Attitude – Grandpa Bob Encouraging Leadership

Living Inside History

Every generation believes it’s living through extraordinary change.

And in a way, every generation is right.

Economic strain, political division, conflict, and rapid technological change appear in different forms, but the underlying tension remains the same.

Ray Dalio describes what he calls the Big Cycle. The rise and decline of nations shaped by debt, money, internal division, and shifting global power. He would say we’re late in that cycle, marked by high debt, widening wealth gaps, and growing competition among world powers.

Harry Dent approaches history through demographics, studying population growth, and generational spending patterns. From his view, today’s economic strain reflects aging populations, slower growth, and the unwinding of decades of expansion.

Different perspectives. Similar conclusions.

Neither claim to predict the future with precision. Debt cycles, demographic waves, generational moods, technological revolutions, and geopolitical tensions move simultaneously. Understanding these forces and their patterns helps us recognize the currents. How we live within them is still our responsibility.

I remember the OPEC oil embargo of the 1970s and gas lines stretching for blocks. I was in elementary school as interest rates climbed above twenty percent. I watched the Reagan Revolution reshape economic thinking and bring supply-side theory into the mainstream.

I lived through the Iranian Revolution in 1979, the taking of US hostages, and the subsequent spread of militant extremism across parts of the Muslim world over the next four decades. I watched an airplane strike the World Trade Center in real time.

I grew up under the shadow of the Cold War, when nuclear conflict felt possible at any moment. I saw the optimism that followed the fall of the Soviet Union and then watched China open to the world after decades of isolation. I remember the theories about how expanding capitalism in China might soften their communist approach to governing.

I witnessed the savings and loan collapse, multiple stock market crashes, the Great Recession, and a global pandemic that disrupted economies, institutions, and families alike. I watched how strongly governments grasp control when certainty disappears.

I saw personal computers and then the internet transform daily life, followed by the digital economy, smartphones, social media, and now artificial intelligence reshaping work itself.

I can think of countless other historical events that have happened in the span of one life. Each moment felt unprecedented. Each reshaped the world, sometimes positively, sometimes negatively.

And yet, life continued.

When history is written, it focuses almost entirely on macro events. The narratives are dominated by wars, collapses, elections, revolutions, and markets. What rarely appears are the countless individual lives unfolding quietly alongside these events.

History does not record families eating dinner together during times of high inflation. Nor does it record weddings that took place during recessions or children born during wars. It overlooks the laughter that survived fear and the quiet courage required to just keep going.

But these individual experiences of life form the definition of humanity.

For every name preserved in textbooks, millions of people were doing what people have always done. They worked. They loved. They raised children. They cared for neighbors. They hoped tomorrow might be a little better than today.

Macro forces shape conditions. They influence opportunity and may narrow our options. They may, unfortunately, end our life or the lives of someone we love. But they don’t define a life.

Inside every macro upheaval exists our “micro” life. The life lived within the headlines rather than dictated by them.

The world may determine interest rates. It does not decide whether we act with kindness. It may influence careers, but it does not control our integrity. It may introduce hardship, but it does not determine how we respond.

Our response is where freedom still lives.

Viktor Frankl understood this more clearly than almost anyone. After enduring unimaginable suffering in Nazi concentration camps, he observed that nearly all external freedoms can be taken from a person. One freedom remains intact. The ability to choose one’s attitude and response to circumstances.

Events may constrain us. They may demand adaptation. They will never own our human spirit.

In my office, I have a wall filled with photographs. Family gatherings. Wedding days. Trips taken together. Beautiful places. Ordinary moments that became lasting memories.

When I step back and look at this wall, patterns appear.

We worked hard.

We made time for one another.

We traveled together.

We celebrated milestones.

We were living out our hopes and dreams, and we still are.

My wall has no charts or financial forecasts. No macro trend lines. But it tells the story of what matters most.

None of these moments waited for ideal conditions. They unfolded alongside inflation, recessions, political change, and uncertainty. The photographs capture lives shaped by ordinary but important choices made amid extraordinary times.

As we traveled, we met families across many countries. Different customs. Different faiths. Different governments. Yet everywhere we went, the hopes sounded familiar. Parents wanting the best for their children. Families striving for opportunity. Communities longing to contribute and belong.

The differences emphasized by the world shrink quickly when people speak about those they love.

Human aspirations remain remarkably consistent.

History changes its outward form. The heart changes very little.

You will live through upheavals of your own. Some will be frightening. Some will be unfair. Some will test your trust in institutions or leaders.

Remember this.

