Advisors
The short answer: Replace "What age do you want to retire?" with questions about the life clients want and the habits they have today. Derek Coburn, author of Let's Retire Retirement, argues that clients who find work they don't hate rarely want to stop at 65, and that planning for a longer working life frees up money and time for health, relationships and family now.
Most retirement conversations start with one question: what age do you want to stop working? On the Visionary Advisor podcast, Alex Kirby, founder of Total Family, talks with a guest who thinks that's the wrong question.
Derek has advised wealthy families since 1998. He sold his practice to private equity in 2019, co-founded the business community CADRE and wrote Let's Retire Retirement. The book started with his father, who developed dementia at 62 and lived with it for about nine years. Derek began writing believing his dad had missed out on retirement. Then, going through family photos around the funeral, he saw how many trips his father had taken and how much he'd enjoyed along the way. His dad had never really been heading for retirement and he hadn't waited for it to enjoy his life. As Derek puts it, "My dad probably was not going to retire even though he talked about it."
Key takeaways
Ask "whether" before "when." A default of 65 drives decades of decisions most clients never really made.
Extra working years change the math dramatically. In Derek's example, retiring at 75 instead of 65 cuts monthly savings by 96%. Plan for an early exit too.
Test dreams against current habits. What clients practice now is what they'll keep.
Widen the plan beyond financial capital. Health, relationships and shared experiences are investments too.
Legacy is lived. Values defined now shape today's choices and what the next generation inherits.
Why is "What age do you want to retire?" the wrong first question?
Because most clients haven't really chosen an age, and the number they're handed shapes everything that follows. Clients rarely walk in having thought hard about it, Derek says, so the advisor suggests 65 "because that's the age that everyone else picks," and that one assumption sets savings targets, sacrifices and expectations for decades.
The number isn't sacred. Derek traces 65 to Germany's first state pension, though Germany's 1889 program actually set the age at 70 and only lowered it to 65 in 1916. The US chose 65 in 1935 for what the Social Security Administration calls "primarily pragmatic" reasons. It was an administrative choice, not a law of nature.
Derek's bigger point is about purpose.
"If you find work that you don't hate, if you find work that isn't sucking your soul, you're probably not going to want to stop at 65," he says.
He cites psychologist Barbara Fredrickson, whose 2013 study of 80 adults linked purpose-driven well-being to a healthier immune gene profile and pleasure-driven well-being to the opposite. It's a small study that didn't track illness or deaths, and its analysis has been challenged, so treat it as suggestive. Alex has seen the human version: when people stop working without a plan for how they'll contribute, "that's when you see rapid deterioration."
What this means for you: Ask whether clients want to retire before you ask when. Alex summed up Derek's advice this way: swap "When do you want to retire?" for "Do you even want to retire?" and then listen.
How much does working longer change a client's savings target?
More than most people expect, advisors included. In Derek's "Tale of Two Tonys," a 45-year-old earning $150,000 with $150,000 saved needs to put away about $2,400 a month, around 20% of his income, to stop at 65. Move the date to 70, and it falls to about $600 a month. Move it to 75, and it falls to about $110, a drop of 96%.
More years of contributions, more years of compounding, and fewer years of withdrawals all pull the same way. "Even financial advisors don't get this math off the top of their head," Derek says. For many clients the result is relief: the pressure to hit a number by a certain age is gone, so they can enjoy more of life now.
Working longer isn't always a choice, though. In the Employee Benefit Research Institute's 2024 Retirement Confidence Survey, workers expected to retire at a median age of 65, but retirees actually stopped at 62, and 49% retired earlier than planned, often because of health problems or changes at their company.
What this means for you: Model 65, 70 and 75 side by side so clients see the trade-off, then stress-test the plan for an earlier exit.
Share with your clients: Ask your advisor to show your plan at three retirement ages, and notice how each one changes what you can spend on your life today.
What questions reveal what clients actually want from retirement?
Questions that test the dream against today's habits. When couples told Derek they wanted to travel the world in retirement, he didn't ask about destinations or budgets. He asked:
"When was the last time the two of you went out on a date?"
Most of the time, he says, they didn't have a good answer.
He asks golfers who plan to play five days a week but haven't played in four years what makes them think they'll have "the physical ability, the friendships, the relationships, the skills" 20 years from now. The more clients travel, play and date their spouse today, the more likely they'll still be doing it in their 70s, "because we're exercising those muscles, we're exercising those relationships."
