Helping Families Flourish


Knowledge, skills and stories left behind create a treasured legacy

August 05, 2018 12:52 PM | Deleted user

A legacy is much more than the material wealth we leave behind upon our passing.  In this, the first in a series of articles, the authors help us adopt a broader view of a legacy: why legacy conversations are so important and how to begin the process.

Legacy Conversations That Matter:

How to Have Meaningful Legacy Conversations

Within Your Family Now

By Sue Rhomberg and John Paolini

This is the first of a series of blogs on how to have meaningful legacy conversations within your family.

I couldn’t believe my ears! Here was Uncle Leo – yes, that Uncle Leo – our just departed mother’s little brother, holding the rapt attention of all three dozen or so of our family and old friends in the room. In glorious disbelief, our collective eyes were wide open as he told one story after another about Mom and Dad, things we had definitely never heard before as our stunned glances at each other with each new tale confirmed. Until now, his role in our extended family seemed limited to saying things that embarrassed us all to no end. But here he was, at what was expected to be a somber memorial for our just departed mother, regaling us with stories about Mom and Dad. (Why did they never tell us these fascinating remembrances?)

Even after Dad died three years ago, Mom had never uttered a word about many of these events, stories that today had everyone in the room laughing hysterically – or, in a few instances, exclaiming in near horror. And, with uncles, aunts, cousins and old friends now excitedly recounting their own stories of our parents, my own brothers and our sister kept glancing at each other with mutual delight (and occasional disbelief) at how this supposedly sad occasion had evolved into a wonderful night of bonding and family discoveries that would surely change each of our views of the family in a profound way.

If you are a baby boomer, you may have experienced an evolution over time in how you think about what you will pass on to your children, your nieces and nephews, your grandchildren – and maybe even the generations beyond them. Without a doubt, part of the “what” is your accumulated wealth – in the form of hard assets such as investments, your home, personal property and the like. And for many readers those assets have already been dealt with by professionals who are skilled in the intricacies of investments, trusts, taxes and philanthropy.


What is legacy?

Legacy means different things to different people, and to some it is quite confusing. If you are like most people, your thoughts don’t just naturally go there. One of the questions that’s probably going through your mind is: “Why do I have to think or talk about my legacy? Won’t it just happen after I die based on how I’ve lived my life? But questions that might also be going through your mind probably include: What if I don’t think about it what is most likely to happen? What will be forgotten and never spoken of again? Am I comfortable with that?

So what is legacy really?

To bring things quickly into focus, we like to begin our discussion of legacy with two (rather simple) definitions:

  1. A gift by will, especially of money or personal property.
  1. Something received from an ancestor or a predecessor.

(Note: As the authors continue to discuss legacy issues, a distinct definition will be developed that will guide readers in generating and transacting for their own legacies. Follow us down the road to learn more.)

The first definition is, obviously, more legalistic. It’s what estate planning attorneys consider when drafting your will or trust documents. The second definition, by contrast, focuses on family history. Your history. It is your family’s history that informs you, your children and the generations that come after them. It includes an array of family trees, personal belongings and heirlooms, cultural heritage, and stories and lore that are passed along from one generation to the next. It is what guides, inspires, educates and gives meaning to the relationships that both constitute your history and shape your descendants’ future.

As you plan for the things that will matter beyond your lifetime, conversations about legacy become an increasingly valuable part of that planning – and of leaving things in good order.

What are legacy conversations and why do they matter?

What’s the difference between a legacy conversation and just a “plain old conversation” with your kids, your parents or your grandparents? Is it a conversation you should be thinking about? When should you be thinking about it?

In fact, it’s not the easiest thing to get started on.

In general, asking questions helps to get the ball rolling – and also helps you to understand something or someone better. At one level, legacy questions are designed to help you better understand and appreciate the people that are important to you. And they often become the basis for those wonderful stories you will share with your grandkids!

