The Hidden Key to a Meaningful Life and Legacy: Looking Back to Move Forward
How reflecting on your past can reveal purpose and legacy
By Jean-Luc Bourdon, CPA, PFS
Over a lifetime, Frank had built a successful avocado farm from nothing. Yet when his CPA suggested estate planning, he'd shut down the conversation every time. "My heirs will get plenty," he'd say dismissively. I was given the chance to work with him and offered him a visualization exercise.
"Imagine you're looking down from heaven," I said. "What do you want to see for your family?"
His face lit up. "I want to see them pick avocados."
That simple statement revealed everything he truly valued: hard work, the understanding that wealth takes effort, and the fulfillment of nurturing something meaningful. Passing on money wasn't enough to motivate him. Passing on his values meant everything.
The Three Questions That Define Us
Rabbi Jonathan Sacks once observed that every introspective person must eventually confront three essential questions: Who am I? Why am I here? And how should I live my life?
These questions aren't easy. Our identity constantly changes—parent, spouse, professional, friend, caregiver. We wake up driven by basic needs, switch roles throughout the day, and face conflicting demands from family and work. No wonder finding consistent answers feels impossible.
Yet these questions are fundamental to living a meaningful life. Imagine having clear, convincing, and consistent answers to all three. Life decisions would become easier. Conflicts would resolve more naturally. Our life direction and legacy would be clear.
The Stories That Shape Us
Here's the surprising truth: we are the stories we tell ourselves about ourselves. Your identity and purpose aren't hidden in some deep philosophical exercise—they're woven throughout the stories of your life.
These stories reveal what we consistently value, how we handle challenges, who matters most to us, and what drives our choices. Consider how we talk about someone who made us angry. What boundaries did they cross? What values were violated? What did we expect instead? These parts don’t just shape the story; they also reveal the values we hold deeply.
We might think we're creating our life story as we go, but here's the paradox: it's actually our life story that's creating us.
Dan P. McAdams from Northwestern University, a leading researcher in narrative psychology, puts it this way: "We are all tellers of tales, and we seek to provide our scattered and often confusing experiences with a sense of coherence by arranging the episodes of our lives." This process of weaving our experiences into coherent stories doesn't just help us remember what happened—it shapes who we become.
We all carry these stories within us. The challenge is learning to listen for their deeper meaning.
The Backwards Path to Purpose
Modern society trains us to look forward, set goals, make plans, and pursue our dreams. However, researchers in psychology and aging have discovered that meaning comes from looking back.
Dr. Gene Cohen identified four developmental stages that we go through as we age, each prompting us to reflect on our lives and make sense of our experiences. It’s a psychological need that is not optional.
Without a past, we cannot find meaning in life. For example, small children are unable to contemplate life's purpose. Meaning develops gradually, requiring the accumulation of experiences, relationships, and choices over time.
The Mixed Bag of Life
When we look back, what do we find? A mixed bag. Some goals we achieved, others we didn't. Some dreams came true, others remained wishes. Painful events we never wanted happened anyway. Unexpected joys surprised us.
The key isn't to judge this mixed bag but to make sense of it. To find the threads that connect disparate experiences into a coherent story. To identify what has been most valuable, most meaningful, most truly you.
This process—what psychologists call "meaning-making"—transforms random events into a purposeful narrative. It's like weaving separate threads into a tapestry, where each thread gains significance from its place in the larger pattern.
Beyond the Campfire
In traditional societies, elders naturally shared their stories around campfires. Communities had established ways to pass wisdom from one generation to the next. Today, we often isolate our elders, losing these natural opportunities for meaning-making.
But the need remains. Therefore, a process needs to be facilitated. Research shows that people who engage in life review—the process of reflecting on and making sense of their experiences—approach aging and even death with greater peace. It is so powerful that life review processes are now commonplace in hospice and palliative care settings.
The Three Types of Legacy
Writer David Solie identifies three types of legacy most people create:
Default Legacy: The "do nothing" approach where others piece together your story from facts and figures after you're gone. Think of genealogy websites—lots of data, little meaning.
Political Legacy: The rushed decisions made in lawyers' offices under time pressure. Expected answers to standard questions that may not reflect what truly matters to you.
Organic Legacy: The kind that emerges from genuine reflection on what has been most meaningful in your life. This is the legacy that captures the essence of who you are and what you've learned.
Your Story, Your Choice
You don't need a professional coach or an expensive program to begin this process. Start by simply listening to your own stories. When you find yourself telling the same story repeatedly, ask yourself: Why does this story matter to me? What does it reveal about what I value?
Pay attention to the moments that still make you proud, the decisions that defined you, the relationships that shaped you. Notice the values that appear again and again in your important stories.
Consider creating opportunities to share these stories with family members, friends, or even through writing. The act of telling meaningful stories to engaged listeners helps refine and clarify their significance.
The Hope in Looking Back
Dr. Haesun Moon, who teaches coaching at the University of Toronto, describes in her book “Coaching A to Z” how a terminally ill patient faced death with hope. This initially seemed like a contradiction to me, but it made sense once I understood the role of a well-defined legacy.
When we can examine the mixed bag of our lives and identify what has been most valuable—our growth, our relationships, and our contributions—and when we can find ways to extend those values beyond our lifetime, we create something larger than ourselves.
This is the true power of legacy: capturing the best of who we are and giving it momentum to endure beyond our lifetime.
The Path Forward
Meaning is found by turning back and evaluating the significance of our lives. When we pursue that meaning during our lifetime, it becomes our purpose. And when we find vehicles to extend that purpose beyond our lifetime, we create a true legacy.
The future will come as it always has. But the wisdom to navigate it meaningfully comes from understanding where we've been, what we've learned, and what we want to pass on.
Your story is still being written. But the chapters you've already lived contain the keys to making the remaining ones—and the legacy you leave—as meaningful as possible.
Like the avocado rancher, your most important legacy might not be what you leave behind, but what you inspire others to pick up and carry forward.
Disclaimer: The views expressed in this article are those of the author and do not necessarily reflect the views of any firm or organization. This content is provided for general informational and educational purposes only and should not be construed as personalized financial, tax, accounting, or investment advice. Although the author is a CPA and holds the PFS credential, no professional services are being offered through this article. Readers should consult their own qualified advisors before making decisions based on this information. The content may include information from sources believed to be reliable but is not guaranteed and may be subject to change without notice.
Copyright: © 2025 Jean-Luc Bourdon, Original text, structure, organization, and editorial revisions created by the human author. The author used AI as a drafting tool, but exercised creative control by rewriting, restructuring, and contributing original analysis, tone, and expression. Disclosure in accordance with U.S. Copyright Office guidance on AI-assisted works.