Humility – Grandpa Bob Encouraging Leadership

Grandpa Bob Encouraging Leadership — A New Podcast

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.

Photo by Patrick Fore on Unsplash

A Parenting Prayer

Parenting is one of the clearest places where faith meets daily life. It calls us to humility, patience, courage, generosity, and the kind of love that stretches us far beyond what we believed we could give.

It invites us to trust God with the people most precious to us, even when the path ahead is uncertain and far beyond our view.

The prayer below is one I’ve been working on for a while. It’s a prayer for parents at every stage of life…those just beginning, and those watching their grown children take their first steps into adulthood. It’s also for those whose children are becoming parents and carrying this calling into a new generation.

It is a reminder that God accompanies us in the noise and the silence, the ordinary and the holy, the days that feel long and the years that pass so quickly.

May this prayer strengthen your heart and deepen your hope as you walk this sacred calling.

A Parenting Prayer

God, please grant me
The wisdom to guide my children with patience, clarity, and love
And the humility to grow alongside them as they grow.
Teach me to choose presence over hurry,
Trust over fear, and connection over control.

Give me the courage to admit when I am wrong
And the grace to show my children that learning never ends,
Not at 7, not at 17, not at 70.

Help me see the world through their eyes,
Eyes that understand wonder,
Eyes that welcome the new with unguarded joy.
Let their curiosity rekindle my own,
So our home becomes a place where questions are celebrated
And imagination roams freely.

Give me integrity in the quiet moments,
When my child is learning from what I do.
Give me a heart strong enough to support them
And gentle enough that they always feel safe coming to me.

Teach me to treasure the small things:
The bedtime stories,
The long drives,
The conversations over tacos,
The ordinary afternoons that turn into lifelong memories.
Remind me that these simple moments
Will matter far more than the schedules we keep
Or the outcomes we chase.

Loving God,
Free me from comparing my family to others.
You did not design my children to fit anyone’s timeline but Yours.
Help me trust the pace of their becoming
And see their strengths even when they are wrapped in struggle.

Guard me from chasing achievements that impress the world
But neglect the souls under my roof.
Let our home be defined by gratitude, peace, and laughter,
With the quiet confidence that love is our foundation.

Help me pass down what truly endures:
Character over perfection,
Kindness over victory,
Service over status,
Gratitude over entitlement.

May the stories I tell, the choices I make,
And the way I show up each day
Become part of the heritage my children carry forward.
Help me become an example worth following,
One who lives with faithfulness, honesty, and a willingness to learn.

Give me strength for the hard times
And calm for the anxious nights.
Give me a long view of parenting,
Seeing not just who my children are today
But who they are becoming by Your grace.

Teach me to listen more than I lecture,
To encourage more than I correct,
And to guide without stifling the person
You created them to be.

Grant me the courage to give responsibility as they mature
And the faith to let them walk their own path,
Even when that path stretches beyond my view.

Lord, may our home reflect Your kingdom,
A place of welcome, forgiveness, generosity, and joy.
Let my children feel seen, valued, and deeply loved,
Not for what they do, but for who they are.

I invite You into every step of this sacred calling.
Walk with me in the noise and the silence,
In the exhaustion and the celebration,
In the days that feel long
And the years that pass too quickly.

Grant me the peace that comes from Your eternal and infinite love,
Now and forever.

Amen.

Photo by Hu Chen on Unsplash

Teachers, Mentors, and the Grace That Carries Us

“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.

We never really travel alone.

Photo by Rafael Garcin on Unsplash

Beautiful Things Don’t Ask for Attention

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’m Not That — What You’re Not Might Be Holding You Back

Sometimes the hardest limits aren’t what we believe we are…but what we’ve decided we’re not.

Leader: I’m hitting a wall. No matter how hard I try, something’s stuck.
Coach: Where?
Leader: Connecting with my direct reports. The one-on-one meetings. All the details. I’m just not wired for any of it.
Coach: You sure?
Leader: I’ve never been good at connection. I’m not super technical. I’m not touchy-feely. I’m not a detail person.
Coach: Sounds like you’ve got your “not” list down cold.
Leader: Isn’t that just self-awareness?
Coach: Could be. Or maybe you’re protecting yourself with that list.
Leader: I’m not trying to be someone I’m not.
Coach: Are you avoiding someone you could become? What if the growth you’ve been chasing is on the other side of “I’m not”?
Leader: What if I do all that work and don’t like what I find?
Coach: Then you’ll learn something real. But what if you find a strength you didn’t know you had?
Leader: That feels like a stretch.
Coach: Growth usually does.

