Writing is less about controlling the process and more about trusting the process. This is a tough first step: just write. Just write and listen to what you think.

There is an ocean of ideas about what “good writing” is. We can drown in it. Rather than discovering what we think, we’ve been taught to write what we think other people want us to think. That’s a bad habit. We’re going to drop that habit, for now. We will practice “good writing” later but first, and for awhile, we are going to just write.

We are taking the journey together. This week, we’ll introduce ourselves, create some spaces for sharing and prepare ourselves for the road ahead.

Lesson contents

This week’s reading

“Simple can be harder than complex: you have to work hard to get your thinking clean to make it simple. But it’s worth it in the end because once you get there, you can move mountains.”

— Steve Jobs

I began my adult life as an aspiring actor and writer. I loved occupying creative potential — the space where we “see” something true and matterful, then do the hard work of bringing it to life. I especially loved doing that work with talented others. Even when we were a wild bunch of melodramatic youngsters who took ourselves too seriously.

For awhile, I combined writing and acting, creating comedy sketches for improv shows. I tried to write the Great American Novel in the morning, while performing in summer theater at night. (That … did not go well.) I “got serious”, bought a Writer’s Market and tried earning money as a freelance writer. I don’t remember what I earned but it definitely didn’t pay my rent.

Eventually, I stopped acting because it’s tricky to balance with parenting. But I never gave up on writing. Writing, for me, isn’t necessarily about publishing. Writing is an embodied practice of listening and crafting and cultivating my thinking.

Writing is creating something from nothing — that then seems like it was always there.

Writing is a constant intellectual challenge with no roadmap. People I respect have hiked the trails: John McPhee, James Glieck, Anne Lammot, David Sedaris, Tracy Kidder, Mary Roach, Micheal Pollan and so many others. They know something about how to avoid being eaten by a bear or dying of hypothermia. They inspire me. But they can not map my journey. Other people can’t know what lessons I need to learn or how I need to learn them.

I have to trust the process.

I was never very good at trusting … anything. Going with the creative flow requires vulnerability, a thing I generally avoid. Instead I try to control the process, with schedules and drama about things tangential to writing, like “omg which website blocker tool should I use”? (Perhaps you’ve worked on technology initiatives run like this? Wanting to change things but making a hot mess instead?) Micromanaging our habits while trying to “flow” is a waste of time and energy. Very little actually gets done. (Again, perhaps that sounds familiar?)

In my 30s, I went back to college and studied both writing and computer science because I couldn’t decide between them. By that age, I’d learned to distract myself endlessly with “getting shit done”. My todo list was more important than my writing schedule. After I finished school, I invested money, earmarked for paying rent while I wrote, in an independent bookstore. I hoped the bookstore would support me. Hahahahahahahaha.

The bookstore was a wonderful adventure and a close cousin to writing. It taught me a lot, while also being a drain on my time, energy, attention and, goodness knows, my bank account. This has been a reoccuring theme in my life, a defect of character: putting myself in situations that were a massive drain on my attention, then wondering why I never got creative work done. It took me too long to learn that focus, gathering my own attention, is the key to writing … and thinking … and being happy.

When I closed the bookstore and moved to the little Silicon Valley of Austin, Texas (USA), I thought I’d quit writing. I’d finally deciding between writing and tech! I just wanted to code. I dove into my new career with gusto. Which means, I was a bit of a workaholic. Which means, I was a workaholic. In part because, as previously mentioned, “get shit done” itis. And in part because I absolutely loved it. Along with coding, architecting, leading teams and initiatives, I gave talks and workshops all over the world. I learned anything and everything that interested me.

I say that I loved my work but the truth is, sometimes, I hated it. In tech culture, there is a constant tension between seeking power and control (see: Twitter at the end of 2022) and actual innovation. The amount of time, energy and attention wasted on ego trippin’ is high.

Over the years, I watched many initiatives get stuck in the same rut I did personally, seeking to maintain control while trying to create. Those two things do not get along. Innovation arises from insightful, well-crafted and learning-driven processes that support people thinking well together, not military deployment.

What I needed was solitude, I thought, time when I was (mostly) free of responsibilities. Then! I’ll! Create! That strategy kinda worked but it mostly didn’t. Regardless, it’s not sustainable. I’ve seen organizations eschew effective social processes, praising individual contributions as the Golden Goose, then deliver nearly nothing but noise.

My work in tech is sometimes maddening and exhausting. Sometimes satisfying and exhilarating. Sometimes all those things and more, simultaneously. Just like life.

