and 75 will compound — for better or worse — across the entire remainder of your life and into your heirs' inheritance. A serious retirement readiness checklist treats tax positioning as a multi-decade discipline, not an annual filing exercise.
Required minimum distributions begin at age 73 (rising to 75 for younger cohorts), and they can push retirees into surprisingly high marginal brackets, trigger IRMAA surcharges on Medicare premiums, and create what advisors sometimes call the “tax torpedo” — a steep effective marginal rate caused by RMDs, Social Security taxation, and capital gains stacking on top of each other.
Roth conversions during the low-income window between retirement and age 73 can be one of the most powerful tax-positioning levers available — when modeled carefully against the full distribution timeline. Asset location — which holdings sit in which account type — is fundamentally a portfolio construction question, and one where custom-built portfolios meaningfully outperform standardized allocations. Tax-loss harvesting, qualified charitable distributions, donor-advised funds, and bracket-management withdrawal sequencing all belong in the conversation.
Question 8: Does Your Estate Plan Match the Life You've Actually Built?
Estate planning is not just for the ultra-wealthy and it is not just about death. It is about ensuring the wealth you spent a lifetime building flows on your terms — to the people, causes, and purposes you choose — with minimum friction, tax, and family conflict.
At a minimum, before you retire, you should have an up-to-date will, durable powers of attorney for finance and healthcare, an advance healthcare directive, and a complete review of beneficiary designations on every retirement account, life insurance policy, and annuity. Beneficiary designations override your will. A 401(k) still listing an ex-spouse will pay an ex-spouse, regardless of what your will says.
Depending on the size and complexity of your estate, revocable trusts, irrevocable trusts, generation-skipping strategies, and lifetime gifting plans may all warrant analysis. The right structure depends on your assets, your family, and your intent — and the way the underlying portfolio is constructed and titled has direct downstream effects on how efficiently it transfers. A complete retirement readiness checklist reviews estate documents, titling, and beneficiary designations as one integrated system, not three separate ones.
Question 9: Have You Honestly Accounted for Inflation?
A retirement that begins at 62 may need to fund living expenses into the early nineties. Over thirty years, even modest inflation does extraordinary damage to fixed-income purchasing power. At 3% annual inflation — roughly the long-run U.S. average — $10,000 of monthly spending today requires more than $24,000 to buy the same goods and services thirty years out.
A retirement readiness checklist that ignores inflation is not a plan; it is a snapshot. Sustainable retirement portfolios are built to grow, not just to pay out. That generally argues for a meaningful allocation to assets with the historical capacity to outpace inflation over long horizons — even for retirees who instinctively want to dial down risk the moment they stop working.
Building a portfolio that grows through retirement — rather than one designed only to distribute — is a deliberate active construction choice, not a default setting. The right balance between protecting against short-term volatility and protecting against long-term erosion is one of the central design questions of any retirement portfolio.
Question 10: Is Your Advisor a Fiduciary — or a Salesperson?
The financial services industry uses the word “advisor” generously. Many people who hold that title are legally permitted to sell you products that pay them more than they pay you. The fiduciary standard — a legal obligation to act in your best interest at all times — is held by registered investment advisors, not by every broker, insurance agent, or representative working under a brokerage banner.
Before you retire, ask, in writing: Are you a fiduciary at all times in our relationship? How are you compensated, in total, including any third-party payments? Do you accept commissions, revenue-sharing, or product-based incentives of any kind? Do you build custom portfolios for individual clients, or do you place clients into pre-built models? Your retirement readiness checklist is not complete until you can answer all of these questions about whoever is managing your money.
A fee-only fiduciary firm — paid solely by the client, with no commissions, no product sales, and no performance fees — eliminates the most common conflicts of interest in the industry. It is the foundation Infinitus Wealth Management was built on, and it is why every Infinitus portfolio is custom-constructed for the individual client rather than slotted into a one-size-fits-all model.
From Retirement Readiness Checklist to Custom Portfolio
A retirement readiness checklist exposes the questions. The portfolio is where most of them get answered.
At Infinitus Wealth Management, we build custom portfolios for each client we serve. Not model allocations. Not goals-based templates. Not glidepaths that drift you toward a generic target date. Every Infinitus portfolio is constructed from the ground up around the specific investor it serves — their withdrawal pattern, their risk capacity, their tax picture, their income stack, and their actual time horizon.
For pre-retirees and retirees, that means:
A portfolio architected for the distribution decades, not just the accumulation years
Sequence-of-returns risk addressed in the construction itself, not bolted on as an afterthought
Asset location across taxable, tax-deferred, and Roth accounts coordinated for tax-efficient withdrawals
Active management that can tilt defensively when valuations and macro conditions warrant it
A reserve structure designed so you never have to sell depressed equities to fund living expenses
An inflation-aware equity allocation built to grow through retirement, not just pay out
We are an independent, fee-only fiduciary. No commissions. No product sales. No performance fees. Our compensation comes exclusively from our clients, which means our incentives are aligned with yours — at every decision, on every position, in every market environment.
If you would like a complimentary, no-obligation review of how your current portfolio is positioned for the ten questions in this article — and a clear, side-by-side look at how a custom-built Infinitus portfolio would address them differently — we welcome the conversation.
Ready for a second opinion? If you’d like an honest, no-obligation review of your current portfolio, fee structure, and investment strategy, I’d welcome the conversation. Schedule a complimentary consultation at infinituswealth.com. |
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Important Disclosures
Infinitus Wealth Management is a registered investment advisory firm. This article is provided for educational and informational purposes only and does not constitute investment, tax, legal, or accounting advice. It is not an offer or solicitation to buy or sell any security or to enter into any advisory relationship. Any references to specific strategies, withdrawal rates, tax provisions, or historical figures are general in nature and may not be appropriate for any individual investor.
Past performance is not indicative of future results. All investing involves risk, including the possible loss of principal. Tax laws are complex, change frequently, and have unique application to individual circumstances; please consult a qualified tax professional regarding your specific situation. Social Security rules, Medicare rules, and retirement account regulations are subject to legislative and regulatory change.
The information in this article was believed to be accurate at the time of writing but is not guaranteed. Readers should consult with their own qualified advisors before making any financial decisions specific to their situation.
