The Pain Train
Chances are: You have arrived here on the same train I rode in on.
You’ve solved a difficult problem. You’ve worked hard to communicate your recommendation — gathering feedback, making visuals, bridging gaps, gluing silos, herding cats. You’ve crafted the slidedecks, maybe even prototyped.
Then: an “easy” answer gets adopted instead -- the one that will make the problem worse in the long run. Or That Guy, the one who’s “been here forever and knows how we do things,” says it won’t work, and your support evaporates. The Product Manager says there’s and the CXO says there's no budget for anything that isn't AI. The engineers say it’s not concrete enough and, anyway, they don’t believe it’s actually a problem.
Eventually, somehow, your recommendation gets adopted. By then, there are new problems to solve. You begin pushing the next rock up the hill, hoping this time it won’t roll back down (and crush you).
Meanwhile, the original problem recurs.
Welcome to The Pain Train. Where the exhausting friction of turning information into shared meaning, decisions, and action makes you question every one of your life choices.
I didn’t have a name for it at first — a system stuck in its own loops. But it became familiar. Across the highs and lows of my technology career, I’ve ridden that train. I might have ridden it all the way to retirement ... if I hadn’t crashed into the wall of reality, like Truman in The Truman Show.
Pirsig summed it up best:
If a factory is torn down but the rationality which produced it is left standing, then that rationality will simply produce another factory
— Robert Pirsig , Zen and the Art of Motorcycle Maintenance
Every “transformation” I experienced eventually reconstructed the same problems in trendy new language. We navigated faster flows of change, the rising river of complexity — and still hit the same icebergs.
Why?
Because, as Pirsig says:
The true system, the real system, is our present construction of systematic thought itself, rationality itself.
As knowledge workers, this is what we do: shape outcomes, structure decision-making, frame the problem space, and adapt as things change. We turn raw information into concepts, recommendations, diagnoses, decisions, and action.
And yet, most of us feel more like cogs in an inexorable, Sisyphean machine. We keep the wheels turning but can’t effectively steer them in another direction. Not without brute force, or some form of dominating power, which is always a temporary fix.
I want to get off the Pain Train.
Will you join me?
If so, you must first stop producing another factory.
This book isn’t about “better, faster, more.” It’s about re-architecting rationality — the invisible defaults — so we get more signal, less noise.
More flow, fewer bikesheds. More groups of people doing what no one can do alone.
Designing systems that generate momentum, coherence, and resilience — people and machines co-creating intelligence that moves across tools, situations, and time.
Rather than being run over by the Pain Train.
The Protean Definition of Knowledge
What is knowledge?
Is knowledge winning at Jeopardy? Performing heart surgery? Coding a complex algorithm? Fixing motorcycles or negotiating a peace treaty?
Is Wikipedia knowledge? Is passing an exam proof that knowledge has been acquired?
When you give advice -- sharing knowledge? Are you passing knowledge onto your kida?
If you answered yes to any of these questions ... how do you know?
How do you know you know?
By now, you are probably waiting for my single, canonical, concrete definition of knowledge. Enough with the rhetorical questions!
Sorry (not sorry). There's isn't one. The definition of knowledge is protean. Proteus, the Greek sea god changed forms. Knowledge is like that, it can appear solid -- until you try to pin it down.
This book is titled Knowledge Flow because knowledge, like water, is a shapeshifter. We'll describe it differently depending on context, purpose, and perspective.
That doesn't mean we can'tl understand it! You can drink a glass of water, add ice cubes to your lemonade, admire puffy clouds, open your umbrella when it rains, and swim in the lake. In each instance, you understand that water is involved. Knowledge Flow describes different experiences, different shapes, but it's still knowledge.
Lest you think "this is too abstract, a bullshit management book, poetically unrelated to my actual job (fluffy clouds indeed)" ... imagine a tsunami.
The depth of the oceans. Your body (80% water) shriveling in the desert after in three days without water. To demand only solidity is to ignore the power of change. The inexorable impact of human mental models on our lives, our work, the planet itself.
Here are two definitions that will keep us oriented. Whatever else knowledge might be ... it is always these two things:
You know what knowledge is because you experience it, every day. Flowing through everything you design, synthesize, shape, focus on, share, and deliver. Every decision you make is sipping knowledge flow. It's what you pay attention to and everything you ignore.
The practice of knowledge flow is a precious investment, both for you personally and for every organization that depends on knowledge work (which is, all of them.)
The Precious Investment
The ability to perform deep work is becoming increasingly rare at exactly the same time it is becoming increasingly valuable.
