Welcome to “FWIW (For What It’s Worth),” a candid advice column about the triumphs, trials and everything in between of running a family business. Rooted in real-world experience and a deep appreciation for the unique challenges family businesses face, this column offers insights that are well-intentioned, practical and sometimes a little unconventional. Need some guidance on a family business issue? You can anonymously submit a question to Jamie right here.
Entrepreneurship is often described as a lonely pursuit: the weight of decisions, the responsibility for others, the second-guessing that comes with doing something new. Yet I often point out to entrepreneurs that family business leadership can be even more isolating! When the people who you might normally turn to for perspective are also shareholders, managers, siblings, parents or successors, it can feel like there’s no neutral ground. That tension between belonging and burden is both real surprisingly difficult to find spaces where these topics can be discussed openly, especially when they feel taboo.
Family business is often portrayed through a dramatic lens: cue the power struggles, boardroom betrayals and “Succession”-style monologues. Yet most families I know are not plotting corporate coups over breakfast. They are trying to do their best, make thoughtful decisions and protect both relationships and results at the same time. There is tension, yes. But there is also humor, pride, loyalty and deep care.
This is why family businesses matter so much to me. They are one of the few forms of enterprise that allow owners to define value on their own terms. Public companies and private equity-backed firms are structured around maximizing shareholder value, typically measured in financial return. Nonprofits prioritize impact over profit. Family-owned businesses have the rare flexibility to pursue both, to build profitable companies while aligning decisions with deeply held personal and family values. That freedom is powerful.
As a first-generation American, I have seen firsthand the opportunity and generational security that business ownership can create. A family enterprise can be more than a balance sheet; it can be a platform for stability, mobility and long-term impact across generations. And, if structured properly, a family business can become connective tissue: a shared endeavor that bridges generations and geography. When I think about my children, nieces and nephews, I love that they will share something that goes beyond holidays and family stories. They will have the opportunity to build, grow and carry forward something meaningful together.
For background, I’m not a formal family business advisor or a lawyer. Instead, my perspective comes from both theory and practice: teaching family business at The University of Chicago Booth School of Business in a course called, “Outperform & Outlast: Operating and Investing in Family Businesses” and leading my own family’s company, Chem-Impex, as president. Those two worlds, classroom and shop floor, have given me a front-row seat to the joys, tensions and real-life tradeoffs families navigate every day.
This column is a space to share stories and ideas that might resonate with your own journey. If something’s been on your mind, big or small, I’d love to hear it. Whether it’s a quick curiosity or a lingering “What do I do now?” moment, your questions might just spark ideas that help others too. And for what it’s worth, even small questions can lead to big insights!
We’re kicking off our inaugural column with a question about what it really means to be “ready” for leadership in a family enterprise.
Dear FWIW,
I’ve built a career outside my family’s business and am now considering joining the family business. I have experience, but not inside our company. How will I know if I’m ready to step into leadership or if I still have more to learn elsewhere first?
Sincerely,
Unsure in Chicago
Dear Unsure in Chicago,
If Whitney Houston has taught us anything, it’s that “How will I know?” is rarely a question with a clear answer. While “How will I know?” sounds like an internal question, it carries two other questions just beneath the surface: “Can I do it?” and “Will others trust I can?” Readiness in a family business is not only self-assessment; it is external validation. (Whether we like it or not!)
Starting with the question: “Can I do it?” In my experience, there is no perfect moment of certainty. At some point, knowing comes from doing. Leadership is learned in motion. Taking from the Taoist philosophy: “The best way to do is to be.”
Particularly for high-achieving people, preparation can become a form of comfort: another role, another credential, another year of “just a little more experience.” But preparation can also become a form of delay. I know I went through this. It often felt like someone else had the “secret sauce” or a hidden playbook I could never know. In reality, much of what I needed was already there, I just needed to start executing. At some point, becoming the leader requires stepping into the role and growing from within it.
That said, stepping forward doesn’t have to mean leaping blindly. Before stepping in, you can gather perspective. What would your actual role look like? Who would you be working alongside? What expectations already exist (spoken or unspoken)? Can you spend a few weeks or days on the job?
The second question, “Will others trust that I can?” is where readiness moves from internal conviction to external validation. Family business scholar Ivan Lansberg calls this the “Tests of the Prince”: the formal and informal trials successors must pass before they are truly seen as leaders. The four tests are:
- Qualifying tests: external markers that signal competence, such as education or outside experience.
- Circumstantial tests: how you respond when a crisis hits or a difficult decision must be made.
- Self-imposed tests: the standards you hold yourself to in situations you create.
- Political tests: navigating family dynamics and organizational relationships with maturity.
At their core, these tests are about trust. They are less about perfection and more about proving that the business, and the relationships within it, are in “good hands”. You do not pass these tests before you step in. You pass them by stepping in. FWIW, readiness, in that sense, is not a feeling you wait for. It is something you prove.
Signed,
Jamie