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 ideas. You’ve gathered feedback from others, made visuals, bridged gaps between perspectives, glued silos, herded cats. You’ve crafted slidedecks — you’ve prototyped.
Then: you watch as an “easy” answer gains support instead – the solution that will make the problem worse in the long run. The Product Manager says there’s no time. That Guy, the one who’s been here forever and knows “how we do things,” says it won’t work. The CXO says there’s no budget for anything but “AI”. The engineers say your idea isn’t concrete enough. They believe the problem can be solved with Kubernetes.
Eventually, your recommendation gets adopted. By then, you are already solving new problems. You’ve begun pushing the next rock up the hill, hoping this time it won’t roll back down (and crush you).
Meanwhile, the original problem recurs. And the cycle begins again.
Welcome to The Pain Train. Where the exhausting friction of turning information into shared meaning, decisions, and action makes you question every single one of your life choices.
Early in my career, I didn’t have a name for it — a system stuck in its own loops. I believed more effort was needed. Work harder and I’ll break on through to the other side.
Over time, the Pain Train became familiar and inevitable. 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.
If I hadn’t seen, across initiatives and organizations, the truth that Pirsig sums 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” eventually reconstructed the same problems, obfuscated by trendy new language.
Every change designed to navigate faster flows of change, the rising river of complexity — hit the same iceberg, the one lurking below the surface.
Why?
As knowledge workers, we turn raw information into concepts, recommendations, diagnoses, decisions, and action. As technologists, we shape those into working code. We produce change.
And yet, most of us feel like we are running on an endless treadmill. Cogs in an inexorable, Sisyphean machine. The wheels keep turning but we can’t effectively steer.
We might apply brute force or dominating power. Then discover: Power is just another temporary fix — and it propels us into the iceberg faster.
I wanted to get off the Pain Train. Do you?
Albert Camus said, “You have to imagine Sisyphus happy.” Accepting that life is meaningless is the key to transformation. Pushing the boulder can become freedom, transforming suffering into a source of personal power.
Pishposh. These metaphors, the Pain Train, punishing gods, the mountain and the boulder … we made them up. Humans invented our systems of labor. Systems that, too often, are antithetical to knowledge work. I want to do knowledge work.
I haven’t figured out how to stop The Pain Train. But I have discovered alternative realities. Pathways and practices that generate better ways of working. And deliver significantly better outcomes.
Less pain, more transformation.
My journey continues — learning to avoid the icebergs and discovering what’s beyond them.
Will you join me?
Activity One: Consider this
Reading is consuming other people’s thinking. Reading is a valuable activity, one of life’s great pleasures. But for this experience, my new reader companion, it is insufficient.
You will be transforming your own thinking, because no real change can happen without that core skill. While I personally like my thinking, and hope you enjoy it too, what matters most is how well (or not) it supports your work.
Perhaps you’ll love the ideas you find here. You’ll probably hate at least one of them. Regardless, you’re in flow with me. We are doing the work together, asynchronously.
As Beetlejuice said, “You’ve got to work with me here.”
Throughout the book, there are “Consider this” prompts. Write your answers. (Or ask yourself a different question, that’s fine too.) Pay attention to your experience.
You can share them but you don’t have to — considering is enough. You are planting the seeds of insight — the only kind that actually grow. When the time is ripe.
Here is your first one:
If you want to consider with others, you can join the Knowledge Flow community. I’ll send an announcement when it’s open to new members.
The Protean Definition of Knowledge
What is knowledge?
Is knowledge winning at Jeopardy? Performing heart surgery? Coding a complex algorithm?
Is Wikipedia knowledge? Is it fixing motorcycles?
When you give advice – are you sharing knowledge?
If you answered yes to any of these questions … how do you know?
How do you know you know?
Central to this book is a single, core premise: Certainty is impossible. In fact, the more you believe you know (or strive to be certain) … the more closed your mind becomes to knowledge.
This is not pessimism or nihilism. This is joyful liberation. As knowledge workers, we arrive at conclusions and take action in the midst of uncertainty. Knowledge is something we craft, in real time, with other people.
We are not performing knowledge acts, showing how much we know or how fast we can produce. We are endlessly nudging ourselves and the world around us in a direction. Whether that direction is good, correct or valuable depends on our circumstances.
Knowledge is not a single fact; it is an artifact — an object made or modified by human beings that is always subject to revision. It does not have to be written down or recorded in any way (though I will encourage you to make artifacts visible.) Artifacts function as pointers to what we call “knowledge”.
An artifact is always made up of three parts, whether or not these parts are explicit (or acknowledged):
- A conclusion or assertion: what we believe we know.
- The reasons that justify it. Are the reasons true? Are they coherent? Do they fit together to form sound support for the conclusion?
- Context: Circumstances are the specific conditions that exist right now. Context is the way we understand and assess those circumstances. A group of people experiencing the same circumstances (like a war) can view them very differently (like who is the good guy), based on their understanding of the wider world.
An artifact is always defeasible — open to revision, valid objection or simply becoming less relevant. Knowledge changes, as does everything.
In technology work, I often hear the word “concrete”. As if concrete is the ideal material for artifacts. But concrete does not iterate and evolve.
Knowledge at rest has ceased to be knowledge.
Artifacts grounded in context help us decide what to do. We do want more of that. But if you strip away context and uncertainty, you strip away knowledge.
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 shaping is a profoundly challenging skill to develop. The infrastructure needed to support our work is often missing, broken, or pushing against us in favor of control. We are surrounded by delusion about what knowledge is and who owns it.
In the next chapter, we will explore those delusions.
