reflection – Grandpa Bob Encouraging Leadership

Six Questions at the End of the Day

For the next two weeks, I’ll be doing something new.

Marshall Goldsmith is encouraging people to ask themselves six questions every day. That’s the whole experiment.

Six questions. Asked at night. Answered honestly.

They all start the same way:

Did I do my best to…

The questions don’t ask what happened to me today. They ask what I did with today.

During his webinar introducing the experiment, Mr. Goldsmith referred to the Rigveda, an ancient poem from India that he described as being thousands of years old. He just mentioned it and moved on.

I had never heard of the Rigveda, so down the rabbit hole I went after his webinar ended.

The Rigveda is a collection of hymns. A lot of it is about everyday things. The sun rising. Fire. Breath. Life continuing. There’s a sense that daily life matters. That how we live each day counts.

People have been trying to figure out how to live a good life for a long time. Way before self-help and leadership books. Way before webinars and podcasts.

St. Ignatius of Loyola comes to mind. He developed something called the Daily Examen. It’s a review of the day. You look back. You notice where you were grateful. You notice where you fell short. You think about tomorrow.

Different times. Different traditions. Same basic ideas.

At the end of the day, pause and ask, “How did I live today?”

Goldsmith’s six questions fit right into that pattern.

Did I do my best to be happy today?

The question hits differently when the day is already over. I can see clearly whether I purposely enjoyed the day or just rushed through it.

Did I do my best to build positive relationships?

Now I’m thinking about the way I spoke to someone. Whether I listened. Whether I gave someone my full attention.

The questions are short. The reflections take some time.

Goldsmith describes happiness as “enjoyment with the process of life itself.” Happiness lives inside the day. It grows out of our engagement with what’s already in front of us.

The writers of the Rigveda seemed to understand that. Ignatius understood it too. They’re asking us to pay attention to our life and actively engage in it.

I’m only a few days into this experiment. Nothing dramatic has happened. No big breakthroughs.

But I know I’ll be answering these six questions later. I move through the day with more awareness. I catch myself sooner. I stay present a little longer. I think twice before reacting.

It’s a small shift…but small shifts repeated over time shape our lives.

Thousands of years have passed since the Rigveda was written. Centuries since Ignatius taught people to examine their day.

Our modern life looks very different, but the question remains the same.

How did I live today?

Here are Goldsmith’s six questions:

–Did I do my best to set clear goals today?

-Did I do my best to make progress towards my goals today?

-Did I do my best to find meaning today?

-Did I do my best to be happy today?

-Did I do my best to build positive relationships today?

-Did I do my best to be engaged today?

h/t – Marshall Goldsmith

Photo by Jonh Corner on Unsplash – looks like an awesome spot to think about these questions.

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

Words Around Christmas

December turns our words to gold,
Tidings, joy, and peace foretold.
Lights like stars along our eaves,
Hope returns on winter’s leaves.

Forgotten words begin to rise,
Childlike wonder in our eyes.
Tinsel, sleigh bells, candle-glow,
Songs of Christmas we all know.

Jingle bells and sleighs take flight,
Rudolph glows through frosted night.
Elves and workshops, North Pole cheer,
Santa’s laughter draws us near.

Snickerdoodles and mulling spice,
Our kitchen’s warmth feels soft and nice.
Welch cakes, pasties, stories told,
Trimmings bright against the cold.

Village lights and carols ring,
Wishes whispered, children sing.
Holly, ornaments, and good cheer
Mark the turning of the year.

Laughter spills from room to room,
Chasing winter’s early gloom.
A gift is only paper bright
Till love folds edges soft and tight.

Traditions bloom in winter air
When generations gather there.
Past and present intertwined,
Stories passed from heart to mind.

Nutcrackers guard, reindeer in flight,
Stockings, holly, silent night.
Sacred stillness gently kept,
In the hours while we slept.

Speak with warmth in every line,
Merry heart and joy divine.
Let kindness shape the songs we sing,
for Christ is born, our promised King.

Let peace on earth be more than art,
let joy take root in every heart.
Let words become the lives we live,
hope to hold, and grace we give.

For all these phrases loved and dear
return to us but once a year.
They point us toward God’s Word,
the sweetest story ever heard.

Love made its dwelling in the hay,
a Child who gave the world its way.
We speak these golden words because
He came to live His love through us.

Photo by Rafał Danhoffer 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

The Pathways to a Rewarding Life

Finding Purpose at Every Age

From thirty thousand feet, the land below looks like a patchwork of roads and fields. Each marks a choice someone once made about where to go. Some stretch straight and steady. Others twist through hills or fade out of sight. Together they form a map of movement and direction, a living story of people who kept choosing the next road.

Life feels the same way. The routes change, but the invitation stays the same. Keep moving to find greater meaning.

The most rewarding paths often pass through three places. Serving others, staying curious, and daring to pursue new goals.

Service opens our heart. When we give to something beyond ourselves, our life expands. For the younger generation, it teaches them that purpose grows through generosity and connection. Helping a friend, joining a cause, or showing up for someone who needs encouragement builds an identity rooted in contribution. Later in life, service transforms experience into legacy. It turns lessons into guidance and presence into impact. Every act of service whispers that we still matter.

