The Family.Inc Newsletter

Newsletter No. 3 – January 26th, 2024
Written by a human. 

“My happiness grows in direct proportion to my acceptance, and in inverse proportion to my expectations.”

Frustration (F) is the result of our perceived (p) reality (R) falling short of our expectations (E.)

Every frustration you experience, from your relationships to your evening commute, stem from this imbalance.

When I was growing up, I showed an interest in going into the family business. I was going to be a cheese man like my father and his father before him. I even dressed as a businessman for Halloween one year, bespeckled and briefcase in hand. I was like the Alex P. Keaton of Plymouth, WI.

However, as I got older, I started wrestling with internal competing interests that didn’t align with this younger version of myself, a self I was still projecting for the seeming appeasement of others. For example, I was quietly nurturing an interest in religious life as a Catholic priest. And, on the other side of the spectrum, I also found I had a remarkably persistent entrepreneurial bug I couldn’t swat away.

When I started living for myself and expressing my interests in the form of the decisions I was making, I know I frustrated those people whose expectations for me did not align with the reality that was playing out before them.

What happened to the cheese man? Their reality (for Josh) didn’t align with their expectations. Simultaneously, I was frustrated by what I saw as a lack of unconditional support; my expectations for approval and encouragement didn’t align with the reality I was experiencing.

I highlight this personal example as I see threads of it in all the work I do with families-in-business. The delta between expectations and reality can cause immense strain on a family system.

So, how do you bridge this difference?

Start by building trust and communicating.

For example, I could have better aligned others’ expectations if I had communicated the fact that the Alex P. Keaton of my younger years had grown up and his aspirations had evolved.

Simultaneously, a precondition for this communication was (me) trusting that it would have been received with grace, warmth, and understanding.

Take two minutes and explore your relationship with the equation.

  • Where in your family system is there frustration?
  • How are you minimizing the difference between expectations and reality?
  • Are you building the conditions for clear, open, and honest communication?


– Josh Gentine

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