I’ve worked with numerous enterprising families in my decades of consulting. One of my favorite sayings is, “Family is tough enough on its own; when sharing a business or other complex wealth, it is a whole lot tougher and more complex.”

One of the (many) sources of that complexity, and one of the most powerful, is the long history that family members share. For better AND for worse (although humans have a tendency to pay special attention to pain). I’m confident that as current and former clients read this blog, many will think that it is about them. That is how common these themes are. You can rest assured that examples are artificial amalgams of dozens of clients—possibly even my own family! 😉

Commonly my work with families takes a detour into events of 20, 30, even 60 years ago! A discussion about fairness around how ownership should be divided, for example, can quickly devolve into a pre-teen experience around lawn-mowing, parents treating one child better or more unfairly than the others, or how the youngest—born and raised during the family’s financially comfortable years after lean years—was spoiled and got more than the older siblings did. I can think of circumstance after circumstance when tough history reared its head in the here-and-now.

Addiction (current or past), divorce, emotional and physical abuse all come into play at times—just like with families with few resources. The trick for enterprising families is to manage all this emotional complexity and history while balancing shared family ownership, leadership, and management of their assets.




LOOK INWARD at what you can change in yourself to improve tensions and heal relationships. It is so easy and common when tensions arise to look at what the other person is doing and to tell them what you believe they need to change. Looking inward before pointing fingers hopefully seems obvious, but is hard and takes intentionality. In my decades of experience, I have observed that the families in which members primarily focus inwardly on what they can change themselves have much better outcomes in terms of business/wealth endeavors and overall family harmony. Simple to say; hard to do.

I say this with all my experience as a family therapist, psychoanalyst, consultant to enterprising families, and a family member within my own family (that had some intense and incredibly helpful family therapy along the way): it is worth the emotional investment for family members to check themselves.

(And, of course, giving feedback is a crucial next step.)

WHEN THE TIME IS RIGHT, GIVE FEEDBACK WITH COMPASSION in order for it to be taken in, considered, and acted upon. I am aware this is not rocket science, and yet it is very difficult to pull off, especially when angry and filled with memories of hurt, unfairness, or worse. The overwhelming majority of people would likely agree that feedback given with sensitivity is significantly more likely to be received well and used for growth. So often feedback in families is given with weapons drawn. This can be sarcasm, harsh criticism which could have been given more gently, poor timing (when receiver of message is already upset or stressed and/or in front of others, causing humiliation), or by needlessly referencing old hurts, to name a few.

While going more deeply into the “how” of pulling off the above is more than a brief blog (meant to be read in a minute or two) can tackle, consider these options:

  • Try individual or family therapy
  • Work with a coach experienced in helping families learn to manage conflict
  • Find a book that speaks to you about managing difficult relationships, giving and receiving feedback, or healing old hurts

These basic rules of thumb are as powerful as they are simple to understand, all while offering an intense level of challenge to those who undertake mastery of them. The rewards reaped for undertaking such a challenge can be the beautiful fruition of family harmony integrated with family wealth in a way that serves the deeply held values of the family, both financial and non-financial.

My professional background includes having worked in my family’s commercial printing business, finding success in a sales/marketing career outside the family business, then training as a family therapist and psychoanalyst. The common theme throughout this unique set of experiences was developing my mastery of helping families dive deeply into emotional and relational dynamics so they could be healed, strengthened, and then meet the hard work of sharing assets and making key decisions related to the leadership and management of those assets, as well as developing the next generation to run with it all in the future.

It takes tending to all of these complex dynamics at once to meet the challenge of family history and family business with open hearts and clear heads.