Over the last 15 years, I’ve written a lot of words.
Words shaped by work and leadership challenges.
Words that grew out of quiet reflection or things that caught my attention at just the right moment.
Many of them were also shaped by family, faith, mistakes, and moments that stayed with me longer than I expected.
More than a few people have suggested I start a podcast. They’d tell me it’s a lot easier to listen than it is to keep up with a bunch of new reading assignments each week.
While my mom was still alive and living with significant vision loss from macular degeneration, I gave the idea serious thought. Listening would have been the only practical way for her to “read” my posts.
Unfortunately, that “serious thought” didn’t turn into action in time for her to benefit.
Ironically, for someone who usually believes in starting, then figuring things out along the way, I let all the steps required to set up a podcast get in the way of beginning.
Until now.
So today, I’m launching a new podcast:
Grandpa Bob Encouraging Leadership
This podcast is a series of short reflections on leadership, life, and learning. I’m sharing them first and foremost with my grandchildren…and with anyone else who might be listening in.
The episodes are intentionally brief, thoughtful, and unhurried.
They’re the kind of reflections you can listen to on a walk, during a quiet drive, or at the start or end of your day.
They’re meant to create space, not fill it.
Who it’s for
At its heart, this podcast is for my grandkids.
Someday, years from now, I want them to be able to hear my voice and know what mattered to me.
The things I noticed. What I learned the hard way. What I hope they carry with them as they find their own way in the world.
But leadership lessons rarely belong to just one audience.
So, if you’re listening, as a parent, a leader, a teacher, or simply someone trying to live well, you’re welcome here too.
What we’ll talk about
Each episode explores a simple idea. Here are some examples:
-Showing up when progress feels slow
-Letting go of certainty
-Choosing gratitude over entitlement
-Learning to wait without drifting
-Leading with trust, humility, and patience
-Paying attention to what’s quietly shaping us
There won’t be hype. There won’t be slogans. There certainly won’t be any fancy edits.
I’ll discuss questions worth talking about, and observations a loving grandfather hopes to pass along to his grandkids.
An invitation
You can find Grandpa Bob Encouraging Leadership wherever you listen to podcasts.
Don’t worry if you can’t listen to every episode.
Please feel free to disagree with anything I say. I don’t have a monopoly on the right answers.
If even one episode helps you pause, notice something new, or steady yourself a little, then it’s doing what it was meant to do.
Thanks for listening.
And if you’re one of my grandkids reading this someday, know that I believe in you and I’m always rooting for you.
If you’re listening alongside them, the same is true for you.
“There is no Frigate like a Book / To take us Lands away.”
Emily Dickinson wrote these words in her quiet room, understanding something I didn’t grasp for decades. The greatest journeys begin within.
I know her poem only because of my 11th grade AP English teacher, Mr. Cox. As a rambunctious and cocky 11th grader, would I have taken any of my “super valuable” time to read poems, sonnets, short stories, even books? No way.
But because of his work (and the work of countless other teachers along the way), I did read. A lot. I learned tons of material and information that didn’t matter to me at the time…but matter a lot today.
My focus back then was simple. Be the best student, get the highest test scores, pass as many AP tests as possible, and earn varsity letters in multiple sports. Mostly, I wanted to beat everyone else, pure and simple. It helped that I was blessed with an almost photographic memory and could recall facts and formulas with ease (sadly, not so much nowadays).
I carried that mindset into college. I loved being the student who defined the grading curve for the class. I was annoyed if I didn’t get every single point on an assignment, midterm, or final. I had an almost uncontrollable drive to outshine everyone…as if that was all that mattered.
I was completely wrong.
On the bright side, that drive and motivation made me a successful student and propelled me into my early career.
On the other hand, seeing everyone as my competition, and less as people, meant I probably missed out on a lot of fun. And lots of friendships that never happened. I was so focused on the destination that I forgot to notice who was traveling with me.
That realization connects me back to Dickinson’s frigate in ways I never expected. She saw the book as a vessel capable of carrying anyone, anywhere, without cost or permission. But what I’ve learned over nearly fifty years since high school is that I was asking the wrong question. It was never “How far can I go?” It was “Who am I becoming, and who’s helping me understand?”
