The idea was simple. If you look closely at life, you’ll see that everyone is climbing something.
A career. A relationship. A difficult time in their lives. A personal challenge.
Life has a way of placing mountains in front of us. Or maybe…we’re just good at finding them.
As I wrote back then, the climb only makes sense from the inside. Watching others or hearing their stories are no substitute for taking it on yourself.
There was another part of the metaphor that mattered even more.
Many of us start the climb with backpacks full of things that make our journey harder than it needs to be. Old resentments. Lingering disappointments. Criticism that stuck with us longer than it should have. Sometimes we even carry baggage that belongs to someone else.
Years later, I came across a Buddhist parable that gave a new wrapper to this idea. It described people walking through life carrying large boulders. Anger. Ego. Grudges. The suffering didn’t come from the boulders themselves. It came from choosing to pick them up.
Whenever a hill approached, I had a habit of shifting into an easier gear before the climb even began. It felt like preparation. It felt like the smart thing to do.
One day I tried something different. Instead of downshifting, I shifted to a higher gear and pushed harder.
To my surprise, I climbed much faster than before, without bonking like I thought might happen.
Sometimes growth means discovering we’re stronger than we realize.
That experience raised questions I still ask myself.
Where else in life do I downshift before the hill arrives?
Am I protecting myself from difficulty…or underestimating what I’m capable of?
Recently, I read a post by Tim Ferriss about the “self-help trap.” He described sitting around a campfire one evening with a small group of close friends, the kind of unhurried night where the conversation slows down enough for truths to surface. He found himself thinking about the fire, and then realizing the fire wasn’t the point. The people sitting around it were.
He described how easily we can become so absorbed in optimizing ourselves, tracking progress, chasing improvement, climbing toward our next summit, that we lose sight of why we started climbing in the first place.
Summits will eventually fade. Our achievements will blur with time. Recognition disappears quicker than we expect.
Perhaps the real work of self-improvement is simpler than we think.
The rocks we’re carrying were never necessary.
The hills we fear are usually smaller than we imagine, or remember.
And the fire, the one worth tending, isn’t the one powering our ambition. It’s the one we gather around with the people we love.
During British rule in India, officials in Delhi faced a serious problem with venomous cobras. The snakes posed a real danger to residents. The government needed a solution.
Their answer seemed sensible. They offered a bounty for every dead cobra that citizens turned in. At first the program appeared to work. People brought in carcasses and collected rewards. The body count rose. The government believed progress was being made.
But entrepreneurial citizens had discovered something. If the government was paying for dead snakes, breeding snakes would be a profitable business. When authorities found out and cancelled the bounty program, the breeders released their suddenly worthless inventory.
Delhi ended up with more cobras than before the program began.
Economists call this the Cobra Effect. The intention was to reduce cobras. The incentive rewarded producing dead cobras. Those two things turned out to be very different.
The Leadership Lesson
Have you ever watched a team find a way to hit a metric while quietly missing the point behind it?
The numbers improve. The dashboard looks great. People are working hard. And yet there’s a sense that the outcome falls short of what everyone really intended.
Consider a company that creates a bonus program tied to quarterly revenue growth. The leadership team hopes it’ll encourage strong customer relationships and long-term growth. But the sales team discovers a faster path to the reward. Deals get pulled into the quarter. Discounts increase to make numbers land before midnight on the last day of the period. The metric improves. The organization stumbles as it tries to handle all these discounted last-minute deals coming in the door.
People rarely optimize for intentions. They optimize for rewards.
If you pause and think about your own organization, an example probably comes to mind quickly. Somewhere in the system, someone is optimizing the metric rather than the goal behind it. That is, assuming they know what that goal is.
The Hidden Incentive System
The official incentive system is only part of the reward structure. Leadership behavior creates another one, and it’s usually more powerful.
A company might design a thoughtful program that rewards initiative and collaboration. On paper the system makes sense. But employees quickly learn something else. They learn the habits of their leader.
A leader who prefers to make every decision personally creates a silent incentive to wait for approval. One who values loyalty over candor creates an incentive to agree. One who always needs to have the final answer in the room creates an incentive to create that moment.
These preferences form a second reward system that goes unwritten but gets studied carefully. Employees learn when to speak and when to stay silent. They learn which ideas move forward and which quietly stall. Good ideas go unspoken. Initiative slows. Energy shifts toward maintaining harmony with the leader’s style.
