Reflections – 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

My Friend, Paul

When I heard that my friend Paul was in the hospital and things weren’t looking good, I can’t say I was shocked. When he passed away a few days later, what stayed with me most was the loss of everything he still had ahead of him.

Paul had been in a self-destructive pattern for a while. I recognized it early, having seen something similar play out in my own family years before. Still, knowing the path doesn’t make the ending any easier.

Paul was my brother’s best friend since high school. More than that really…another brother. Like brothers often do, they didn’t agree on everything, but they agreed they were in it together, and that wasn’t going to change.

I first met Paul when he was probably a sophomore or junior in high school. I was home visiting from my freshman year in college. I remember that mullet like it was yesterday. Business up front, party in the back. He wore it with absolute confidence, as if it were the only reasonable hairstyle.

He was quick-witted and cocky, but in a good way. Sure of himself, without yet knowing what his future held. Which, in hindsight, makes him a lot like the rest of us at almost any age.

Paul had a way of knowing everyone. If he didn’t already know you, he would by the end of the day. His personality filled whatever space he walked into. He remembered names after meeting someone once, a gift I’ve always envied. He asked questions, was genuinely curious about people, and he made everyone feel seen. Paul appreciated people, and people felt that.

He was always ready to dive into big ideas and big projects. He liked to say, “I don’t have a stop sign on my chest.” While others talked about racing off-road “someday,” Paul made it real. With my brother and a group of equally committed friends, he jumped headfirst into building and racing a Class 10 buggy.

What did Paul know about off-road fabrication or racing at speed in the desert? Not much. That didn’t stop him. He’d figure it out along the way. Thursday nights in his garage turned into a ritual. Fabricating, wrenching, laughing, getting ready. Lots of Saturdays were spent in the desert testing and tuning, trying to make the car race ready.

My brother was his co-driver, mentor, and probably the unofficial crew chief. I don’t know how many races they finished, maybe one or two, but they often led the first lap and looked great until something small failed. A cheap part. A loose wire. A power steering pump. One tiny thing ending the day.

They were frustrated, but they didn’t quit. Eventually the Class 10 car gave way to a Class 8 truck. Everything got bigger. More horsepower, bigger suspension, more parts, higher speeds. More complexity. More commitment. More Thursdays. More Saturdays. More races.

Paul used to joke that the only things standing between him and winning were experience, capability, and funding. All probably true. Where most people would see that as a reason to stop, Paul saw it as part of the adventure. He believed he’d learn as he went, and he’d have fun doing it.

I was lucky to pit for Paul at a few of his races. But where I really got to see him shine was pitting for Team Honda in Baja and Team Kawasaki in Nevada. I learned that Paul knew the words to every Metallica song, and nearly every other song that came on the radio…rap, country, classic rock. He knew them all.

One Nevada race stands out. We were assigned the first pit of the day, then relocated to be the final pit later the same day. It’s always fun to be able to do two pits in the same day.

We scouted the location the day before. A desolate stretch of desert about 50 miles from the start. We rolled out early from our little motel the next morning in the dark to get set up.

We thought it would be cool to have an official Kawasaki awning over the spot where the bikes would stop for gas and service. It looked great. We forgot one detail. Securing that awning.

As the first rider, a Kawasaki (of course), came rolling in, Paul had the fuel dump can ready. We could fill a tank in about ten seconds. Everything was smooth. Then the desert wind kicked up, and the awning took off, cartwheeling across the landscape in spectacular fashion right as fueling began.

There was nothing to do but keep going. Rider one laughed as he pulled out. Did I mention there was film crew there? They laughed. We laughed. Thirty seconds later, rider two came in and out just as fast.

When we finally went to retrieve the awning that had rolled about a half mile away, we expected wreckage. Instead, it was mostly fine. Scratched, dusty, but intact. At the final pit of the day, we remembered to tie it down.

When I think of Paul, that’s what comes to mind. The sprinkling of chaos. The laughter. The way nothing ever quite went according to plan, and how little that bothered him or any of us. We were having fun together and that’s what mattered.

I’ll miss Paul’s infectious grin, his laugh, and his refusal to wait for perfect conditions. He left too early. But he left us with stories, friendships, and a reminder that life isn’t meant to be watched from the sidelines.

Rest in peace, my friend.

Photo – a selfie back when selfies were taken with film cameras, at least 30 years ago. Three knuckleheads driving to the desert way too early. That’s my brother and I on the left and my brother’s other brother, Paul, on the right. We’ll miss you, Paul.

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

Simplifying 2026, One Decision at a Time

Every December, I return to a familiar practice. I reread a few of my older posts, looking for threads that might help clarify my thinking about the year ahead. Last year, on the final day of 2024, I wrote a short post on my goals for 2025:

-Serve the quests of others over my own
-Offer insights and advice, not direction
-Push beyond my comfort zone and inspire others to do the same
-Bring the loaves and fishes, and trust God with the rest

I see that I longed for simplicity without mentioning it directly. I wanted more presence, more clarity, more intention, and a little less noise in a world that seems to generate more every year.

This week, as I listened to Tim Ferriss speak with Derek Sivers, Seth Godin, and Martha Beck about simplifying life, I realized this desire has been with me for a long time. More than a decade ago, I wrote a short post called Becoming a Chief Simplicity Officer, describing how organizations thrive when they remove friction and create clean intuitive paths so people can focus on what truly matters. The idea was straightforward. When systems run smoothly, people flourish.