Practicing knowledge skills is what enables us to avoid “simply building another factory.” As Pirsig goes on to say:
The true system, the real system, is our present construction of systematic thought itself, rationality itself. — Pirsig
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.
This book is titled Knowledge Flow because knowledge, like water, is a shapeshifter. We’ll describe it differently depending on context, purpose, and perspective.
Knowledge is both an artifact and a flow, the same way that electronics are both particles and waves. — Dave Snowden
That doesn’t mean we can’t understand it! You know what water is even though you drink a glass of it, add ice cubes to your lemonade, admire puffy clouds, open your umbrella when it rains, and swim in the lake. Knowledge Flow describes different artifacts and methods of making them, different experiences, different shapes. But it’s still knowledge.
It is creating the infrastructure we need to generate knowledge.
Rather than being run over by the Pain Train.
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
Here are 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 it.
- 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 … these are not the primary reasons for practicing knowledge flow.
Experiencing knowledge is its own reason. The experience of time, energy and attention converging into insight, action and meaning is inextricable from a life well lived.
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
Knowledge work, well done, is probably not reason enough if you are responsible for economic viability. We are all responsible for organizational viability, if we want 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.
Economic viability depends on developing these systems because the future is knowledge flow. That’s reason enough, isn’t it?
You are already paying for it … if you’re lucky
Knowledge workers are expensive. Organizations invest billions of dollars a year seeking “top talent”.
Talent is still commonly defined as “what do you already know?” In small teams and big organizations like Google, Amazon and IBM, technology knowledge is tested on a whiteboard or other coding test. (Often before the applicant interacts with a human.)
When I poll audiences at technology conferences, 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.
Increasingly, the most important skill is responding appropriately to organizational challenges, adapting as things change.
Where’s the whiteboard test for that?
How do my JavaScript skills help me work effectively with non-technical people to design innovative solutions to our customers’ challenges? Is the investment generating growth, innovation, and a more-intelligent system?
Then squandering it
Business processes designed for production systems focus on reductionism, speed, “efficiency” and managerial control. This approach isn’t just a bad fit for modern needs — it wastes the accumulated benefits of knowledge work.
Most technology workers leave a role within 2-3 years. The number one reason they give is: stagnation. The pressure to change while keeping everything the same. Stagnation in the technology stack, in their personal growth, and in the lack of knowledge generation.
When they leave, their network of relationships collapses — emergent connections that generate value for the organization. Their replacement must build another one in order to be effective.
Imagine a cellular network that had to replace every cell tower, at random intervals, every two years. Imagine how staggeringly expensive that would be. And how little time they’d have for expanding the system.
Yet, most organizations fail to change the infrastructures that reinforce this outcome.
And chasing it away
The bigger the knowledge gaps between organizational silos (product and tech, for example), the more valuable work falls into the space between them. Like Gandalf and the Balrog, knowledge flow falls into the gap, never to be recovered.
The people with proven capacity for relational leadership become bridge roles. They “glue” teams together, overcome organizational silos.
These connectors, innovators, bridge builders, enthusiastic knowledge flow leaders carry big responsibility with little authority. As stagnation increases, their change-focused recommendations are pushed aside in favor of short-term fixes — they are increasingly ignored.
Then the organization hits a roadblock. They need a “transformation” — new bridges so they can escape the downward velocity of silo’d processes.
Uh oh! The people they most need, the ones who design bridges … have all walked out the door.
Your future depends on flow
Your org chart architects your technology system. Innovation is a product of the ways people and technology think, communicate and act in concert.
In a world of increasingly distributed information, fast-changing contexts, industry disruption, unproven AI integration and data meshing … fast technology deployment can only get you so far.
When you’ve reached the edge of your knowledge flow network, you’ve reached the end of the line.
The Journey Ahead
There are as many ways to explore knowledge flow as there are ideas. I’ve mapped some pathways. You can read the book cover to cover. (Obviously, I recommend this.) You can dive into the digital space and explore one practice area. You can read books in the knowledge flow domains. You can start practicing activities in the Knowledge Studio or facilitating activities in your organization. You can join the community and share your experiences. (Beta Group launches soon.)
Ideally, you will do all of these things, expanding your ways of knowing as you grow.
Our primary journey will be along Six Spiral Paths that move us aways from the Six Dominant Delusions (of Unusual Size) towards the Six Inconceivable Truths. (Warning: there will be snarky jokes and movie quotes on this journey.)
Along these paths, you’ll be practicing. Making artifacts, learning skills, opening your mind, shifting your perspective. No doubt you’ll disagree with me. And you’ll learn how to express that disagreement in ways that generate better insight.
Here’s a peek at what’s ahead.
We’ll develop temporal intelligence by shaping knowledge with our time, energy and attention, rather than managing or stockpiling it.
We’ll cultivate coherence with relational reciprocity — think better, together, rather than reinforce hierarchical authority.
We’ll generate emergent meaning — solutions we could never create on our own — with well-designed systems of people, technology, and practices rather than simply go faster.
We’ll steward distributed decision making with relational leadership rather than trying to command and control everything.
We’ll build learning loops into our daily work so we can navigate towards signal, rather than just delivering more noise.
We’ll mastermind cognitive ecologies and solve hard problems with diverse ways of thinking, rather than just Mr. Spock’ing everything.
This journey is fraught. There is no “easy way” to get from here to there. Knowledge work is hard. And the better you get at it — the harder it is. Because doing hard things is … actually the point.
Like James when he faced the decision about whether to join Men in Black, you might ask me, “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. If you’re strong enough 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 Two: 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 continue your journey. Beginning with the core compentencies.