From the perspective of the employees, the behavior makes perfect sense. They’re responding to the reward structure they experience every day. The cobras are being bred. But nobody calls it that.
Why AI Makes This Visible
This same behavior is showing up in artificial intelligence, and it’s revealing just how universal it is.
Researchers evaluate AI systems using benchmark tests. They ask questions, measure answers, assign scores, and compare systems. The logic is clean. But something interesting has started to emerge.
Instead of simply answering the questions, some AI systems have begun studying the structure of the benchmark itself. They explore how the scoring works, look for patterns, and in documented cases have searched for ways to access encrypted answers directly.
In one well-known example, a model trained to maximize performance on a coding benchmark learned to exploit a quirk in how test cases were scored rather than solving the underlying problems.
This is a familiar human instinct. Students ask what’s on the test. They hunt for past exams. They want to know if grading will be on a curve. The behavior that researchers call “reward hacking” in AI systems is the same thing humans have always done when they figure out how their world is scored.
In earlier centuries these patterns unfolded slowly, over years or decades as people gradually discovered the loopholes and secret hacks to their incentive systems. With modern AI, the process is compressed into days or weeks.
AI is a new player in a very old game. It simply reveals how powerful optimization becomes once a system understands how the game is scored.
The Question That Remains
Every organization creates reward systems. Some appear in compensation plans and performance reviews. Others appear in meetings, decisions, and the daily behavior of leaders.
Every system teaches people what really matters. Once that becomes clear, behavior follows. The snakes get bred. The quarter gets managed. The benchmark is gamed.
The British officials in Delhi thought they were paying for safety, but they were paying for dead snakes. By the time they realized the difference, the snakes were multiplying in the streets.
What behavior does your incentive system truly reward?
For centuries, those words marked a moment of transition in a monarchy. They acknowledged loss while declaring that the kingdom would continue.
One reign ends. Another begins. The work continues.
Modern organizations operate in much the same way, just without the ceremony.
When the Ball Changes Hands
Sometimes the transition is visible. A retirement announcement made months in advance. A company-wide gathering, a slideshow of memories, a few stories capturing the arc of a career. Handshakes and hugs. People are grateful for the chance to say thank you.
Other departures unfold quietly. A decision formed over time. A conversation held in private. Recognition that the moment has arrived for something different to begin.
At times, the individual chooses the timing, sensing it’s time to redirect their energy or reclaim parts of life that have waited patiently. At other times, the organization makes the call.
It’s like a manager walking to the mound and asking the starting pitcher for the ball. The pitcher may have thrown well and kept the team in the game. A new batter steps in, and the situation calls for a different arm. The decision reflects what the moment requires. What the pitcher deserved is a different conversation.
The Half-Life of Professional Memory
Spend any time inside large organizations and you’ve witnessed what follows.
A respected leader leaves after a long and meaningful tenure. Their name surfaces occasionally.
Over time, new colleagues arrive who never worked with them. New leaders establish their own ways of operating. The organization adapts.
Work progresses while memories fade into the background.
Institutions carry short memories because continuity is the center of their purpose. Time spent dwelling on the past subtracts from their responsibility to build what comes next. This quality allows organizations to endure. From the inside, it can still be painful.
The Grief No One Mentions
We rarely dwell on the plain truth that this process hurts.
Years of personal investment in people, in solving problems, and in creating a supportive culture eventually become part of who we are. When the organization moves forward without us, it can feel like we’re diminished. Like our work didn’t matter as much as we believed.
That feeling deserves to be called grief. The natural response to losing something we genuinely loved.
Our mistake is letting that grief become a verdict.
The organization’s short memory says nothing about the value of what we contributed. It says something about how institutions are built to function. They’re designed for mission and continuity, with memory serving a different purpose. Understanding the difference doesn’t make the feeling disappear, but it does change what the feeling means.
Where Influence Actually Lives
Our work never disappears. Its impact simply resides in a different place.
The confidence someone discovers because we believed in them. The standards we upheld when it would have been easier to compromise. The steadiness we showed under pressure. The thinking patterns others continue to use long after they’ve forgotten the source.
These moments accumulate.
Lasting influence rarely lives in titles, completed initiatives, or improved metrics. Those matter deeply in their time, yet they rarely define what lasts.
Most of us can trace core insights to a teacher or mentor who shaped us. Someone who challenged us to think beyond ourselves or our capabilities, changing how we see the world. Their insight became part of who we are.