You are not responsible for controlling history. You are responsible for how you live inside it.

You will not choose the history that surrounds you. You will choose the values you carry through it.

You choose how you treat people.

You choose how to adapt.

You choose how you show up for your family.

You choose whether uncertainty hardens you or deepens your compassion.

You choose whether fear leads or faith steadies you.

These are your choices. Always.

Humanity endures because ordinary people continue to build their lives amid uncertainty. They love, they work, they fail, they adapt, and they hope, even while larger forces move around them.

While empires rise and fall, families persist.

That is the quiet march you belong to. Rarely captured by historians yet carried forward by generations.

History happens around you.

Life happens within you.

Live your life well. Love deeply. Work honestly. Stay flexible. Hold your faith. Care for one another.

If you do that, you will live a meaningful life regardless of when you were born.

As I was finishing this post, I found these quotes from George Bernard Shaw. The words come from two different writings of his from the early 1900’s. Together they express something important about what it means to live well within whatever history hands us.

“This is the true joy in life, the being used for a purpose recognized by yourself as a mighty one; the being a force of Nature instead of a feverish, selfish little clod of ailments and grievances complaining that the world will not devote itself to making you happy. “

“I am of the opinion that my life belongs to the whole community, and as long as I live it is my privilege to do for it whatsoever I can. I want to be thoroughly used up when I die, for the harder I work the more I live. I rejoice in life for its own sake. Life is no ‘brief candle’ for me. It is a sort of splendid torch, which I have got hold of for the moment; and I want to make it burn as brightly as possible before handing it on to future generations.”

h/t – Atkins Bookshelf

Photo by Federico Giampieri on Unsplash

If this post resonated with you, feel free to share it with someone who might appreciate it as well.

You can also listen to the Grandpa Bob Encouraging Leadership Podcast, where I share short reflections on leadership, life, and learning.

Thanks for reading!

When the Disruptors Get Disrupted

For most people in IT, change is constant.

New platforms arrive. Old tools fade. Processes are reworked. Skills must evolve.

In that sense, disruption has long been part of the job description.

Software developers create new and improved tools. They streamline workflows. They automate tasks that once required entire teams. Over time, they have reshaped and disrupted how work gets done across nearly every industry.

This pattern has been in place for decades.

For software developers, something different is happening now.

With the arrival of AI-assisted development tools, including systems like Anthropic’s Claude Code, disruption has begun to turn inward. These tools are reshaping how developers approach their own work.

For many in the profession, this feels unfamiliar.

Software development continues, but the definition and details of the role are shifting. Tasks that once required sustained manual effort can now be generated, refactored, tested, and explained with remarkable speed.

A developer who once spent an afternoon writing API integration code might now spend fifteen minutes directing an AI to produce it, followed by an hour reviewing edge cases and security implications. The center of gravity moves toward judgment and direction rather than execution and production.

When job roles experience disruption, responses tend to follow predictable patterns. Some people dismiss the change as temporary or overhyped. Others push back, trying to protect familiar and comfortable ways of working. Still others approach the change with curiosity and engagement, interested in how new capabilities can expand what’s possible.

Intent Makes the Difference

An important distinction often gets overlooked when discussing pushbacks.

Some resistance grows from denial. It spends energy cataloging flaws, defending established workflows, or hoping new tools disappear. That approach drains effort without shaping new outcomes. It preserves little and teaches even less.

Other forms of resistance grow from professional judgment.

Experienced developers often notice risks that early enthusiasm misses. Fragile abstractions, security gaps, maintenance burdens, and failures that appear only at scale become visible through lived experience. When developers raise concerns in the service of quality, safety, and long-term viability, their input strengthens the eventual solution. This kind of resistance shapes progress rather than attempting to stop it.

The most effective developers recognize this shift and respond deliberately. They move away from opposing new tools and toward advocating for their effective use. They ask better questions. They redesign workflows. They establish guardrails. They apply experience where judgment continues to matter.

In doing so, they follow the same guidance developers have offered others for years.

Embrace new tools.
Continually re-engineer how work gets done.
Move upstream toward problem framing, system design, and decision-making.

Greater Emphasis on Judgment

AI generates code with increasing competence. Decisions about what should be built, which tradeoffs make sense, and how systems must evolve over time still require human judgment. As automation accelerates, these responsibilities grow more visible and more critical.

This opportunity in front of developers calls for leadership.