My journey from that hyper-competitive teenager to what I hope is a much more caring, thoughtful, empathetic, nuanced, and life-giving person has been propelled by those same teachers I mentioned earlier, and a longer line of guides who keep showing up at the right time in my life.
I didn’t realize it then, but those books, poems, and teachers were all part of my fleet of frigates. Each one quietly helped me close the distance between knowledge and understanding, between my ambition and wisdom.
My mentors, family, and friends have all been vessels that carried me through changing seas. Some taught me to sail straight into the wind. Others reminded me that drifting for a while can be part of my journey as well. Each lesson mattered, even the ones that didn’t make sense at the time…especially those.
Over time, life has a way of sanding down our sharper edges, revealing something deeper underneath. My focus slowly shifted from being the best at something to becoming the best version of myself.
Now, when I think about Emily Dickinson’s frigate, I picture something far greater than a book. I picture a lifetime of learning, carried by the people who invested their time, wisdom, and patience in me. Mr. Cox, and others who gave freely of their time and wisdom, helped me see that the destination isn’t solely becoming the top of the class. It’s finding a profound depth of understanding, the expansion of empathy, and the ability to see beauty and meaning in small, unexpected places.
If I could go back and talk to that 16-year-old version of myself, I’d tell him the real tests aren’t scored on paper. They’re graded every day in how we treat people, how we listen, and how we show grace.
I’d tell him that the frigate he thinks he’s steering alone has always been guided by grace. The true measure of his voyage will be how much space he makes for others to come aboard.
We’re all learning to sail, carried by the steady hand of God.
Writing a song is like fishing, Kenny Chesney once said. Some days you catch something beautiful. The melody, the moment, the truth. Other days, you sit there all day with nothing but frustration and a stubborn belief that it’s still worth being out there.
That kind of wisdom transcends genres. Ernest Hemingway spent his life circling the same idea. That real art happens when we show up. Whether facing a blank page, a marlin that wouldn’t bite, or a battle that couldn’t be won, he believed the only way to live fully was to move, to act, to engage.
His work embodied a simple truth. The shortest answer is doing the thing. For him, wisdom wasn’t found in thinking about life, but in living it. No clever phrasing. No shortcuts. Just the act itself. Simple, honest, alive.
We spend so much of life thinking about what we might do, planning what we should do, waiting until we feel ready to begin. But readiness rarely arrives on its own. The line stays slack until you cast it. The song stays silent until you play it. The story remains untold until you write it.
Sometimes we catch something incredible. Other times, nothing.
Either way, we were there. Present. Awake. Participating in the work and wonder of life.
Maybe that’s the whole point.
A life well-lived must first be lived.
Photo by Shojol Islam on Unsplash – I wonder if he’ll catch something on this cast. Maybe. Maybe not. But, he’s in the game, giving it his best shot and that’s what matters.
I saw The Secret Life of Walter Mitty on an airplane ride recently. At a significant moment in the story, we hear the line, “Beautiful things don’t ask for attention.”
The photographer in the story chooses not to take a coveted photo of the elusive snow leopard. Instead, he simply enjoys the beautiful moment with his own eyes.
Real beauty doesn’t need to perform. It’s authentic and humble, whether anyone stops to notice or not.
A person of character lives this way. They have no need to prove themselves. They show up with kindness, consistency, and honesty. The neighbor who shovels snow from an elderly woman’s driveway before dawn, leaving no trace. Or the teacher who stays late to help a struggling student, never mentioning it to anyone.
The beauty of their character reveals itself in the way they live each day.
Humility makes this possible. It allows a life to shine without glare, to influence others by being genuine. Like mountains that reflect the glow of sunrise or wildflowers blooming unseen in a meadow, people of quiet integrity embody a beauty that doesn’t depend on recognition.
In our culture that rewards noise and spectacle, this is easy to forget. We’re told to broadcast accomplishments and measure our worth by attention. Yet the most meaningful lives belong to those who live true to themselves, free from the need for applause.
