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AI Business IBM Management

Making It Up As We Went Along

There was a building along Route 270 in Gaithersburg, Maryland where people kept secrets for a living. Not the cloak and dagger kind. The corporate kind, which in its own way requires just as much discipline. The IBM Washington Systems Center occupied a two-story modern building that looked, from the outside, like any other outpost of late twentieth century American business. Inside it was something else. It was where IBM sent its hardest problems, and where the largest IBM customers in the world โ€” the ones whose names you would recognize immediately โ€” sent their most urgent ones back.

I worked there as a manager. But before I was a manager there, I was a hire. And before I was a hire, I was like every other IBM professional on the outside of a particular line โ€” a line I didnโ€™t fully understand until I crossed it.


At IBM there was a protocol so embedded in the culture it had almost ceased to be a rule and become something closer to a religious observance. New products were not discussed until they were announced. Not hinted at. Not alluded to. Not whispered about with a favored customer over lunch. The announcement came in the form of something called a Blue Letter โ€” a formal communication from senior leadership that functioned as the official moment a product entered the world. Before the Blue Letter, the product did not exist in any conversation you were permitted to have. After it, you could talk about nothing else.

Violation was not a career setback. It was a firing offense. Full stop.

That clarity had a kind of elegance to it. You didnโ€™t have to calibrate how much you could say or navigate gray areas. The line was absolute. And because it was absolute, and because everyone knew the consequence of crossing it, the culture enforced itself. You didnโ€™t need surveillance. You needed people to understand the stakes, and they did.


What I didnโ€™t understand, from the outside, was what that line was doing to my imagination.

When you canโ€™t see the roadmap โ€” when the strategy and the unannounced products and the long arc of where the company is going are all behind a wall you have no access to โ€” you donโ€™t experience that as absence. You experience it as depth. The things you donโ€™t know feel like they must be there for a reason. The gaps in the announced picture feel like the gaps in a great iceberg โ€” whatโ€™s visible is impressive, but whatโ€™s below the surface must be more impressive still.

I had faith in IBMโ€™s strategic intelligence the way you have faith in things you canโ€™t fully see. And faith, uncontradicted by evidence, tends toward beauty. The hidden roadmap wasnโ€™t just unknown โ€” it was, in my imagination, a thing of coherence and intention and vision. It had to be. The alternative was too unsettling to consider.

Then I got hired into the Washington Systems Center and crossed the line.


There was no single moment of disillusionment. No specific product that shattered the dream, no strategy document that read like a disappointment. It was more like a gradual adjustment of the eyes โ€” the way they adapt when you move from bright sunlight into a room lit quite differently than you expected. The room isnโ€™t dark. Itโ€™s just not what you anticipated. And once your eyes adjust you can see perfectly well, but you can never quite recover the image you had of the room before you entered it.

The reality on the inside was messier than the dream on the outside. More improvised. More human. We were, in ways I hadnโ€™t anticipated, almost making it up as we went along. Not carelessly โ€” the people at WSC were extraordinary, the work was serious, the commitment was real. But the beautiful coherent roadmap I had constructed in my imagination from the outside bore only a partial resemblance to the actual thing. Strategy, it turned out, looked different up close. Less like architecture. More like weather.

I absorbed this alone. Nobody sat me down and named what I was experiencing. Nobody had the conversation with me that I would later learn to have with others. I found my way through it by degrees, the way you find your way through most things that donโ€™t come with instructions.

What came out the other side wasnโ€™t cynicism. It was something more useful โ€” a clearer eye, a more grounded relationship to the institution I was part of. The faith hadnโ€™t been wrong exactly. It had just been innocent. And innocence, once lost, canโ€™t be recovered. But what replaces it, if youโ€™re lucky, is something steadier.


Years later I was the manager. And I was hiring IBMers โ€” good ones, experienced ones, people who had spent serious careers on the other side of the blue line. They knew the products cold. They knew the customers. They knew how to work. What they didnโ€™t know, couldnโ€™t know, was what waited for them on the inside of the wall they were about to cross.

I knew it. Because I had been them.

There is a particular expression that crosses a personโ€™s face when the actual roadmap becomes visible for the first time. It isnโ€™t dramatic. It doesnโ€™t announce itself. Itโ€™s more like a subtle recalibration โ€” a slight stillness, a momentary adjustment behind the eyes. The person in front of you is doing quiet interior work, reconciling what they imagined with what theyโ€™re now seeing. The gap between those two things is doing something to them, and theyโ€™re not sure yet what to do with it.

I learned to watch for that expression. And when I saw it I knew what was coming if I didnโ€™t get ahead of it.


The danger wasnโ€™t disappointment. Disappointment is temporary, and smart people move through it. The danger was what disappointment hardens into when it isnโ€™t named and worked through โ€” a corrosive cynicism that poisons not just the person carrying it but everyone around them. A talented IBMer who had invested a career in faith, discovered the faith was misplaced, and decided the whole enterprise was therefore hollow โ€” that person could do real damage to a team. I had seen it happen, or the early stages of it, which was enough.

So I developed what I came to think of as the god is dead conversation.

The name came from Nietzsche, though the application was strictly practical. What Nietzsche meant โ€” or one of the things he meant โ€” was that when the organizing faith of a civilization collapses, the collapse doesnโ€™t leave nothing. It leaves a vacancy that has to be filled with something else, something built rather than inherited. The god is dead conversation was about helping someone through that vacancy quickly, before they filled it with the wrong thing.

It wasnโ€™t a long conversation. It didnโ€™t need to be. What it needed to be was honest, and direct, and delivered before the cynicism had time to set.

I would tell them what I saw happening. I would tell them it was normal, expected, that everyone who crossed this particular line felt some version of it. I would tell them the dream theyโ€™d carried on the outside wasnโ€™t foolish โ€” it was a reasonable response to incomplete information, and the information had been incomplete by design, and the design had served real purposes. None of that made them naive. It made them human.

And then I would tell them what Iโ€™d learned on my own, without anyone to guide me through it. That the messiness on the inside wasnโ€™t a failure of IBMโ€™s intelligence or intention. It was just what strategy actually looks like when youโ€™re close enough to see the seams. Every institution looks more coherent from the outside than it does from the inside. Thatโ€™s not a scandal. Thatโ€™s organizational life.


The conversations were tricky. There was real care required. You were asking someone to grieve something โ€” the beautiful imagined roadmap, the faith in a hidden coherence โ€” without tipping them into bitterness about what replaced it. You were trying to accelerate a process that, left alone, might drag on for months and quietly corrode their effectiveness. And you were doing it while also being their manager, which meant you needed them functional and engaged on the other side of the conversation, not just unburdened.

What I had going for me was credibility. I wasnโ€™t delivering a message from outside the experience. I had made the same crossing. I knew the specific texture of what they were feeling because I had felt it myself โ€” the diffuse quality of it, the absence of a single dramatic moment, the gradual adjustment of the eyes. When I told them I understood what was happening to them, I actually did. I think they could tell.

Trial and error had taught me the shape of it. What didnโ€™t work I had found out the hard way, at some cost, early on. What I arrived at had been load tested by real people in real situations. It wasnโ€™t a framework from a leadership seminar. It was something I owned completely, which meant I could adapt it in the moment rather than execute a script.


Most of them came through it well. Better than well, actually.

What I hadnโ€™t fully anticipated โ€” though in retrospect it makes complete sense โ€” was what replaced the faith once it was gone. It wasnโ€™t the steadier, clearer-eyed pragmatism I had found my way to alone. It was something more potent than that. Something that surprised me the first time I saw it and then became one of the things I quietly counted on.

They came out the other side feeling superior.

Not arrogant. Not dismissive of colleagues still on the outside. But quietly, privately elevated โ€” because they were now keepers of the secrets they had once only believed in. The blue line that had shaped their entire professional identity, that had defined the boundary of what they could know and say and imagine, was now behind them. They were on the inside. They had access. They had been trusted with the actual roadmap, the real strategy, the unannounced products that the rest of the world was still constructing faith-based pictures of.

The believer had become the keeper. And keeping, it turned out, was a more powerful identity than believing. The believer is passive โ€” sustained by what they imagine. The keeper is active, responsible, trusted. They carry something real rather than something projected.

It solved my practical problem neatly, though that wasnโ€™t why it moved me. What moved me was watching people find their footing on the other side of a genuine loss and discover that the ground there was solid โ€” different from what theyโ€™d imagined, but solid. They hadnโ€™t just survived the crossing. Theyโ€™d been changed by it in a way that made them more valuable, more grounded, more fully present to the actual work.

Which was, I suppose, what the god is dead conversation had been for all along.


I think about that blue line often these days.

We are living through a moment when artificial intelligence is advancing faster than most people can track, and the organizations building it โ€” the labs, the research teams, the companies placing enormous bets on where this technology is going โ€” have their own version of the wall. Not identical to IBMโ€™s. The competitive and legal architecture is different. The culture is different. But the basic structure is the same: there is what has been announced, and there is everything else, and most people are working entirely from the announced side.

Which means most people are doing what I did before I crossed the line at WSC. They are filling the gaps with faith. And faith, uncontradicted by evidence, tends toward beauty.


