Leave a Legacy

Loaded Words


Leaving a legacy.

Your legacy.

What a loaded finance word, right? We know it has depth and meaning, but we don’t always really know what it looks like practically.

From a Friend’s Perspective

Let me start with a story, a story I’m quite familiar with.  This is a story about my best friend.  Honestly, he’s more of a brother than a friend, we just don’t share DNA.

It was nearly two decades ago that we met, and we were in similar stages of life.  We were at an age where we still felt like we were kids, yet in a technical sense, the world considered us adults.  So, we were just trying to figure out what “adulting” looked like.  Both of us had aspirations of a career, family, and the like, but we lacked the specific direction or clarity of what exactly that would look like.

We were roommates at the time. I remember leaving the house one day and telling him that I thought I’d like to go back to school to study finance.  He chuckled a bit and asked, “Why?” Nothing of my past – interests or experience – would lead anyone to believe this was the direction I’d choose.  Yet, here we are today.  My friend, on the other hand, decided that he wanted to follow in his father’s footsteps and work in the family business.

I had a front-row seat for this season of life, and I can tell you that he wasn’t choosing the easy path.  His motivation wasn’t simply to take over the family business.  His dad was a great provider, had built an incredible business, and had an impressive reputation in the industry he served.  Yet, the physical toll of the labor wasn’t ideal for his age and stage of life.  My friend showed up when his dad needed him; what he did was honorable.  I watched him do the grueling commute daily, I saw him put in the long hours, and I was there when he’d work some days until 2:00 a.m.  His assessment of all of this? He embraced it.  He loved the quality time he had with his dad – whether that was in the midst of a project or a traffic jam.  This is a quality/desire that I can only pray my boys will imitate.

In the blink of an eye, his dad is now retired, they navigated a sale of the business from one generation to the next, and my dear friend leads a flourishing enterprise.  What was once a one-man show – an employee count of one – is now a business that employs 24 individuals.  Behind these employees are spouses, children, and families that glean from this flourishing.  This was always the dream of my friend that this business would expand its impact and influence.

From Good to Great

So, what does this all mean? Why share this account? I share this because this was my first exposure to what legacy actually looks like.  This was the rare case where the second generation built upon the foundation that was laid by the first generation.  Nothing was squandered.  Where we typically find atrophy, we saw a strengthening.  The quality and reach of the business did not deteriorate. Instead, it was taken from good to great.

Legacy should be important to you.  Unfortunately, what I described above is often the exception, not the rule.  Countless studies will lead you to the same conclusion – most often, the second generation destroys and squanders wealth.  Sure, you could simply conclude that since they didn’t earn it, they won’t revere it.  This line of thinking gives you an easy out because then it’s just an inevitability that legacy is fiction.  Yet, I know it’s not.  I’ve seen it firsthand, and I know it’s not easy, but it is possible.  It takes awareness and intentionality.

So, let’s dive in; let’s discuss the steps to leaving a legacy.

(1) Give them wisdom.

Whether your kids are toddlers, teenagers, or mid-lifers, they need wisdom.  Wisdom is the knowledge and experience you’ve accumulated over time.  You need to look for opportunities on how to deliver this wisdom.  There will be those opportune moments where your words of wisdom will be the exact puzzle piece your children are in search of.

It all starts with a relationship.  Regular engagement and conversation (1) builds trust and (2) gives you visibility on where they are at.  You obviously will need to meet them where they are at, and the weight of the wisdom you deliver will need to be commensurate with their maturity – their ability to carry that truth.

My best friend’s father taught him the craft, the mechanics of the business, and, most importantly, how to treat customers in a manner that builds a lasting reputation.  He left a legacy, and it all started with passing down wisdom.

(2) Give them Seeds.

Give them seeds, but not an orchard.

My friend spent much of his beginning years in the business doing grunt work.  His sweat and efforts probably greatly outweighed his compensation.  This was good for him; this is a needed ingredient for leaving a legacy.

I remember hearing an executive from the privately held company, In-N-Out, speak about their people strategy.  He said, “Everyone starts in fries.”  He talked about even the heir apparent to the business starting from an entry-level position.  This was their example of giving a seed (of responsibility), not the orchard.

Why? It’s the journey that builds character, and when wealth or responsibility outpace character, it never ends well.

(3) Give them Autonomy.

Don’t be a helicopter parent.

Allow room for failure.  Part of leaving a legacy is casting vision while letting the next generation forge the path.

If the next generation always uses you as a safety net – financially, physically, or mentally – then they will never have the strength to carry the torch on their own.  Autonomy builds resilience, confidence, and competency.

Give them space; give them autonomy.

(4) Give them Guidance.

This may seem counter to my last point, but hear me out.

Let me add an adjective here, and we will call this Socratic Guidance.  Yes, I don’t want you to helicopter and tell the next generation what to do, but I do want you to ask them thought-provoking questions.  I want you to help guide them through their own thinking.

At this stage, I want questions, not comments.  “What led you to that conclusion?” “What obstacles might you face?” “What resources will you need?”

They have the answers in there somewhere, you just need to help them surface.

(5) Develop them.

To me, this last step/stage is all of our calling.  This is a lifelong endeavor.  Yes, if your son or daughter is 70 years old, I am absolutely saying that you should continue to help them develop.  None of us are perfect, nor will we ever be, so there is always an opportunity for us to sharpen one another.

What does this practically look like? I’ve heard some describe it as the ability to deliver both grace and truth.  Always holding these two realities in tension.  I want to frame this a bit differently.  To develop the next generation, I want you to (1) encourage and (2) correct.  Look for gifting and strength, encourage these qualities, and use words of affirmation to do so.  Most of us are comfortable with that side of the coin, yet we really don’t exercise the art of encouragement enough.  It’s the other lever that we shy away from pulling.  Whether you want to call it feedback, constructive criticism, or correction, I don’t have a strong opinion.  I simply want you to operate in candor and know that correction is part of the development process.  A relationship steeped in trust can shoulder this type of feedback.

Remember, they are called blind spots for a reason.  We need another set of eyes, we need another vantage point to really help us develop into our full potential.

So, if your legacy matters to you, then commit to always helping to develop the next generation.

A Beautiful Legacy

If you saw my friend’s business today, you might find it interesting, you might even find it fascinating.  Perhaps you’d marvel at the growth and achievements they’ve accomplished.  Yet, you wouldn’t see the beauty that I do.  You just didn’t have that same front-row seat that I did.  This is legacy.  This is what we should aspire to.  The echoes of our voice, leadership, and decisions should reverberate through the next generation.  This is the goal, and as stated above, those are the steps.

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About the Author

Trevor Cummings

Private Wealth Advisor, Partner

Trevor is a Partner and Director of our Private Wealth Advisor Group.

As the author of TOM [Thoughts On Money], Trevor endeavors to write and speak about financial concepts and principles in a kind of “straight” talk demeanor and posture.

He received his Bachelor’s degree in Organizational Leadership from Biola University and his MBA from California State University, Fullerton.


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