I THINK IN DECADES
Family enterprise does too. Maybe that’s why I’m so interested in what comes next.
Someone recently thought I was their VA.
I corrected that pretty quickly. Ha.
There are probably several layers to unpack in that interaction, including some old ideas about women, leadership and who is assumed to be doing what work.
But mostly it made me laugh because I realized something:
I think in decades.
I always have.
I don’t necessarily care what we’re doing Tuesday at 2:00. I want to know what we’re building, what is changing around us, what isn’t working anymore, who is going to matter, and what all of that might mean ten years from now. It’s one of the reasons I’m fascinated by family enterprise.
Families with meaningful wealth understand decades. They almost have to. They’re making decisions today that may affect people who aren’t old enough to sit at the table yet. Sometimes people who haven’t even been born.
And I think we are entering a period where that kind of thinking is going to matter enormously.
WHAT WORKED BEFORE MAY NOT BE WRONG
One of the lenses we’ve been exploring at Believe Crew comes from Human Design.
Human Design describes the period from roughly 1615 through 2027 as the Cross of Planning—a long era associated in that system with bargains, institutions, collective structures and our ability to organize ourselves together.
I don’t need someone to believe Human Design is literally predicting the future for the idea to be interesting.
Look at what we built.
Governments. Universities. Corporations. Banks. Healthcare systems. Public markets. Career ladders. Large institutions designed around the idea that if enough people participate in the system, the system can provide some degree of stability in return.
Go to school. Get the credential. Get the job. Buy the house. Contribute to retirement. Trust the institution.
Follow the path.
For generations, that was pretty reasonable advice.
In many cases, it still is. But something is changing. We’re watching entrepreneurs stay private longer. Enormous pools of capital are moving through private markets. Family offices invest directly. Sellers participate in financing their own transactions. People assemble portfolios of businesses instead of building one career. Technology allows very small teams to create enormous leverage.
None of these individually proves that we’re entering some grand new human era.
Put enough of them beside each other, though, and I get curious.
They seem to point toward something similar: More agency is moving toward the individual. And agency sounds wonderful until you realize what comes with it.
Responsibility.
THE NEXT GENERATION MAY NOT WANT WHAT WE BUILT
Imagine spending 40 years creating something extraordinary.
You sacrificed. Took risks. Built the company. Created the wealth. Established relationships. Built the family office. Created governance. Found the advisors. Protected the assets.
Then the next generation arrives and says: I don’t want that.
Not necessarily because they’re entitled.
Maybe because they’re seeing the world differently.
The previous generation can experience that as rejection. The incoming generation can experience the existing structure as confinement.
And both can love each other deeply.
That’s where I think the human work becomes incredibly important. The answer can’t always be convincing the next generation to appreciate what the previous generation built. And it probably shouldn’t be burning down everything that came before either. There is wisdom in both. The work is learning to discern what remains useful and what has completed its purpose.
Human Design calls what comes next the Cross of the Sleeping Phoenix.
Again, I hold this as a lens, not a certainty. But I find its themes fascinating: individuality, inner authority, vitality, spirit and knowing what is correct for oneself.
That sounds beautiful. It can also sound terrifying if your entire model for keeping a family safe has been built around predictability. Because the question changes.
It isn’t only: How do we prepare the next generation to manage what we’ve built?
It becomes: How do we prepare humans to trust themselves in a world we cannot completely prepare them for?
That’s a different assignment.
NOT EVERYONE IN THE FAMILY IS SUPPOSED TO SEE WHAT YOU SEE
One person sees ten years ahead.
Another notices the risk everyone else missed.
Someone understands people. Someone understands capital. Someone needs enormous amounts of research before making a decision.
Someone else learns by touching the stove.
More than once.
Ha.
Families can waste enormous energy trying to make everyone process information the same way.
Maybe differentiation becomes an asset.
The goal isn’t getting everyone to think like the founder.
It’s helping each person understand how they know.
What is a real yes for me? What is fear? What is pressure? What belongs to someone else? What happens when I get it wrong? Can I recover? Can I change direction? Can I trust myself again?
That isn’t soft work.
I think it becomes increasingly valuable as the future becomes less predictable.
MAYBE WEALTH ISN’T ONLY ABOUT PRESERVING WHAT WORKED
For generations, wealth stewardship has understandably focused heavily on preservation. Protect the assets. Reduce unnecessary risk. Create structures. Diversify. Transfer wisely. Preserve optionality. All important. But I wonder if the next era asks families to think more expansively about what they’re actually preserving.
Because the greatest asset may not be the portfolio.
It may be a family full of differentiated humans capable of meeting a world their grandparents couldn’t have anticipated. Humans who know how to think. Discern. Collaborate. Experiment. Recover. Create. And trust themselves.
The future is unknown. It always has been.
We just built extraordinarily good systems that occasionally allowed us to forget that.
Maybe the next chapter isn’t about predicting what’s coming perfectly.
Maybe it’s about developing humans we trust to meet it.
Including ourselves.
That’s the kind of work I want to spend the next several decades thinking about.
Definitely not your VA.
With love and belief,
Jaime & Kevin