On a sunny day in March of 2020, I first heard the word “covid”. I don’t remember the exact date, but I do know that a magic realization arrived sometime afterwards. I hadn’t “quit” anything. The processes and patterns I’d learned through writing were present in my technology career. (Except the poverty part, I earn more than enough to pay my rent.) But otherwise …

I loved occupying the creative potential of building technology, the space where I do the hard work of “seeing” something true and tangible and impactful, then bringing it to life. I loved doing that work with talented others, even when we were a wild bunch of mostly guys who took ourselves too seriously.

Coding and technology architecture isn’t only about what you push to production. It’s an embodied practice of listening and crafting and cultivating your thinking and problem-solving recommendations. It’s creating something from nothing that then seems like it was always there.

Building modern technology is a constant intellectual challenge with no roadmap. People I respect have traveled the path: Peter Senge, Eberhardt Rechting, Donella Meadows, Russel Ackoff, Eric Evans, Kent Beck, Netflix, Spotify and so many others. They know something about how to build performant systems, avoid constructing the same thing again and again with different tools, wasting millions of dollars “transforming” nothing. Other people’s experiences help. But they don’t describe what this software or system needs. Other people can’t know what lessons we need to learn or how we, as a team or an organization, need to learn them.

We have to trust the process.

I discovered that I was better than most organizations at trusting. Going with the creative and intellectual flow, discovering, requires vulnerability, a thing most organizations generally avoid. They want “transformation” without risk. So they make a lot of unnecessary drama along the way. So much noise, endlessly distracting ourselves with “getting things done” for the sake of it.

My career has taught me a lot. It has also been an unnecessary drain on my time, energy and attention. The bigger the drain, the fewer the results delivered. The more a situation spun out of control, the more control got added, which increased the blame but not the transformation.

When my teammates and I could focus on figuring out tough challenges, work hard and invest our attention in activities that lead to impactful insights, we moved mountains. And, generally, we were happy together doing it.

Apparently, there is little difference between the lessons writing teaches me and the lessons technology systems teach me. Different languages. Different, less poetic, group of colleagues. But overall … crafting knowledge is crafting knowledge.

As knowledge workers … we craft knowledge. Regardless of our role, we endlessly weave other people’s ideas and experiences into our own. We construct recommendations. We hope our ideas will benefit the technology system, people processes, products and organizations whose mission we serve.

We try to see what is not yet visible and bring it to life.

Alas, despite our good intentions, we often become lost in the forest of strong, disparate opinions. We head down a promising path and discover a dead end. We do this again and again. When we do find a path that leads to change … almost nobody follows us.

Buffeted by the forceful winds of organizational politicking, we are screaming into the wind.

Crafting knowledge involves constructing something whole and actionable from the raw materials of abstract ideas. This requires consistently creating conceptual integrity. Conceptual integrity helps us figure out what is best to do, rather than simply doing what we are told to do.

Responsibility to yourself means refusing to let others do your thinking, talking, and naming for you; it means learning to respect and use your own brains and instincts; hence, grappling with hard work.

— Adrienne Rich

Unfortunately, we are truly terrible at creating or maintaining integrity of thinking, in ourselves and with others. Unless we practice. Fortunately, writing is inherently the practice of crafting conceptual integrity.

We can use writing to strengthen our metacognition – awareness and understanding of our own thought process. Thinking is a process we can observe, understand and improve.

Writing can be used as a method of inquiry. We write to explore questions, assertions, new ideas and insights. We reflect on, and detangle, our experiences. We consider new pathways and invent new, better, questions.

We can use writing to structure learning. When we proactively learn and grow, we improve our ability to navigate uncertainty.

Writing can synthesize knowledge, experience and sound judgement into the best-possible recommendation, in the midst of ever-changing circumstances. When we write, we are not making things concrete, except when we need concrete. We are synthesizing. Synthesizing and prioritizing, when done together as a team, becomes thinking well, together.

Thinking well together generates better outcomes. And makes daily life more enjoyable for everyone. When people cooperatively strengthen their thinking, and reasons for acting, they make better decisions together.

All these practices strengthen conceptual integrity. When we are good at creating conceptual integrity … we can lead learning teams and structure sociotechnical systems where knowledge grows and people flourish. This is integrative leadership — a strong foundation for generating true and lasting change.

What to do this week

  1. Select a notebook and pen
  2. Set a timer for 10 minutes and write your story … why are you here? (Share it with me, if you want to.)
  3. Select a creative nonfiction book to read
  4. Make a little space in your morning

What we’ll do in class

This week, we’ll introduce ourselves. We’ll make sure everyone has access to everything they need. And I’ll briefly describe the activities we’ll be doing over the next eight weeks. You don’t have to start daily writing practice this week … but I will recommend you do. I’ll also recommend you choose a book to read.

Further reading

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