Let’s rewind to 1913. After being widowed, my great-grandmother Ella Sindorf took over Sindorf’s “Staples and Fancy Groceries” on Hadley Street in Milwaukee, WI. A businesswoman by necessity, not by design, she ran the show. Eventually, her son – my grandfather – joined her and expanded the operation into a full-service butcher shop (Sindorf’s Market) while still offering the aforementioned “Staples and Fancy Groceries”. It wasn’t exactly an empire, but it was theirs. As it later turned out, my mother was an only child. So was I. So is my daughter. And thus, the family business quietly closed the moment my grandfather retired in the early 1970s. No heirs, no handoff, no dramatic boardroom exit. Just a clean close of the ledger.
Family businesses live at the intersection of commerce and kinship, and that’s a notoriously precarious place to set up shop. Decisions are freighted with emotion and conversations double as referendums on relationships. Conflicts don’t end at the office door – they follow you to Thanksgiving dinner and echo in the passive-aggressive tone of family text chats.
And while the idea of “working with family” might sound cozy on paper, it can be a bit like mixing spaghetti with glitter – impossible to separate, somehow everywhere, and always harder to clean up than you expected.
Add to this the logistical complications – succession planning, equity division, leadership transitions – and you start to see why family businesses, though romanticized, can be an emotional and organizational minefield.
Governance Deficiencies: Who’s Actually in Charge?
One of the most consistent challenges in family-owned businesses is a lack of formal governance. Titles are often ceremonial (“Let Mikey be the VP of Something”), and decision-making tends to follow either seniority or sheer volume – the loudest voice wins. The absence of clear roles, responsibilities, and structured decision processes creates confusion and inefficiency.
When cousin Angie is supposedly “handling marketing” but also thinks she’s leading operations – and Uncle Tony is “weighing in” on every email thread despite technically being retired – you’re not running a business. You’re starring in a low-budget workplace reality show.
Establishing defined roles, clear reporting lines, and transparent processes isn’t about bureaucracy – it’s about survival. Good governance doesn’t diminish the family’s influence but does allow it to function productively.
Misalignment of Goals: We’re Family, Not Mind Readers
Just because everyone shares DNA doesn’t mean they share vision. In fact, divergent views on where the business is going, what it stands for, and how success is defined can create deep fissures.
One sibling might want to modernize operations and expand digitally. Another might cling to the “way Dad always did it.” Maybe one generation is ready to sell while another insists on legacy preservation at all costs. And someone – usually the one doing the accounting – just wants to get paid.
Without open dialogue and a mechanism to align priorities, the business stalls. Or worse, it splits. You need a forum (formal or informal) to check assumptions, reconcile differences, and recalibrate direction. Family businesses don’t fail because of disagreements; they fail when those disagreements never get discussed.
Too Few Heirs, Too Many Cousins
Succession isn’t just a topic for strategic off-sites – it’s often a simmering source of stress. What if no one wants to take over the business? What if everyone does? How do you navigate inheritance, leadership transition, and ongoing involvement without setting off a decades-long feud?
On one hand, there’s the quiet heartbreak of a founder realizing none of the next generation wants the keys to the shop. But on the other hand, what if you have too many family members – siblings, cousins, maybe a nephew who once took a business class and now thinks he’s automatically the next CEO? The pressure to “keep it in the family” can be overwhelming, even when it’s clear that not every family member is destined to become an operational asset.
The answer lies in succession planning that starts early, includes open dialogue, and (here’s a radical idea) allows for “outsiders” to be hired when necessary; just because it’s a family business doesn’t mean every role must be filled by a family member.
Why It’s Worth It
For all the complications, family businesses remain a bedrock of the economy and community. They often operate with a deep sense of purpose, resilience, and care that’s hard to replicate. But none of that happens by accident; it takes intentional effort to keep the “family” from overwhelming the “business.”
The family business requires boundaries, structure, and the occasional reality check which may mean saying no to hiring your cousin’s underqualified boyfriend or acknowledging that your kid would rather be a marine biologist than a fourth-generation milliner. And sometimes it means getting outside help – a neutral party who can see beyond Aunt Linda’s feelings and help you make smart, sustainable decisions.
Running a family business is part logistics, part legacy, and 100% navigating the emotional landmines that come from merging personal and professional lives. But if you can balance it all – and, let’s be honest, sometimes just survive it – you’ll have something even better than a successful business: you’ll have a story worth telling for generations.
