Courage – Grandpa Bob Encouraging Leadership

Decision Time

A decision sits in front of us, waiting.

We turn it over in our head. We ask a few more questions. We look for one more data point. We check with another person whose opinion we respect. We wait for the timing to feel right.

And still, we hesitate.

We tell ourselves we need more information. More time. More certainty.

Indecision usually grows from very human places. Fear of being wrong. Fear of being blamed. Fear of choosing a path that can’t be undone. Fear of embarrassment.

Add decision fatigue to the mix and postponement starts to feel reasonable.

Meanwhile, the cost of waiting accumulates quietly. Teams stall. Momentum fades. Confidence erodes. What began as a thoughtful pause turns into drift.

Most leadership decisions are made without perfect information. Progress rarely waits for certainty.

So, what is our hesitation really telling us?

Sometimes, it’s a clear no. A request pulls us away from what matters most. We don’t like what we see, but we’re not sure why. Maybe a partnership doesn’t sit right with our values. In these moments, extended thinking isn’t searching for clarity. It’s searching for a way to explain our decision.

Other times, we hesitate because the decision stretches us. It introduces uncertainty. It raises our visibility. It asks more of us than we feel ready to give. Growth decisions usually feel uncomfortable before they feel right.

At some point, the data stops improving and the waiting stops helping.

Start small. Take a step that tests the decision rather than locking it in. Forward motion reveals new information…something thinking alone can’t.

A decision that turns out to be wrong isn’t failure.

It’s feedback.

And feedback points us toward our next decision.

“Whenever you see a successful business, someone once made a courageous decision.”
— Peter F. Drucker

Photo by ChatGPT’s new image generator, which is way better than prior versions of the tool.

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.

The Opportunity to Level Up

Ego may be our biggest barrier to learning.

It’s like having a guy working the door at a nightclub, deciding who or what gets in.

We assume we already know everything, so we stop listening. We nod politely. But inwardly we’ve already dismissed the person speaking. Or the article. Or the correction.

There’s often good reason for our defensiveness. Being wrong about something important can have real consequences. Our ego is trying to protect us from the genuine discomfort and potential costs of being mistaken.

The paradox is that the very thing protecting us from being wrong in the moment often prevents us from being more right in the future.

What if instead of having a bouncer who turns everyone away, we hired a smarter gatekeeper? One who doesn’t just protect us from being wrong, but actually helps us get better at being right?

What if we treat new information, even the stuff that contradicts what we think we know, as an invitation?

An opportunity to level up. To upgrade our understanding. To sharpen our thinking.

What happens when we level up? Our predictions start getting more accurate. Our explanations become clearer and more useful to others. We catch our own mistakes faster…sometimes before they even leave our mouth. We become more curious about the very areas we feel most certain.

The next time someone disagrees with you or presents information that challenges what you believe, pause before your ego’s bouncer slams the door.

Ask yourself, “What if they’re right? Can I learn something new?”

This doesn’t mean accepting everything that comes your way. But you can listen. Examine the ideas. Question them. Test them against what you know.

That’s true intellectual courage.

And it’s the only way to keep growing in a world that never stops changing.

“It is impossible for a man to learn what he thinks he already knows.” – Epictetus

Photo by Vinay Tryambake on Unsplash

Starting is the Hardest Part

The blinking cursor on a blank document. The empty stretch of land where you’ll soon be building a shop. The new web application your company wants to develop that will revolutionize your industry. These are just a few examples of standing on the edge of something new, something important, yet feeling completely unsure of where to begin.

You might have a vision of the final result—the finished document, the completed shop, the fully functioning app. But that doesn’t mean you know how to get there.

It’s easy to get lost in the variables and the endless possibilities. What if I make the wrong decision? Are there more resources out there? What do other people think? Should I read more articles? Watch more videos? Seek more advice? What if I mess it all up?

In every case, the hardest part is starting.

It’s taking that first step. Writing the first sentence. Sketching out the first screen of an app. Nailing the first stakes into the ground—the ones you’ll attach a string to, so you can visualize where your new shop will go.

It’s a commitment to action over hesitation. A moment of bravery that marks the beginning of making something real.

An amazing thing happens when you start. Your mind shifts from a place of endless “what-ifs” to a place of positive motion. You begin to focus on the next steps and real solutions. All the challenges you imagined before starting—that, in many cases, won’t even come to pass—are forgotten. The path ahead becomes clearer, and each small step forward makes your next decision easier.

Does this mean everything goes perfectly after you start? Of course not. You’ll make mistakes, adjust, learn, and pivot along the way.

But here’s where starting becomes crucial: it provides a tangible foundation. It gives you something to measure against, something to refine, something to edit. You might completely change your initial idea, but you wouldn’t have discovered the need to change if you hadn’t started.

Starting is hard, but it’s also the most important part.

Take the first step, even if it feels uncomfortable. You’ll learn more from those first few steps than you will from standing still…wondering what might happen.

Once you start, momentum kicks in. And from there, the possibilities are endless.

Photo by Jon Tyson on Unsplash

Navigating Fear…A Personal Guide to Freedom and Growth

Fear is like that well-meaning friend who occasionally oversteps boundaries. It’s a survival instinct, a leftover trait from our ancestors who needed it to avoid becoming someone else’s lunch. It can guide us toward wise choices and help us steer clear of danger.

