Perspective: Legacy Lessons from Legends

January 22, 2025 | G. Derek Henderson


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“The future is uncertain, and the end is always near.” - Jim Morrison

Good Mornin’

Well…it’s the beginning of December, and the snow has arrived here in Ontario, time to start planning for the holiday season, and the inevitable and exciting new year ahead.

Other than the changing of the seasons, there are a few things that we can know for sure during our journey in life, and ironically, one of these things is that, eventually, our lives will end. While we don't know anything for sure about what happens before we are born or after we die, death marks an unavoidable destination in the path of every human being, which can either be felt as a certainty we can embrace or a looming threat, depending on how you look at it.

The phrase “memento mori” is Latin for “remember you must die.” It reflects on the impermanence of life and is a constant reminder not to take your time on earth for granted and not to worry about things beyond your control.

Often perceived as somber, "memento mori" is an invitation to appreciate the everchanging and fleeting nature of life. The phrase translates not merely to "remember that you will die," but more accurately, "remember that you must die"—a subtle yet vital distinction that emphasizes the need for us to be thoughtful about, and preparing for, the eventual end.

Legacy Lessons from Legends

Jim Morrison, James Dean, and John F. Kennedy have little in common besides their historical iconic status, and the fact that throughout various stages of my life, I have delved into the stories of each of these remarkable figures. While their paths were uniquely distinct, each left an indelible mark on history, encapsulating a blend of inspiration and tragedy—tales rich with lessons that captivate those seeking them. They exemplify courage, curiosity, charisma, creativity, and leadership—all attributes from which we can draw insights about legacy planning.

Legacy Planning intertwines two well-known human discomforts: confronting a significant life event for the first time and contemplating our mortality.

A 2022 report from RBC Royal Trust and The National Institute on Ageing revealed that 91% of Canadians believe "Wills are a critical part of an estate plan." Yet, astonishingly, less than 48% have created one. Why this discrepancy?

JFK once proclaimed that “change is the law of life. And those who look only to the past or present will surely miss the future.” Contemplating what happens after one’s death is indeed daunting, and it's not uncommon to feel fear, uncertainty, and perfectionism, which can lead to planning paralysis. Understandably, discussing such matters can feel as vulnerable as Jack Kennedy riding in a convertible through a Dallas parade. Many clients face psychological barriers; some believe themselves too young to begin planning for wealth transfer, while others are unsure of where to start. Cognitive biases often contribute to procrastination, such as present bias (prioritizing immediate gratification over future needs) and loss aversion (avoiding choices that might lead to loss).

Legacy planning is a profound act of selflessness, ensuring that your loved ones experience a seamless transition, free from conflict, confusion, or resentment that could last a lifetime. Wealth transfer can be a flashpoint for unresolved family disputes, leading to emotional turmoil and financial costs. This complexity increases when considering assets that hold value beyond mere dollars and cents, such as a family business, a cottage, or an art collection. Establishing a tailored plan can help mitigate familial discord, and starting early can make a substantial difference.

What better way to understand the importance of planning but looking back in history to see if we can gather some lessons from legends….

The Will of the Lizard King

Despite The Doors' short career span—active from 1965 to 1973—Jim Morrison became a legend in his own right, passing away at just 27 years old on July 3, 1971. Many might assume that a wild and unpredictable rocker would not draft a will, but Morrison did actually take that important step. His turbulent relationship with his parents fueled his desire to prevent them from inheriting his assets upon his passing. Instead, his long-time partner, Pamela Courson—who was ultimately recognized as his common-law spouse—was named the sole heir to his estate. His will stipulated that if she passed within 90 days of Morrison’s death, his siblings were designated as alternate beneficiaries.

This clearly illustrated Morrison's wish that, if Courson were not around, his brother and sister would inherit his wealth. As fate would have it, Courson lived for two years after his death, and the court ruled that she was entitled to the assets as per the will’s provisions. However, after her own passing, she died intestate, leaving her parents as her heirs. Morrison’s parents contested this verdict, resulting in a settlement that divided ongoing royalties and remaining estate assets.

