Encouragement – Grandpa Bob Encouraging Leadership

Nothing Is Easy

Many of us have felt it. That quiet, persistent yearning for life to just settle down for a while.

We imagine a stretch of road where the strain lets up, the demands lighten, and we can move forward without so much weight on our shoulders. We tell ourselves that after enough years, enough lessons, enough work, and enough milestones, there ought to be a time when things begin to coast.

That hope is understandable. We carry a lot. We get tired. We get worn down.

But easy rarely waits for us around the bend. More often, what comes instead is something better.

Perspective. Wisdom. A clearer sense of what’s worth our energy and what’s worth leaving behind.

With time, we may carry life with more grace. We may stop pouring ourselves into things that never deserved that much from us. We may learn the wisdom of laying down false guilt, unnecessary fear, stale resentment, and the crushing expectations that come from trying to live someone else’s life.

A good bit of suffering comes from carrying weight we were never meant to bear.

Of course, knowing what to set down is its own kind of work. It takes honesty to name what we’ve been carrying needlessly. It takes courage to actually let it go.

But even after we set those things down, effort remains. That’s a feature, rather than a flaw, in life’s design.

Work requires our attention. Relationships ask for our patience. Growth brings discomfort. Purpose calls for sacrifice, and faith asks for trust.

Effort remains part of a life that’s awake and engaged.

Sometimes what we call easy is really just familiarity. We know the terrain. We know the language. We know how to move around in it. That can feel easier, but familiar things can still cost us. They can still ask for endurance, humility, steadiness, and resilience.

Maybe relief is the most honest word for what we’re seeking.

We want a little less pressure. A little less uncertainty. A little less disappointment. A little less striving. We want room to breathe.

There’s nothing wrong with that. Relief is human. Rest is holy. Recovery matters.

But relief differs from a life free of demands. And deep down, most of us would find such a life unsatisfying.

We may say we want to coast. We may fantasize about “easy street.” We may imagine how nice it would be if everything just ran smoothly for a while. But too much ease has a way of hollowing us out, leaving us restless, a little purposeless, quietly bored with ourselves.

We were made for engagement. We want to build, help, solve, shape, encourage, contribute, and grow. We want to know that our presence still counts for something.

That’s why a completely easy life, if such a thing existed, would probably disappoint us pretty quickly.

We were made for meaningful effort, and that’s where we find ourselves most alive.

The question, then, is less about whether life will ever become easy and more about whether we’re giving ourselves to things that build something in us and around us. Things connected to purpose, love, responsibility, service, growth, and calling.

Giving ourselves to the right things helps us stop feeling sorry for ourselves and start paying attention again. It steadies us for the chapter we’re in, rather than the imaginary one we hope will arrive.

As long as we’re here, there’ll be something in front of us asking for effort.

That’s our life inviting us in.

Photo by Nadya Spetnitskaya on Unsplash – Bread doesn’t rise without the work. Neither do we.

After the Fumble

A fumble changes everything.

One second the play is moving. The runner has the ball. The blockers are engaged. The drive has life. Then suddenly the ball hits the ground, bodies are diving, momentum has shifted, and what was yours a moment ago is theirs.

A fumble tests everyone.

The one who dropped the ball.

The coach.

The team.

For the player who fumbled, the moment is immediate and personal. He cost his team field position, momentum, or more. He’ll think about that play long after the whistle.

His pain rarely comes from the mistake alone. It also comes from the exposure. He was carrying something important, and now everyone can see that he mishandled it.

He comes to the sideline knowing what he did.

He doesn’t need it explained. He doesn’t need the replay. He felt the ball leave his hands. He already knows what it cost.

What he doesn’t know is what comes next.

That depends largely on who’s standing on the sideline with him.

A weak coach sees only the mistake. A careless coach brushes past it. But a strong coach understands something both miss. This player, in this moment, is deciding, maybe without knowing it, whether he can still trust himself.

Correction matters. Accountability matters. But there’s a difference between a coach who corrects and a coach who restores. One addresses what happened. The other addresses what happens next.

Real leadership does both.

It says, “Yes, that mattered. Yes, you need to learn from it. And yes, you’re still capable of more than this moment.”

Correction is the easy part. The rest is belief.

People rise to the level of belief placed in them after they’ve failed. That’s one of the most dependable things about human beings. A good coach knows this. A great one acts on it.

What about the team?

They saw it.

That fumble belongs to everyone now.

Do they quietly create distance from the one who dropped the ball? Do they look away? Do they let frustration show in ways that make him feel more alone?

Or does someone move toward him?

Not to fix it. Not to instruct. Just to be close enough that he knows he hasn’t been cut loose.

Great teams are built by people who know what to do when somebody fumbles. That knowledge is built over time. Through the kind of culture a team creates long before the ball hits the ground.

That’s true in every organization, every family, every group trying to do meaningful things together.

Eventually someone will drop the ball. Someone will let something important get away. Someone will have a moment they wish they could take back.

Failure doesn’t create a team’s culture. It exposes it.

A lot of people carry the weight of old fumbles.

A business decision that went wrong.

A missed opportunity.

A sentence that should have stayed unspoken.

A responsibility handled poorly.

A relationship moment they wish they could take back.

That weight is real. The costs were real. The embarrassment was real. There’s no use pretending otherwise.

But the fumble doesn’t have to be the end of the story.

Sometimes the growth that follows a mistake runs deeper than anything that came before it. Failure exposes what needs to be seen. A weakness, a blind spot, a lapse in discipline. It creates a moment that can be used, or wasted.

