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Writer's pictureRoelf Botha

Overcoming the cycle of “shirtsleeves to shirtsleeves”

The process of passing wealth and leadership across generations is a cornerstone of family businesses and dynasties. Legacy wealth involves building, protecting and transferring wealth within families over time, and it is crucial for maintaining financial stability, preserving values and creating a lasting impact. However, the successful transfer of wealth and leadership is not always guaranteed. Statistics indicate that many families lose their wealth by the third generation, a phenomenon often referred to as “shirtsleeves to shirtsleeves in three generations”.


This pattern occurs when the initial generation accumulates wealth through hard work, the second generation maintains and possibly expands it, but the third generation often sees it dissipate due to mismanagement, entitlement, or lack of purpose. Yet, history shows that some legendary families have successfully countered this trend. This article explores the key factors that have enabled such families to preserve their wealth and legacy across generations.


Legacy Planning: The Strategic Foundation


“Legacy is not about what you have achieved, but what you leave behind”.


Legacy planning is the strategic foundation of overcoming the paradox of intergenerational wealth. It involves committing to a unified long-term vision and shared values, ensuring that future generations understand and uphold the meaning behind the inherited wealth. This approach emphasises the transfer of family values, stories and traditions.

Effective legacy planning includes developing strategies for managing and distributing wealth, protecting family members, minimising taxes, and having a lasting impact through charitable giving, business succession or establishing trusts. Its goal is to maintain family harmony, provide for loved ones, and leave behind a legacy that reflects personal beliefs and aspirations.


Succession Planning: Ensuring Leadership Continuity


“Leadership is the capacity to translate vision into reality”.

Warren Bennis


Cultivating the next generation’s leadership is vital for maintaining a family’s legacy and protecting it against future uncertainty. By identifying and grooming future leaders from a young age, families can ensure that their businesses and assets are in capable hands when the current leaders step down.


The Plantin-Moretus Printing dynasty, founded by Christopher Plantin in the 16th century in Antwerp, stands as one of the most remarkable examples of a family legacy that endured over centuries. Plantin’s printing house, renowned for innovation and craftmanship, flourished in Europe during the Renaissance. Despite having only daughters, Plantin involved them in the business from a young age. To ensure continuity, he chose his son-in-law, Jan Moretus, as his successor. This thoughtful succession planning enabled the business to thrive for nine generations, demonstrating that well-executed leadership transitions contribute to enduring family enterprises.


Succession planning ensures that each generation is led by individuals who share the family’s vision, perseverance and dedication.


Estate Planning and Family Governance: structuring for success


“Proper communication will always be a main ingredient for building family solidarity and permanence”.

Marvin J. Ashton


Successful families rely on financial planners, legal advisers, and tax experts to navigate the complexities of wealth management, ensuring their assets are optimised for long-term growth. They also use estate planning tools such as trust, diversified investments, and wealth transfer mechanisms to safeguard their wealth from mismanagement, market volatility and other risk factors.


Alongside expert advice, strong governance structures like family councils and regular family meetings foster transparency, harmonious relationships and shared decision making. These forums engage younger generations in financial dialogues, preparing them to make informed decisions while staying true to family principles and objectives. By blending professional insight with clear communication, families create a foundation of trust and cohesion, which is essential for sustained success.


Education and skill development: Preparing the next generation


“Education is for improving the lives of others and for leaving your community and world better than you found it”.

Marian Wright Edelman


Investing in the education of younger generations is essential for preserving a family legacy. A well-rounded educational approach covers fundamental knowledge and emphasises the development of critical thinking, ethical decision-making and leadership skills. This preparation equips heirs to engage meaningfully with their inherited assets and responsibilities.


In addition to general education, specialised skill development related to the family’s traditional trades or business ventures can further strengthen the connection to the family’s heritage. While not all family legacies revolve around a specific trade, targeted skill development bridges the gap between inherited wealth and active stewardship, empowering heirs to enhance the family’s legacy with confidence and competence.


Philanthropy: Extending the legacy through giving


“We make a living by what we get, but we make a life by what we give”.

Winston Churchill


Philanthropy plays a central role in sustaining wealth across generations by fostering a sense of purpose and responsibility. Families that contribute to society with their wealth create unity and a shared mission, helping to counteract entitlement and encouraging the younger generation to see themselves as stewards of both financial and social capital.

The Rockefeller family exemplifies this approach. John D. Rockefeller, the patriarch, believed that wealth came with a responsibility to give back to society. His philanthropic efforts were groundbreaking, focusing on education, public health, and scientific research. He established several major institutions, including the University of Chicago and the Rockefeller Foundation, which have made enduring contributions to society.


With philanthropy woven into the family’s culture, wealth becomes a tool for creating positive change, and the family legacy extends beyond mere financial success.


Integrating legacy planning, succession planning, philanthropy, education and estate planning, creates a robust framework for preserving and enhancing a family’s wealth and values over time. Legacy planning provides the strategic foundation, ensuring that the family’s values and vision are preserved. Succession planning secures capable leadership, while estate planning and family governance structures facilitate effective wealth management and transfer. Education and skill development prepare the next generation to manage responsibilities with confidence, and philanthropy adds a dimension of purpose and societal impact.


By building these elements into a unified strategy, families can address the challenges of intergenerational wealth transfer, ensuring that their legacy endures and flourishes across generations, preserving their wealth, values and impact for the future.


References

  • Hausner, L, Freeman, DK. The Legacy Family. 2009.

  • Mestre, J. Plantin-Moretus: A Museum for Book Lovers. OldWorldVoyages.com. 2022

  • Rockefeller Archive Center.

  • Ungerer, M, Mienie C. A Family Business Success Map to Enhance the Sustainability of a Multi-Generational Family Business. 2018.

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