It turns out this Chief Simplicity Officer role fits in life just as well as leadership. Someone needs to step into the work of reducing complexity, eliminating friction, and clearing space for the things that deserve attention. Someone needs to guard the essentials by shedding the excess.

That someone is me, and it’s you in your life.

From Tim Ferriss’s Podcast

Derek Sivers: Simple Isn’t Easy, but It Is Freedom

Derek Sivers says simplicity requires intention. It doesn’t appear just because we cut a few tasks or say no occasionally. It takes shape when we clear away commitments that no longer belong and choose what contributes to the life we want to live. He often talks about building life from first principles instead of living on top of default settings.

Every recurring obligation fills space that could hold something meaningful. Every dependency adds weight. Every unfinished task pulls at the edges of our attention.

What possibilities would rise if complexity stopped crowding the edges of your life?

Seth Godin: Boundaries Create Clarity

Seth Godin approaches simplicity through the lens of clarity. When you know exactly who your work is for, you stop bending your days around expectations that were never meant to guide your decisions. Clear boundaries turn vague intentions into choices you can actually live out.

Simplicity often follows sharper edges. Define your edges, and the path through each day becomes easier to walk.

Martha Beck: Choose Joy, Not Habit

Martha Beck speaks of simplicity in the language of joy. She tells a story from her twenties when she made a single choice that reshaped her life. She turned toward joy and stepped away from misery, even when the joyful path cost more in the moment. Joy has a way of clearing the fog. It cuts through distraction and highlights what brings life.

Her words invite us to examine the decisions we’ve kept out of habit or comfort. Some habits strengthen our soul. Others only multiply clutter. Joy reveals the difference.

Ten Simplicity Moves for the Start of 2026

These actions are small, but each one lightens the load. They remove stones from a shoe you may have been walking with for years without realizing.

Cancel one subscription that no longer serves you. Even a small change can create a surprising sense of clarity.
Choose one non-negotiable time boundary and honor it. Maybe evening email and scrolling limits or a weekly focus block on your calendar. Small open spaces accumulate over time.
Simplify one recurring decision. Automate it, template it, or eliminate it entirely.
Pause one habit you maintain out of inertia. Give yourself a week to assess its value.
Identify one activity that consistently brings joy and schedule time for it this week.
Unsubscribe from three email lists that add noise instead of value.
Clear one surface you see every day. A calm space refreshes the mind.
Revisit your goals from last year and carry forward only what still matters. Release the rest.
Decide who you are working for. Clarity about your audience sharpens the work you choose to do.
Ask yourself one grounding question: What do I truly need to live the life I want? Let your answer shape what stays and what goes.

Looking Back at 2025 and Forward Into 2026

My goals for 2025 were aimed at deeper alignment with the things I care about. They served me well and opened my heart to possibilities I never would have imagined. I’ll carry these goals into 2026 (and beyond).

For 2026, I’m adding one specific goal to my list. I started working on this goal a few months ago, and it’s pushing me way outside of my comfort zone. While it’s a personal quest (and not one that serves the quests of others over my own), I believe it will serve others on their journey. I’ll be bringing the loaves and fishes and trusting God to do the rest. I’ll share more details later.

A Closing Invitation

Simplicity grows as unnecessary weight falls away and clarity rises in its place. You don’t need a title or a plan to begin.

You only need to choose.

Choose clarity.

Choose boundaries.

Choose joy.

Choose to be the Chief Simplicity Officer in your own life.

Let this be the year you simplify your days and rediscover the freedom and clarity that come from intentional living.

Photo by Paul Earle on Unsplash

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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.

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.

Seeing What Comes Next

The difference between reacting to the moment and preparing for it.

Most leaders spend their days responding. A problem surfaces. They fix it. A crisis hits. They mobilize.

Urgency crowds out importance. By Friday they’re exhausted from fighting fires they never saw coming.

This is leadership without anticipation.

Every action sets something in motion.

-Launch a product without considering support capacity, and you’ll be drowning in angry customers in three months.

-Promote someone before they’re ready, and you’ll spend the next year managing the fallout.

-Ignore the quiet signals in your market, and you’ll wake up one day wondering how you got disrupted.

Some outcomes can be seen in advance. Leadership is the discipline of noticing what’s coming and readying your team to meet it.

Wayne Gretzky once said, “I skate to where the puck is going to be, not where it has been.”Most leaders skate to where the puck was. They optimize for yesterday’s problem. They staff for last quarter’s workload. They strategize for a market that no longer exists.

Leaders who matter skate differently. They think past the first step and see how decisions unfold across time. When they make a choice today, they’re already anticipating the second and third-order effects.

They connect short-term actions to long-term outcomes, asking not just “Will this work?” but “What happens after it works?”

When you cultivate this habit of anticipation, something shifts. You stop being surprised by the predictable. You create space before you need it. You move with a quiet confidence that comes from seeing the terrain before you cross it.

Your team feels it too. It’s the difference between reactive and ready, between scrambling and intentional.

We can’t eliminate uncertainty. The future will always bring surprises. But we can change how we manage it. We can choose to be the leader who sees what’s coming rather than the one who’s perpetually caught off guard.

Dwight Eisenhower said, “In preparing for battle I have always found that plans are useless, but planning is indispensable.” Plans will change. They always do. But the act of planning, of thinking through trajectories, testing assumptions, and imagining scenarios, prepares you to lead when the moment arrives.

The leader who anticipates doesn’t wait for clarity. They sense it forming and courageously move toward it. They shape the path while others are still reacting to it.

Photo by Aleksander Saks on Unsplash

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