The Common Struggles in Maintaining a Family Legacy

Fewer than a third of family businesses make it to the second generation, and only a fraction survive into the third. Behind those numbers lie not just business failures, but fractured relationships and lost legacies. Anyone who has lived through the ups and downs of a family enterprise knows that legacy is not set in stone. It is fragile, human, and in constant need of care.

When families try to pass on more than wealth, when they want to hand down values, reputation, and a sense of belonging, the struggles are real. And they tend to show up in the same patterns, generation after generation.

In this article, I share some of the struggles I’ve seen families face when trying to maintain a legacy, and why naming them is the first step to overcoming them.

Keeping the next generation engaged 

One of the first challenges is making sure the next generation cares. Too often, younger family members feel little connection to the stories and sacrifices that built the enterprise. If all they inherit is responsibility without meaning, legacy starts to feel like a burden.

Families who succeed bring younger voices in early. Not with token roles, but with real opportunities: projects, ventures, or initiatives that matter to them. It might be philanthropy, sustainability, or even a new business idea that carries the family name forward. Engagement is never about forcing the past, but inviting them to co-create the future.

Succession avoidance 

Every family knows succession is important, yet many avoid it until it is too late. The result is confusion, mistrust, and fights that could have been avoided. According to PwC’s Global Family Business Survey 2023, fewer than 25 percent of family businesses have a formal succession plan.

The deeper reason is often fear. Founders worry about becoming redundant or forgotten. For many, the business is their identity and handing it over feels like handing away their purpose.

Holding on may feel safe, but it leaves everyone else in uncertainty. Succession is not just about choosing who comes next. It is about helping the older generation find dignity and a new sense of purpose, while giving the younger generation room to lead. Families who set timelines and speak openly reduce the risk of conflict. Those conversations are rarely comfortable, but they often prevent years of tension later.

When values start pulling in different directions 

Another struggle is when generations drift apart in what they value most. Founders often focus on stability and preservation, while younger members want innovation, impact, or sustainability. Both are valid, but when ignored, tension grows.

These aren’t just business debates. They play out at kitchen tables and holidays. A disagreement over whether to reserve profits or expand into new markets is also a disagreement between father and daughter, or between siblings with different worldviews.

James E. Hughes Jr. puts it well: the real work of wealth preservation is not to prepare the money for the family, but to prepare the family for the money. Part of that preparation is allowing values to evolve without fracturing the bonds between people.

Gaps in preparation 

Successors rarely answer to anonymous shareholders. They face relatives with strong voices and strong opinions. The pressure is constant: Will I measure up? What if I lose what they built? What if the others never see me as legitimate? These doubts can paralyze as much as lack of training.

Preparation is not only about financial literacy or governance courses. It is about building resilience, confidence, and a sense of purpose. Families who encourage mentoring, gradual responsibility, and outside experience give successors space to grow into leadership instead of being thrown into it.

When successors are allowed to earn trust step by step, through learning, failing, and contributing, they carry the legacy with competence and humility rather than fear.

Forgetting to preserve the story 

Finally, there is the struggle of memory. Families pour energy into assets and strategies but often forget the stories, rituals, and identity that give legacy its soul.

When traditions are not passed on, they are lost. When stories are not told, they fade. Owen Eastwood, in Belonging, writes that our identity is carried in the stories we share and the rituals we practice. Families who capture and celebrate their history are the ones whose legacy feels alive. As Maya Angelou said, “You can’t really know where you are going until you know where you have been.”

What all this means 

What I’ve learned working with families is that continuity is never about the money or the assets. The real struggles are human: the fear of letting go, the pressure of living up, the clash of values, the lack of structure to protect relationships, and the slow fading of the family story.

These struggles are predictable. I see them again and again, whether in small businesses or global enterprises. And because they are predictable, they can be addressed. It starts with naming them. Once families can say, “This is what we are up against,” the work of renewal begins.

Legacy survives when both generations find courage at the same time: when the older can step back with dignity, and the younger can step forward without being crushed by pressure. Governance, preparation, and storytelling all help, but at its core, sustaining continuity comes down to love, trust, and the willingness to keep talking, even when it is uncomfortable.

This is not only a private concern for families. They shape industries and anchor communities. When a family enterprise falters, the ripple effects extend far beyond the boardroom. That is why sustaining one cannot be measured in wealth, but in bonds that last, conversations that stay alive, and values carried forward with pride.

And in the end, families who thrive are the ones who dare to name these struggles openly. They protect the roots but also allow new branches to grow.

Written by René Sonneveld.

Have you read?
The Citizenship by Investment (CBI) Index evaluates the performance of the 11 nations currently offering operational Citizenship By Investment (CBI) programs: St Kitts and Nevis (Saint Kitts and Nevis), Dominica, Grenada, Saint Lucia (St. Lucia), Antigua & Barbuda, Nauru, Vanuatu, Türkiye (Turkey), São Tomé and Príncipe, Jordan, and Egypt.