Category: Leadership

Teachers, Mentors, and the Grace That Carries Us

“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.

We never really travel alone.

Photo by Rafael Garcin on Unsplash

When an Idea Stops Being Yours Alone

There’s a quiet moment in meaningful work when your idea begins to live in someone else. You see it in the way they talk about it. You hear it in their enthusiasm. You notice how they add their experience and their language to it until the idea carries their imprint as much as yours.

It can feel strange the first time it happens. You know the origin, but they suddenly feel the spark of the idea for themselves. That’s the moment you know your idea has begun to grow.

Real success often arrives like this, but we don’t always notice it. People begin to adopt your idea, reshape it, and eventually believe in it with a conviction that can be surprising. They explain it to others in their own voice. They defend it. They improve it. If the idea spreads far enough, some will forget where it began. Your name may fade from the origin story. That loss of attribution can sting if you hold the idea too tightly. It should feel like success instead.

Leaders have a responsibility here. Ideas rarely spread through logic alone. They spread through emotional ownership that grows when people discover a piece of themselves in the idea. When that happens, they carry the idea farther than you ever could by insisting on authorship.

A leader’s task is to create the conditions for this transfer. You offer the early shape of the idea, then invite others to step inside and help build the next version. You ask for their insight, their experience, and their concerns. You let their fingerprints gather on the surface until the idea becomes a shared creation. People support what they help to shape.

As others begin to adopt your idea, they’ll need to feel safety in their new enthusiasm. They need to know they’re not the only ones who believe in this direction. A wise leader pays attention to this. They take the people who have embraced their idea and introduce them to others who have done the same. They form new connections, helping to create a small community where confidence strengthens and courage grows. When people see others adopting the same idea, they feel validated, understood, and ready to act.

This is how ideas gain momentum inside organizations. One person sees the promise. Another begins to shape it. A third begins to feel inspired. Before long, it becomes a shared narrative. It starts with your imagination, but it continues through their belief and conviction.

Once people begin to adopt your idea, you must release it. You may or may not receive credit for it. Either outcome is acceptable.

The goal was never to build a monument to your creativity. The goal was to move the organization forward. When others bring your idea into new conversations without you, your contribution has done its job.

Your attention can return to the horizon. There’s always another idea waiting for you, another possibility that needs your curiosity, another problem that needs new framing.

Good leaders plant seeds. Great leaders celebrate when those seeds take root across the organization.

Inspired by Dr. Michael Levin’s post, h/t – Tim Ferriss

Photo by Alex Beauchamp on Unsplash – a new idea taking root and growing beyond its beginning.

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. 

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

How Limits Bring Art to Life

Inspired by G. K. Chesterton

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.”

Photo by pine watt on Unsplash

Seeing What Comes Next

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

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

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

This is leadership without anticipation.

Every action sets something in motion.

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

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

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

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

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

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

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

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

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

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

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

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

Photo by Aleksander Saks on Unsplash

Bring Them On the Journey

You can tell people what to do, and sometimes that’s the right call. Yet, direction without participation creates compliance instead of commitment.

When people understand the purpose, see where they fit, and have a voice in the direction, they’ll take emotional ownership.

The best leaders invite that ownership by asking questions that open doors to insight. What are we missing? What would you try? Where do you see the risk? These questions are invitations to shape the work and the results.

When a product manager asks her team, “How would you approach this?” instead of presenting a finished plan, the solutions that emerge are sharper, and the team building them gets stronger.

Humans are built for both independence and belonging, desires that often pull in different directions. Wise leaders guide this tension well. They give people space to grow while connecting them to something larger than themselves.

To bring others on the journey is to build together. Growth is shared. Trust expands. When the path gets steep, they’ll keep climbing with purpose.

They remember the reasons, because they helped shape the path.

Photo by Powrock Mountain Guides on Unsplash – Unsplash has a ton of amazing hiking photos, mountain climbing photos, pictures of maps, legos, and winding paths. All would have represented the themes of this post admirably. But this photo caught my eye.

How do you see it connecting to this post? What makes this photo stand out? How hard do you think it is to hike across to that gleaming white mountain in the distance?

The Mirage of Strategic Clarity

Strategic Planning That Can Survive Reality

It was the second day of a two-day strategic planning retreat. Revenue projections stretched across the screen. The CFO walked through all the assumptions in his spreadsheet. Customer acquisition costs will flatten, churn will improve by two points, and the new product will capture eight percent market share within six months.

Everyone nodded along, acting as if these forecasts represented knowledge rather than elaborate guesses built on dozens of assumptions, any one of which could be wrong.

Three months later, a competitor launched an unexpected feature. Customer behavior shifted. The CFO’s projections became relics of a reality that never existed. The entire strategic planning process had been built on an illusion.

What we pretend to know

In his 2022 memo The Illusion of Knowledge, Howard Marks explored how investors mistake confidence for clarity. He began with a line from historian Daniel Boorstin:

“The greatest enemy of knowledge is not ignorance, it is the illusion of knowledge.”

Leaders face a brutal paradox. Boards expect forecasts. Teams want confidence. Investors demand projections. The machinery of leadership demands certainty.

So, we build elaborate forecasts and make decisions based on assumptions we know to be fragile. We treat detailed guesses as facts.

Physicist Richard Feynman once said, “Imagine how much harder physics would be if electrons had feelings.” Electrons follow discrete laws, unlike people. People innovate, resist, panic, and occasionally do something amazing nobody saw coming. Competitors behave differently than our models assume. Markets shift for reasons we never thought possible.

Marks describes forecasting as a chain of predictions. “I predict the economy will do A. If A happens, interest rates should do B. With interest rates of B, the stock market should do C.” Even if you’re right two-thirds of the time at each step, your chance of getting all three predictions correct at once is only about thirty percent.

Leadership forecasts work in a similar way. We predict customer adoption rates. If adoption hits those numbers, we’ll need a certain operational capacity. With that capacity, we can achieve specific margins. Those margins will attract investment.

Each assumption depends on the previous one. The chain is only as strong as its weakest link.

The tools we trust

Walk into any strategic planning session and you’ll likely encounter two frameworks treated as gospel:

-SWOT analysis (strengths, weaknesses, opportunities, and threats)

-SMART goals (specific, measurable, achievable, relevant, and time-bound).

Business schools teach them. Consultants recommend them. Leaders deploy them with confidence. Each relies on assumed knowledge that may not exist.

A SWOT analysis claims to know which possible developments count as opportunities versus threats. It’s a snapshot of assumptions masquerading as strategic insight. An opportunity exists only if you can identify it, execute against it, and do so before circumstances change. The framework provides no way of acknowledging uncertainty.

SMART goals often confuse precision with accuracy. “Increase market share” becomes “increase market share in the Northeast region from 12% to 15% by Q4 2026.” It sounds specific, and therefore rigorous. It’s easy to be precise about something unpredictable.

And how do we know a goal is achievable? We make assumptions about resources, market conditions, and competitor behavior, then write a goal that treats our assumptions as facts.

Both frameworks serve a valuable purpose. They force structured thinking. But they also seduce leaders into believing they know more than they do.

What should we do instead?

To be clear, this isn’t an argument for abandoning planning. Organizations need direction, priorities, and coordinated action. The question is how to plan in ways that acknowledge what we can’t know while still making decisive progress.

A better path involves changing how we plan and how we talk about the future.

Distinguish between direction and destination. Amazon knew it wanted to be “Earth’s most customer-centric company” without knowing exactly what that would look like in year ten. “We’re moving toward increased automation” carries more truth than “we’ll reduce costs by seventeen percent by Q3 2026.” The first creates direction. The second creates false precision.

Separate what you know from what you assume. Customer complaints increased forty percent this quarter. That’s knowledge. Saying the trend will continue is extrapolation. Predicting that fixing the issue will increase retention by five points is speculation. Present plans that show what you know, what you’re inferring, what you’re assuming, and what you’ll do if you’re wrong.

Build optionality into everything. Create strategies that work across multiple futures. Hire people who can do, or think about, more than one thing. Build modular systems with flexibility in mind. Create decision points where you can change course.

Use familiar tools differently. Run a SWOT analysis, then list three ways each opportunity might fail to materialize. Write SMART goals, then document the assumptions those goals depend on and how you’ll adapt if they prove incorrect.

Here’s a concrete example. You’re deciding whether to build a new product line. The traditional approach creates a detailed business case with market projections and revenue forecasts. You present it. People debate assumptions. A decision gets made.

An alternative approach defines what success means, then identifies what must be true to achieve it. You sort those conditions into things you can validate quickly, things you can validate over time, and things you can validate only much later. Stage investments to match the timing of the validations, rather than an arbitrary quarterly schedule.

The difference in these approaches is critical. In the first, the business case pretends to represent knowledge. In the second, it becomes a set of hypotheses to test over time.

The harder path

Amos Tversky observed, “It’s frightening to think that you might lack knowledge about something, but more frightening to think that, by and large, the world is run by people who have faith that they know exactly what’s going on.”

We select leaders for their ability to project confidence about an unknowable future. We reward decisiveness over doubt. Then we wonder why strategies fail when reality diverges from our projections.

Most of us live in this system. We’ve built organizations that demand the illusion of knowledge.

Real leadership creates organizations resilient enough to find answers as circumstances unfold. It builds teams that can adapt rather than simply execute a plan written many months ago.

When did you last change a forecast because reality diverged from your assumptions?

When did you last reward someone for identifying that a plan was failing?

Start small. Pick one decision where you can be explicit about uncertainty. Structure one investment to test assumptions instead of betting on a forecast. Have one conversation where you separate what you know from what you’re guessing.

Plan in ways that acknowledge uncertainty and position your organization to learn. Lead with confidence about principles while staying adaptable around specifics. Build organizations that can adapt when reality diverges from the plan.

Because it will. The measure of leadership lies in how well your culture can face that truth.

The CFO’s spreadsheet was never the problem.

The illusion that it represented knowledge was.

Photo by Michael Shannon on Unsplash

The Gift of Grace

There are times when we are firmly in the right. The facts are clear. The other person made a mistake or caused harm. In that moment, we face a choice. We can leverage our position of strength and press our advantage. Or we can give grace.

Grace is the strength to let go of proving a point. The willingness to give someone space to recognize what went wrong and find their way back. Every one of us needs that space, because every one of us makes mistakes.

Grace holds truth in one hand and love in the other. It sees what happened and names it honestly. It also holds out the invitation to begin again. In this way, grace strengthens relationships and helps keep them whole.

Grace looks to the future. A person rarely grows when held down by another’s righteousness. They grow when they feel the freedom to face their mistakes with dignity. Grace creates space for that freedom.

The flow of grace is a gift that we depend on. It honors truth. It protects relationships. When we give grace, we often find that it changes us as well.

We may discover that the person we extend grace to carries burdens we never knew about. When we choose grace over vindication, we become more human, more aware of our own weaknesses, and more capable of genuine compassion.

“Put on then, as God’s chosen ones, holy and beloved, heartfelt compassion, kindness, humility, gentleness, and patience, bearing with one another and forgiving one another, if one has a grievance against another; as the Lord has forgiven you, so must you also do.” – Col 3:12–13

Photo by Mrugesh Shah 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