The things that endure, whether in people or in nature, carry their beauty without fanfare. They simply are.
There’s a paradox in writing about something that exists most powerfully in silence. Maybe that’s the point. Celebrating this kind of beauty without claiming it for ourselves.
But we can learn to recognize it. To be shaped and inspired by it. And, in our quieter moments, we can strive to live it.
Photo by Patrick Schaudel on Unsplash – some of my fondest memories involve waking up in a tent on crisp mountain mornings, basking in the beautiful glow of the rising sun.
I recently turned 59. Not the big 60 milestone but knocking on the door. In honor of this “almost-milestone” birthday, here are 59 lessons or truths I’ve picked up along the way that may be helpful for you:
Family is the greatest treasure. I’ve learned this from countless dinners, phone calls, and quiet moments of simply being together.
Love grows when you give it away.
Small kindnesses matter more than big speeches. Holding a door, writing a note, or showing up means more than most people will admit.
A campfire has a way of pulling people closer. Some of our best conversations happened with smoke in our face and stars overhead.
Walks in the woods teach patience. The trail never hurries, but it always leads you somewhere good, even if the trail leads back to where you started.
Listening is often better than speaking.
Start, even if you don’t know the finish line.
Forgiveness frees the forgiver.
Work hard, but not so hard you miss the laughter at the dinner table. That laughter is life fuel.
Friendships need tending like gardens.
A calm mind shapes a calm day. How you manage your thoughts sets the tone for how you live, not just how you lead.
Prayer steadies shaky ground.
Scars are inevitable but can become footholds.
Your children and grandchildren remember the times you kept your word. Integrity is how love earns trust over a lifetime.
Music can heal a weary spirit.
Laughter with grandchildren is holy ground. Even the silliest joke can create amazing memories.
Take pictures but also put your phone down.
The best conversations happen unplanned, often on the way to somewhere else.
God shows up in ordinary moments.
Start with what you have, not what you lack.
Be quick to encourage. A word of encouragement can feel like oxygen to someone gasping for air.
Time with your spouse is the best investment you’ll ever make.
A sunrise reminds us the story isn’t over.
Be generous with money, with time, and with grace.
Don’t underestimate a good meal shared…even a bad meal shared.
Patience is a form of love.
Read good books slowly. And read them aloud. I’ll never forget the nights of reading Harry Potter chapters to my kids, one voice carrying us all to another world.
Children teach us as much as we teach them.
A soft answer turns away wrath.
Slow down for sunsets.
Stay curious, even at 59.
Hold babies gently, but often.
Let go of what you can’t control.
Keep your promises, even the small ones. If you can’t be trusted in the little things, no one will trust you with the big ones.
Coffee or a meal with a friend beats any meeting.
Rest is productive.
Gratitude doesn’t just brighten the day. It multiplies joy in ways you can’t measure. It shifts ordinary moments into holy ones.
The journey matters more than the finish line.
Never be too proud to say, “I was wrong.” Or “I don’t know.”
Faith isn’t about knowing all the answers.
Celebrate progress, not perfection.
Trails are better with company. I’ve seen some of the deepest conversations unfold at mile three.
Be the first to say “thank you.”
Find work you believe in, but don’t let it define you.
Love is the legacy worth leaving.
Don’t compare. Contentment is wealth.
Your words can build or break. Choose to build. Always.
A long hug can mend a broken heart. I’ve felt that healing in the arms of family.
Keep learning, keep growing. Continuous improvement matters. Even the smallest step forward is still forward.
Tradition ties generations together, especially if that tradition involves an old family recipe that takes hours and lots of teamwork to make.
Tell stories. Your family needs them. Stories pass down more than facts. They carry history and identity.
Choose wonder over cynicism.
You can’t outgive God, but you can follow His example.
Every season has its beauty. Even Oklahoma summers with their heat and humidity have sunsets worth pausing for (clearly I appreciate sunrises and sunsets).
Be present. Tomorrow isn’t promised.
Family trust is sacred. Break it once, and it may never return the same. Protect it as carefully as you protect your home.