That moment rarely turns on the person who fumbled. It depends on what they find when they look up.

The leader who steps in with exactly the right mix of truth and trust. The teammate who moves toward them instead of away. The voice that says you’re still capable of more than this moment.

What looks like the end of the drive is sometimes the moment the real game begins.

Photo by Tim Mossholder on Unsplash

The Rocks, A Higher Gear, and Campfires

In 2013, I wrote a short post called We Are All Mountain Climbers.

The idea was simple. If you look closely at life, you’ll see that everyone is climbing something.

A career. A relationship. A difficult time in their lives. A personal challenge.

Life has a way of placing mountains in front of us. Or maybe…we’re just good at finding them.

As I wrote back then, the climb only makes sense from the inside. Watching others or hearing their stories are no substitute for taking it on yourself.

There was another part of the metaphor that mattered even more.

Many of us start the climb with backpacks full of things that make our journey harder than it needs to be. Old resentments. Lingering disappointments. Criticism that stuck with us longer than it should have. Sometimes we even carry baggage that belongs to someone else.

Years later, I came across a Buddhist parable that gave a new wrapper to this idea. It described people walking through life carrying large boulders. Anger. Ego. Grudges. The suffering didn’t come from the boulders themselves. It came from choosing to pick them up.

In 2015, I wrote about riding my mountain bike.

Whenever a hill approached, I had a habit of shifting into an easier gear before the climb even began. It felt like preparation. It felt like the smart thing to do.

One day I tried something different. Instead of downshifting, I shifted to a higher gear and pushed harder.

To my surprise, I climbed much faster than before, without bonking like I thought might happen.

Sometimes growth means discovering we’re stronger than we realize.

That experience raised questions I still ask myself.

Where else in life do I downshift before the hill arrives?

Am I protecting myself from difficulty…or underestimating what I’m capable of?

Recently, I read a post by Tim Ferriss about the “self-help trap.” He described sitting around a campfire one evening with a small group of close friends, the kind of unhurried night where the conversation slows down enough for truths to surface. He found himself thinking about the fire, and then realizing the fire wasn’t the point. The people sitting around it were.

He described how easily we can become so absorbed in optimizing ourselves, tracking progress, chasing improvement, climbing toward our next summit, that we lose sight of why we started climbing in the first place.

Summits will eventually fade. Our achievements will blur with time. Recognition disappears quicker than we expect.

Perhaps the real work of self-improvement is simpler than we think.

The rocks we’re carrying were never necessary.

The hills we fear are usually smaller than we imagine, or remember.

And the fire, the one worth tending, isn’t the one powering our ambition. It’s the one we gather around with the people we love.

Photo by Marc Zimmer on Unsplash

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

One Hundred Years from Now

I saw an inspirational sign over the weekend. It said…

I saw an inspirational sign over the weekend. It said:

One Hundred Years from now it will not matter what kind of house I lived in, how much money I had, nor what my clothes were like, but the world may be a little better because I was important in the life of a child.

All of us are children, some just older than others. We each have the capacity to inspire, and to be inspired. We each have the capacity to challenge, and to be challenged. We certainly have the capacity to teach, and to be taught.

Our openness to both sides of the equation is what’s most important.

What Are You Saying?

When talking to your friends, family, employees, or anyone else, do you use encouraging words, or discouraging words?

The words and tone you choose matter. They reflect, and impact, your attitude. Your words are the window into your perspective on the world.

Choose discouraging words, and you actively create a discouraging environment for those around you.

Choose encouraging words, use encouraging questions, and guess what…you create an encouraging environment.

The power to create an encouraging environment, an encouraging attitude, is in your hands everyday.

Here’s an exercise for you. Seek out three people to encourage today. Encourage them with your words, your questions, and your actions. Show them that you are genuinely interested in what they have to say. Be appreciative of their unique efforts and skills. Actively consider how to help them be more successful in achieving their goals. Repeat this exercise everyday.

Does this exercise make you uncomfortable? If so, maybe you should be the first person you seek out to encourage.

Everything Looks Easy…

Everything looks easy (from the grandstands)…

A pro golfer smacks a 325 yard drive off the tee. He has modified his swing perfectly so the ball draws to follow the dog-leg turn in the fairway at about the 225-yard mark. He bends over and picks up the tee, strolling casually away as if this is just a routine shot. For him, it is routine.

A pitcher throws a ball 98 miles per hour, straight down the middle for a strike, and follows that up with an 80 mile per hour change-up with the exact same throwing motion…fooling the batter with both pitches.

A Cirque de Soleil performer soars through the air upside-down, holding on with one hand to what appears to be a satin sheet hanging down from above. The soaring routine lasts 7-10 minutes, and the entire time the performer is merely hanging onto the satin sheet.

A freestyle motocrosser performs a no-handed back-flip across an 80 foot jump and lands it effortlessly.

A figure skater performs a jump combination that includes a triple spin in the air, followed by another triple spin in the opposite direction…landing flawlessly.

A general contractor and his crew convert an empty lot into a custom-built home, complete with custom landscaping, in less than 180 days.

A CEO gives an inspiring talk to 500 employees gathered in an auditorium. There are also 25,000 others watching remotely on the web. Every word is clear, precise, and each employee connects with the CEO’s message.

The audience only sees the final product. They don’t see the countless hours (often, years) of dedication, practice, and failures that have made the difficult look easy.

Where are you spending your time? In the grandstands where everything looks easy? Or, in the game where commitment, and a willingness to fail on the way to success, are the price of admission?