-- Cal Newport , Deep Work
Some pretty awesome reasons for reading this book and practicing knowledge flow:
- You are more likely to do work that interests you and be economically sustained by that work.
- You are more likely to generate sound, cohesive ideas and solutions to difficult challenges..People are more likely to trust your judgement, insight,and leadership.
- You are more likely to see systemic patterns. You are less likely to be persuaded or manipulated by faulty arguments.
- You are more likely to have a positive impact on the world around you.
These are true. You'll experience at least some of these benefits. And yet ... they are not the primary reasons for practicing knowledge flow.
Experiencing knowledge is its own reason. The experience of knowledge is inextricable from a life well lived. Your time, energy and attention converging into insight, action and meaning.
This book describes knowledge work, well done. Isn’t the reason enough?
The Competitive Advantage
Those companies that don’t adapt to understanding knowledge as a force of production more important than land, labour and capital, will slowly die, and will never know what killed them. – Larry Prusak
If you are responsible for organizational leadership, knowledge work, well done, is probably not reason enough. Economic viability is needed to support people who need health coverage and competitive wages. Why should organizations care about shaping their investment of time, energy and attention with knowledge flow?
- They are already paying for it.
- Then squandering it by
- Chasing away relational leaders and innovators.
The future is knowledge flow ... economic viability depends on developing these systems. That's reason enough, yes?
You are already paying for it ... if you're lucky
Knowledge workers are expensive. Organizations invest billions of dollars a year seeking "top talent". People who generate profitable returns with their time, energy and attention.
Talent is still commonly defined as "what you already know and can do." In small teams and big organizations like Google, Amazon and IBM, technology workers take whiteboard coding tests to prove competency is a particular tech stack. Often, this happens before they talk to a human about the work.
Great, organization hires people who can code on a whiteboard, even when stressed. Will those people abandon those skills next year when the technology landscape changes?
Do they have the self-awareness necessary to change their own minds?
When I poll audiences at technology conferences, at least half the room says they are using skills they did not have 2 years ago. A Harvard Business Review study found similar results: the half-life of many technology skills is 2.5 years.
Do I have temporal intelligence -- the ability to respond appropriately to organizational challenges by adapting systems so they accelerate, rather than suffocate, change?
Where’s the whiteboard test for that?
Sure, tt's important that I can write J
Sure, tt's important that I can write Javascript, if that's my job. I want my heart surgeon to know how to do heart surgery too.
It's also important that I can do something with Javascript that makes a difference. Can I work effectively with non-technical people to design innovative solutions to our customers’ challenges? Can I help other developers improve their skills?
If you are paying for knowledge generators, ensure that their knowledge can generate growth, innovation, and an intelligent system.
Then squandering it
Organizations put knowledge work inside of business processes designed for production systems. Focus on one thing, do it faster, more efficiently and as directed by management.
This isn't just a bad fit for current needs. It sabotages people’s desire to think for themselves. The knowledge generators burn out.Most technology workers leave a role within 2-3 years. The number one reason they give is: stagnation. Stagnation in the technology stack, in their personal growth, and in the lack of knowledge flow (though they might not know to call it that).
When they leave, they take with them what they know. In most orgs, that’s a one-to-one tradeoff … they hire someone with that knowledge.But remember, knowledge is relational – it arises primarily between nodes workers. Each worker has built a network of relationships, emergent connections that generate value for the organization. When one node / worker leaves, that network goes offline. The replacement node/worker might rebuild it but the network will function differently … forcing each node/worker to adapt.Imagine: what if this knowledge system was the cellular network our phones depend on. Imagine how staggering expensive that would be and how frustratingly disruptive.
Yet, most organizations accept it as the cost of doing business.
And chasing it away
Organizational silos create gaps between knowledge areas. The bigger those gaps (between product and tech, for example) the more valuable work falls into those gaps, like Gandalf and the Balrog, never to be recovered.
Organizations promote people who demonstrate command and control approaches, gap makers, more often than not. Rather than promote people with a proven capacity for relational leadership, they create roles to bridge the gaps, "glue" teams together, overcome organizational inertia.
Thus tossing money into the gap, never to be recovered. When this profoundly expensive cost of doing business gets too high … they lay off the glue people.
Or, and I’ve seen this again and again over my career – they don’t have any glue people to lay off. As stagnation increased, the changemakers were increasingly ignored, pushed aside, or burned out. The people who facilitate change, the connectors, innovators, enthusiastic knowledge flow leaders … have walked out the door.
