What If Keeping the Family Together Isn’t the Goal?

Jaime White
1 day ago
5 min read

I’m not entirely sure I’m ready for this idea myself.

I spent most of my life in a family business. Well into my 40s.

For a long time, I thought getting more of the family involved was the goal.

Of course we wanted our kids to have access to opportunities. We wanted them to understand business, investing and entrepreneurship. We imagined them proposing new businesses, asking for investments and creating things of their own.

That was just part of our family culture.

Some families are sports families. Some are education families. Some hunt or fish or travel or spend every weekend at a hockey rink.

We talked about business.

We played Cashflow and Acquire. We played Settlers of Catan, Rook and Pit.

And when we weren’t playing games, sometimes we were cleaning out rental properties together.

This was normal.

And honestly, I still love a lot of it.

Then our kids started becoming themselves.

That’s where things got more interesting.

As we’ve given our children more room to explore outside the expectations of family business, we’ve watched very different humans emerge.

We’ve got rock climbing—including a kid who free solos—parkour and mountain biking.

One is fascinated by affiliate marketing and online trading.

Another became an HVAC technician.

Another is writing a book, creating an entire game world and figuring out how to use AI to help him build it.

They support each other.

But they aren’t the same.

And they’re definitely not miniature versions of us.

Maybe that’s the point.

Opportunity and identity aren’t the same thing.

I’ve always believed that being resourced creates opportunities.

I still do. But I’m learning that being resourced isn’t the same as believing money solves the problem.

Sometimes what our children need isn’t another opportunity we can provide.

Sometimes they need another person.

We’ve encouraged our kids to find outside mentors and invest in themselves. Partly because I began realizing they needed people who weren’t us. Sometimes another person could say almost exactly what I had been saying and somehow my kid could hear it differently.

Annoying?

Absolutely.

Also healthy.

Because their lives aren’t supposed to be built entirely through us.

Then they started telling us things we didn’t necessarily want to hear.

At one point, some of our kids were willing to give up the perks and opportunities that came with being connected to the family business.

They didn’t want the same culture.

They didn’t agree with some of the values they saw being lived. And they said so.

One of the comments that has stayed with me was essentially:

“Mom, we don’t understand why you’re staying. We don’t like the way Grandpa treats women.”

That’s an interesting moment as a parent.

And an even more interesting moment in a multigenerational family.

Because what’s normal in one generation isn’t necessarily normal in the next.

What’s tolerated by one generation may be unacceptable to another.

What one generation calls loyalty, another may experience as codependency.

What one generation calls respect, another might experience as silence.

And what one generation proudly calls legacy might feel like an obligation to the person expected to carry it.

That’s where this gets complicated.

Successful families have a gravitational pull.

When a family has built something significant—especially over 50 or 100 years—it carries weight.

There’s history.

There’s opportunity.

There’s pride.

There’s identity.

There’s usually a person somewhere in the story who became larger than life.

I sometimes call this person the giant in the family.

Maybe it’s Grandpa.

Maybe it’s Mom.

Maybe it’s the founder whose personality, success, expectations and approval have enormous gravitational pull.

Nobody necessarily decided that person’s desires should determine everyone else’s lives.

It just happens.

And sometimes everyone gets very good at orbiting the giant.

That’s where artificial harmony can start looking a lot like family unity.

Everyone gets along.

Everyone shows up.

Nobody rocks the boat.

But nobody asks:

Is this actually who I want to be?

I’ve seen the gravitational pull from the other side, too.

We recently talked with a NextGen family member who wasn’t working in the family enterprise.

She was an industrial designer.

The family was asking her to consider coming into the business, where she could quickly find herself working at an extraordinary level—including exposure to people like the Secretary of Defense.

That’s an incredible opportunity.

I don’t think the answer is:

Don’t join the family business. Go prove yourself somewhere else first.

I actually disagree with that as a universal rule.

Why should someone automatically walk away from extraordinary access, mentorship, relationships and opportunities simply because their family created them?

There can be tremendous value in bringing NextGen into the enterprise early.

There can also be tremendous value in leaving.

The question isn’t:

Should they stay or should they go?

The question is:

Who is this person, and what path allows them to become more fully themselves?

Maybe we need to stop deciding what success looks like for them.

One child may be wired to run the empire.

Another may build something completely unrelated.

Another may care far more about people than profit and spend significant parts of their life volunteering or serving.

One may want responsibility for family assets.

Another may want very little to do with them.

That doesn’t automatically make one ambitious and another entitled.

It doesn’t make one successful and another unsuccessful.

They’re different humans.

Our job isn’t to make them the same.

And I think this is one of the hardest things for successful families.

We’ve spent decades learning what works.

We have resources.

We have relationships.

We have experience.