“Ego is as much what you don’t think you are as what you think you are.”
– Joe Hudson

We usually spot ego in people who overestimate themselves. Their arrogance and swagger enter the room before they do.

But ego has a quieter side. It hides in the limits we quietly accept. Not in who we think we are, but in who we’ve decided we’re not.

“I’m not technical.”
“I’m not good at details.”
“I hate public speaking.”

These negations, the things we distance ourselves from, might feel like declarations of strength and clarity.

But often they are boundaries we’ve unconsciously placed around our identity. Once we’ve drawn these lines, we stop growing beyond them. They protect us from challenges, discomfort, and the hard work we know will be required.

Leaders who define themselves by what they aren’t often:

-Avoid feedback that challenges their identity.

-Miss chances to adapt or grow.

-Choose the path of least resistance.

-Struggle to connect with different types of people.

-Dismiss skills they haven’t developed (yet).

If you’re feeling stuck, ask yourself:

-What am I avoiding by saying, “I’m not that”?

-What am I protecting by holding on to that story?

-What might open up if I let it go?

Sometimes the next chapter of growth begins not with a new strength, but with a willingness to loosen our grip on the stories we tell ourselves.

If you want to grow as a leader—or help others grow—it’s not enough to ask, “Who am I?”

You also have to ask, “What am I willing to become?”

Photo by Amir Mortezaie on Unsplash

The Freedom of Humiliation

We usually think of humiliation in its negative context, since we’ve allowed it to matter…

Consider how much time and energy we devote to avoiding humiliation. We’re taught early in life to strive for being right. Quickly understanding, and then knowing the answer…especially to the questions that’ll be on the test.

Think back to your first job, your second job, in fact, every job you’ve ever had. How was your first day? What about your first month? How comfortable were you? What type of impression did you want to make on your new boss? Your new co-workers?

I bet your main goal was to avoid screwing up, learn what it takes to be successful, and by all means, don’t embarrass yourself.

It’s the same in just about any new environment. Meet a new group of people and one of the first things in your mind is how to present the best image of yourself to this group. Don’t let them see your flaws, your fears, your anxieties. Don’t let them know you’re completely uncomfortable. For now, your goal is to fit in, get to know who’s who in the group and, don’t embarrass yourself.

“True humility is not thinking less of yourself; it is thinking of yourself less.” ― Rick Warren

What if you approached all these situations and nearly every other in your life without fear of humiliation or embarrassment. In fact, imagine if you sought situations where humiliation was a distinct possibility.

What if you approached that new software tool, or the new sales program with the confidence of knowing that you’ll be learning something new…rather than worrying about arguments against them, or how they’ll push you out of your comfort zone?

We usually think of humiliation in its negative context, since we’ve allowed it to matter. But, humiliation is closely related to humility, and humility is the first step toward real learning.

Once you approach a subject with the humility of a beginner, regardless of your tenure or experience, only then will you be fully prepared to learn.

The humble learner doesn’t allow themselves or their ego to come between new ideas and their pre-conceived notions of the truth. They allow these new ideas to penetrate the veneer of pride and self-righteousness where many of us hide. Then, they can truly assess and make a judgment about the new ideas.

Too often, we don’t even allow the new idea to enter. We’re too busy coming up with reasons that our own ideas are correct, the only direction, the only way. The new idea is like a foreign invader to be repelled at the gate.

A new and potentially rewarding relationship is placed behind a well-crafted wall of pride and imagery that hides our fears of humiliation or of letting this new person visit the deepest parts of ourselves.

All these walls and anxieties have their root in our fear of humiliation. We can’t face the risk of being wrong, of being weak, of being vulnerable. We are right, and our focus is on ensuring we reinforce this “fact” to anyone or anything we encounter…especially to ourselves.

“There is nothing noble in being superior to your fellow man; true nobility is being superior to your former self.” ― Ernest Hemingway

The freedom of humiliation is a freedom to be open: to new ideas, new people, new directions, new beliefs, and even new perceptions of truth. When we’re free from the fear of humiliation, we don’t have to defend ourselves from new situations. We turn the threat of the new into an opportunity.

This doesn’t mean giving up on our definitions of right and wrong, our definitions of how to live a virtuous life or our core beliefs.

It means dropping that wall of protection we place around ourselves and our ideas and allowing them to roam freely and interact with others.

“A true genius admits that he/she knows nothing.” ― Albert Einstein

Photo by Joshua Earle on Unsplash