Celebrate the small wins. A child’s smile, a project finished, or a quiet evening with family. Cherish these moments.
Joy often hides in the small, ordinary things.
Life is a gift. At every age, unwrap it with wonder.
4 Bonus Lessons (which means I came up with four more that I didn’t want to exclude)
Adapt or be left behind. If you’re the best buggy whip maker, prepare to adapt when automobiles come out. Don’t cling to the past so tightly that you miss the future.
The quiet miracle of savings and compound interest. Einstein was right. Compound interest is the most amazing thing. Steadily and quietly setting aside a portion of your income builds your wealth over time. It also provides peace of mind and freedom for your future self.
Learn outside your lane. Take time to study things that don’t seem connected to your work. The most important lessons often come from entirely different fields.
Travel opens two windows. When you visit a new country, you learn about their culture, their food, their people. But you also return seeing your own home differently…with gratitude, with perspective, and with fresh eyes.
“If you could erase one memory, what would it be?”
We all have memories that sting. Failures. Regrets. Accidents. Loss. Moments we wish had gone differently. It’s easy to imagine how much lighter life might feel if certain days had never happened.
I wouldn’t erase any of them.
Every memory, good and bad, shapes who I am today. The hard ones give me resilience, humility, and perspective. The joyful ones give me hope and fuel. Together, they’ve woven the story that brought me to this moment.
If I erased regret, I’d lose the lessons.
If I erased pain, I’d lose the growth.
If I erased loss, I’d lose the clarity it gave me about the value of life and love.
I carry each memory with gratitude. Gratitude that even the hardest chapters are part of a larger story. Gratitude that none of it was wasted.
Gratitude that grace has been big enough to redeem even the parts I once wished to forget.
Photo by Jason Thompson on Unsplash – because grace brings life out of the hardest places.
I don’t remember a lot from Mrs. Olsen’s first grade class. One event that stands out is the day we planted a bunch of seeds in a garden. First grade Bob enjoyed digging in the dirt, making small seed holes, dropping each seed into its place, and writing the plant names on popsicle sticks that we plunged into the dirt next to the seeds.
Then came the bad news.
We wouldn’t be able to see the plants we’d planted until weeks later, and they wouldn’t reach maturity (whatever that meant) for at least a year.
To a first grader, weeks (and especially a year) meant forever. First grade Bob was extremely disappointed. I never saw the plants that came from the seeds we planted that day. It would be decades before adult Bob would go to the trouble of planting seeds or transplanting potted plants into a garden.
Recently, I watched an Essential Craftsman video where he planted 25 new trees. He worked the soil, designed a hand-made watering system, dug 25 holes with exactly the right spacing, brought in a truckload of special soil, mixed it with his existing soil, and then carefully placed each tree in the ground.
At various points in this multi-week project, he worked alongside his grandsons, his wife, and one of his good friends. He said that working with them over the years, especially his wife, had made him a better person.
The finished line of trees looked amazing and will look even better over the next 10 – 20 years.
He reflected that it’s easy to take for granted the shade we enjoy from trees planted decades before. The journey from seed to shade provider is a long one, but it always begins with the person (or Nature) planting that seed.
So, what kind of “shade” are we planting today? Is it the kind that shelters others through encouragement, love, wisdom, opportunity, or sacrifice?
The things we do now may not seem significant in the moment. They may never fully bloom while we’re around to enjoy them. A kind word to a child. A story passed down. A habit of generosity. A newly taught skill. A quiet act of integrity. These are the seeds we plant for the future.
Sometimes, like first grade Bob, it’s easy to get frustrated when we don’t see results right away. We live in a world that loves fast feedback and instant gratification. But shade trees don’t grow overnight. Neither do strong families, good character, or traditions worth passing on.
What if our job, the most important job of all, is to plant and build for a future we’ll never see? To create a little more shelter for the people coming after us?
Few will notice what we’re planting. But that’s okay. We do it anyway. And someone else will get to rest in that shade.
That’s the kind of impact I hope to make. Something that lasts beyond my lifetime, even if no one remembers exactly which trees I planted.
