I Thought My Retirement Was Set — Until I Answered These 3 Questions

A simple wooden block with the number 3 on it.

One of my goals in life is to outlive my father. He passed away just a few days shy of his 48th birthday.

It reshaped the way I look at time. When I was younger, I thought anyone who reached their 50s was old. Now that I’m here, slouching toward midlife, I see how much my father missed: the birth of his grandchildren, graduations and marriages. He never saw my writing published. I know now that he really did die too young.

Life events like these put things into perspective — what’s possible, what you wish for and what really matters.

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The three questions approach

Traditional retirement planning generally considers questions such as "Have I saved enough money?" Or "How will I afford health insurance and travel?" Those are legitimate retirement concerns, but they tend to focus too narrowly on financial issues, often before we've even explored what kind of retirement we truly want. That's why George Kinder developed a new approach to financial planning.

Kinder, founder of the Kinder Institute of Life Planning, pioneered the "life planning" approach, which centers financial decisions around a person’s deepest values, goals and sense of purpose. Advisers who complete the Institute’s training earn the Registered Life Planner (RLP®) designation.

Kinder may be best known, however, for three deceptively simple, yet powerful, questions designed to move people beyond thinking only about money and toward what truly matters in their lives.

Over the years, I’ve heard many financial advisers reference these questions when helping clients set goals. Scott Frank, a CFP®, RLP® and founder of Stone Steps Financial, says the questions help people "prioritize the elements of life that are essential for them to flourish."

Yet I had never given them much thought myself. I’ve often found it difficult to think deeply about my future life — and I’m not the only one. Social psychologists find that people often fail to make long-term positive choices because they feel emotionally disconnected from their future selves.

But as I approach the 20-year mark since my father passed away, I’m reminded how quickly time moves and how important it is to think about the time I may have left. So I decided to work through these questions myself (and I encourage others to do the same).

I found the exercise highlights the central challenge of life planning: making the most of your life with limited resources. These questions can help point you in the right direction. As J. Robert Oppenheimer put it, "To be able to ask a good question is already half of the solution of a problem."

Here’s what I discovered about who I am today and who I hope to become.

Question 1: Design your life

"Imagine you are financially secure. You have enough money to take care of your needs, now and in the future. How would you live your life? What would you do with the money? Would you change anything? Let yourself dream."

"It’s the old ‘if you won the lottery’ question," says Lisa Kirchenbauer, who has been an RLP® since 2005 and is a founding partner of Omega Wealth Management.

Without money as a constraint, this exercise opens your thinking and helps uncover your deeper values and desires.

In my mind, after waking before the sun as usual, I step outside into the cool air and see the same old truck. There is no Ferrari, no long driveway leading to a private gate, no butler greeting me "good morning." I wouldn’t want luxurious things; I would want more experiences. Research consistently shows that experiences bring greater happiness. I would travel more, try new activities and fund adventures with friends and family.

Most of us rarely spend time reflecting on our values, so this question can be surprisingly revealing. Kirchenbauer says she has seen "couples look at each other and say, 'I didn’t know you wanted to do that.'"

As I reflect further, the question nudges my conscience. I see how much of my time is spent chasing money, status and success — building security for the future — yet something is missing: service. I feel an urge to volunteer and contribute more meaningfully.

In the end, my answers come down to adventure, relationships and service — priorities that daily demands can easily drown out.

As Frank notes, "Everyone’s answers are different. Some long to dedicate time and energy to a new career because they feel the current one is soul-sucking; others want to start a family; while others want more creativity or spirituality back in their lives."

Question 2: Remember, you’re living on borrowed time

"Now imagine your doctor tells you that you have five to ten years left to live. You won’t feel sick, but you will have no notice of the moment of death. What will you do in the time you have remaining? Will you change your life? How will you live out your remaining years?"

This question introduces mortality into the equation. It sharpens your priorities. Frank says the goal is to "feel the weight of limited time and feel what matters most."

The writer George Saunders once said that as we grow older, "everything in the universe is giving you the memo that you’re temporary." This question forces us to confront that reality.

If I had that time horizon, I would attempt to finally write a novel. Yet I would also struggle to balance time spent writing with time with my children. The reality, of course, is that they’d have their own lives to live. So, the challenge is using time intentionally while we still share it.

If possible, I would scale back work — becoming more efficient, working fewer hours, perhaps transitioning to part-time — while pursuing more things that give me joy, whether it’s learning to paint or meditate. I would also consider sleeping and complaining less while hugging and laughing more.

Five to ten years is both short and long. As Bill Gates famously said, "Most people overestimate what they can do in one year and underestimate what they can do in ten years."

Kirchenbauer notes that this type of planning "is not about the money — it’s about time, relationships, creativity, spirituality or perhaps a special place."

This perspective also leads to what illustrator and writer Tim Urban calls "depressing math," calculating how many times we may realistically experience the moments we value most. My grandmother is in her 90s and I see her once a year; simple math suggests only a handful of visits remain. Sure, it’s not a pleasant thought, but it’s a powerful motivation to prioritize.

Question 3: Seizing the day

"Finally, imagine your doctor tells you that you have just 24 hours left to live. Notice what feelings arise as you confront your mortality. What did you miss? Who did you not get to be? What did you not get to do?"

This question hits hardest, forcing reflection on regrets, identity and meaning. As Frank says, "It cuts to the core — what is the untapped potential of your life?"

It echoes the Stoic concept of memento mori, the contemplation of your own death. In fact, research suggests that contemplating mortality can motivate positive life changes and even increase happiness.

Steve Jobs captured this idea in a 2005 commencement speech: "Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life. Because almost everything — all external expectations, all pride, all fear of embarrassment or failure — these things just fall away in the face of death, leaving only what is truly important."

On my computer sit unfinished books. On my desk are maps of places I’ve dreamed of visiting. And on my bookshelf, there is a picture of my father and me that reminds me of all the memories we didn’t get to share.

If I were to die tomorrow, I would ask whether I had been the best father I could be. I’d wonder what my children will remember about me. Will they live better lives because of what I did, or inherit traits I wish I had changed?

Experiences like these remind us how easily regrets form when life’s pressures crowd out what matters most. As Kirchenbauer notes, it is not uncommon for people to share with her regrets about having worked so long and hard.

The reality is that we are all moving toward the same endpoint, but until then, we are still living and still have the chance to seize the day. As Seneca wrote, "We do not suddenly fall on death, but advance toward it by slight degrees. We die every day."

Where do you go from here?

I came away from these questions with a different perspective on money and planning for the future. It’s not all about hitting a certain number or chasing the highest possible return.

That’s the beauty of these questions. As Kirchenbauer says, they help people "refocus more broadly on living more intentionally going forward."

Ultimately, I now see even more clearly that retirement is something I need to enter with intention, rather than something to simply stumble into.

As Frank puts it, "Retirement is simply a frame for a phase of life. The three questions help you clarify what you really want in that stage."

But maybe that’s true for any stage. As the professor Randy Pausch wrote in The Last Lecture, "The key question to keep asking is, 'Are you spending your time on the right things?' Because time is all you have."

Jacob Schroeder is a financial writer covering topics related to personal finance and retirement. Over the course of a decade in the financial services industry, he has written materials to educate people on saving, investing and life in retirement.

With the love of telling a good story, his work has appeared in publications including Yahoo Finance, Wealth Management magazine, The Detroit News and, as a short-story writer, various literary journals. He is also the creator of the finance newsletter The Root of All (https://rootofall.substack.com/), exploring how money shapes the world around us. Drawing from research and personal experiences, he relates lessons that readers can apply to make more informed financial decisions and live happier lives.