Over twenty years of sitting across from people who are finally getting serious about their later years, I keep noticing the same thing. It doesn’t matter if someone walks in with a seven-figure portfolio or something far more modest. The worry in their voice almost always circles back to one question—and they usually wish they’d asked it ten years earlier.
Most clients show up thinking the big question is, “Do I have enough?” That one gets plenty of airtime. Calculators, spreadsheets, Sunday supplements—they’re all built around it. But the number on a statement rarely answers what people are really trying to understand. The deeper question slips by until the runway gets uncomfortably short.
The Question That Surfaces Too Late
I’ve come to call it the “what now” question, though nobody ever says it in those exact words. A client might be six months from leaving a thirty-year career. The financial plan checks out, the paperwork is in order, the pension election forms are ready to sign. Then they lean forward and say something like, “I keep waking up at three in the morning. I’m not worried about running out of money. I’m worried I won’t know what to do with myself.”
That’s the real one. It’s not about asset allocation or withdrawal rates. It’s about purpose, structure, and identity when the job title disappears. And it’s a question that benefits from years of thought, not weeks.
Why the Question Gets Pushed Aside
There are sensible reasons people avoid this territory. For two or three decades, the priority has been accumulation. Pay down the mortgage. Fund the college accounts. Max out the retirement plan. The checklist is long, and ticking boxes feels productive. Thinking about how you’ll spend a Tuesday morning when you’re sixty-seven feels fuzzy next to this quarter’s bonus or a child’s tuition bill.
There’s also a quiet fear that asking the question will invite uncomfortable answers. If your work has been the scaffolding for your social life and daily rhythm, imagining life without it can feel like staring into a void. It’s easier to tell yourself you’ll sort it out once you get there.
But the clients who have the smoothest transitions are the ones who started wrestling with this years before their last day. They didn’t need a perfect blueprint. They just needed to stop treating the question as an afterthought.
The Financial Plan Is Only Half the Picture
I have a responsibility to make sure the numbers work. That’s non-negotiable. A retirement income plan has to account for longevity, inflation, sequence-of-returns risk, tax efficiency, and a dozen other variables. But a spreadsheet can’t tell you whether you’ll feel useful on a Wednesday afternoon.
When I sit with a client who is five or ten years out, we spend time on the technical side. Then I ask something that sometimes catches people off guard: “Tell me about a typical day, two years after you stop working.”
The answers vary. Some people describe a blur of travel, hobbies, and grandchild time. Others go quiet. That silence tells me more than any monologue could. It means we have work to do that has nothing to do with basis points or required minimum distributions.
I’m not a therapist, and I don’t pretend to be one. But I’ve watched enough retirements unfold to know that the financial piece and the life-design piece aren’t separate conversations. They feed each other. A person who has a clear sense of what they’re retiring to—not just what they’re retiring from—tends to make steadier financial decisions. They’re less likely to panic during a market dip because their sense of security isn’t anchored solely to a brokerage balance.
The Cost of Waiting
When the question gets delayed until the final months, the options narrow. Someone who hasn’t cultivated relationships outside of work may find their social circle shrinks overnight. Hobbies that were always deferred start to feel hollow without the contrast of a busy week. Marriages that functioned well with built-in time apart can hit friction when the calendar suddenly empties.
I think of a client—let’s call him Robert—who retired at sixty-four with a portfolio that was more than adequate. He’d done everything right on paper. He’d also spent forty years in a demanding profession that left little room for anything else. Six months in, he told me he felt like he was “waiting for something to happen.” His golf game improved, but his mood didn’t. It took him two years and some false starts to build a rhythm that felt meaningful. He said later, “I wish someone had told me to start practicing retirement before I actually retired.”
That phrase stuck with me. Practice retirement. Not as a dress rehearsal where you live on a reduced budget for a month. Practice in the sense of deliberately building the non-financial infrastructure you’ll need: the relationships, the pursuits, the causes, the daily rituals.
What the Question Looks Like When Asked Early
Clients who begin exploring this in their mid-fifties have a different energy. They come to meetings with observations, not just anxieties. They’ve tried volunteering on Saturday mornings and discovered they love mentoring. They’ve taken a class in something completely unrelated to their career. They’ve had honest conversations with their spouse about how much togetherness feels right and how much feels suffocating.