So I’ll keep planting. I’ll keep building. I’ll keep encouraging…investing in the people I know will grow far beyond me.
Because someday, someone will enjoy the shade I may never see.
Adult Bob loves that.
“If your plan is for one year, plant rice. If your plan is for ten years, plant trees. If your plan is for one hundred years, educate children.” – Confucius
I sat down recently to write a letter to my cousin (technically my first cousin once removed), who just started basic training in the Air Force.
What began as a quick note turned into something more. A personal reflection, a bit of a manifesto, and a stack of lessons I wish someone had handed to me when I was just setting out.
By the time I hit “save,” I realized this may be worth sharing with any young person taking their first real steps into the adult world.
The letter was full of life updates, jokes, birthday party planning, movie recommendations, and the occasional 10-year-old version of myself asking random questions. But the main message was you can do hard things, and you’re not alone.
What follows are some ideas that come from years of learning, leading, failing, and reflecting. These are lessons for anyone who finds themselves on the edge of something new.
Leadership begins and ends in your head. Most of your real battles are internal. That voice in your head? It can lift you up or hold you back. Especially in an environment full of rules and pressure, how you think will define who you become. Supportive self-talk, resilient thinking, steady choices. These are the foundational traits for leadership.
Start before you’re ready. Showing up takes more courage than people realize. You will rarely have everything figured out before you begin. Your best opportunities for growth will come from figuring things out while under pressure. That discomfort you feel is a sign that you’re on the edge of growth.
Do the next right thing. When life gets overwhelming (and it will), it helps to stop trying to solve everything all at once. Pause. Breathe. Do the next right thing. That’s enough. The bigger picture tends to take care of itself when we’re faithful and focus on the next indicated step.
You belong here. The feeling that maybe you’re not ready, or that someone else would be better suited for the challenge in front of you. That’s normal. But it doesn’t mean you don’t belong. The truth is you do belong. You’ve earned the right to be where you are. And you’re growing stronger every day, even if it doesn’t feel like it in the moment.
Respect is the foundation of everything. Not just the kind of respect that comes from rank or titles, but the kind you live out through humility, consistency, and quiet honor. When you offer that kind of respect, you build trust. And trust is what makes people want to follow your lead.
When the going gets tough, remember why you started. Every hard day will test your resolve. Every early morning, every setback, every lonely hour…these are the places where you’ll either lose sight of your purpose or anchor more deeply into it. Purpose doesn’t remove difficulty, but it gives meaning to the difficulty. And that’s enough to carry you through.
Discipline equals freedom. I shared this piece of advice that comes from Jocko Willink, former Navy SEAL, war veteran, and a powerful voice on discipline and leadership. He says, “Discipline equals freedom.” The more discipline you have, the more freedom you gain.
Discipline gives you control. Over your body, your mind, and your choices. Freedom to choose your future. Freedom to trust yourself. Freedom to follow through, especially when motivation fades.
You won’t always feel motivated. That’s okay. Stay disciplined. Show up. Do the work. That’s how you earn freedom. One decision at a time.
“Don’t wish it were easier. Wish you were better.” A classic quote from Jim Rohn. There’s no shortage of obstacles. The goal isn’t to escape them. It’s to grow strong enough to rise above them. The learning curve is real. Learn, adapt, overcome…become better and things will become much easier.
About those movie recommendations I mentioned earlier. It’s probably more accurate to call them story recommendations. Stories about honor, resilience, human ingenuity, and the willingness to keep going when things are difficult.
We Were Soldiers, an amazingly good movie about strategic servant leadership (which is my preferred style of management), bravery, and the love that comrades in arms have for one another. It’s a great tribute to the men who fought (many who gave their lives for the guy next to them) and their brave families back home. I think I’ve seen it at least 25 times and I’m happy to watch it anytime. Each time I watch it, I tear up in at least 2 or 3 places in the movie.
Ocean’s 11 and The Sting, two films that focus on creative problem solving and teamwork…though our “heroes” in these movies are con men and thieves.
The Princess Bride made the list. The value of honor (even among combatants), mixed with the comedic and spoofy scenes make it a classic. Even in a world of duels and danger, kindness, respect and loyalty still matter.
