Castles in the Air

In a family business, everyone at the table has already built a future. Most of them have never said it out loud.

Family members discuss the future of their business around an office table.

There is a word in Swedish and Norwegian that I first heard from my wife, and came to know well in my years in Sweden.

Luftslott.

A castle in the air.

Magnificent from a distance... towers, windows, light... but with nothing underneath to hold it up.

Most European languages have a version of it. Each one compares foolish or impossible dreams to fortresses built out of thin air.

Over the years, I have seen a great many of them. Most often around a family table.

Some years ago, I was asked to sit with a family preparing to pass on a business the father had spent forty years building.

Around the table were the parents, their three adult children, and the children's spouses.

Every one of them arrived with a future already built.

The father saw the business carrying on as it always had. The same name over the door. The same customers. One of his sons at the desk. And himself, still coming in most mornings, just to keep an eye on things.

His wife saw something else. For years she had been waiting for a life that did not revolve around the business. Travel. Time with the grandchildren. A husband who was finally home for dinner.

The son who worked in the business saw himself running it his own way. New markets. New partners. And a father who would, at last, let him make the decisions.

His brother and sister had built their lives elsewhere. Each assumed that whatever happened would be fair to them. Neither had asked what fair meant. No one had ever told them.

And the spouses had built castles of their own. Some together with their partners... a house, a school, a plan that quietly depended on how this conversation would end. Some on their own, in thoughts they had never shared, even at home.

Eight people.
More castles than chairs.
Each one beautiful. Each one built quietly, over years.

None of them had ever been described out loud.

Nobody sets out to build a luftslott. It is built from assumptions that are never checked. From hopes that feel too personal to say. And from silence, because raising the question might start a conversation no one wants to have.

So the castle grows. And the longer it stands, the more it feels like a promise.

Then succession arrives, and the castles meet.

That day, they met all at once. Positions hardened. Voices rose. Old hurts that had nothing to do with the business found their way into the room.

And I could see where it was heading. Not toward a bad agreement. Toward something far worse.

A family that might never sit around the same table again.
No holidays together.
Cousins growing up as strangers.
Grandchildren who would only hear stories about the other side of the family.

A family feud, built on castles in the air.

So I had to bring some reality into the room. I asked one question.

"What would have to happen for everyone here to be able to sit around the same table next holiday... and every holiday after that?"

It is a question I have learned to ask in rooms like this one.

The room went quiet.

For the first time that day, no one was talking about what they were owed. They were talking about what they could not bear to lose.

And underneath the castles, quieter things began to surface. A father afraid of becoming irrelevant in the company that carried his name. A mother who wanted, for once, to be chosen ahead of the business. A son who wanted to be trusted. A brother and sister who wanted to know they still belonged. Spouses who needed to know their own families' futures were safe.

None of that was in the shareholder agreement. How could it be?

This is where the Compass helps.

Clarity: to separate what has actually been said from what has only been assumed.
Curiosity: to ask about the future each person is picturing, before deciding who gets what.
Courage: to name the gap when the castles do not match.
Care: for the family as well as the business, because the family will still be gathering long after the papers are signed.

And Presence: to stay in the room when the castles begin to crack.

Henry David Thoreau once wrote: "If you have built castles in the air, your work need not be lost; that is where they should be. Now put the foundations under them."

That is what this family did.

Over many, many months, and a lot of difficult conversations, they worked together to build a strong foundation.

And on it, they could finally envision, and build, one castle.
One with rooms for everyone.

In a family, the foundation is the conversation.

Who you are is how you negotiate.
How you show up determines what happens next.

The conversations that matter most ask more of us than words alone can provide.
We need to have better conversations for a better world.

So here is a question to carry with you this week.

What future have you been imagining for someone you love... and have you ever described it to them out loud?

If this resonated, hit reply and tell me. I read every one. And please forward it to someone who needs to hear it.

— Howard

First published November 6, 2026 in True North, Howard's weekly newsletter. Read it on Substack.

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