Developers who work fluently with these tools, guide their thoughtful adoption, and help their teams and organizations navigate the transition become trusted guides through change. Their leadership shows up in practical ways:

-pairing new capabilities with healthy skepticism

-putting review processes in place to catch subtle errors

-mentoring junior developers in how to evaluate results rather than simply generating them

-exercising judgment to prioritize tasks that benefit most from automation

Disruption has always been part of the work.

The open question is whether we meet disruption as participants, or step forward as guides.

Photo by AltumCode on Unsplash

Always Improve Your Position

A few days ago, I was listening to Jocko Willink speak about the quiet discipline behind Brazilian jiu-jitsu. I’m not a jiu-jitsu person, but one idea landed for me. It’s a truth I already knew but had never heard spoken so simply:

Always improve your position.

In jiu-jitsu, nothing happens all at once. A submission arrives like lightning, but only to the untrained eye. What looks like a sudden victory is really the final expression of dozens of subtle movements that came before it. A hip shifts. A grip tightens. An elbow gains an inch of space. Most of these moves go unnoticed. Each small adjustment creates a little more room, a little more leverage, a little more advantage.

I’ve always believed real progress works this way. It’s rarely dramatic. It’s quiet and patient. The accumulated effect of showing up, learning something new, adding a bit more care, and preparing a little more than required.

Breakthroughs rarely come from a single moment of inspiration. They come from the quiet work no one sees. The thoughtful practice that sharpens your skills, the trust built over months of ordinary conversations, the time spent learning before making a decision. When opportunity arrives, it looks sudden to others. To you, it feels like the next logical step.

This truth showed up clearly for me after a derecho tore through our property on Father’s Day weekend a few years ago. Ninety-mile-per-hour winds knocked down at least thirty trees across multiple acres. When I walked our land the next morning, everything felt broken and overwhelming. The cleanup looked like a project that would take months. I didn’t have months to devote to it.

But I did have mornings. So, I decided to work for an hour and a half every day before work. I cleared a small section each morning. It was incredibly slow. I dragged branches, cut trunks, chipped debris, split firewood, and made countless trips to our local dump. Small steps, small progress, one morning at a time.

Over the course of a year (maybe more), I worked my way across our entire property. Along the way, I cut in new hiking trails and removed a number of unhealthy trees. What started as a mess became a healthier stand of trees and a network of paths that look like they’ve been here forever.

Out of destruction came a daily habit that changed my life. I still work outside every morning. Clearing brush, trimming trees, expanding trails, building chicken coops, restoring a rustic barn. All in small ninety-minute bites. It’s like a time-lapse video created through countless quiet mornings of small improvements.

The pattern I saw on my land is exactly what Jocko described on the mat. I didn’t need a grand plan or a burst of superhuman effort. I needed to improve my position every day, just by a little.

Improve your position today, even by an inch, and tomorrow becomes easier. Improve it again tomorrow, and the day after that reveals options that didn’t exist before. You don’t need surges of motivation or dramatic reinvention. You only need the willingness to keep moving, always improving.

Careers grow this way. Trust grows this way. Faith deepens this way. Families strengthen this way.

Progress won’t always be linear. Some days distractions will pull us off course, or setbacks will undo work we thought was finished. All of this is part of the journey. Even then, the way forward still comes through small steps. Imperfect, uneven, but the work of always improving our position remains the same.

We improve our position slowly, almost without noticing. That’s enough. Tomorrow, we’ll improve again. Then one day, we’ll find ourselves able to take a step that would have felt impossible a year ago.

Focus on the next inch. The miles will take care of themselves.

Photo by Walter Martin on Unsplash – a great rendition of my early morning work environment for at least a year.

Why Curiosity Is the New Competitive Advantage

Imagine two managers sitting at their desks, both using the same AI tool.

The first asks it to write the same weekly report, just faster. Three hours saved. Nothing new learned. Box checked.

The second uses the AI differently. She asks it to analyze six months of data and search for hidden patterns. It reveals that half the metrics everyone tracks have no real connection to success. Two new questions emerge. She rebuilds the entire process from scratch.

Same tool. Different questions. One finds speed. The other finds wisdom.

This is the divide that will define the next decade of work.

For a long time, leadership revolved around structure and repetition. The best organizations built systems that ran like clockwork. Discipline became an art. Efficiency became a mantra.

Books like Good to Great showed how rigorous process could transform good companies into great ones through consistent execution. When competitive advantage came from doing the same thing better and faster than everyone else, process was power.

AI changes this equation entirely. It makes these processes faster, yes, but it also asks a more unsettling question. Why are you doing this at all?

Speed alone means little when the racetrack itself is disappearing.