Our imagination, on the other hand, is a bit of a storyteller, especially when it comes to tales that can hold us back. With all our experiences and secrets tucked away in our minds, our imagination can whip up some remarkably dreadful future scenarios. And our lizard brains? They thrive on responding to fear.

Fear is undoubtedly real. The fear of failure, loss, embarrassment, injury, loneliness, helplessness, and death can have profound impacts on our thoughts and actions. However, if we recognize, understand, and confront these fears head-on, it will be like flicking on the lights in a dark room – suddenly, the monsters lose their scariness.

By acknowledging that fear is a living part of us, we can take steps toward asserting our control over it. Fear shouldn’t be in the driver’s seat.

“Yea, though I walk through the valley of the shadow of death, I will fear no evil: for thou art with me; thy rod and thy staff they comfort me.” – Psalm 23

We aren’t alone in this journey of conquering fear. We have a loving God, supportive family, and caring friends to help us face our fears. They can offer a broader perspective and lend a hand when we need it most.

Life is a rollercoaster of unknowns, and fear hates rollercoasters. Instead of fearing the unknown, befriend it. New ideas, experiences, and relationships? Embrace them as opportunities, be curious, and let the adventure unfold.

Life is rarely easy, and sometimes truly terrible things happen to us. But, fear should be the backseat driver, not our navigator.

“I must not fear. Fear is the mind-killer.

Fear is the little-death that brings total obliteration.

I will face my fear. I will permit it to pass over me and through me.

And, when it has gone past, I will turn the inner eye to see its path.

Where the fear has gone there will be nothing. Only I will remain.”

–Paul Atreides in the novel Dune, by Frank Herbert

Photo: Why hot air balloons? Well, taking a ride in a hot air balloon would not be possible if we let fear make the decision. I’m happy to report the balloon ride was amazing!

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Beyond the No Wake Zone

True adventure happens out past the buoys…

I get seasick easily, especially on sailboats (and fighter jets). I’ve been on a few sailing trips. They all had one thing in common. Once we’re outside the no wake zone, my nausea starts. Things go downhill from there until my head is buried under a towel and I try to sleep until we get to dry land. Needless to say, I avoid sailing trips.

I don’t have a problem on cruise ships, except in rough seas. Cruise ships are engineered to deliver a smooth ride for their passengers. Most swells go unnoticed. Passengers wake up in a new port almost every day, and the food and entertainment are usually spectacular.

Harbor cruises work for me. I can handle cruising around inside the no wake zone, looking at all of the boats in their slips, the nice homes on the shoreline, and passing other boats as they make their way out to sea. Christmas time, with all the lights and decorations is the best. It’s relaxing and safe. There are no swells to cause nausea and seasickness.

Every sailor knows the opportunity for new discovery lies beyond the no wake zone. True adventure happens out past the buoys, past the breakwater, and out in the wind and waves. Riding around in the harbor, or lazily enjoying a multi-course dinner on a cruise ship are fun and sometimes exotic. But, neither compare to the adventure of plying the seas in a forty-foot sailboat, with your hand on the tiller.

What about the risks? Staying on shore has risks. Cruise ships certainly carry risk (and sometimes, viruses). We may take comfort that others are managing our risks for us, but nothing is risk free. Storms and rough seas will hit, no matter who drives the boat. Understanding the risks, planning and preparing for them, and facing our challenges head-on is the only consistent winning strategy…at sea, and in life.

What about seasickness? I remember talking with a sailor in Tahiti. We had flown in for a vacation, and met my mother-, and father-in-law, who were sailing their boat across the South Pacific. The sailor was a friend of theirs. I mentioned my problem with seasickness, and how it would prevent me from making such a voyage.

He laughed and said, “The seasickness usually passes after three days at sea. After that, it’s an adventure of a lifetime.”

He was right.

The Bargains We Make

I bargained with Life for a penny…

I came across this classic poem recently:

My Wage

I bargained with Life for a penny,

And Life would pay no more,

However I begged at evening

When I counted my scanty store.

For Life is a just employer,

He gives you what you ask.

But once you have set the wages,

Why, you must bear the task.

I worked for a menial’s hire,

Only to learn dismayed,

That any wage I had asked of Life,

Life would have willingly paid.

–by Jessie Belle Rittenhouse (1869-1948)

My Question for You

What is your bargain with Life?

Are you working for a penny, or something more?

How about your end of the deal?

Are you even keeping score?

If we get out of Life,

Only what we ask,

I say go for the Moon,

And reach for the stars.

But, are you willing to bear the task?

Remembering to Breathe

Nearly all sports are the same (at least on one level).

Nearly all sports are the same (at least on one level). It doesn’t matter if that sport is soccer, baseball, golf, archery, skeet shooting, curling, downhill skiing, long distance running, ice skating, motorcycle racing, or competitive yodeling.

They each start with the same fundamentals:

Relax and stay loose
Calm your mind
Visualize success
Bend your knees
Don’t forget to breathe.

One could make a case that each of these fundamentals are of equal importance, but my money is on the last one. Consciously remembering to breathe puts us in the right state of mind to remember the other fundamentals.

We each face challenges on a daily basis. Some are small, and some are huge (at least from our perspective). Here’s a strategy for tackling each of them: