Stone by Stone: Lessons in Leadership and Grit from My Grandparents

In the legal profession, we talk a lot about innovation, fresh ideas, and staying ahead of the curve. All of that is important.

But sometimes the most powerful lessons don’t come from what’s new - they come from the people who’ve already walked the path before us. Mentors, colleagues, family members, community leaders … their wisdom has a way of grounding us in what truly matters.

With Grandparents Day this weekend (Sunday, September 7), I’ve been thinking about those lessons in a more personal way. It’s a gentle reminder to reach out to your grandparents if you’re fortunate enough to still have them or to take a moment to remember the people whose guidance and example shaped your life. (I have some “bonus grandparents” in my life and the lives of my children, and I sent them a card, too.)

For me, that’s my Grandma Bennett. She’ll turn 93 this year, and I get to spend time with her this weekend at my cousin’s wedding. Every time I’m with her, I’m reminded of resilience, grit, and the importance of keeping both hands on the work in front of you.

When Grandma and Grandpa were just out of high school in the same small town in northern Illinois where I grew up, they married and started their family right away with two of their five children coming in the first couple of years of their life as a married couple.

Starting from nothing, they decided to take a leap into the rock and quarry business, taking a huge risk in taking out loans to buy land, equipment, end loaders, etc. (My first job full-time summer job as a teenager was weighing semi-trucks full of rock at those quarries.)

Grandpa worked from sunup to sundown - literally building a business stone by stone - while Grandma raised five kids and ran a hair salon out of the front room of their house to help support the family until the quarry became profitable. 

It wasn’t glamorous. It was exhausting. And yet, it was also deeply inspiring. Through hard work and sheer tenacity, they eventually built a thriving business that still exists today and is run by my uncles. Their belief in themselves, their clear vision, and their hard work made the seemingly impossible a reality.

Later, they built their dream home, where Grandma still lives independently at almost 93 years old (Grandpa passed away several years ago). And to this day, she tends her garden daily, keeps the house organized and beautifully decorated, and moves and thinks with an energy that amazes us all!

Lessons from Grandma Bennett (and those who came before us)

1. Hard work matters. Success rarely comes quickly. It’s the daily commitment - showing up again and again - that builds something lasting.

In practice: Legal skills, reputations, and trusted client relationships are built the same way - over time, through steady, consistent effort.

 2. Tenacity pays off. Challenges will always come. The real test is whether you keep going.

In practice: The lawyers and professionals who build long, meaningful careers aren’t the ones who never stumble. They’re the ones who keep moving forward when it gets hard, asking for help when and where they can.

 3. Resourcefulness creates resilience. Grandma’s salon wasn’t fancy, but it kept the family going until the quarry could stand on its own.

In practice: In the legal world, creativity and flexibility - whether in managing matters, solving client problems, or balancing priorities - are what keep us steady when pressure rises.

 4. Growth takes patience. Just like Grandma’s garden, success takes nurturing, tending, and time.

In practice: Professional growth and organizational culture both flourish when we give them consistent care and attention, not quick fixes.

 5. Well-being is cultivated. For Grandma, her garden is more than flowers. It’s joy, ritual, and a way of caring for herself and her world. Grandpa and Grandma taught us to balance the hard work with regular moments and breaks for appreciating beauty, resting, traveling, being in nature, and enjoying family.

In practice: Well-being in our profession works the same way. It isn’t a box to check once and for all. It’s something we cultivate daily through tending to our brains and bodies, taking time to recover, and investing in the relationships and habits that help us thrive personally and professionally.

The Bigger Lesson: Learning from Others Ahead of Us on the Journey

Grandparents Day is a perfect reminder that we don’t have to figure everything out alone.

Whether in our families or in our legal organizations, there is enormous value in learning from those who came before us - like our grandparents, our mentors, and others who have walked a path before us. Their stories, insights, and examples can guide us toward building careers and lives that are not only successful, but also sustainable, caring, and full of meaning.

So this weekend, I encourage you to pause and reflect: 

Whose wisdom are you carrying forward? 

How can you honor that wisdom, not just by remembering it, but by living it in the way you practice law, lead others, show up for those you care about, and shape your own well-being?

(And don’t forget to send a card/text or call your grandparents (or someone who has played that role for you) - just to let you know you’re thinking of them! ♥️ )

Recommended Resources

[Article] Learning from Past Generations | Psychology Today

[Video] Cinthia Manuel: Why is Mentoring Backwards? | TED Talk

[Article] Five Ways to Tap Into Other People’s Wisdom | Greater Good Magazine | The Greater Good Science Center at the University of California, Berkeley