These aren’t grand gestures. They’re small experiments that accumulate into self-knowledge. And they have a practical financial benefit: they reduce the risk of making a rushed, expensive decision—like relocating to a dream destination that turns out to be a poor fit, or sinking a lump sum into a business venture that was really just a search for purpose.
This isn’t fluffy advice. It’s risk management of a different kind. The risk of a well-funded but hollow retirement is real, and it can undo the careful work of decades. I’ve seen it happen.
Bringing It Into the Planning Process
If you work with an adviser, you should expect more than a monologue about Monte Carlo simulations. A good planning relationship leaves room for the conversation that has no ticker symbol. That doesn’t mean your adviser needs to be your life coach. It means they should be willing to ask the question you might be avoiding, and to connect it back to the financial decisions you’re making today.
If you’re navigating this on your own, the discipline is the same. Schedule time to think about the non-financial side with the same seriousness you give to rebalancing your portfolio. Write down what a satisfying week might look like. Talk to people who are ten years into retirement and ask what they wish they’d known. Pay attention to the parts of your current life that give you energy, because those are clues about what you’ll want more of later.
One resource I’ve found useful in these conversations is a piece I wrote a while back, The Question You Should Be Asking Years Before You Retire. It walks through a framework for thinking about identity and purpose well ahead of the transition, and it pairs naturally with the income planning work we do together.
The Fiduciary Angle
I work under a fiduciary standard, which means I’m obligated to act in my clients’ best interests. That obligation doesn’t stop at the edge of the brokerage account. If I see a client heading toward a retirement that is financially sound but personally adrift, I haven’t done my job. The best interest includes the whole person—their relationships, their health, their sense of contribution.
This isn’t a novel idea, but it’s easy to lose in an industry that often reduces retirement to a single number. I push back against that reduction because I’ve seen the consequences. A retirement that looks perfect on a spreadsheet can feel empty in real life. A retirement that looks modest on paper can be deeply rich when it’s built around the right things.
Practical Steps You Can Take Now
If you’re still working and retirement is on the horizon, here are a few concrete moves that cost nothing but attention:
Start a “retirement practice” journal. Once a month, jot down what you did over the weekend that felt meaningful. Patterns will emerge. Those patterns are data.
Talk to your partner early. Don’t assume you have the same vision. Ask things like, “What does a good weekday look like to you?” and “How much solo time do you think you’ll need?” Differences are normal. Discovering them late is the problem.
Test-drive a pursuit. If you think you want to consult part-time, try doing a small project on the side while you’re still employed. If you picture yourself volunteering, commit to a regular shift for six months and see how it feels. Small stakes now prevent big regrets later.
Build relationships outside your industry. Join a group, take a class, reconnect with old friends who don’t share your professional background. The broader your social base, the less your identity will depend on a job title.
Revisit your financial plan with purpose in mind. When you model different spending paths, don’t just stress-test for market crashes. Consider what your spending looks like if you decide to work part-time in a lower-paying but fulfilling role. That scenario might change your required portfolio size in a way that opens up options.
Frequently Asked Questions
Why do people avoid thinking about life after work until it’s almost here?
Most of us are busy with careers, family, and the demands of daily life. Thinking about retirement feels like a distant luxury. There’s also an emotional barrier: contemplating a major identity shift can be unsettling, so it gets postponed. The irony is that the earlier you engage with the question, the less unsettling it becomes.
How does the “what now” question affect financial decision-making?
When someone has no clear picture of their post-career life, they tend to make financial choices based on fear or vague assumptions. They may oversave and live unnecessarily frugally, or they may chase risky investments in search of a sense of direction. A well-defined purpose anchors financial decisions and reduces the likelihood of reactive moves during market volatility.
Can a financial adviser really help with the non-financial side of retirement?
A fiduciary adviser should at least raise the question and connect it to the planning work. While an adviser isn’t a therapist or life coach, they see patterns across many retirements and can point clients toward resources and frameworks that have helped others. The best planning relationships make space for the whole picture, not just the numbers.
What’s the single most important thing someone can do ten years before retiring?
Begin deliberately investing in the non-financial side of life. That means nurturing relationships, exploring interests, and building routines that don’t depend on a job. Think of it as diversifying your identity. Just as you diversify a portfolio to manage risk, you diversify your sources of meaning to manage the risk of a hollow retirement.
The question I wish more clients would ask early isn’t complicated. It’s simply, “Who will I be when the work stops?” You don’t need a complete answer. You just need to start asking it while there’s still plenty of time to shape the answer.