I suggested Seveneves by Neal Stephenson. A science fiction novel (my favorite genre for at least the past 10 years) about human survival, adaptation, and rebuilding civilization after catastrophe. The premise is that an asteroid causes the moon to shatter. What starts out as an oddity in the sky becomes a calamity as the moon breaks up into a ring and then begins to rain down to Earth (something they call the Hard Rain). Great sci-fi, lots of human ingenuity and adaptability, and a story that covers about 5,000 years. It’ll take some time to read, but it’s worth it.
Two books by Andy Weir. The first is The Martian (which became a movie starring Matt Damon), and the second is Project Hail Mary. Andy wrote The Martian in 2011 and self-published it on Amazon. It picked up fans and became a bestseller without an “official” publisher. His second book was called Artemis (takes place on the Moon). It was good, but not quite as good as The Martian (which is a high standard, so I’m probably being unfair).
His third book was Project Hail Mary. This one is also being made into a movie, starring Ryan Gosling. It is excellent.
The big thing about Andy’s books is that they are scientifically accurate. His characters deal with extremely complex challenges that require thinking and ingenuity to overcome. He writes in a way that entertains and teaches things you never knew.
I love that Andy wrote his first book from beginning to end without any publisher involved. Nobody was there to tell him what he was doing was the right thing. He believed in himself, believed in the story he was telling, focused on the work, delivered a high-quality product, and proceeded to find his audience one reader at a time.
All these stories reflect truths about the path ahead. Your journey will be hard. You’ll need grit, creativity, and perseverance. You’ll need others (family, friends, mentors, even strangers). More often than not, the tools to overcome life’s challenges will come from within yourself, quietly shaped by the stories you carry and the habits you form.
Whatever new thing you’re stepping into, whether it’s basic training, a new job, a cross-country move, or a new phase in your life, know that it’s okay to be unsure. It’s okay to feel stretched. Just remember your “why,” do the next right thing, and keep showing up with courage.
And who knows? Maybe decades from now you’ll be the one writing a letter like this, passing along what you’ve learned…
I received an email from Noah Kagan this week. Not because we’re personal friends, but because I subscribe to his newsletter. Noah, the CEO of AppSumo, often shares practical insights and thought-provoking questions from his journey in the tech world.
This particular message stood out. He talked about being fearful for his 10-month-old daughter’s future. With all the chaos in the world, the deepening divides, the rise of AI and robotics, the general noise of modern life, he wonders what kind of world she’ll inherit.
But instead of spiraling into worry, Noah laid out how he’s choosing to respond: by creating clarity, limiting distractions, and doubling down on the things that matter most. He’s building a foundation, not just for his own peace of mind, but for his daughter to inherit.
His email reminded me of a quote often attributed to Mark Twain: “The future is in the hands of a generation that isn’t ready for it.”
We didn’t have AI, social media, or the internet back in Mr. Twain’s day. But even then, concerns about “the next generation” were nothing new. Parents, teachers, and elders across every era in history have wondered if the next generation is truly ready.
Noah’s concern isn’t just that the next generation might be unprepared. It’s that the world itself might be too broken to navigate well. But history offers some perspective.
Every generation has faced challenges. Wars, famines, political collapse, pandemics, technological upheaval, moral drift. And yet, the world moves forward. Somehow, each generation rises to meet its moment…even if their preparation feels lacking.
We don’t get to control the future, but we do influence it by how we live, what we model, and what we choose to pass on. We can’t predict what our children and grandchildren will face, or how they’ll respond. But we can teach them how to think, how to hold on to timeless values, and how to walk through hardship with strength and grace.
It’s natural to worry.
Let’s not forget that hardship doesn’t cancel out beauty.
Struggles don’t erase joy.
There will be triumphs ahead, too. If we’ve taught them well, they’ll learn to spot their small victories, celebrate them, and then pass along what matters to those who come after.
The future always arrives in the hands of the young—and the young are never quite ready. But then again, neither were we.
