Remember those ING commercials from the early 2000s in which people walked around with a giant hologram of their projected retirement number floating over their head? The ads were memorable because they distilled retirement planning to one figure: the amount of capital someone needs to maintain their lifestyle in the post-working years.
Of course, there’s a lot more to retirement math than estimating a client’s “number.” It requires us to think in multiple dimensions and find a path that makes sense for each client. Two clients of the same age and net worth might need very different strategies depending on where they live, how active they are and their risk tolerance. Three clients from the same metro area with the same net worth—one a baby boomer, one Gen Z, one millennial—will need three very different conversations.
Still, I’ve found three questions useful across nearly every long-range retirement conversation, regardless of age or circumstance:
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What is your number—the capital you need at retirement?
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How much more do you need to save to reach that number?
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What’s the best way to invest to maximize your odds of getting there?
“What’s your number?” is a great opener. Most clients haven’t thought hard about it. They know they need to save, and they’re diligently contributing to a 401(k), maybe an IRA or a Roth IRA. But unless they’ve inherited money or had a major liquidity event, they likely won’t have meaningful non-qualified assets until much closer to retirement. Even so, “What’s your number?” is a meaningful way to kick off the “how much is enough?” conversation.
These three questions are hard to answer because they lack universal formulas—they depend on unpredictable human variables rather than hard facts. Advisors leaning solely on financial projections that shift with every life change will struggle to keep up. As advisors, our real job is to manage expectations and apply judgment to help clients see risks and opportunities. “What’s your number?” is simply the starting point.
1. What Is Your Number? (Your Target Net Worth)
There’s no one-size-fits-all magic number. The answer hinges on lifestyle goals, healthcare costs, risk tolerance, longevity, and inflation—plus how well a client adapts to a new identity as a “retiree” rather than a business owner, CEO or family provider.
Problem: People rarely know what they’ll actually spend in retirement. Spending shifts across the go-go, slow-go and no-go years, and you also have to account for potential long-term care needs—dementia, stroke, cardiac or respiratory issues.
Reality: You can generate a rough number by multiplying expected expenses using Bengen’s 4% rule, but that target shifts dramatically with unexpected medical costs, heavy travel plans or above-average inflation. Someone earning $150,000 today at age 50 might need roughly $225,000 in purchasing power by 75—but their health, Social Security benefits and other income sources will move that number considerably in either direction.
2. How Much Do You Need to Save?
Many advisors hesitate to name a flat savings rate (say, 10% of pay) because income and expenses fluctuate, and family obligations—kids, aging parents—complicate things further. I find it more useful to anchor a target number first, then work backward to the desired savings rate. This naturally opens up conversations about inheritance, gifting, and estate planning.
Problem: Life isn’t linear. Job changes, home purchases, market swings and shifting tax brackets aren’t predictable and call for dynamic budgeting, not a fixed formula. Contributions and growth don’t move in a straight line either, so it’s important to track progress against the original benchmark.
Reality: Rules of thumb—like “10x your income by age 67” or “8x by age 60”—are only a rough starting point. Depending on age, some clients simply won’t have enough time to hit their number without seriously disrupting their current lifestyle. In those cases, the conversation shifts to other levers that can offset a shortfall in savings, which leads to the third question.
3. “What Is the Best Way to Invest for the Highest Probability of Success?”
There’s no universal answer here either, since every advisor has a different philosophy. What matters is being able to explain clearly and confidently why your approach works. Every client has an inflection point on the efficient frontier. That’s where the highest return they could theoretically achieve with their assets is balanced against their psychological tolerance for volatility and loss.
Problem: In my experience, there are two types of investors: those who believe they (or an algorithm) can outperform the market (gamblers), and those who want a predictable, consistent methodology (investors).
Reality: You can tell the first type, the gamblers, that they can chase the market or let the market lift them. Either way, you need to be able to articulate exactly why you’re the right answer to question three—because if you can’t, artificial intelligence increasingly will. That’s the challenge every advisor will face in the coming years. The second type of client, the investor, wants someone who understands long-term strategy, isn’t chasing fads, and takes the time to genuinely listen. Otherwise, they can get the basics from a retail brokerage or an AI chatbot.
Before Asking the Big Three
Before diving into those three questions, make sure you understand these foundational ones:
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What does money mean to you? Building from advisor coach Bill Bachrach’s classic conversation starter question: “What’s important about money to you?” when you ask clients what money means, it’s a powerful open-ended question. The answers reveal a client’s values—stewardship, generosity, freedom, prestige and security. You can’t help them answer “the three questions” without understanding what money represents to them emotionally.
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What were your earliest memories of money? Research shows that people’s relationship with money is heavily shaped by the messages they absorbed growing up—scarcity, conflict, Depression-era caution, or comfortable abundance. Even the advice advisors give is often colored by their own experiences with money at an early age.
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What are your biggest money fears? Most financial anxiety isn’t really about inflation or interest rates—it’s about catastrophic scenarios: a market crash, job loss or realizing too late one didn’t save enough. That underlying anxiety drives poor decisions, or worse, paralysis. As we know, the biggest threat to investment returns isn’t the investment itself—it’s client behavior during volatile markets. Surfacing that anxiety early can make a real difference.
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How much do you consider taxes in your investing? Are tax brackets likely to rise or fall in retirement? Taxes typically take a bigger bite out of equity returns than fixed income, and most active funds lose roughly 1% a year to taxes. Helping clients think through tax-location strategies or tax-managed products—and developing a clear philosophy around taxes, as they might around ESG investing—can meaningfully boost net returns.
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How do you feel about leaving an inheritance? Some clients want to pass on a business or significant assets. Others worry that a large inheritance will diminish their children’s motivation. Some plan to spend their last dollar on their last day, leaving little to heirs or charity. Knowing where a client falls on this spectrum is essential to building a plan around their actual goals — and it starts with being a good listener and factfinder.
Conclusion
We tend to equate “smart” with intelligence, but in the age of AI, that needs to be rethought. Knowledge is now instantly available to anyone. Being smart is knowing what to do with that knowledge; wisdom is knowing how to do right by the people in front of you. As advisors, intelligence alone isn’t enough—clients want wisdom, and wisdom comes only from experience.