The unrevealed AI roadmap looks, from the outside, like a thing of coherence and intention. The capabilities that havenโ€™t been announced yet must be more impressive than the ones that have. The strategy must be more considered than whatโ€™s visible. The gaps in the public picture feel like depth rather than uncertainty โ€” like the part of the iceberg below the surface, which must be vast because the part above is already remarkable.

I am not saying this faith is wrong. I held the same faith about IBM and it wasnโ€™t wrong exactly โ€” it was innocent. The people constructing faith-based pictures of where AI is going are doing a reasonable thing with incomplete information. The information is incomplete partly by design, for reasons that make competitive and strategic sense, just as IBMโ€™s secrecy made sense. None of that makes the faith naive.

But Iโ€™ve been inside enough walls to know what the inside tends to look like. And I think itโ€™s worth saying, clearly and without cynicism, that the reality is probably messier than the dream. More improvised. More uncertain. More human. The people building these systems are extraordinary โ€” the work is serious, the commitment is real โ€” but they are also, in ways that might surprise you, almost making it up as they go along. Not carelessly. But without the complete map that the outside imagines must exist somewhere, fully drawn, waiting to be revealed.

Strategy, up close, looks less like architecture and more like weather.


This isnโ€™t a counsel of despair. Itโ€™s almost the opposite.

The IBMers who crossed the line and survived the god is dead conversation didnโ€™t end up with less than they started with. They ended up with more โ€” a clearer eye, a more grounded relationship to the institution, a more useful kind of engagement with the actual work. The faith they lost was the innocent kind. What replaced it was steadier and more durable.

I suspect something similar is available to anyone willing to look at the AI moment with clear eyes. Not the disappointed cynicism of someone who expected a beautiful coherent roadmap and found a human institution instead. Not the breathless faith of someone still on the outside of the wall, filling gaps with generous assumptions. Something in between โ€” harder to sustain, more honest, ultimately more useful.

The technology is real. The progress is real. The stakes are real. None of that requires the roadmap to be a thing of beauty. It just requires it to be worked on seriously by people who understand what they donโ€™t yet know โ€” which, from everything I can observe, it is.


What I couldnโ€™t give those IBMers, and what nobody can give you, is the experience of crossing the line yourself. The god is dead conversation only works because the crossing has already happened โ€” because the person sitting across from you has already seen the actual roadmap and is already processing the gap between what they imagined and what they found. You canโ€™t have the conversation in advance. The disillusionment has to be real before it can be worked through.

Most of us will never cross the line into the AI labs. Weโ€™ll stay on the outside of the wall, working from the announced picture, filling the gaps as best we can. Thatโ€™s not a failure โ€” itโ€™s just the condition most of us are in, the same condition those IBMers were in for their entire careers before I hired them.

But knowing the wall exists, and knowing what walls do to imagination, seems like it ought to change something about how we hold our faith. Not abandon it. Just hold it a little more lightly. Stay curious about the seams. Remain open to the possibility that the most important thing about the unrevealed roadmap isnโ€™t whatโ€™s in it โ€” but what weโ€™ve projected onto it.

The blue line is still there. Most of us are still on the outside of it.

And the hidden roadmap still looks, from here, like a thing of beauty.

Categories
AI Business Consulting

The Toll Bridge and the Terrain

For fifteen years of my life, I lived inside the fortress of information asymmetry. I was part of a payments consulting business, and our model was exactly what Andrew Feldman described on a recent Moonshots episode when he pointed a sharp finger at traditional professional services.

His observation was simple, cutting, and entirely true:

“Their role today is to stand between ordinary people and obscure knowledge. And the application of that obscure knowledge to everyday problems.”

When I heard him say that, it landed with a quiet thud of recognition.

For a decade and a half, my colleagues and I were the ones standing in that gap. The payments industryโ€”with its labyrinth of interchange fees, compliance structures, clearing networks, and legacy tech stacksโ€”is a monument to obscure knowledge. Clients didn’t come to us because we possessed some divine, unreplicable wisdom. They came to us because the map was locked in our heads, and navigating the terrain without us was a recipe for an expensive disaster.

We charged for our time, and we earned it. We untangled complexity and solved real, everyday business problems for people who just wanted to move money safely from point A to point B.

But looking back now, I can see the architectural flaw disguised as a premium service. The economic foundation of that entire era relied on friction. It relied on the fact that it took an immense amount of human energy to retrieve a piece of obscure data and map it onto a specific business dilemma. You weren’t just paying for strategic guidance; you were paying a premium on artificial scarcity.

We are living through a moment where the marginal cost of intelligence is rapidly trending toward zero. When the barrier of “obscure knowledge” evaporates, the traditional toll bridges begin to look absurd.

For anyone starting a consulting business today, the playbook would have to be entirely different. When an LLM can parse thousands of pages of network operating rules, interchange tables, and regulatory compliance frameworks in a handful of seconds, the gatekeeper’s standing ground liquefies.