The first step isn’t as hard as you think: just start with a simple question or two. And suddenly you’re talking. YOU and THEM talking. Really talking about things that matter. Not like talking to your kids about what happened at school today or having the talk with them – you know, those awkward conversations of “growing up” and “doing the right thing.” It’s not asking grandma if she won at Bingo last night but instead asking her why she plays and what about it is fun for her.

How many of you are having meaningful conversations with the important people in your life? Regularly? Sometimes? At least a couple meaningful ones each year? Do you wish you were (or know you ought to be) having them more frequently?

Legacy conversations begin when people connect with who they are and what matters to them – and convey what matters by sharing not just their experiences and their stories but their feelings about those experiences and stories.

For some of the people who have had the greatest influence on your life – deceased grandparents or parents, for example – it’s already too late. But for many key people in our lives, it’s not too late to engage in these important conversations. They might even be waiting to be asked! The kids may care more about the great grandparents they never met if they could learn a little something about them. It’s all the same bloodline, and your similarities and traits have all been passed on in some way.

In our experience, people love to connect the dots about why they are the way they are and understand where some of it came from. Peace of mind may be the hidden gift that comes from just understanding it all a little bit better. Maybe you, as you read this, are realizing that you have stories that ought to be passed along and you are the only one who can tell them. If you don’t, who will?

Or maybe not – maybe you or the “elders” in your family are not thinking at all about legacy. You (or they) may feel they are just living an ordinary life like everybody else. “What’s so interesting about my life? I’m just your average guy/gal who goes to work every day, plays golf on the weekend and jokes with my grandkids.” “Haven’t I said it all already? What else do you want to know?

Food for thought: Have you ever asked your kids or grandkids if there is anything they would like you to talk about? Sometimes we overlook what we haven’t said yet – what we might think is routine or even boring – but that may be insightful and interesting for others to hear.

Where to begin?

We often begin legacy conversations with two basic questions: (1) “What does the word ‘legacy’ mean to you?”; and (2) “Is leaving a legacy important to you?” More often than not we find that we are soon asking, “Why?” The “why” (as long as it is asked neutrally and not taken as a confrontational question) gets at the heart of what people value, what experiences have shaped their lives and what motivates them to move forward. Without this, you will likely miss important aspects of who these people are deep inside – and they may not feel the need to move into action. Really knowing someone and the experience of being known is at the core of feeling connected as a human being – and granting someone the experience of being known is one of the greatest gifts you can give. The cherry on top is what you receive from the generosity of their sharing and your listening.

We love legacy conversations and we know that others do too. There is a richness to sharing and discovering what these questions unveil – about ourselves and where we’ve come from. It may also help, whether you are the storyteller or the story capturer, to answer a few of your own questions. As you talk or listen to stories, some sort of light bulb usually goes on!

Clearly, there are many more questions ahead; we’ve only begun to address some of them here. But hopefully we’ve raised new questions to ponder about why legacy conversations matter. Part of our rationale for writing Legacy Conversations in a serial format is to emphasize that these topics comprise an exploration that unfolds over time.

We look forward to guiding you as you embark on a journey of your own personal legacy – and your family’s legacy as well. We know it can influence the richness of your life and provide continuity to those in future generations. Enjoy your journey!

Here’s what’s ahead in our upcoming articles:

How do I prepare to have meaningful legacy conversations with my family? How do I even create the right environment to begin?

What values and traits from your ancestors are a part of your legacy? How do you think you will be remembered?

How do you want to be remembered? Issues around family businesses Achieving your philanthropic desires

and more

Sue Rhomberg is a legacy consultant who captures stories that celebrate life and build legacy and supports individuals and families in identifying and expressing their own personal and family legacies. Sue is also a member of the Chicago Trustee Collaboratory.

John Paolini is a wealth management consultant and certified executive coach who specializes in helping families articulate – and perpetuate – their legacies and the values that support their philanthropic activities.

The Chicago Trustee Collaboratory

Helping Families Flourish! The Chicago Trustee Collaboratory is a not-for-profit professional association helping families and their trusted advisors understand and manage their family trusts.

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