Curiosity in the age of AI means something specific. It asks “why” when everyone else asks “how.” It uses AI to question assumptions rather than simply execute them. It treats every automated task as an opportunity to rethink the underlying goal. And it accepts the possibility that your job, as you currently do it, might need to change entirely.

That last part is uncomfortable. Many people fear AI will replace them. Paradoxically, the people most at risk are those who refuse to use AI to reimagine their own work. The curious ones are already replacing themselves with something better.

Many organizations speak of innovation, but their true values show in what they celebrate. Do they promote the person who completes fifty tasks efficiently, or the one who eliminates thirty through reinvention? Most choose the first. They reward throughput. They measure activity. They praise the person who worked late rather than the one who made late nights unnecessary.

This worked when efficiency was scarce. Now efficiency can be abundant. AI will handle efficiency. What remains scarce is the imagination to ask what we should be doing instead. Organizations that thrive will use AI to do entirely different things. Things that were impossible or invisible before.

Working with AI requires more than technical skills. The syntax is easy. The prompts are learnable. Connecting AI to our applications isn’t the challenge. The difficulty is our mindset. Having the patience to experiment when you could just execute. The humility to see that the way you’ve always done things may no longer be the best way. The courage to ask “what if” when your entire career has been built on knowing “how to.”

This is why curiosity has become a competitive advantage. The willingness to probe, to question, to let AI reveal what you’ve been missing. Because AI is a mirror. It reflects whatever you bring to it, amplified. Bring efficiency-seeking and get marginal gains. Bring genuine curiosity and discover new possibilities.

Here’s something to try this week. Take your most routine task. The report, the analysis, the update you’ve done a hundred times. Before asking AI to replicate it, ask a different question. What would make this unnecessary? What question should we be asking instead?

You might discover the task still matters. Or you might realize you’ve been generating reports nobody reads, tracking metrics nobody uses, or solving problems that stopped being relevant two years ago.

Efficiency fades. What feels efficient today becomes everyone’s baseline tomorrow. But invention endures. The capacity to see what others miss, to ask what others skip, to build what nobody else imagines yet.

The curious will see opportunity. The creative will see possibility. The courageous will see permission. Together they will build what comes next.

The tools are here. The door is open. Work we haven’t imagined yet waits on the other side. Solving problems not yet seen, creating value in ways that don’t exist today.

Only if you’re willing to ask better questions.

Photo by Subhasish Dutta on Unsplash – the path to reinvention

Choosing Curiosity Over Fear

When we look toward the future, two voices compete for our attention. Fear tells us to run away. Curiosity invites us to step forward.

Fear whispers, “It’s too much. I can’t keep up. Better to stop trying.” Curiosity responds, “I don’t understand…yet. Let’s see what happens.”

Fear closes.

Curiosity opens.

Fear imagines disaster.

Curiosity imagines possibilities.

Fear isolates.

Curiosity connects.

The world is changing quickly. The pace can feel overwhelming. Many will react with fear. A curious spirit asks questions. It wonders what could be.

Curiosity doesn’t remove uncertainty but transforms how we deal with it. When we lead with curiosity, we move from paralysis to participation. We see the unknown as a chance to grow.

“Never let the future disturb you. You will meet it with the same weapons of reason which today arm you against the present.” – Marcus Aurelius

We already have the tools we need. Curiosity and our ability to learn. What we need is the courage to use them.

Photo by ALEXANDRE DINAUT on Unsplash

The Noonday Devil and the Lie of Boredom

Psalm 91 promises safety from dangers both visible and invisible, from “the terror by night” to “the arrow that flieth by day.”

In verse 6, we read: “Nor for the pestilence that walketh in darkness; nor for the destruction that wasteth at noonday.”

The Desert Fathers, those early Christians who left the cities around the third and fourth centuries to live in the desert, drew on this verse to describe one of their deepest spiritual struggles. They called it the noonday devil.

This devil represents an interior battle, a weariness of the soul that crept in at midday when the sun beat down, the silence grew heavy, and the temptation to abandon their prayer and vocation felt overwhelming.

They named this struggle acedia. Sometimes it’s translated as sloth, but it is much more than that.

How many kids have said to their parents, “I’m bored.” We remind them that boredom is in their heads. They can use their imagination, find a book, or play outside. And if that doesn’t land, we parents always have another cure for their boredom: chores.

It’s amazing how quickly boredom vanishes when a child is handed a rake, a shovel, or a basket of laundry to fold.

Boredom is what happens when we can’t see the meaning in what we’re doing. Acedia is boredom’s older cousin. Spiritual weariness with much deeper stakes.