If your value proposition is merely standing between a client and a hidden database, your business model isn’t just flawedโ€”itโ€™s obsolete.

Yet, this collapses into a fascinating paradox. You might assume that when you democratize expertise, you eliminate the need for the expert. But as Dan Shipper recently observed, the reality of AI is completely counterintuitive.

Shipper points out that AI effectively packages up “yesterday’s competence” and makes it cheap and ubiquitous.

Suddenly, anyone can generate a complex contract, a software pull request, or a payments flow strategy with the click of a button. But when cheap competence skyrockets, adoption explodes, resulting in an unprecedented glut of generic outputโ€”what the internet has collectively taken to calling “slop”. Itโ€™s the default, lazy answer that lacks soul, context, and nuance.

When everything begins to look and smell the same, a strange thing happens: the market’s demand for genuine difference sky-rockets.

The shift we are facing across all professional servicesโ€”whether legal, financial, or consultingโ€”isn’t about eliminating the expert. It is about changing the expert’s job from data-retriever to orchestrator and judge. The floor has been raised. Yesterday’s ceiling is today’s baseline.

What remains is the ability to read a room. To watch a clientโ€™s shoulders tighten when you present an option thatโ€™s technically correct but organizationally impossible. To notice the glance exchanged across the table before anyone speaks. No LLM parses that. The map is universal now; the guide still has to be in the room.

We don’t need fewer guides; we need fewer toll booths. The future of consulting doesn’t belong to those who hoard the map. It belongs to those who use a universally available map to help people actually walk the terrain.

Categories
Inspiration Living Reflection

Exploring the Seams of Freedom

โ€œAll of us have little fissures in our lives that provide us greater than normal moments of freedom. You play the seams when you identify those moments and seize them.โ€

Neal King (American Ramble)

We often conceive of our lives as following fairly rigid scripts and routines. We wake up, go to work or school, come home, eat dinner, maybe squeeze in some hobbies or time with loved ones, then go to bed and repeat. The cycles feel inescapable, like train tracks laid out before us.

But if we look closer, there are tiny fissures and fault lines running through even the most regimented of daily grinds. Moments where the iron grip of obligation loosens ever so slightly. A traffic jam that makes you late, forcing you to take an alternate route. A cancelled meeting that clears an unexpected hour in your calendar. A power outage that shuts down the office and sends everyone home early. A flat tire that happens at the worst possible time and place – like happened to me yesterday!

These are the seams that Neil King refers to in the quotation. Little rips and tears in the fabric of our routines that create momentary pockets of freedom. Openings where the rules don’t quite apply and we can slip through the cracks of the scheduled order.

The key, as King notes, is to first identify these seams when they occur, and then seize them rather than letting them pass by unnoticed or unremarked upon. It’s about being present enough to your circumstances to recognize when one of these fissures opens up, and then brave enough to diverge from the mapped out path to explore it.

After all, some of life’s greatest adventures and discoveries have happened during these “off script” moments. Yesterday, my conversation with a tow truck driver opened my eyes to the steps he took to fend off a mountain lion attack on a 5 AM run in the dark! I hope I never have to apply his techniques but I did find our conversation about his encounter fascinating!

Of course, these serendipitous detours and unplanned paths are easy to romanticize after the fact, when we know they turned out well. In the moment when the seams first crack open, it can be daunting to jump through them into the unknown. Sometimes we have to but our ingrained instinct is to stick to our set schedule, to get back on course as quickly as possible.

There’s comfort and safety in routines. Seizing those fissures when they present themselves means trading certainty for adventure, the familiarity of a well-worn groove for the risk and exhilaration of going off road into the unknown. It requires being able to quiet that voice of fear inside us that clings to control and embrace one of spontaneity and serendipity in where the detour might lead.

The rewards of following those detours down their winding paths are often worth it. While not every seam we slip through will result in a life-altering event, they allow us to break up the monotony, to experience something different from our repetitive routine, even if just for a little while. Those moments add texture and vibrancy to our days. They’re the asides and ad-libs to the main scripts we follow. Often they provide those special moments we vividly remember and want to share with others.

So keep your eyes peeled for those little fissures and unexpected openings in your routine. Don’t just impatiently wait for life to reset to its default settings once these moments arise. Seize them while you can and see where they lead you. You might just stumble into a beloved new local cafe, or finally muster the courage to start writing, or meet someone who changes your life’s trajectory and opens even more new possibilities.

The seams are there, waiting to be played whenever we’re bold enough to follow their diverging paths. All we have to do is watch for the fissures and be willing to step through into the open spaces of freedom they reveal. Who knows what new experiences and challenges await us on the other side? What new learning might result?