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  • Writer's pictureHannah Boundy, CFA®, CFP®

How Exploring Regret Can Help You Live a Meaningful Legacy

I recently came across George Kinder's three-question framework for building what he refers to as a “life plan.” The questions are basically three variations on: "what would you do if you had a limited amount of time left to live." Of course, the basis of these questions isn't hypothetical for any of us. We all face a finite amount of time on this earth and must answer the question, put more eloquently by the poet Mary Oliver: "What is it you plan to do with your one wild and precious life?" When it comes to financial planning, this question is no less relevant. What are you saving for, and what will you do with your hard-earned wealth when the time comes to spend it?

Perhaps most beneficial about Mr. Kinder's approach is the time frames built into his questions. The first version of the question is broad. It asks you to envision yourself in a position of abundance, with more than enough resources to meet all of your needs. What does a full life look like for you? How do you spend your time? What are your greatest hopes and dreams and how do you fulfill them?

The next question introduces a more finite time frame. It asks you to consider a scenario in which you only have five to ten years to live. Now that there is a more tangible boundary to your time, what becomes most important? The goal of this question is to encourage you to begin prioritizing. You would likely enjoy many things but realistically can't do them all. In that case, exploring which items are most important is essential.

This brings us to Mr. Kinder's final question: individuals are asked to imagine a scenario where they have been given 24 hours to live. There is no time left. What do you regret not doing? Without a doubt, this is a complex and intimate question and one worth giving some thought to. It may seem more straightforward to brush it off and to pronounce an intention to live without regrets, and while that may be an admirable approach in some contexts, it negates the beauty of this exercise.

For most of us, time is not running out so quickly. But because of that, we face no urgency in making our hopes and dreams a reality. What's so valuable about this third question is that it encourages us to self-reflect and uncover what is most valuable to us. For myself, I would regret the time I spent on logistics instead of relationships. This should cause me to pause. What areas of my life are being wasted on administrative tasks instead of time with my family?

Of course, there is a delicate balance to everything. I'm not suggesting that you quit your job and book a worldwide trip tomorrow. Administrative tasks are an unfortunate reality. Bills must be paid and appointments made. But being mindful of what we might regret in the version of life we're currently living invites us to explore an alternative approach to life. One in which we are more active in making what matters most to us a reality.

When it comes to your living legacy, we hope you have the tools you need to embrace the lifestyle and types of activities that are truly meaningful for you. In the past, we've written about how if you don't fly first class, your heirs will. In many ways, this three-question framework is an extension of that idea. If you don't actively engage in building your legacy, it won't materialize on its own. These questions are important and worth spending time on – individually and with those you love.

If you'd like to explore these questions and what they might mean for your living legacy, we would love to sit down with you and have that conversation in our recently remodeled office living room. We have intentionally created a space in our new office for conversations like these, and we would love to host you. Please don’t hesitate to reach out if that’s something that would be of value to you.


“George Kinder Delivers the 3 Questions | What Is Life Planning & How Is It Different?” YouTube, Kinder Institute of Life Planning, 8 Mar. 2022, Accessed 11 Jan. 2023.

Oliver, M. (1992) 'Poem 133: The Summer Day', in New and Selected Poems, 1992. Boston: Beacon Press.


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