It’s restlessness, a refusal to care, a loss of joy in the very things that give life meaning. It can show up as distraction or busyness. Acedia tempts us to walk away when the middle of the journey feels too long and too heavy.

I think of the countless days spent inching along in rush-hour traffic, morning after morning, just to get to work. I’d put in a full day’s work, then crawl through another hour or more of brake lights to get home. The next day brought the same routine. After a while, it was easy to think maybe the whole thing had no meaning.

That’s the noonday devil at work.

The midpoints of life test us in a similar way. Paying bills, the daily grind of a career without clear progress, responsibilities that seem to grow heavier without much relief. Our internal voice asks, “How can I escape? Should I look for something easier?”

Jean-Charles Nault’s The Noonday Devil: Acedia, the Unnamed Evil of Our Times says this ancient struggle is alive and well today. It shows up in constant scrolling, in working ourselves to exhaustion to avoid deeper questions, in chasing novelty because the present moment feels too heavy.

The Desert Fathers found the answer was to persevere through, but with far more than sheer willpower. Keep praying, even when prayer feels dry. Stay faithful to commitments, even when they feel heavy. Lean into your community rather than isolating from it. Practice humility and remember that perseverance is possible only by God’s grace.

What does this look like? When we feel the pull toward endless scrolling, we might instead text a friend or call a family member. When work feels meaningless, we can remember the people our efforts serve, even if indirectly. When prayer feels empty, we show up anyway, trusting that faithfulness itself has value beyond our feelings in the moment.

The noonday devil tempts us to think that only extraordinary lives matter. But as Oliver Burkeman points out in his idea of “cosmic insignificance therapy,” recognizing our smallness frees us to find profound meaning in ordinary acts.

The daily work of caring for children, preparing meals, or showing up for neighbors and friends carries as much weight as anything could. These acts may never make headlines, but in God’s eyes they shine with eternal value.

Persevering in small, steady commitments resists acedia and helps us discover joy in the very places where meaning often hides.

Psalm 91 carries a promise, “He shall cover thee with his feathers, and under his wings shalt thou trust.”

God invites us to rest beneath His wings, to trust Him in the heat of the day, and to discover joy at the very heart of our journey.

Faithfulness in the ordinary is never wasted. Under His wings, even the smallest acts take on eternal meaning.

h/t – Hallow app – Noonday Devil; Tim Ferris – Oliver Burkeman’s Cosmic Insignificance Therapy

Photo by Mauro Lima on Unsplash

Providing Room to Fail

Organizational culture, not technology, is the hardest part of innovation

How many of your projects are truly innovative? If you have any, what’s your success rate? Would you consider your success rate to be all-star caliber?

This baseball analogy is almost a cliché, but it holds up. A professional hitter with a .300 average is considered excellent (all-star?). That means they fail seven times out of ten.

Now imagine applying this to innovation. What if only 30% of your projects succeed? At first glance, that sounds like a losing record. But if the successful projects provide 10x productivity increases, transform your customer’s experience, or massively boost profitability…30% success would yield incredible results for your organization.

This is the kind of opportunity in front of us today with AI. Tools are maturing quickly. The potential is staggering. Every company, large or small, is beginning to experiment.

Some will tiptoe. Others will dive headfirst. All will face a mix of breakthroughs and busts.

There will be tools that don’t deliver on promises, pilots that fizzle, and teams that struggle with adoption. But there will also be amazing homeruns. Projects that reshape the business and redefine what’s possible.

Many leaders today are focusing on which AI tools to purchase and how to train their teams. That’s the easy part.

The harder part is creating space for both the hits and the strikeouts. If people feel they must succeed every time, they probably won’t swing at all. They’ll play it safe and stick with what they know.

Innovation will grind to a halt.

Providing room to fail doesn’t mean celebrating mistakes. It means making sure your team knows that experiments, even the ones that fall short, are part of making progress. Leaders who demand perfection get compliance. Leaders who make room for failure get innovation.

As you lead your organization into AI and beyond, remember that your job isn’t to guarantee every swing is a hit.

Your job is building a culture where people are willing to keep taking swings.

