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.
One of the best parts of the Iron Man movies is Jarvis, the ever-present AI system that acts as an extension of Tony Stark’s mind. Jarvis is a collaborator. A research analyst. A pattern finder. A problem solver. He handles logistics, runs calculations, surfaces insights, and stays ready in the background until Tony needs him.
Jarvis amplifies and extends Tony’s genius.
Recently, I introduced a friend to ChatGPT. He hasn’t jumped into any AI tools yet, but he can see that people around him are finding real value in them. Like many thoughtful people, his first questions weren’t about features. They were about data privacy. About whether these tools were simply repackaging other people’s work. About what was really going on under the hood.
At one point, he asked a simple question:
Is it like having Jarvis around whenever you need him?
To me, the honest answer is yes.
But it’s also important to realize that Jarvis isn’t perfect. And neither are the AI tools available to us today.
The First Questions Matter. Almost every serious conversation about AI tools begins in the same place.
Is my data safe?
Who owns the output?
Can I trust what I’m getting back?
These are the same questions we ask whenever a new digital tool emerges.
At a basic level, paid versions of tools like ChatGPT don’t use our conversations to train public models. Even with that protection in place, I still guard my data carefully. If I’m asking questions related to finances, health, or legal matters, I use hypothetical scenarios rather than personal specifics. I’m the first line of defense when it comes to my personal information.
In professional and commercial environments, organizations using business or enterprise versions gain additional protections around data isolation, encryption, access controls, and audit logging. At the enterprise level, some platforms even allow customers to manage their own encryption keys on top of the platform’s security.
The tool doesn’t decide what’s appropriate to share. We do.
Who Owns the Output? We do. The tool doesn’t claim authorship. It doesn’t retain ownership of what it produces for you. The output becomes yours because you directed the work, supplied the context, and decided how the result would be used.
But ownership is only part of the story. Responsibility matters just as much.
The tool doesn’t know your intent. It doesn’t understand your audience. And it doesn’t bear the consequences of getting something wrong. That responsibility stays with the human in the loop. That’s us.
In that sense, using AI isn’t fundamentally different from working with many other analytical tools we may have used for decades. The work becomes yours because you shape it, refine it, and ultimately stand behind it.
A Note on Sources and Attribution. Owning the output also means owning the responsibility for its accuracy and integrity. This is especially important when it comes to research and citations.
AI tools can pull together large volumes of information, synthesize ideas across many inputs, and present them in clean, compelling language. That capability is incredibly useful. But it doesn’t remove the author’s responsibility to understand where ideas come from and how they’re represented.
The tool may summarize research. It may surface commonly known concepts. It may produce language that sounds authoritative and polished. What it doesn’t guarantee is proper attribution or assurance that content isn’t too closely mirroring a specific source.
That responsibility stays with the human.
When I use AI for research or writing, I treat it as a starting point. I ask it to surface each source. I follow links. I read original material. And when an idea, quote, or framework belongs to someone else, I make sure it’s credited appropriately. This step also helps catch hallucinations that sound amazingly accurate.
Ownership requires standing behind the integrity of the work to the best of your ability.
Can I Trust What I’m Getting Back? Usually. Only with supervision. AI tools are very good at consuming information, identifying patterns, and accelerating first drafts. They are less reliable when precision, nuance, or real-world verification is required.
They can be confidently wrong. They can lose context. They can blend accurate information with outdated or incomplete details.
AI tools hallucinate regularly, though this tendency improves with each new model release. These aren’t reasons to dismiss AI as a tool. They’re reminders to understand what AI is and what it isn’t.
Trust paired with skepticism is the right approach. AI tools are fast-thinking assistants, never the final authority.
Verification still matters. Judgment still matters. Experience still matters. In fact, the better your judgment, the more valuable these tools become.
Why Memory Changes the Equation. Most people use AI tools like a smart search engine. Ask a question. Get an answer. Move on.
That works. But it barely scratches the surface of what’s possible. The real multiplier happens when the tool is allowed to remember context.
ChatGPT includes a memory capability that lets you intentionally store preferences, patterns, and reference material across conversations. Used well, this transforms the tool from something you query into something you can collaborate with.