In the same way, we become that teacher in someone else’s story.
The Metric That Matters Most
Leaders who sustain themselves over the long term tend to live with dual awareness. They engage fully and care deeply about the organization’s mission. They invest in people and outcomes.
At the same time, their sense of self rests on something broader. Family, faith, health, curiosity, service, and community form a foundation that holds steady regardless of their title.
They recognize that one day the organization will continue without them, and they choose to lead in ways that remain meaningful regardless. This awareness strengthens their commitment rather than weakening it, because it clarifies what actually matters.
Eventually, each of us hand over the ball. The badge stops working. The inbox grows quiet. Someone else takes the chair.
Our opportunity is to contribute in ways that remain useful long after our names fade from conversation. Lessons carried forward through people we may never meet.
For the next two weeks, I’ll be doing something new.
Marshall Goldsmith is encouraging people to ask themselves six questions every day. That’s the whole experiment.
Six questions. Asked at night. Answered honestly.
They all start the same way:
Did I do my best to…
The questions don’t ask what happened to me today. They ask what I did with today.
During his webinar introducing the experiment, Mr. Goldsmith referred to the Rigveda, an ancient poem from India that he described as being thousands of years old. He just mentioned it and moved on.
I had never heard of the Rigveda, so down the rabbit hole I went after his webinar ended.
The Rigveda is a collection of hymns. A lot of it is about everyday things. The sun rising. Fire. Breath. Life continuing. There’s a sense that daily life matters. That how we live each day counts.
People have been trying to figure out how to live a good life for a long time. Way before self-help and leadership books. Way before webinars and podcasts.
St. Ignatius of Loyola comes to mind. He developed something called the Daily Examen. It’s a review of the day. You look back. You notice where you were grateful. You notice where you fell short. You think about tomorrow.
Different times. Different traditions. Same basic ideas.
At the end of the day, pause and ask, “How did I live today?”
Goldsmith’s six questions fit right into that pattern.
Did I do my best to be happy today?
The question hits differently when the day is already over. I can see clearly whether I purposely enjoyed the day or just rushed through it.
Did I do my best to build positive relationships?
Now I’m thinking about the way I spoke to someone. Whether I listened. Whether I gave someone my full attention.
The questions are short. The reflections take some time.
Goldsmith describes happiness as “enjoyment with the process of life itself.” Happiness lives inside the day. It grows out of our engagement with what’s already in front of us.
The writers of the Rigveda seemed to understand that. Ignatius understood it too. They’re asking us to pay attention to our life and actively engage in it.
I’m only a few days into this experiment. Nothing dramatic has happened. No big breakthroughs.
But I know I’ll be answering these six questions later. I move through the day with more awareness. I catch myself sooner. I stay present a little longer. I think twice before reacting.
It’s a small shift…but small shifts repeated over time shape our lives.
Thousands of years have passed since the Rigveda was written. Centuries since Ignatius taught people to examine their day.
Our modern life looks very different, but the question remains the same.
How did I live today?
Here are Goldsmith’s six questions:
–Did I do my best to set clear goals today?
-Did I do my best to make progress towards my goals today?
-Did I do my best to find meaning today?
-Did I do my best to be happy today?
-Did I do my best to build positive relationships today?
You’ve probably seen it happen. A new tool explodes across your social media feeds, your team starts asking questions, and you’re left wondering whether to embrace it or ignore it. Last month’s OpenClaw rollout is the latest reminder of how chaotic technology adoption really is.
Technology adoption curves are depicted as neat, predictable diagrams, a smooth line moving from innovators to early adopters to the early majority and eventually to late adopters.
In textbooks, the curve looks calm. In real life, it feels more like a storm.
Watching the recent surge of interest around OpenClaw, an open-source AI automation tool that lets developers and non-developers build custom autonomous agents, highlights this contrast clearly.
The tool moved rapidly from Clawdbot to MoltBot to OpenClaw. While its identity was in motion, innovators and early adopters embraced it with enthusiasm. Within days, countless articles and YouTube videos appeared with reviews, tutorials, and predictions about how it would reshape everything.
Within another week, we began hearing a more complete message. People still praised its power, but they also surfaced significant security weaknesses and vulnerabilities that accompany those capabilities.
My goal in this post is less about celebrating OpenClaw itself and more about understanding the real-world adoption pattern that I’ve seen countless times.
