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Early in my career, I had a mentor who was masterful at asking thoughtful questions during meetings with clients. She would cut straight to what actually mattered — not the surface-level details, but the issues that determined whether a client’s retirement plan would succeed or not.
I think about that often when working with people approaching retirement. Most retirement planning conversations get buried in the details — portfolio allocation, Social Security breakeven calculations, Roth conversion strategies. All of it matters. But underneath the mechanics, there are a handful of questions that truly determine whether your retirement will succeed or not. Answer them well, and you're in good shape.
Here are the five questions we ask every client who is approaching retirement — and what honest answers look like.
This is the foundational question of retirement planning, and it's more nuanced than it appears.
Most people frame it as: 'Do I have enough money to retire?' But that's actually the wrong question. The better question is: 'Will my money last as long as I need it to — through market downturns, rising inflation, unexpected expenses, and a retirement that might last 30 years or more?'
Start with your spending. Not your current spending — your projected retirement spending. These are different numbers for most people. Some expenses disappear at retirement (commuting costs, work wardrobe, saving for retirement itself). Others increase — healthcare, travel, hobbies, helping adult children. Most people underestimate the second category.
Once you have a realistic annual spending figure, calculate how much of it is covered by guaranteed income: Social Security, a pension if you have one, rental income, or any other fixed source. The gap between your spending and your guaranteed income is what your investment portfolio needs to cover.
The sustainable withdrawal rate — the percentage of your portfolio you can draw each year without running out of money over a 30-year retirement — has historically been in the 4% to 5% range. A portfolio of $2 million, for example, can support approximately $80,000 to $100,000 in annual withdrawals with a reasonable degree of confidence.
But this isn't a set-it-and-forget-it number. Markets fluctuate. Inflation erodes purchasing power. Healthcare costs tend to rise faster than general inflation. A retirement income plan that doesn't account for these realities isn't a plan — it's wishful thinking.
The honest self-assessment: Can you fund your desired lifestyle from guaranteed income plus a sustainable draw from your portfolio? If the math is tight, the solution isn't necessarily to work longer — it may be to right-size your spending, optimize your Social Security timing, or identify tax efficiencies that free up additional cash flow.
Healthcare is the expense that derails more retirement plans than any other single factor. Yet it remains the most commonly underestimated line item in retirement budgeting.
If you're retiring before age 65, you're retiring before Medicare begins. That gap — between your retirement date and your Medicare eligibility — needs to be funded. Private health insurance for a couple in their late 50s can easily run $2,000 to $3,000 per month or more depending on the plan, the state you live in, and your income level (which affects ACA subsidies). That's $24,000 to $36,000 per year in healthcare costs before you've paid a single medical bill.
Even after Medicare begins at 65, the costs don't stop. Medicare Parts A, B, and D, along with a supplemental Medigap policy, currently run a typical couple roughly $6,000 to $10,000 per year in premiums alone — before any deductibles, copays, or out-of-pocket costs. And those premiums increase with income, thanks to IRMAA surcharges. A couple with combined income above $212,000 in 2026 pays significantly more for the same coverage.
Then there are the costs no one likes to think about: long-term care. The average cost of a private room in a skilled nursing facility now exceeds $100,000 per year in most major markets (much more here in San Diego). Assisted living, in-home care, and memory care are similarly expensive. The probability of needing some form of long-term care during your lifetime is not small — roughly 70% of people over age 65 will require it at some point, typically later in life.
Beyond healthcare, life has a way of presenting unexpected bills. A new roof. A car replacement. An adult child who needs help. A divorce. A parent whose own finances require your support. These aren't hypotheticals — they're the kinds of events that arrive without warning and cost real money. Your retirement plan needs a buffer for the unpredictable.
The honest self-assessment: Does your retirement budget include a realistic healthcare cost estimate that covers both the Medicare gap years and ongoing costs after 65? Have you thought seriously about long-term care — whether through insurance, self-funding, or a hybrid approach? If not, these are the numbers to work through before you retire, not after.
Most retirees draw income from multiple sources: Social Security, a taxable brokerage account, a Traditional IRA, perhaps a Roth IRA, and maybe a pension or rental income. Each of these sources is taxed differently. Social Security can be 0%, 50%, or 85% taxable depending on your total income. Traditional IRA withdrawals are ordinary income. Roth IRA withdrawals are tax-free. Long-term capital gains from a taxable account are taxed at preferential rates. The order in which you draw from these accounts — and in what amounts — can dramatically affect your annual tax bill.
This is where tax bracket management becomes powerful. Many retirees find themselves in a unique position in the years before Required Minimum Distributions (RMDs) begin: their income is relatively low, their tax bracket is lower than it was during their working years, and they have an opportunity to fill that bracket intentionally — through Roth conversions, strategic capital gains harvesting, or simply drawing from tax-deferred accounts before they're forced to.