Over the past year and across hundreds of prompt conversations, I’ve shared:
-My writing voice and stylistic preferences
-A digital copy of a leadership book I wrote over a decade ago (about 65,000 words)
-An autobiography I wrote for my children and grandchildren (about 90,000 words)
-Hundreds of blog posts published over the past 13 years (roughly 240,000 words)
-How I like to structure projects and approach new work
In total, I’ve trained the tool with nearly 400,000 words of my original content. This began as an experiment to see if I could reduce generic responses and encourage the tool to approach questions from my foundational perspective.
The difference is tangible. Early on, whether I was drafting communication, analyzing problems, or organizing ideas, the tool would produce polished but generic output that required extensive rewriting. Now, it reflects my priorities, uses frameworks I’ve shared, and produces work that feels aligned with how I think. I still edit quite a bit, but I’m refining rather than rebuilding.
Collaboration Requires Judgment. My friend asked me another important question.
Do you still feel like the writing you produce with it is yours?
Yes. Completely.
Every project I’ve worked on with these tools begins with my original content, reinforced by reference material I created long before AI entered the picture. Hundreds of thousands of words written over more than a decade. Clear intent about audience and purpose, using a defined process I’ve established before drafting anything.
The tool supports rather than replaces my judgment. Drafts usually require significant edits, shifts in tone, and sometimes complete rewrites.
Where it excels is in synthesis. In retrieval. In pattern recognition across large bodies of work. In accelerating first drafts that already have direction.
Large projects require constant supervision. Threads get crossed. Context gets muddled. The tool needs redirection, clarification, and sometimes retraining as the work evolves.
This is simply the nature of collaboration.
Why the Hype Misses the Point. There’s a popular narrative circulating that anyone can now write a book, write a complex software application, create a website, start a business, or become an expert with just a few well-written prompts.
This misunderstands both the tools and the craft associated with each of these tasks.
I think of AI the way I think of a great camera. We can all buy the same equipment. That doesn’t guarantee an amazing photo. The quality still depends on the eye behind the lens, the patience and skills to frame the shot, and the willingness to edit ruthlessly afterward.
Ansel Adams once said that asking him what camera he used was like asking a writer what typewriter he used. The tool matters. But it has never been the point.
The same is true with AI tools.
Without intent, taste, and care, straight AI output feels flat and formulaic. Readers will notice. Substance can’t be faked. Depth doesn’t appear by accident.
These tools reflect the discipline of the person using them.
Hitting the Ground Running. For someone just getting started, the biggest mistake is expecting magic. The better approach is to build understanding and training into the process (for you and the AI tool).
Explain what you’re trying to do.
Tell the tool how you think.
Correct it when it’s wrong.
Guide it when it drifts.
Treat it like a junior collaborator. One that’s fast, tireless, and remarkably capable…but still dependent on direction and context.
If you’re looking for a practical first step, try this. Find an article you’ve read recently and ask the tool to summarize it. Compare that summary to the original. Notice what it captured, what it missed, and what it misunderstood. This simple exercise reveals both the tool’s strengths and its limitations in a low-stakes way.
From there, you might ask it to help you draft an email, outline a presentation, or brainstorm solutions to a problem you’re facing. Start with tasks where you can easily evaluate the quality of the output and provide feedback on what the tool provides.
Over time, you’ll notice the quality improves. That’s when the tool begins to resemble the Jarvis we imagined. It isn’t perfect, but it becomes more aligned with what you value most and how you like to approach your work. At the same time, your understanding of its strengths and limitations becomes clearer through consistent use.
AI doesn’t replace thinking. It requires it.
Used carelessly, it produces noise. Used deliberately, it sharpens your insights.
The question is whether we’re willing to slow down at the beginning, set expectations, and engage AI tools with proper intention.
Only then can these tools truly serve us well.
Photo by Chris Haws on Unsplash – photographers often say, “It’s about the photographer, not the camera.”
If this post was helpful, please feel free to share it.
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.
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.
“There is no Frigate like a Book / To take us Lands away.”
Emily Dickinson wrote these words in her quiet room, understanding something I didn’t grasp for decades. The greatest journeys begin within.
I know her poem only because of my 11th grade AP English teacher, Mr. Cox. As a rambunctious and cocky 11th grader, would I have taken any of my “super valuable” time to read poems, sonnets, short stories, even books? No way.
But because of his work (and the work of countless other teachers along the way), I did read. A lot. I learned tons of material and information that didn’t matter to me at the time…but matter a lot today.
My focus back then was simple. Be the best student, get the highest test scores, pass as many AP tests as possible, and earn varsity letters in multiple sports. Mostly, I wanted to beat everyone else, pure and simple. It helped that I was blessed with an almost photographic memory and could recall facts and formulas with ease (sadly, not so much nowadays).
