Bringing Mentoring Back to Legacy Planning

By Peter Johnson

Even now, I feel vulnerable and embarrassed sharing the following story. It’s a painful legacy to recall.

In the early ‘70s, I was a young man living in Los Angeles with a vague dream of making a living in the music business. I was a junior college dropout from an upper middle-class family, drifting. Then, boom! On my 21st birthday, I received a trust, valued at $130,000 (or a little over $750,000 in today’s dollars). At the time, I hadn’t had any mentoring or preparation whatsoever in money. What do you suppose happened?

Yes, some very predictable things occurred. I continued to avoid real work or a formal education for a few years. I tinkered at being a music producer and invested a little in a growing music studio. But mostly I stayed up late, partied, and avoided facing life head-on. In addition, some other, less-expected things happened. Some of my closest friends grew distant, angry with me for having money when they didn’t. I also discovered that I didn’t have the ability to say no when people asked me for money — even people I didn’t particularly like or trust. My phone rang constantly with people asking for loans. It was a very lonely time.

Eventually, my story had a happy ending: the money ran out, and I was fortunate enough to be able to return to college and find a career I love.

Here’s what now strikes me as exceedingly odd, which informs my life’s work. Although there must have been a reason, an aspiration, a hope for what this money could mean in my life, no one ever talked to me about it. Not. One. Peep. No one sat me down and asked basic questions of me — questions like “What difference could this trust fund make in your life?” or “How long do you think the money will last?” No one said, “Here are some of the things you can expect other people to say or do, and here’s how you can handle that.” What was missing was mentoring.

The Shadow Legacy™

The point is, I inherited a legacy of unintended consequences. A human legacy that typical estate and gift planning often doesn’t account for. A yawning chasm between intention and outcome. Unforeseen, damaging, and all too common. I inherited a Shadow Legacy.

The term shadow was used by the famed psychologist Carl G. Jung to describe the repressed or denied part of the self. But in this work, I use the term shadow to describe “the unconscious or denied aspects of our impact on others as it applies to our legacy.” It’s our blind spot.

Now, let’s zoom out to the bigger picture. My trust fund story is but one small example of a shadow legacy. The issues are compounded when a death occurs and multiple heirs are involved. Then wealth and precious family relationships can be at risk. Estate documents alone can never replace engagement, communication, and mentoring. Talk to any estate planning attorney, and she can share countless examples of failed legacy: families torn apart over mistrust, fear, greed, unresolved childhood issues, and yes, even over the cherished clock on the mantle. It’s such a common occurrence that most of us have personally seen instances of it, whether in our own lives or in the lives of our friends and acquaintances. The suffering it creates often has a lasting impact on individuals, inherited wealth and relationships.

But the term failed legacy is a misnomer. There was and is a legacy, all right, just not the one which was originally intended. Rather, legacies are entirely consistent with the foundation laid through years of interactions and experience, and not primarily the result of a handful of estate documents, or the wishes behind those documents.

Bringing Light to the Shadow

The good news is that shadows dissipate quickly in the light. Unintended suffering can be ameliorated or avoided more easily than you might imagine. The moment that I became aware that mentoring was the crucial element missing in my own painful financial journey — as well as my siblings’ journeys — my life took a dramatic turn, both personally and professionally. My shame was replaced with the desire to help families build powerful, sustainable legacies through connection and preparation.

It’s important to take a moment to reflect on what mentoring is. At its best, mentoring provides intellectual and emotional support, and gives mentees a safe place to turn with questions. It’s not about imperious lecturing or the conveyance of pedantic facts. It’s about discovery, and drawing out the gifts of those being mentored. It’s a journey of encouragement that is accepting of mistakes and stumbles.

Specifically, if I were mentoring the young man I used to be, I would explore the following:

  • I would have the family benefactors share, in their own words, their intentions behind the gift. This is a significant opportunity to convey heartfelt values and to paint an aspirational picture, deepening family connection.
  • I would explain that this is an opportunity to learn how to handle money, including knowledge and skills that will be useful for a lifetime.
  • As I have done for so many clients, I would graphically show how long the money might last at different spending rates (including taxes and inflation). This is often an eye-opener and always useful in terms of getting a sense of the bigger picture.
  • I would ask my mentee to identify and prioritize possible life goals, and to consider how the money might be used to achieve them, with the understanding that goals and priorities will change over time.
  • Finally, if the inheritance or gift were of adequate size, I would recommend hiring a hands-on, fiduciary financial planner who has a passion for coaching, to work with the beneficiary over time.

Now Is the Time

In speaking with many families, I have found that there is resistance to engagement with other family members and having conversations about estates and legacy. Families are bogged down by cynicism, resignation, and a lack of urgency. But there are people, processes and structures that can be highly effective in bringing families together to create compelling shared visions and possibilities, and, when necessary, to work out estate conflicts successfully. There are almost countless ways to build intergenerational trust, wisdom, and connection. What successful legacy requires is awareness, communication, trust, and support. Engagement is not transactional; it is transformational. It’s an opportunity for creativity, joy, and regeneration.

Families fail to pass wealth on successfully because they fail to address the human element in estate planning effectively. Enormous potential is missed. Without the requisite skills and context, money can easily wind up being detrimental to inheritors. Mentoring is essential. Fortunately, this work doesn’t have to be hard. And it’s never too late. Get help if you need it. Professionals who may be able to help include estate planning attorneys, mediators, Collaborative Practice professionals, family meeting facilitators, family business consultants, trustees and financial planners.

Just being aware that we all have a Shadow Legacy is a beginning. We have some time, now to make a difference. Our legacies ripple out and touch others in countless ways, and for generations to come. Imagine what a clear focus on our actual legacies could mean for our families, our descendants, the larger community, and yes, for us. We’re not meant to do life alone. Family is one our greatest opportunities in this life to suffer, or to thrive.

We’re all ancestors in training. What legacy will you leave?

For more articles on legacy planning, click here to subscribe to Legacy Arts Magazine.

07 Peter Johnson headshotPeter Johnson works with families to unlock potential and create sustainable legacies. Where appropriate, his work incorporates interdisciplinary teamwork, as well as nature connection, to provide the deepest and most meaningful family experiences possible. He is a pioneer in Collaborative Practice Trusts & Estates and is a member of The Purposeful Planning Institute. Peter has run a successful wealth advisory business for over 25 years. Learn more at and Peter can be reached at