Photo by Chris Chow on Unsplash

59 Lessons at 59

I recently turned 59. Not the big 60 milestone but knocking on the door. In honor of this “almost-milestone” birthday, here are 59 lessons or truths I’ve picked up along the way that may be helpful for you:

Family is the greatest treasure. I’ve learned this from countless dinners, phone calls, and quiet moments of simply being together.
Love grows when you give it away.
Small kindnesses matter more than big speeches. Holding a door, writing a note, or showing up means more than most people will admit.
A campfire has a way of pulling people closer. Some of our best conversations happened with smoke in our face and stars overhead.
Walks in the woods teach patience. The trail never hurries, but it always leads you somewhere good, even if the trail leads back to where you started.
Listening is often better than speaking.
Start, even if you don’t know the finish line.
Forgiveness frees the forgiver.
Work hard, but not so hard you miss the laughter at the dinner table. That laughter is life fuel.
Friendships need tending like gardens.
A calm mind shapes a calm day. How you manage your thoughts sets the tone for how you live, not just how you lead.
Prayer steadies shaky ground.
Scars are inevitable but can become footholds.
Your children and grandchildren remember the times you kept your word. Integrity is how love earns trust over a lifetime.
Music can heal a weary spirit.
Laughter with grandchildren is holy ground. Even the silliest joke can create amazing memories.
Take pictures but also put your phone down.
The best conversations happen unplanned, often on the way to somewhere else.
God shows up in ordinary moments.
Start with what you have, not what you lack.
Be quick to encourage. A word of encouragement can feel like oxygen to someone gasping for air.
Time with your spouse is the best investment you’ll ever make.
A sunrise reminds us the story isn’t over.
Be generous with money, with time, and with grace.
Don’t underestimate a good meal shared…even a bad meal shared.
Patience is a form of love.
Read good books slowly. And read them aloud. I’ll never forget the nights of reading Harry Potter chapters to my kids, one voice carrying us all to another world.
Children teach us as much as we teach them.
A soft answer turns away wrath.
Slow down for sunsets.
Stay curious, even at 59.
Hold babies gently, but often.
Let go of what you can’t control.
Keep your promises, even the small ones. If you can’t be trusted in the little things, no one will trust you with the big ones.
Coffee or a meal with a friend beats any meeting.
Rest is productive.
Gratitude doesn’t just brighten the day. It multiplies joy in ways you can’t measure. It shifts ordinary moments into holy ones.
The journey matters more than the finish line.
Never be too proud to say, “I was wrong.” Or “I don’t know.”
Faith isn’t about knowing all the answers.
Celebrate progress, not perfection.
Trails are better with company. I’ve seen some of the deepest conversations unfold at mile three.
Be the first to say “thank you.”
Find work you believe in, but don’t let it define you.
Love is the legacy worth leaving.
Don’t compare. Contentment is wealth.
Your words can build or break. Choose to build. Always.
A long hug can mend a broken heart. I’ve felt that healing in the arms of family.
Keep learning, keep growing. Continuous improvement matters. Even the smallest step forward is still forward.
Tradition ties generations together, especially if that tradition involves an old family recipe that takes hours and lots of teamwork to make.
Tell stories. Your family needs them. Stories pass down more than facts. They carry history and identity.
Choose wonder over cynicism.
You can’t outgive God, but you can follow His example.
Every season has its beauty. Even Oklahoma summers with their heat and humidity have sunsets worth pausing for (clearly I appreciate sunrises and sunsets).
Be present. Tomorrow isn’t promised.
Family trust is sacred. Break it once, and it may never return the same. Protect it as carefully as you protect your home.
Celebrate the small wins. A child’s smile, a project finished, or a quiet evening with family. Cherish these moments.
Joy often hides in the small, ordinary things.
Life is a gift. At every age, unwrap it with wonder.

4 Bonus Lessons (which means I came up with four more that I didn’t want to exclude)

Adapt or be left behind. If you’re the best buggy whip maker, prepare to adapt when automobiles come out. Don’t cling to the past so tightly that you miss the future.
The quiet miracle of savings and compound interest. Einstein was right. Compound interest is the most amazing thing. Steadily and quietly setting aside a portion of your income builds your wealth over time. It also provides peace of mind and freedom for your future self.
Learn outside your lane. Take time to study things that don’t seem connected to your work. The most important lessons often come from entirely different fields.
Travel opens two windows. When you visit a new country, you learn about their culture, their food, their people. But you also return seeing your own home differently…with gratitude, with perspective, and with fresh eyes.

Photo by Mantas Hesthaven on Unsplash

Which Memory Would You Erase?

“If you could erase one memory, what would it be?”

We all have memories that sting. Failures. Regrets. Accidents. Loss. Moments we wish had gone differently. It’s easy to imagine how much lighter life might feel if certain days had never happened.

I wouldn’t erase any of them.