I carried that mindset into college. I loved being the student who defined the grading curve for the class. I was annoyed if I didn’t get every single point on an assignment, midterm, or final. I had an almost uncontrollable drive to outshine everyone…as if that was all that mattered.
I was completely wrong.
On the bright side, that drive and motivation made me a successful student and propelled me into my early career.
On the other hand, seeing everyone as my competition, and less as people, meant I probably missed out on a lot of fun. And lots of friendships that never happened. I was so focused on the destination that I forgot to notice who was traveling with me.
That realization connects me back to Dickinson’s frigate in ways I never expected. She saw the book as a vessel capable of carrying anyone, anywhere, without cost or permission. But what I’ve learned over nearly fifty years since high school is that I was asking the wrong question. It was never “How far can I go?” It was “Who am I becoming, and who’s helping me understand?”
My journey from that hyper-competitive teenager to what I hope is a much more caring, thoughtful, empathetic, nuanced, and life-giving person has been propelled by those same teachers I mentioned earlier, and a longer line of guides who keep showing up at the right time in my life.
I didn’t realize it then, but those books, poems, and teachers were all part of my fleet of frigates. Each one quietly helped me close the distance between knowledge and understanding, between my ambition and wisdom.
My mentors, family, and friends have all been vessels that carried me through changing seas. Some taught me to sail straight into the wind. Others reminded me that drifting for a while can be part of my journey as well. Each lesson mattered, even the ones that didn’t make sense at the time…especially those.
Over time, life has a way of sanding down our sharper edges, revealing something deeper underneath. My focus slowly shifted from being the best at something to becoming the best version of myself.
Now, when I think about Emily Dickinson’s frigate, I picture something far greater than a book. I picture a lifetime of learning, carried by the people who invested their time, wisdom, and patience in me. Mr. Cox, and others who gave freely of their time and wisdom, helped me see that the destination isn’t solely becoming the top of the class. It’s finding a profound depth of understanding, the expansion of empathy, and the ability to see beauty and meaning in small, unexpected places.
If I could go back and talk to that 16-year-old version of myself, I’d tell him the real tests aren’t scored on paper. They’re graded every day in how we treat people, how we listen, and how we show grace.
I’d tell him that the frigate he thinks he’s steering alone has always been guided by grace. The true measure of his voyage will be how much space he makes for others to come aboard.
We’re all learning to sail, carried by the steady hand of God.
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.
I’ve come to believe what Chesterton once said. Art is limitation, and the essence of every picture is the frame. It took me time to see that truth.
Many of us grow up thinking freedom creates great work. Unlimited time. Unlimited canvas. Unlimited choice.
But if you’ve ever stared too long at a blank page, you know what real freedom can feel like. Paralyzing.
Nothing takes shape until the edges appear. A story waits forever if the writer can’t decide where it begins. Music is noisy until the composer chooses a key. The frame gives the work its purpose.
The same is true in leadership and life. A budget helps us decide what we value. A deadline turns a dream into something real. A small team learns to trade excess for imagination. Limited resources push us to invent new ways to adapt. The frame brings focus.
Still, the frame itself matters. A picture can feel cramped when the frame becomes too tight. A project can drift when the wrong thing fills the center. When the boundaries are off, the whole image loses clarity. That’s why wise leaders spend time defining the edges before the work begins.
Whenever I work on a puzzle, I start by finding all the edge pieces. Once the border comes together, I can see how everything else might fit. The same principle applies to creative work and leadership. The edges give us context. They help us imagine where the middle pieces belong and how the picture will come to life.
Frames should change as we grow. The world shifts. We learn more about what we’re building. Every so often, we step back and see whether the picture still fits. Sometimes the frame needs widening. Sometimes the colors need more light. Adjusting the frame keeps the beauty true.
Constraints give possibility its shape. They reveal what truly matters. Choosing the right limitations helps us see what is essential.
When you feel boxed in or limited, pause before you push against the edges. The frame around your work may be the very thing helping the picture appear. And when the picture becomes clear, refresh the frame so the beauty within it continues to grow.
Thanks to James Clear for sharing this G. K. Chesterton quote: “Art is limitation; the essence of every picture is the frame.”
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 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.
Grandpa Bob Encouraging Leadership 
You must be logged in to post a comment.