We know about Maslow’s Hierarchy of Needs and how our wants and desires are like a pyramid that goes from our basic needs up to our desire for self-actualization. The Pareto Principle reminds us that 80% of our results come from 20% of our efforts, helping us focus on what truly moves the needle. Saint Ignatius’s Spiritual Exercises guide us through discernment, teaching us to distinguish between what brings life and what drains it.
But there’s another framework worth considering: the evolution of what we consider important throughout our lives.
As kids, we know what’s most important. It usually revolves around attention, followed by winning at whatever we are doing, which we think will get us more of that attention we crave. Everything feels urgent. Every disappointment feels permanent. The world revolves around us, and that’s exactly as it should be for a child learning to navigate life.
Teenagers start to focus on freedom, independence, and figuring out what they’re going to do when they grow up (whatever that means). They often reject what their parents value. Sometimes for good reasons, sometimes solely because rebellion feels necessary for finding their own path. What matters most is breaking free from the constraints that feel suffocating, even when those constraints were designed to protect them.
As young adults, we’re getting started, establishing our independent life, our financial foundations, our career foundations…at least we’re trying to get these things established. We’re in acquisition mode: getting the job, the apartment (maybe a house), the relationship, the respect (something we crave more than attention at this stage). We often dismiss advice from older generations, convinced they don’t understand how different the world is now.
Then something interesting happens.
As the decades flow by, what was important a few years ago, isn’t. We start to think about how to serve others, help our kids flourish, help their kids flourish. The shift is gradual but profound. From getting to giving, from proving ourselves to improving the lives of others.
Major life events accelerate this evolution. A health scare makes us realize that all the success in the world doesn’t matter if we’re not here to enjoy the fruits of our labor. The birth of a child or grandchild suddenly makes legacy more important than achievement. The loss of a parent reminds us that time is finite, and relationships are irreplaceable.
Sometimes the shift happens more quietly. Earlier this week, two co-workers were discussing the NBA finals and asked me what I thought of Game 2. I had to admit that I haven’t followed basketball since the Magic Johnson era of the Lakers. As we talked, it became clear to me that I haven’t followed any sports—except for the Savannah Bananas baseball team’s shenanigans—in many years.
What captures my attention now? I’m drawn to watching people live their best lives in rural settings, building homesteads for themselves and their families. I find myself rooting for others to succeed in their chosen vocations, nothing more, nothing less. It’s not that sports became unimportant because they were bad. They just became less important than something else that feeds my soul more deeply.
As we get older, preserving our health, and the freedom that comes with it, moves toward the top of our priority list. Interesting how the freedom we sought as teenagers is still important to us in our senior years, but for different reasons. Then, we wanted freedom and thought we were ready for responsibility.
Now, we want freedom to focus on what truly matters. Freedom to be present for the people we love, freedom to contribute in meaningful ways, freedom from the noise that once seemed so important.
There’s a beautiful irony in how we often spend the first half of our lives accumulating things, achievements, and accolades, only to spend the second half learning to let go of what doesn’t serve us. We chase complexity when we’re young and value simplicity as we mature.
Questions worth considering:
– What would happen if we could skip ahead and see what our 70-year-old self considers important? What about our 80-year-old self? Would we make different choices today knowing what they know?
– Why do we have to learn the hard way that some of the things we chase don’t matter? Is there wisdom in the struggle, or are we just stubborn?
– How can we be more intentional about evolving our priorities on our terms instead of waiting for time to do it?
– What if we could honor the lessons each life stage provides without completely losing face and dismissing what came before?
The evolution of importance isn’t about getting it right or wrong at any particular stage. It’s recognizing that growth means what we value will shift.
That’s not a bug in the system. It’s a feature. The teenager’s desire for freedom isn’t foolish. It’s necessary for their development. The young adult’s focus on building a foundation isn’t shallow. It’s essential for future stability.
Perhaps the real wisdom comes in staying curious about what matters most. Knowing that the answer will keep evolving. And maybe, just maybe, we can learn to trust that each stage of life has something valuable to teach us about what’s truly important.
The key is staying awake to the lessons, even when they challenge what we thought we knew for certain.
Grandpa Bob Encouraging Leadership 
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