15 Apr Beyond the Binary: Exploring New Paths for Family Business Owners

By: Mike Schmitt, The Rubra Group, LLC

Every family business owner eventually finds themselves at a crossroads. Perhaps you’re feeling frustrated with your current operations, fatigued by daily challenges or stifled by long-standing dynamics. Or maybe you’re contemplating selling the company entirely, only to be haunted by a deeper sense of regret, as if you might be turning your back on your family’s legacy.

This internal debate—should I stay, or should I go? — is often framed as a binary choice. But here’s the truth that too few advisors tell you: it doesn’t have to be.

There are more options than simply holding on out of obligation or selling under duress. In fact, some of the most successful transitions in multigenerational enterprises happen when owners step back, assess with clarity, and choose a third or a fourth, or a fifth option. This week, we’ll explore some powerful alternatives to the “all or nothing” decision that many business owners face, and we’ll offer a broader framework to help you reimagine what’s possible.

1. Elevate a Professional Management Team

One of the most empowering decisions a family business owner can make is to shift from “operator” to “owner-strategist.” This doesn’t mean removing yourself completely—but it does mean empowering others to handle day-to-day operations while you focus on long-term vision, legacy planning, and stewarding capital.

Bringing in a professional management team, or elevating key non-family talent already within your company, allows the business to grow beyond the limitations of any one individual’s time or energy. It also creates space for you to rediscover joy and meaning in your role, possibly as board chair, family council leader, or innovation champion.

If the thought of professionalizing your company is daunting, remember this: systems and talent can be developed. You don’t need to hand over the keys tomorrow. You just need a plan.

2. Consider a Partial Liquidity Event

Another powerful option is a partial sale or recapitalization. This allows you to take some chips off the table—preserving your family’s financial security—without walking away from the enterprise entirely.

Through recapitalization, you can retain control, invite strategic partners into the business, or shift some equity to a next generation who are ready to lead. In doing so, you create breathing room. You gain liquidity, de-risk your future, and make space for strategic pivots or succession planning.

Liquidity events don’t have to mean the end of a legacy. In fact, they can provide the fuel to sustain it.

3. Build a Structured Leadership Development Plan

Many families assume that leadership transitions must either happen organically or not at all. But the most successful family enterprises take a strategic approach to developing the next generation.

If no family members are ready to lead today, that doesn’t mean the dream is dead. It just means it’s time to build a bridge. Structured development plans can identify potential next-gen leaders, offer them mentoring, external work experience, and eventually, a leadership path within the business.

What’s more, these plans can be designed to foster inclusion—not just for those who want to be CEO, but also for those interested in innovation, governance, impact investing, or family philanthropy. Leadership in a family enterprise comes in many forms.

4. Restructure for a Multi-Generational Future

A decision to restructure your enterprise—perhaps by splitting it into operating and holding companies or introducing new governance tools like a Family Constitution—can open the door to creative, future-proofed solutions.

When properly designed, these structures create separation between ownership, management, and family influence. That separation allows the business to operate efficiently while honoring the voice and vision of the family. It also paves the way for clarity in succession, easier capital decisions, and better alignment across generations.

As we’ve seen with many of our clients, even a few modest changes in structure can transform not just the business—but the family’s confidence in their shared future.

5. Pursue Legacy Projects Without Selling the Core

For some owners, the biggest point of friction isn’t just operational stress, it’s feeling uninspired. If you’ve spent decades building something, you might now feel called to something new: philanthropy, a new venture, impact investing, or mentorship.

You don’t need to sell your business to pursue that calling.

Instead, consider carving out time, capital, or even a team to build a “legacy project” alongside the core enterprise. This allows you to explore your next chapter while keeping the family business intact. And often, those legacy projects enrich the family brand and culture in profound ways.

Reframing the Choice

The decision to stay, exit, or transform your business should not be made under pressure or from a place of fatigue. Instead, it should come from a place of vision.

Take a moment to ask yourself: What role do I want to play in the next chapter? What do I want my legacy to be? And what will most empower the next generation—not just with capital, but with confidence?

If you feel like you’re standing at a fork in the road, know this: there are more paths available than you think. The key is to pause, assess, and design with intention.

And remember, you don’t have to do it alone.

If this sparked something for you, forward it to a fellow leader or family member. Or reply — we’d love to hear how your family is cultivating a culture of stewardship or thinking about what the future looks like.

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