Every memory, good and bad, shapes who I am today. The hard ones give me resilience, humility, and perspective. The joyful ones give me hope and fuel. Together, they’ve woven the story that brought me to this moment.

If I erased regret, I’d lose the lessons.

If I erased pain, I’d lose the growth.

If I erased loss, I’d lose the clarity it gave me about the value of life and love.

I carry each memory with gratitude. Gratitude that even the hardest chapters are part of a larger story. Gratitude that none of it was wasted.

Gratitude that grace has been big enough to redeem even the parts I once wished to forget.

Photo by Jason Thompson on Unsplash – because grace brings life out of the hardest places.

100 Lessons for Playing (and Winning) the Long Game of Leadership

Ideas and wisdom often arrive with familiar roots.

My views on leadership come from my lived experiences and lessons I’ve learned from great builders and thinkers like Andrew Carnegie, Peter Drucker, Tom Peters, Ken Blanchard, Marshall Goldsmith, Zig Ziglar, Stephen Covey, Jack Welch, Seth Godin, Jeff Bezos, Gary Vaynerchuk, Tim Ferriss, Jocko Willink, James Clear, and countless others.

I’ve also worked with amazing managers and mentors over many decades, including a few who taught me what not to do.

Since I find myself often returning to these lessons, I thought it would be useful to write them down in a list for easier reference.

Leadership Foundations

1. Leadership begins in your mind long before it shows up in your actions.

2. Self-awareness is a leader’s first and most enduring responsibility. Know how your actions land, then lead on purpose.

3. Character outweighs credentials over the long haul.

4. Integrity compounds like interest. The longer you hold on to it, the more it grows.

5. Values are the compass that keep you on course when circumstances shift.

6. Humility is the strength to put others first.

7. Influence comes from trust, not job descriptions.

Vision and Direction

8. A leader’s vision must be big enough to inspire, but clear enough to act on today.

9. Clarity reduces fear. Ambiguity fuels it.

10. Momentum builds when people see the destination and believe they can reach it.

11. Vision is not just what you see. It’s what you help others see.

12. The clearer you are about the goal, the less room there is for fear to grow.

13. Purpose is the map. Storms are just temporary detours.

14. Belief in the destination turns small steps into powerful strides.

15. Every action should feel like part of the same bigger story.

16. Sometimes waiting is the boldest move you can make. Strategic patience is powerful (and extremely difficult).

People and Relationships

17. The right people in the right roles multiply results beyond what you can imagine.

18. A culture of respect will outlast a culture of urgency.

19. Listen like the person speaking might hand you the missing puzzle piece.

20. Pass the applause to others but keep the accountability close to your chest.

21. Trust is invisible, but when it’s gone, everything feels heavier.

22. Relationships need regular deposits of attention, not just withdrawals of effort.

23. Helping someone else win creates a tailwind for your own success.

Decision-Making

24. Good decisions blend facts, values, and the courage to act.

25. The first idea is often just the trailhead. Walk farther.

26. Energy without wisdom burns out. Wisdom without energy gathers dust.

27. Choose the option you can defend in the daylight and live with in the dark.

28. A quick, small decision can open doors a perfect plan never reaches.

29. It’s easier to fix a wrong turn early than to build a new road later.

30. Never cash in tomorrow’s credibility for today’s convenience.

Resilience and Adaptability

31. A setback is a classroom, not a graveyard.

32. Flexibility is a skill, not a personality trait. Practice it.

33. Change is the proving ground where talk becomes action. Priorities sharpen, assumptions get tested, and leadership shows up in decisions, owners, and dates. If nothing changes (no decision, no owner, no date) it was only talk.

34. Adapt your tactics, but never your core.

35. The best views are earned with effort you once thought impossible.

36. Challenges test your limits so you can discover you’re stronger than you ever imagined.

37. Sticking with it usually turns “almost” into “done.”

Growth and Learning

38. The best questions are the ones you don’t yet know how to answer.

39. The moment you stop learning, you stop leading. Sometimes before you notice.

40. Pride blocks the front door to growth. Curiosity leaves it wide open.

41. Ask for feedback before circumstances force it on you.

42. Teach your knowledge, always remembering that your actions teach your values.

43. Every conversation nudges someone closer to, or further from, their best self.

44. Failure carries lessons that success hides. Corollary: High water covers a lot of stumps.

Impact and Legacy

45. Success without significance is empty.

46. The influence you have on people’s lives will outlast your achievements.

47. Your legacy is written in the lives you touch, not in the titles you hold.

48. Leadership is something you borrow from the future. It must be returned in good condition.

49. The most meaningful titles are the ones people give you, not the ones on your nameplate.

50. Think in decades when deciding what to plant today.

51. Your success is multiplied when others stand taller because of you.

52. The best proof of leadership is when growth continues without your hand on the wheel.

53. Leave every place and every person better than they were when you arrived.

Communication & Culture

54. Say the quiet part kindly and clearly. Clarity without kindness bruises. Kindness without clarity confuses.

55. Stories travel farther (and faster) than memos. Stories move people. Memos inform them. Stories turn intention into action.

