Why Family Businesses Are the Ones That Stay With Me

If you run or work in a family business, you've probably felt this weight before.

Not because you don't love it. But because nothing is ever just business.

Decisions follow you home. They sit at the dinner table. They show up in conversations that trail off because no one wants to say the wrong thing.

When something isn't working, you don't just feel it at work. You carry it everywhere.

How I Got Here

I didn't always realize how much I love working with family-owned businesses. It kind of snuck up on me.

At first, I thought I liked them because they're entrepreneurial, scrappy, and deeply committed. And that's true.

But the longer I've done this work, the more I've realized it's the relationships that pull me in.

Family businesses are different. Nothing is ever just business. Decisions don't end at 5pm. They follow you home. 

That kind of complexity doesn't scare me. It feels familiar.

I grew up around a family-owned plumbing, heating, and air conditioning business. I watched what it looked like to build something together—and carry the weight of it together too.

I learned early on that when family and business overlap, emotions don't get neatly separated.

My first job out of school was working for a husband-and-wife team running a pharmaceutical startup. I remember noticing how hard it was for them to switch off. A disagreement at work didn't stay at work. A business challenge became a personal one. And I saw how often hard conversations were delayed because the relationship mattered too much to risk.

Later, I built businesses with my own husband while I was practicing clinical medicine and operating as Chief of Staff to a physician founder.

Between us, we've owned multiple small businesses, managed teams, and operated a real estate portfolio. On any given day, we're responsible for a lot of moving parts and a lot of decisions that affect real people.

And over the past few years, I've worked with dozens of family-owned businesses—insurance agencies, HVAC companies, medical practices, staffing agencies, restaurants, fitness centers.

Different industries. Same themes.

What I See Most

It's not a lack of effort or intelligence. It's hesitation.

Someone knows a role isn't working but doesn't want to hurt a family member.

Someone feels exhausted but doesn't know how to loosen control.

Someone keeps thinking, "I'll deal with this after the next busy season."

So people work around the issue instead of dealing with it.

They ignore it. They work harder to try and camouflage it. They carry it quietly.

But here's what I've learned the hard way, both personally and professionally:

Avoiding a hard decision doesn't protect the relationship. It slowly wears it down.

Tension doesn't disappear when it's ignored. It just shows up as stress, resentment, or distance. And eventually, it costs more emotionally than the conversation ever would have.

What Makes the Difference

The family businesses that grow and stay healthy aren't the ones that avoid discomfort.

They're the ones that decide to face it sooner, with honesty and care.

That might mean redefining roles.

It might mean setting expectations that were never clearly stated.

It might mean bringing in outside support or perspective.

It might mean finally saying the thing you've been rehearsing in your head for years.

None of it is easy. But it's real.

And here's what I've seen: the conversation you're avoiding? It's probably not as complicated as it feels. It's just emotionally loaded.

The actual words you need to say are usually pretty simple. It's all the fear wrapped around them that makes it feel impossible.

If This Feels Familiar

You're not alone. And you're not doing anything wrong by finding this hard.

It's hard because it matters.

The business has your name on it. The people you're making decisions about? You'll see them at Thanksgiving. The legacy you're trying to protect? It's not just about revenue—it's about what you're passing down.

That kind of pressure is real. And it deserves more than just "work harder" or "toughen up."

It deserves someone in your corner who gets both sides—the business mechanics and the human reality.

I'd Love to Hear From You

If this resonates, I'd genuinely love to hear your story.

Reply to this email and tell me a little about your family business. What you love about it. What feels heavy right now.

Sometimes just putting it into words is the first step forward.

And yes, I read every reply.

Cheers to you and your family-owned business,

Kasey