What this means for you: For every retirement goal a client names, ask how often they do it now. The gap between the dream and the calendar is where the real planning starts.
Share with your clients: Pick one thing on your retirement list and do it this quarter.
Why should advisors talk about health, relationships and time, not just money?
Because a plan can be financially sound while the client's life isn't. "We have an opportunity in our role as a financial advisor when we're talking with people to do things that meaningfully improve the lives of our clients," Derek says. Running numbers for a client who sleeps five hours a night, or a couple disconnected from their children, does them a disservice.
Alex uses Total Family's five forms of family capital to widen the lens. Health is human capital, so a gym, a specialist or, in Derek's words, "a $200 pillow" is an investment. So are dinners with adult children and family trips that build a shared culture. As Alex says, "it's really expensive to be in bad health as well."
Time is the scarcest asset. Tim Urban's essay "The Tail End" estimates he'd used up 93% of his in-person time with his parents by the end of high school. Derek calculated about 1,500 hours left with his eldest son at home, so most afternoons he stops work by 3 o'clock. And in the Harvard Study of Adult Development, the people most satisfied in their relationships at 50 were the healthiest at 80.
This approach has a cost. Derek estimates he left $5 million to $10 million on the table when he sold his firm, after 20 years of telling clients to buy the vacation home rather than add to their accounts. It also gave him relationships that have lasted. Alex puts the question bluntly:
"Are you really being a fiduciary if you have these ideas in your head, but you're still telling people to save, save, save, save, save, and you're getting paid on AUM?"
Derek doesn't blame advisors who avoid this. "These are hard conversations to have," he says. But few clients have anyone else to talk it through with, so the advisor is often "one of the only people that they have in their lives who can challenge them."
What this means for you: Give health, relationships and experiences a line in the plan. When a client says a relationship is strained, ask how they're investing in it.
Where does legacy fit if clients should be living for now?
In how they live now. This was the one point where Alex and Derek disagreed. When Alex asked Derek to make legacy planning part of the core financial plan, Derek pushed back: "I think that legacy planning is more of a luxury," especially for clients who are tired, stressed and struggling at home. His message is that "right here, right now can be amazing if you want it to be."
Yet Derek's own legacy came from exactly that kind of living. His father turned down a partnership at a big Baltimore accounting firm to work from home in the mid-1980s and was "at all my games and all my events and all my big moments." Derek now models the same for his boys.
Alex's answer is to start with values:
"Most people that we come across aren't walking around with a set of defined values. Once you do that, that is a very helpful step prior to all of this work around your financial plan or your estate plan."
Letters and family history then show children that a parent "didn't just have it figured out."
What this means for you: Start with values, not legacy documents. Values give clients a filter for every spending, saving and working decision, which is how a lived legacy gets built.
How do you bring this into your practice?
Start small and practice it yourself.
Change the first question. Ask whether the client wants to stop working at all before you ask when.
Test goals against today. For travel, golf or family time, ask, "How often do you do that now?"
Model three ages and an early exit. Show savings at 65, 70 and 75, then plan for work ending sooner.
Budget beyond the portfolio. Give health, relationships and experiences their own lines, starting with values using Total Family's Vision tools.
Lead by example. Derek asks: "we're telling our clients to do this, but is this something that we actually want to do for ourselves?" Total Family treats July as a quiet month, telling clients in January and reminding them at Memorial Day. It's one answer to a wider problem: Pew Research Center found that 46% of US workers with paid time off take less than they're offered.
Frequently asked questions
Should financial advisors stop asking clients what age they want to retire?
Not entirely, but it shouldn't come first. Ask what the client wants their life to look like and whether they want to stop working at all. The retirement age then becomes an output of the plan, not an assumption.
Is working longer a realistic retirement plan?
For many clients, yes, especially those who enjoy their work. But nearly half of retirees in EBRI's 2024 survey stopped earlier than planned, so include a scenario for an earlier exit.
Listen to the Full Episode
The full conversation with Derek Coburn is available now on Apple Podcasts, Spotify, and YouTube.
If this episode gave you a new way to think about retirement conversations with your clients, subscribe to Visionary Advisor and share it with another advisor who wants to help families do legacy better.
