KENNESAW, Ga. | Jan 8, 2026

The United States is entering a pivotal moment for family businesses. Trillions of dollars, much of it tied to privately held businesses, will transition to the following generation in the next two decades. According to Federal Reserve data, Baby Boomers still hold the largest share of U.S. wealth, but that balance is already shifting to Gen X and Millennials. At the same time, the nation has entered what demographers call the “Peak 65 Zone.”

The Peak 65 Zone refers to a historic four-year period from 2024 to 2027, during which the largest number of Americans in history will reach the traditional retirement age of 65. Often described as a “silver tsunami,” this milestone marks the retirement of the final wave of the Baby Boomer generation. For family businesses, this demographic shift accelerates the urgency of leadership and ownership transitions—many of which are still unresolved.

This moment presents both opportunity and risk. Thoughtful planning can preserve family relationships, strengthen leadership continuity, and position businesses for long-term success. Avoiding the conversation, however, can lead to confusion, conflict, or rushed decisions that erode value and legacy.

Key realities family business leaders should keep in mind:

• Trillions of dollars are poised to change hands. Much of this wealth is embedded in family-owned companies, real estate, and long-term investments, making succession planning a strategic business priority.
• It’s never too late to start the transition conversation. Whether transition feels distant or imminent, open dialogue around leadership, ownership, and expectations builds trust and reduces uncertainty across generations.
• No family should navigate transition alone. Peer groups, advisors, and transition experts offer valuable perspectives, shared experiences, and practical guidance during times of change.

At the Family Enterprise Center, we continue to see how early and honest conversations can make all the difference. In our recent webinar with Elizabeth Ledoux and Andrea Carpenter of The Transition Strategists, we explored practical approaches to leadership and ownership transitions. Whether you're just starting to consider a leadership transition or already have a plan in place, this webinar is definitely worth watching.

Finally, as the Peak 65 Zone unfolds, open conversations and clear expectations matter more than ever. Preparing today helps ensure that when leadership and wealth transition tomorrow, your family business is ready.

Want to learn more? America's Great Wealth Transfer is Coming. Here's What Heirs Really Think

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Leadership development doesn’t happen in isolation. It’s shaped by the relationships, experiences, and communities we engage with along the way. For family businesses of all sizes, supporting the rising generation means encouraging them to step beyond their roles inside the company and into the broader local business community.

Across chambers of commerce, young professionals groups, and business associations, next-generation leaders gain access to something that can’t be taught in a classroom: meaningful connection. Local involvement exposes them to peers facing similar challenges, community leaders who model effective leadership, and experienced professionals willing to share insight. These relationships often become sources of guidance, opportunity, and long-term collaboration.

Business growth and leadership readiness are still deeply rooted in trust, and trust is built through consistent, person-to-person interaction.

Why Local Involvement Matters:

• It strengthens networks that support long-term growth. Conversations at a chamber breakfast or association meeting can lead to referrals, partnerships, and new perspectives.
• It builds confidence and communication skills. Representing the business publicly helps emerging leaders develop presence, clarity, and credibility.
• It creates access to mentorship and coaching. Trusted mentors provide perspective, accountability, and encouragement, especially during times of transition.

Many local chambers are intentionally investing in young professional programs that connect rising leaders with seasoned executives through leadership development and community engagement. These initiatives demonstrate the power of intentional connection—not just for individual growth, but for the long-term health of businesses and communities alike.

Encouraging the next generation to engage locally isn’t just about networking. It’s about equipping future leaders with relationships and perspectives that will serve them and the businesses they lead for years to come.

For many family businesses, the idea of stepping away for a two- or three-day planning retreat can feel indulgent or even unrealistic. There is always work to be done, decisions to be made, and customers to serve. Yet for families navigating growth, transition, or generational change, an annual planning retreat can be one of the most valuable investments they make all year.

When done well, a retreat creates space to rise above daily operations and focus on what truly matters: direction, alignment, and relationships. So what do family businesses actually talk about for two or three days? More than you might expect (and it's normally less about what's on the spreadsheets).

Productive retreats typically include a mix of strategy, structure, and people. Families revisit their shared vision, values, and long-term goals. They assess what is working and what is not in the business, clarify roles and expectations, and discuss upcoming transitions related to leadership, ownership, or governance.

Just as important, retreats provide time to address communication patterns and decision-making processes that do not always surface in day-to-day conversations. The key to success lies in how the retreat is designed.

What Makes a Planning Retreat Productive and Inclusive

• Clear objectives and an agenda. Everyone should know why they are there and what outcomes are expected.
• Inclusive participation. Create space for all voices across generations and roles, not just the loudest or most senior.
• Neutral facilitation. A trusted outside facilitator can keep discussions focused, manage tension, and ensure progress without personal dynamics derailing the conversation.

Retreats are not about solving every issue in one weekend. They are about alignment. They give family members shared clarity, renewed trust, and a practical roadmap for the year ahead. For family businesses committed to continuity and healthy leadership transitions, an annual planning retreat is not time away from the business. It is time invested in its future.

Want to learn more? Boost Your Family Business Success With A Family Retreat