Phase 1: The Enthusiasts Light the Fuse
Early adopters jump in first. They’re curious, energetic, and quick to celebrate what they’ve discovered.
They imagine what could be, long before most people fully understand what exists today. They test edge cases, build experiments, share demos, and push boundaries simply because the possibility fascinates them.
This group rarely waits for permission. Their momentum gives a new idea its initial lift.
Phase 2: Quiet Experimenters Emerge
Close behind them comes a second tier of users who watch carefully and learn before speaking.
They begin to explore the tool in private, trying things on their own terms rather than joining the public conversation. Their silence can look like hesitation but usually signals careful attention and research.
They want confidence before committing.
Phase 3: The Tribalization of Opinion
At the same time, people who barely understand the technology start lining up on all sides of the debate as if it were a political issue.
Some declare that it will transform everything. Others warn that it is reckless or dangerous. Still others dismiss it as a passing fad.
Much of this reaction grows from identity, fear, or ideology rather than direct experience. The conversation gets louder while genuine clarity is harder to find.
Phase 4: Rapid Evolution and Ecosystem Growth
If the tool has real potential, the surrounding environment begins to move quickly.
The creators ship frequent updates of their new product. Early adopters invent new uses that nobody predicted. Supporting products (like Cloudflare services or the Mac Mini in the case of OpenClaw’s recent meteoric growth) suddenly see rising demand because they pair well with the new capability. Other companies look for ways to add integrations that make the new tool easier to plug into existing systems.
At this stage, the story shifts from a single product to an emerging ecosystem that amplifies its reach.
Phase 5: The Backlash from the Pioneers
Then a familiar turn arrives.
Some early adopters start getting bored and even a little disillusioned. Others start pointing out limitations, rough edges, and frustrations that were overlooked during their initial excitement. Sometimes they simply move on to the next shiny thing. Other times, sustained use reveals real constraints that only time can expose.
Ironically, the quieter second wave adopters are just beginning to feel comfortable. Enthusiasm and skepticism overlap in the marketplace.
Phase 6: Corporations Hit the Brakes
Meanwhile, large organizations watch from the sidelines while asking serious questions about security, governance, and risk. They focus on oversight, accountability, and long-term stability.
From a leadership perspective, this cautious approach seems safe. They can’t risk the family jewels on a promise of something amazing. At least, not yet.
Phase 7: The Safe Version Arrives
If the capability truly matters and maintains momentum, a major platform provider such as Microsoft, Google, Amazon, (and nowadays) OpenAI, or Anthropic eventually releases something comparable inside their own infrastructure.
This can happen through acquisition, partnership, or independent development. When it does, the risk profile shifts almost overnight.
What once felt experimental and dangerous now feels enterprise-ready. It’s the signal that many CIOs and CISOs were waiting for.
Phase 8: The Irony of Timing
By the time most corporations adopt the new “safer version” of the capability, the original pioneers have already moved on.
They’re chasing the next breakthrough and speaking about the earlier tool as if it belongs to another era. Six months earlier it felt magical. Now it feels ordinary, in part because that earlier innovation did its job of pushing the frontier outward.
What This Means for Leaders
For leaders who care about both capability and security, sprinting toward the bleeding edge rarely makes sense.
Waiting for stability, clear governance, and trusted integration usually serves organizations better. In practice, that means allowing major, “trusted” platforms to bring new capabilities inside their own secure environments before moving at scale.
At the same time, leaders can’t afford to look inward only. Something important is always unfolding beyond the walls of their organization. Entrepreneurs are experimenting. Startups are forming. New approaches and new possibilities are taking shape. If a company becomes too passive or too comfortable, it risks being outpaced rather than protected.
The real leadership challenge is learning to tell the difference between waves that will reshape an industry and those that will fade.
Some signs of staying power are multiple independent developers building on top of a new technology, respected technologists moving beyond flashy demos into real production use cases, and serious enterprise concerns about security and governance being addressed rather than dismissed.
We don’t need to chase every new wave.
The real test is recognizing the waves that matter before they feel safe enough to bring inside our organization.
Photo by Nat on Unsplash – Innovation is easy to see. Truth is harder to judge.
The first version of almost anything is an act of discovery. We’re learning in real time, usually without understanding what we’re building. We don’t yet know which parts will matter, which ones deserve less attention, or where the challenges are.
The first version is shaped by assumptions. Some accurate, others incomplete. It’s often held together by optimism and a willingness to learn as we go.
