America is staring down a succession planning crisis, and the numbers are getting harder to ignore. According to research from private equity firm Enventure, an estimated 57–67% of family-owned businesses in the U.S. are uncertain about how they will pass leadership to the next generation. With baby boomer founders retiring at a rapid clip, and the economic environment in flux, this gap threatens not just individual businesses—but entire communities built around them.

Nowhere is this more evident than in places like Chicago, a city where family-owned businesses form the backbone of neighborhoods and local economies. According to the Family Business Center at Loyola University Chicago, nearly 80% of businesses in Illinois are family-owned, employing over half of the state’s workforce. From iconic food manufacturers to long-standing printing companies and logistics firms, many of Chicago’s enterprises face a reckoning: who takes over next?

“The stakes are high,” says Ankit Shrivastava, Founder & Managing Partner of Enventure, a U.S.-India private equity firm that works closely with family-run companies undergoing generational transition. “To successfully advance while preserving heritage, family businesses need to clearly define their objectives around succession, digital transformation, and innovation.”

Shrivastava argues that this isn’t just a leadership problem—it’s an operational and strategic one. As older generations step away, younger family members are often either uninterested or unprepared to take over. Many are pursuing careers elsewhere or lack the experience needed to modernize operations. Meanwhile, founders are hesitant to give up control or bring in outsiders who don’t understand the culture they spent decades building.

This hesitation can be especially pronounced in legacy-heavy cities like Chicago, where a company’s reputation and relationships often span generations. The fear of disruption is real. But failing to plan, experts warn, is far riskier. Without clear succession strategies, companies can fall into decline—losing customers, employees, and value in a matter of years.

That’s where new tools, particularly AI and data-driven decision-making, may offer a solution. “Embracing tools such as AI-driven analytics can significantly streamline operations, reveal market opportunities, and facilitate informed decision-making,” Shrivastava explains. Technologies that can identify customer trends, optimize supply chains, and improve financial forecasting can make the leap between generations less daunting.

In practice, this means shifting away from ad hoc planning and toward systems that codify institutional knowledge, evaluate successor readiness, and clarify performance metrics. AI and automation can also reduce dependency on founder-led decision making, creating room for more collaborative governance structures.

At Enventure, this transformation is paired with strategic capital—often through co-ownership models that allow founders to stay involved while new leadership scales the business. The approach has proven popular among companies in the Midwest, where founders are often more focused on legacy and long-term impact than fast exits.

Chicago’s own family business landscape reflects both the promise and the peril of this moment. The city has already seen several high-profile generational handovers in recent years—from the sale of Ferrara Candy Company to investment firm L Catterton, to the digital transformation of regional logistics firms. But for every success, there are dozens of small and mid-sized companies flying under the radar, quietly grappling with the same questions.

Who will lead? How will we grow? And how do we preserve what made us different in the first place?

The answers, Shrivastava believes, lie in blending tradition with transformation. It’s not about replacing founders—it’s about evolving their vision. “Succession isn’t an endpoint. It’s a pivot,” he says. “It’s a chance to take everything that worked and make it work for the next decade.”

If more family businesses take that view—and leverage tools like AI to do it—the succession crisis might not be a crisis at all. It might be an opening.

But that window won’t stay open forever. In a city like Chicago, where history is an asset but change is a constant, planning for what comes next may be the most important decision a business ever makes.