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Legacy Planning: A Fool's Advice and a Knave's Rebuttal

Legacy Planning Process: Who is a stakeholder? Who is heard? Who is talked about in absentia? Who speaks for whom? Who makes decisions on whose behalf? Who lives with those decisions after the fact?

Stakeholders: Parents, children, grandchildren, generations unborn; nonprofits and society at large; living creatures large and small; those employed by or customers and constituents of family controlled entities (businesses, trusts, foundations, lobbying arms, newspapers, think tanks, social ventures, nonprofits, governmental entities, oval offices, moats, and dungeons); the attorney, CPA, trust officer, insurance professional, financial advisor, family psychologist, philanthropic consultant, fundraiser, religious and moral advisors.

Scope of The Wealthy Family's Vision, Mission, Strategies, Tools, Tactics, Implementation
: Personal wealth and personal time and talent; family wealth time and talent; connections, board positions, "pull";  societal needs; the capacities of others to be led, mobilized, activated, or deluded whether within hierarchies, publics, or lattice structures of friends and  friends of friends (movements, cabals, private societies, taste making, trend-setting, heroism).

The Dynastic Dance: In the dance of the elements above who leads and who follows over what range and in what order?

  • Who leads as to the vision of a better life for the family, of better family members (more fully developed as ethical, capable and engaged human beings) in a better world for all?
  • Who is heard when the wealth is set up for the children? Are they?
  • Who speaks for the complexity of the plan, and how all the entities and tools will be managed?
  • Who visualizes and scripts the ongoing family chronicle, the story of the family and its origins and ends?
  • Who works across the generations, and the silos of expertise, to make the plan, like a Constitution, a living tradition?
  • Who governs and manages the ongoing work of the plan, and the entities it controls?

Leverage Points For Social and Family Good


  • Advisors who say, "Whatever you want, Boss, I am here to serve" are necessary, like soldiers whether in the army or the mob, but they are not to control the process of setting the vision, the tone, the spirit, the meaning or the purpose.  They may call themselves "Trusted Advisor" and compare themselves to Richelieu, but they are Toadies all the same, unless they challenge as well as serve the vision.
  • Parents who make decisions as to vision, goals, end results wanted, without consultation with their own better angel, without consultation with other stakeholders, such as children employees, nonprofits of importance to the family, and fellow citizens.
  • Advisors, heirs, and others who seek to win at the other's expense, jockeying for power, wealth, access, and control as in the court of the Medicis.


  • Clients and advisors who see giving as a tool or technique of tax reduction, and never get around to talking about social purpose and effect.
  • Trusted Advisors who thoughtfully elicit but never challenge vision and values. ("Values-neutral values-based planners.")
  • Fundraisers and planned giving officers who extract cash and assets for social good without knowledge of, interest in, or concern for, the larger plan of which the giving is a part.
  • Moral and religious professional advisors who preach a general sermon, then bow on the church steps and shake the wealthy parishioner's hand, or invite the wealth holder to a private supper to discuss the vestry committee and its works, leaving any particular discussion of the donor's morals aside.


  • Parents who include children and other stakeholders early in the process to help crystalize the vision.
  • Advisors who convene rather than control, who listen for vision, not just opportunities for this or that tool or planning technique.
  • Advisors who work as a team, keeping one another informed within a sense of common purpose.
  • Advisors who have the courage and skill to play devil's advocate, or Socratic questioner, around an emerging vision that is shallow, half considered, or riven with contradictions, family dysfunction, and vanities.
  • Nonprofits who have an effect at the vision level, not just around a gift, but around a sense of what it is for the family to live a good, ethical, or noble life, within a good or just society within a thriving natural world.
  • Children who do their own planning well, and ask parents if they can be included in the larger family planning sessions at least as to goals. (" But Dad we would rather have a foundation get that money.....")
  • Fools who turn the world upside down, if only by aping the advisors with their long faces, long ears, and long tails.

My Own Tutor's Rebuttal

Well, I showed this post to my mentor, the Happy Tutor, Dungeon Master to the Stars, over in Wealth Bondage, America's Most Wonderful Company. I wanted to make sure that this post was not offensive in any way to the higher ups. I don't want Candidia, our mutual boss, to be upset with me. I need a job and I need the money, such as it is.  Teaching philanthropy may be a load of crap, but it sure beats loading body parts into the freezer in the Chill Room.  Tutor's comment was, "Never send a Fool to  do a  Sadist's job, Phil. Send those wealthy sons of bitches over here and I will beat into their bottoms what you fail to drive into their numb skulls." Tutor was drunk at the time, and it is probably unfair to quote him out of context -  a Dumpster full of Garbage where he holds court, naked and unashamed on his own time, after work.

Closing Comment to My Fellow Professionals in Wealth Bondage

We can't save the wealthy from themselves, contrary to what Tutor may think. But we can get rich off them, and escape a beating ourselves, if you follow my advice above. Moderation all things. If you get too idealistic you are setting yourself up to fail. It is not our decision whether the client wants to save the world, rule it, or destroy it. Give the customer what the customer wants, make a ton of money, and give your own opinion, when it is less risky to do so. Now, back to work, there is a fresh load of body parts down on the loading dock.  Get it cleaned up fast. The motorcade from DC is arrives in 30 minutes. We got a Dynasty to plan here folks.

Managing Investments, Managing Relationships

Take a quick glance here, at Private Wealth Management, and their lead article/puff piece on Bessemer Trust: Managing Investments, Managing Relationships. If these men in suits were managing your multi-generational family's money, and managing the relationships with your family's decision makers, and with you, and if they were guiding not only your allowance, but your philanthropy, how would you feel? And what would you do to shake things up? I am not sure where true social change will start, but not with these fellas, managing investments, managing relationships.  But in what sense is it your money, not theirs?  To what extent should you be managing the money and the relationships with those who manage it for you?  They won't, I suspect, be eager to have you take the lead, nor may your parents.  If you feel sullen, demoralized, dizzy when you think of your money, maybe it is not you. Maybe dizzy or foggy is fine. Maybe that keeps you where you need to be - passive and in the dark. If you are inclined to lead, you are not alone. Happy to introduce you to The Happy Tutor, Dungeon Master to the Stars at Wealth Bondage. He is incorrigible. I, on the other hand, like the fellas in the photo, just want to be a good steward of your family's resources, manging the money and managing you.

Tracy Gary comes from such a background, a family who would make good Bessemer prospects. She  got herself unmanaged years ago. She and I are working on helping heirs and others to lead or partner in the dance of advisors, donors, and nonprofits. Check Appendix A for a taste. But it starts with you, with your getting clear on who you are, the roles you want to play in life, and how you want to affect the world for the better. That comes down to conversation, reading, experimentation, and reflection. To the extent you can master this art of leading from within such a complex closely guarded context, you more than most of us, can make the saving difference.