56. Consistency in small signals (tone, timing, follow-through) builds culture faster than slogans.

57. Meetings should create movement. Reserve live time for decisions and collaboration. End with owners and dates. If it’s just a podcast, send an email. If only two people need to talk, make it a call and give everyone else their time back.

58. Celebrate progress out loud so people know what “right” looks like.

59. Honesty scales when leaders go first. Name the hard thing and show how to address it.

60. Culture forms around what you tolerate as much as what you teach.

Execution & Accountability

61. Strategy stalls without a calendar. Put names and dates on intentions.

62. Start now. Ship one useful thing today. Ride the wave of momentum that follows.

63. Priorities aren’t what you say first. They’re what you do first.

64. When everything is urgent, nothing is important. Choose the one thing that unlocks the next three.

65. Inspect what you expect. Review, refine, and recommit in frequent loops.

66. Own the miss publicly and fix it quickly. Speed heals trust.

67. Scoreboards matter. People work smarter when progress (or lack thereof) is visible.

Faith, Purpose & Centering

68. Quiet time isn’t empty time. It’s where courage and wisdom refuel.

69. Purpose steadies the hands when the work gets heavy.

70. Gratitude turns pressure into perspective.

71. Servant leadership begins by asking, “Who needs strength from me today?”

72. Hope is a discipline. Practice it especially when results lag.

Leading Through Change & Uncertainty

73. Name the uncertainty. People handle the unknown better when it has boundaries.

74. Trade predictions for scenarios. Prepare for several futures, not just your favorite one.

75. Replan without blame. The map changes when the terrain does.

76. Communicate more than feels necessary. The vacuum of silence fills quickly with speculation.

77. Keep experiments small and reversible, so learning is fast and affordable.

78. Endurance is contagious. Your calm can be the team’s shelter in a hard storm.

Coaching & Talent Development

79. Grow people on purpose. Make development a standing agenda item.

80. Coach with questions that build judgment and ownership.

81. When you delegate the result, delegate the authority to achieve it. Authority and responsibility should be in balance.

82. Set intent and boundaries. Agree on check-ins. Then step back so the team can step up.

83. Size stretch work to the person’s readiness. Provide the right challenge, real help, and visible sponsorship. It’s okay if they reach the result by a different route than yours.

84. Build a bench before you need one. Succession begins on day one.

Supportive Organizational Behavior

85. Make it safe to disagree. Invite the view that challenges yours.

86. Credit ideas to their source. Recognition fuels contribution.

87. Write agendas as outcomes, not topics.

Systems Thinking & Process

88. Correct the mistake and improve the system that allowed it.

89. Turn recurring work into checklists and rhythms so excellence is repeatable. Then automate it.

90. Map the flow of work end to end. Prune any step that adds no value. Unblock the rest.

91. Measure what matters. Review it at a pace that improves the work.

Stakeholders & Customer Focus

92. Start with the customer and work back to today’s priorities.

93. Define success in customer outcomes, then align processes, metrics, and rewards.

94. Close the loop by telling people what changed and why.

Conflict & Courageous Conversations

95. Address tension early while the knot is small.

96. Separate the person from the problem. Aim at the issue, not the identity.

97. Put the real issue (the skunk) on the table. Agree on facts before you debate fixes.

Energy & Well-Being

98. Protect time for deep work and recovery so decisions are sharp.

99. Model healthy boundaries. Your example sets the team’s norms.

100. Choose a sustainable pace over heroic sprints. Consistency wins the long game.

Leadership is a skill to be learned and practiced over a lifetime. It grows through steady reflection, small improvements, course corrections, and new discoveries. These reminders pull us back to what matters when life and work get noisy.

Whether you lead a company, a classroom, a project, or a family, your influence reaches far beyond the moment.

The truest measure of leadership is the people we serve and the leaders they become.

Photo by Marcus Woodbridge on Unsplash – I love the idea of a lighthouse showing the way, standing firm and steady especially when the waves are their scariest.

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4 Bonus Lessons (which means I came up with four more that I didn’t want to exclude)

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