Curiosity keeps that whisper alive. It invites discovery and reminds us that wonder never expires. For young adults, curiosity shifts attention from comparison to possibility. It fuels creativity and builds resilience (because nobody said it would be easy). For those further down the road, curiosity revives joy. Learning something new, exploring unfamiliar tools, or asking deeper questions renews their spirit.

Big goals complete the trio. Ambition alone can fade, but big dreams shaped by purpose bring hope to life. For the young, bold goals turn uncertainty into motion. For the experienced, they rekindle the thrill of becoming. The thrill of pursuing. Every goal, whether to build, create, teach, or grow, reminds the soul that movement still matters. Hope rises with every goal we dare to pursue.

Many people never take these paths. Fear of failure, fear of embarrassment, fear of losing face…they each build fences where we can hide. Quiet excuses convincing us to play small and call it wisdom.

Fear says, “Stay comfortable.” Curiosity says, “Let’s see what happens.”

When fear wins, both young and old lose sight of their forward motion. The young adult who fears being judged easily drifts into hopelessness. The older adult who hesitates to dream again slips into quiet surrender. The reasons sound different, yet the root feels the same. Fear has taken the wheel. Stagnation and hopelessness follow.

Purpose waits just ahead. It lives in the next act of kindness, the next mystery to be solved, the next dream still worth chasing.

The pathways to a rewarding life have no finish line. Every act of service, every curious step, every daring goal breathes new life into our soul.

When we explore these paths, joy and fulfillment will be our companion.

Photo by Line Kjær on Unsplash – I wonder what’s in the next valley. Let’s go find out.

How Limits Bring Art to Life

Inspired by G. K. Chesterton

I’ve come to believe what Chesterton once said. Art is limitation, and the essence of every picture is the frame. It took me time to see that truth.

Many of us grow up thinking freedom creates great work. Unlimited time. Unlimited canvas. Unlimited choice.

But if you’ve ever stared too long at a blank page, you know what real freedom can feel like. Paralyzing.

Nothing takes shape until the edges appear. A story waits forever if the writer can’t decide where it begins. Music is noisy until the composer chooses a key. The frame gives the work its purpose.

The same is true in leadership and life. A budget helps us decide what we value. A deadline turns a dream into something real. A small team learns to trade excess for imagination. Limited resources push us to invent new ways to adapt. The frame brings focus.

Still, the frame itself matters. A picture can feel cramped when the frame becomes too tight. A project can drift when the wrong thing fills the center. When the boundaries are off, the whole image loses clarity. That’s why wise leaders spend time defining the edges before the work begins.

Whenever I work on a puzzle, I start by finding all the edge pieces. Once the border comes together, I can see how everything else might fit. The same principle applies to creative work and leadership. The edges give us context. They help us imagine where the middle pieces belong and how the picture will come to life.

Frames should change as we grow. The world shifts. We learn more about what we’re building. Every so often, we step back and see whether the picture still fits. Sometimes the frame needs widening. Sometimes the colors need more light. Adjusting the frame keeps the beauty true.

Constraints give possibility its shape. They reveal what truly matters. Choosing the right limitations helps us see what is essential.

When you feel boxed in or limited, pause before you push against the edges. The frame around your work may be the very thing helping the picture appear. And when the picture becomes clear, refresh the frame so the beauty within it continues to grow.

Thanks to James Clear for sharing this G. K. Chesterton quote: “Art is limitation; the essence of every picture is the frame.”

Photo by pine watt on Unsplash

Doing the Thing

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.

Now and Then

The days feel long, but our years disappear. I’ve been thinking about how easily “someday” turns into “back then.” We spend so much of life working toward what’s next that we sometimes forget we’re already living the moments we’ll one day remember with gratitude.

This truth reaches us at every age. Whether we shape our future with intention or let it unfold on its own, it arrives and quietly invites us to participate. This reflection is about the sweetness of now and noticing that these moments become the story we’re creating together.

Each day arrives on its own, small and full of potential. It doesn’t ask for much. Only our attention, our care, and our willingness to be here. The hours move like honey, slow and golden, rich with sweetness if we take time to notice. Yet the years rush by quietly. One morning we look up and realize the future we worked toward has become the past we cherish.

What we dreamed about for so long is happening now. This day, with its imperfections, interruptions, and small joys, is the life we once hoped to reach. It’s the tomorrow we imagined, already unfolding beneath our feet.

Time helps us see backward with gratitude and forward with wonder. We remember the faces and laughter that have softened into memory. We hold them gently, realizing how meaning hides in ordinary moments.

Each day is a life of its own. Complete, sacred, and fleeting. When we let its minutes open slowly, like sunlight through leaves, we find gratitude sweetening everything it touches. Our wonder grows in quiet places.

“Then” is always born of “now.” When we live this moment with attention, kindness, and a sense of awe, it never really fades. It simply changes shape, becoming the stories we tell, the lessons we pass along, and the love that lingers long after the moment has gone.

Photo by Stephen Crane 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.