Rebel Without a Cause

It's been over 60 years since the tragic death of James Dean, and Hollywood continues to seek “the next James Dean.” His filmography includes only three major films, with titles like *East of Eden* (1955), *Rebel Without a Cause* (1955), and *Giant* (1956). His untimely demise at age 24 on September 30, 1955, forever immortalized him as the quintessential icon of youthful rebellion. Yet, Dean’s legacy took a different course; he passed without a will, leaving his estate to his father under intestate laws.

Over the years, the James Dean estate has thrived, thanks to dedicated efforts to enhance and protect his image. However, the estate has faced legal challenges, including a notable lawsuit from Warner Brothers regarding the rights to market his name and image. Jimmy Dean’s lack of planning starkly illustrates the need for sound estate planning; even a young star with assets should immediately set up a will. Were James Dean alive today, one must wonder if he would have wanted his father and, ultimately, his father's relatives to control his image and fortune. Because of his lack of estate planning, the law dictated the future of his legacy, not his wishes.

The Dynasty

The name Kennedy is synonymous with American political and social influence. Beyond their illustrious public service, the Kennedys have successfully navigated the complexities of financial management, ensuring the sustainability of their wealth across generations.

The Kennedy fortune traces back to Joseph P. Kennedy, the family patriarch. A shrewd businessman, he built an impressive portfolio through stock market investments, entertainment ventures, and real estate. Joe’s strategic financial management established a legacy that supported his immediate family and set up a wealth management framework benefitting the Kennedy lineage for years.

Key Strategies of the Kennedy Legacy

  • Financial Diversification
  • Philanthropy and Social Investment
  • Political Acumen
  • Educational Prioritization
  • Protecting Wealth Across Generations

The Kennedy family’s estate planning offers a comprehensive blueprint showcasing how wealth can be a tool for influence and positive change. They have built a legacy that resonates through astute trust management, political engagement, charitable giving, and sound investments.

This narrative underscores the importance of a holistic approach to estate planning, blending financial strategies with long-term aspirations and values. Whether dealing with family trust challenges or aligning wealth with societal responsibility, the principles of the Kennedy family provide invaluable guidance.

In today’s intricate climate, the Kennedy family's achievements remind us that with careful foresight, a clear vision, and strategic execution, safeguarding a family's wealth and ensuring its growth across generations is feasible. Their enduring legacy inspires anyone to navigate the complexities of modern estate planning.

I could write a book on these iconic stories…and I just might be

In addition to these legendary names, others such as Jimi Hendrix, Bob Marley, Kurt Cobain, James Brown, Prince, Princess Diana, Sonny Bono, and Philip Seymour Hoffman also serve as examples of legends who left behind inadequate planning.

Discovery is the Journey

James Dean once said, “The prime reason for existence, for living in this world, is discovery,” and “If you’re afraid to die, there’s no room in your life to make discoveries.” You have dedicated yourself to caring for your family, but what have you done to prepare for what happens when you are no longer in control? The Legacy planning process is a reflective, introspective process and can lend itself to discovery.

Reflecting on our mortality encourages us to detach ourselves from trivial pursuits and embrace life’s pleasures. Recognizing the inevitability of death can liberate us from fear, doubt, and burdensome habits, prompting us to live each day fully.

Planning for your legacy need not be an overwhelming endeavor. The reality is straightforward: You will pass, and while that is unavoidable, the chaos left for your family doesn’t have to be.

In our planning, we focus on Five Elements of Legacy planning.

The Core Components of an Estate Plan

  • Defining Your Legacy: An estate plan clarifies your intentions for the future.
  • Protection for Future Generations: Estate planning safeguards your family amidst unforeseen circumstances.
  • Tax Strategies: Optimize your estate plan to minimize tax implications.
  • Philanthropic Opportunities: Consider incorporating charitable pursuits into your estate plan.
  • Family Harmony: A well-structured estate plan fosters family unity during transitions.

Planning provides an opportunity to clarify our intentions, help ensure our wishes are honored, and, importantly, reduce the likelihood of conflicts over finances among family members.

JFK was right when he proclaimed, "Children are the world's most valuable resource and its best hope for the future." Approach legacy planning proactively, distribute gifts meaningfully, and make a difference while you’re still here. Today, you can take charge of your legacy—cultivating a heritage of love and clarity, not conflict and regret, before you… break on through to the other side.

Be well and enjoy the moments,

Derek Henderson