RMDs, which begin at age 73 or 75 for most people under current law, can significantly change the tax picture. A retiree with a large Traditional IRA who takes no proactive steps may find themselves forced into much higher income in their 70s than they anticipated — with resulting spikes in Medicare premiums, Social Security taxation, and overall tax liability.
The tax tail shouldn't wag the retirement dog — but ignoring taxes entirely leaves real money on the table. The goal is an income plan that funds your lifestyle while keeping your tax burden as low as the law allows.
The honest self-assessment: Do you know which accounts to draw from first, second, and third in retirement — and why? Have you modeled the impact of RMDs on your future tax bracket? Is there a window between now and age 73 where Roth conversions could reduce your long-term tax burden? If these questions feel unfamiliar, they're worth working through with your advisor.
Social Security is one of the most valuable and most misunderstood assets in most people's retirement plan. For a couple who are both entitled to benefits, the lifetime value of Social Security — properly optimized — can easily exceed $1 million. The difference between a good claiming decision and a poor one can be measured in the hundreds of thousands of dollars.
The core tradeoff is simple: claim early and receive a smaller monthly benefit for a longer period of time, or delay and receive a larger monthly benefit for a shorter period of time. Full retirement age for most people is between 66 and 67. Claiming at 62 — the earliest possible date — reduces your benefit by as much as 30%. Delaying to 70 increases your benefit by 8% per year beyond full retirement age, for a total increase of 24% to 32% above your full retirement age benefit.
The breakeven calculation — the age at which the cumulative value of delaying exceeds the cumulative value of claiming early — typically falls in the late 70s for most individuals. If you live past that age, delaying paid off. If you don't, claiming earlier would have been the better financial decision. Since most people in reasonably good health at 62 will live into their 80s, delaying is often the optimal financial choice.
But the decision is never purely financial. If you have significant health concerns, a family history of shorter lifespans, or a compelling need for income now, claiming earlier may make sense. For couples, the calculation is even more complex — survivor benefits, age differences between spouses, and the ability to bridge to age 70 using other assets all factor into the optimal strategy.
The honest self-assessment: Have you modeled different Social Security claiming scenarios — not just the breakeven calculation, but the impact on survivor benefits, Medicare premium calculations, and overall retirement income? Have you thought about how you'll fund living expenses between retirement and your optimal claiming age? Social Security is worth the time it takes to get this right.
This is the question most financial plans don't address — and it may be the one that matters most.
Studies on retirement consistently show that financial security, while necessary, is not sufficient for a fulfilling retirement. Research has found that retirement increases the probability of depression by 40%. That statistic surprises most people. It shouldn't. Work provides more than a paycheck. It provides structure, purpose, social connection, intellectual stimulation, and a sense of identity. When those things disappear without a deliberate plan to replace them, the consequences can be significant — regardless of how well-funded the retirement account is.
The most common mistake we see among soon-to-be retirees is planning obsessively for the financial transition while giving almost no thought to the human one. They know exactly what their withdrawal rate will be on January 1 of their retirement year. They have no idea what they'll do on January 2.
Think about what your days will look like. Where will your sense of purpose come from? Who will you spend your time with? What will you be curious about, learning, building, contributing to? The research on happiness in retirement points consistently to the same factors: strong relationships, engagement with community, meaningful activity (paid or not), physical health, and a sense of purpose that extends beyond oneself.
The people who thrive in retirement typically aren't the ones who stopped doing things — they're the ones who transitioned into doing different things. Volunteer work. Part-time consulting. A second act career in a field they're passionate about. Travel with intention. Grandchildren. Craftsmanship. Service.
And practically speaking: what happens if one spouse is ready to retire and the other isn't? What does your social life look like when you're no longer defined by a professional role? Have you had honest conversations with your partner about what retirement looks like for both of you — not just the financial plan, but the life plan?
The honest self-assessment: If you retired tomorrow, what would your days look like in six months? In two years? In ten? If the answer is vague, that's worth taking seriously — not as a reason to delay, but as an invitation to build a vision for the non-financial side of your retirement before you make the leap.
No single question on this list is more important than the others — they work together. Financial security gives you the freedom to pursue a fulfilling life. Purpose and engagement give you a reason to want to stay healthy. Healthcare planning protects the financial plan. Tax strategy amplifies what you've already saved. Social Security optimization provides a foundation of guaranteed income that reduces the pressure on everything else.
Successful retirements don't happen by accident. They're built — deliberately, over time, with honest answers to hard questions.
At Arcadia Private Wealth, working through these questions with clients — and building a plan that addresses each of them — is exactly what we do every day. If you're approaching retirement and want a clear assessment of where you stand on all five, we'd welcome that conversation.
Disclosure: This article is for informational purposes only and does not constitute personalized tax, legal, or investment advice. Tax rules are subject to change. Please consult a qualified financial advisor and CPA for guidance specific to your situation. Arcadia Private Wealth LLC is a Registered Investment Adviser in the state of California. Advisory services are only offered to clients or prospective clients where we are properly registered or exempt from registration.
Grant Webster, CFP®, TPCP®
Founder, Wealth Advisor