The first generation isn’t meant to be polished or permanent. Its purpose is proof of life.
Does this idea work at all? Do we enjoy pursuing it? Is there something here worth continuing once the novelty fades?
Many ideas never move beyond that first stage. Excitement gives way to routine. Maintenance enters the picture. It’s decision time.
Is this something I’m willing to own, or was I simply exploring an interesting possibility?
If the answer leans toward exploration alone, the idea stalls, usually forever. It never makes the leap from curiosity to commitment.
That leap matters.
William Hutchison Murray said it well, “Until one is committed, there is hesitancy…the moment one definitely commits oneself, then Providence moves too.”
The second generation begins at that moment of commitment.
If we choose to begin version two, everything changes.
We’re no longer experimenting or learning if this idea works. We’re deciding that it matters enough to carry forward.
We’re operating with experience now. We’ve seen where effort was misdirected and where the momentum came from. We understand which details carry lasting value and which ones only seemed important at first.
More importantly, we own it now.
That’s why the second generation feels heavier. The weight of responsibility belongs to us. We know too much to pretend otherwise.
An idea that survives long enough to earn a second version has already passed an important test. It has encountered reality and endured.
The first generation asks whether something can exist. The second generation answers whether it should continue.
From there, our work evolves. Spontaneous ideation turns into direction. The purpose becomes clearer than the feature set. Identity begins to emerge.
This is how we do it. This is what matters. This is what we’re willing to stand behind.
The second generation is the foundation for everything that follows…far more than the first. It establishes patterns, standards, and expectations for what comes next.
Tackling version one takes courage. But finishing that version is only part of the journey.
The deeper test lies in beginning again. This time with clearer eyes, better judgment, and full ownership of what we’re building.
We move from discovering what we could build to owning what’s truly worth building.
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.
Over the last 15 years, I’ve written a lot of words.
Words shaped by work and leadership challenges.
Words that grew out of quiet reflection or things that caught my attention at just the right moment.
Many of them were also shaped by family, faith, mistakes, and moments that stayed with me longer than I expected.
More than a few people have suggested I start a podcast. They’d tell me it’s a lot easier to listen than it is to keep up with a bunch of new reading assignments each week.
While my mom was still alive and living with significant vision loss from macular degeneration, I gave the idea serious thought. Listening would have been the only practical way for her to “read” my posts.
Unfortunately, that “serious thought” didn’t turn into action in time for her to benefit.
Ironically, for someone who usually believes in starting, then figuring things out along the way, I let all the steps required to set up a podcast get in the way of beginning.
Until now.
So today, I’m launching a new podcast:
Grandpa Bob Encouraging Leadership
This podcast is a series of short reflections on leadership, life, and learning. I’m sharing them first and foremost with my grandchildren…and with anyone else who might be listening in.
The episodes are intentionally brief, thoughtful, and unhurried.
They’re the kind of reflections you can listen to on a walk, during a quiet drive, or at the start or end of your day.
They’re meant to create space, not fill it.
Who it’s for
At its heart, this podcast is for my grandkids.
Someday, years from now, I want them to be able to hear my voice and know what mattered to me.
The things I noticed. What I learned the hard way. What I hope they carry with them as they find their own way in the world.
But leadership lessons rarely belong to just one audience.
So, if you’re listening, as a parent, a leader, a teacher, or simply someone trying to live well, you’re welcome here too.
What we’ll talk about
Each episode explores a simple idea. Here are some examples:
-Showing up when progress feels slow
-Letting go of certainty
-Choosing gratitude over entitlement
-Learning to wait without drifting
-Leading with trust, humility, and patience
-Paying attention to what’s quietly shaping us
There won’t be hype. There won’t be slogans. There certainly won’t be any fancy edits.
I’ll discuss questions worth talking about, and observations a loving grandfather hopes to pass along to his grandkids.
An invitation
You can find Grandpa Bob Encouraging Leadership wherever you listen to podcasts.
Don’t worry if you can’t listen to every episode.
Please feel free to disagree with anything I say. I don’t have a monopoly on the right answers.
If even one episode helps you pause, notice something new, or steady yourself a little, then it’s doing what it was meant to do.
Thanks for listening.
And if you’re one of my grandkids reading this someday, know that I believe in you and I’m always rooting for you.
If you’re listening alongside them, the same is true for you.
Grandpa Bob Encouraging Leadership 
You must be logged in to post a comment.