Then, the organization hits a roadblock; they need a “transformation” to escape the downward velocity of outdated processes. Uh oh! In a constantly-shifting technology landscape, they have not optimized for change.
Your future depends on flow
Your org chart architects your technology system. Innovation is a product of your social system – interrelationships that design the ways people and technology think, communicate and act in concert. can adapt by sharing expertise across an organization.
In a world of increasingly distributed information, fast-changing contexts, industry disruption, unproven AI integration and data meshing, fast technology infrastructure and continuous deployment can only get you so far. When you’ve reach the edge of your knowledge flow network, you’ve reached the end of the line.
How You Will Learn to Flow
We have bad habits that drain our precious time, energy and attention. I call these the Six Dominant Delusions (of Unusual Size).
We believe in them, or at least some of them. Delusions that generate the Sysyphian rock you push up the organization hill. Then it rolls back down and crushes you into a splatty puddle of bug juice.Like in The Princess Bride, the Delusions of Unusual Size live in the Fire Swamp, where myths about knowledge hide in plain sight.
To find your way out, follow the Spiral Paths, habits that lead towards the Six Inconceivable Truths. Yes, yes, I’m mixing metaphors, the Emerald City on the other side of the Fireswamp. But that’s okay, the Truths are true everywhere, even in your daily life.
Here’s the map of our journey – a peek at what’s ahead.
🔒 → ⏳ → 🌊
We’ll avoid the mesmerizing piles of treasure guarded by dragons, the delusion that knowledge is a static possession. And tip toe into the flux of knowledge in constant motion. With temporal intelligence, we’ll shape knowledge with our time, energy and attention, rather than managing it, trying to hold it still.
🏛 → 🌿 → 🤝
We’ll unmask the antiHero, the one shouting commands as if knowledge is hierarchical authority. And arrive in the land where knowledge is relational reciprocity, a font that springs up between knowledge parts. There, we can design processes and practices, that cultivate coherence, the magic of decisions guided by shared meaning.
⏩ → 🌀 → 🏗
We’ll discover that we are shadowboxing, believing knowledge is efficiency of execution. We’ll invent knowledge architectures that generate emergent meaning, well-designed systems of people, tools, and subsystems, that improve our shared capacity for hitting the target.
👑 → 🤝 → ⚖️
We’ll escape knowledge leadership as command and control. And run towards relational leadership, creating an ecosystem in which people (and technology) can effectively contribute, decide, and adapt. We’ll facilitate trust and autonomy by stewarding distributed decision making.
📦 → 🔄 → 📚
We recognize the siren song of knowledge is just delivery. And steer towards knowledge engineered through learning. We’ll build learning loops into our daily work so we can navigate towards signal, rather than noise.
📊 → 🧠 → 🌐
We awaken from knowledge as pure rationality, dissociated analysis, data and Vulcan logic. And solve hard problems with diverse cognitive modes, many ways of knowing. We will mastermind cognitive ecologies, thinking systems for cross-functional decision making in dynamic environments, that give us the super powers we’ve sought but never found.
This journey is fraught. Knowledge work is difficult. There is no “easy way” to get from here to there.
Like James in Men in Black, faced with the decision about whether to join, you might ask, "Is it worth it?"Like Agent K, I can only say, "Oh yeah, it's worth it ... If you are strong enough."If you are strong enough to step off the Pain Train. To stop producing another factory.
Are you ready to:
- Focus on the framing the right questions, rather than getting the right answers?
- Examine your current beliefs about knowledge?
- Envision knowledge flow (as a practice and a system)?
- Walk the paths that get you from here to there?
- Change how you do things?
If you are still reading … you are ready. I’m here with you, looking forward to our journey together.
Let’s begin.
Activity One: Build Your Home
Throughout this book, you’ll build a knowledge repository. Forget everything you think you know about what knowledge, repository, or even creating means. Chances are, your definitions will change.
To begin, set up a practice area — your experimental home. It can live anywhere you like, using any tool you prefer. I’m so not the boss of you. But here’s one constraint that will help you down the road:
Use Coda.
That’s it. Create an account and set up a few starter tables.
Visit the Knowledge Studio
Okay, maybe that’s a bit too constrained. Other good tools include Obsidian, Notion, Airtable, Heptabase, Google Sheets, Figma, or Miro (if you’re visually inclined). You can Luddite this and use a notebook (or a reMarkable), but capturing links will be harder. If you still work by hand, I'm sure you’re not averse to a little sweat.
Once you’ve built your home, come back and explore: “What the heck is knowledge, anyway?”
Field →
Practices →
Read →
