Author: Jim

“The cure for boredom is curiosity. There is no cure for curiosity.” – Dorothy Parker

This has been the tagline here since near the beginning, although there is some question about its provenance (Quote Origin: The Cure for Boredom Is Curiosity. There Is No Cure for Curiosity – Quote Investigator®). One of the forces contributing to my starting this experiment was Dave Winer, whose ur-blog Scripting News just celebrated its 30th birthday (The blogosphere is in full bloom. The rest of the internet has wilted).

When I created an MBA-level course on knowledge management at the Kellogg School, Winer donated licenses to his blogging software tool, Radio UserLand, so that my students could experiment with blogging. The experiment was not terribly successful. I made a slew of mistakes in how I set up and ran that particular experiment. Winer has a theory that some people are what he labels Natural-born bloggers.

Perhaps.

I do think there are some perspectives or attitudes you can bring to blogging (or writing in general) that make a difference. Nicole van der Hoeven offers a perspective that particularly resonates for me when she talks about learning in public. This ties into what I’ve said in the past about the observability of knowledge work.

Curiosity is at the root of all of this. I write as part of figuring out the world and what I think about it. Sharing what I learn is about the excitement of discovering something new and interesting. It’s the toddler showing off the frog she found in the backyard. If you’re lucky you show it to someone who shows you where to find another one in the creek nearby.

But it all starts with committing to your own curiosity.

I have this fuzzy memory of a standoff with my mother when I would have been about five years old. I was playing by myself in the front yard and she called for me to come in. I mouthed off somehow about not being ready or interested in doing what she wanted at that moment.

She responded with a “what did you just say?” in a tone that did not bode well for my immediate future. I remember thinking to myself “what can I say this instant that will get me out of trouble?” A quick “I love you” was sufficient to defuse the situation. While I did indeed love my mother, what sticks with me to this day is the sense of quickly thinking about how to manipulate the conversation to my advantage.

Another early reinforcement for speed and quickness as a default response.

While I think I’m on to something important in focusing on rhythm and cadence in my writing, I also need to sort out this speed response. This is something other than being an adrenaline junkie. I’ve never been one to seek out thrills for the sake of thrills. But I do find that I get impatient when the world around me unfolds too slowly for my tastes. Took me a long time to break myself of the habit of finishing other people’s sentences, for example.

I feel as though most other people tune into the rhythm of situations more easily than I do. For me, it depends on whether the underlying rhythm aligns with my natural “clock speed”. I’m fine when everything is moving briskly. Makes me a good consultant and problem solver.

Most of the time.

When the circumstances say “slow down,” I have to be very deliberate and mindful to match my outside to the appropriate pace. Whether my insides slow down can be another story. A story that will likely take some time to unpack further.

Some things you have to be taught. Others you learn largely on your own. I’ve gotten lots of feedback and editing on my writing over the years. And I got plenty of training on the mechanics of grammar in my youth. But 99% of that input came after I had produced something to react to. I can’t ever recall getting any input on how to create something in the first place.

There was a nun at some point who taught me something about preparing outlines, but I took the same lesson from that as any middle schooler, which was to produce the outline after you’d finished the piece. There’s Anne Lamott’s classic advice on “shitty first drafts.” And I did eventually learn about freewriting somewhere along the way.

For all the writing I’ve done, it isn’t at all clear how much of a process exists behind it. I’m reminded here of an observation that Peter Drucker once made that “whenever we have looked at any job – no matter how many thousands of years it has been performed – we have found that the traditional tools are wrong for the task.”

We feel our way to methods that work for us. When we succeed, we try to repeat what we think we did that worked. When we fail, we change something and try again.

For large scale, industrial, processes we’ve developed a body of knowledge and techniques for improving a process until it can reliably hit measures of performance, output, and quality. We don’t have a similar body of knowledge for creative work, although we pretend that we do. That’s because we can scarcely measure performance, output, or quality. And, whatever crude metrics we do cobble together don’t tell us which aspects of what passes for process connect to what we struggle to measure.

Once you start looking for it, you can find advice on aspects of the writing process. I can’t speak to any of the fancy programs on creative writing or what’s to be found within MFA programs. I have no aspirations to write the great American novel, so I haven’t looked in that direction. I never cracked the code of writing for academic journals. I suppose I’m an amateur writer in the sense of liking to have written.

I’m competent at something that many people find intimidating. Over time, I’ve become interested in getting better at this craft. I’ve sought out the advice and work of those who’ve demonstrated their great skill and graciously set down their thoughts on how this process works for them.

Among the other things I can claim some competence at is the analysis and design of systems and processes. The challenge here, of course, is akin to the old saw that a lawyer who represents themselves in a case has a fool for a client. It’s remarkably hard to coach yourself. How do you stand outside your process effectively enough to improve it?

I’m at a point in this draft, for example, where I’m struggling with what to do next. Do I pull back a bit to see if there is a better high level structure or flow to try? Do I push this line of thought to something that might resemble a close or conclusion of some sort? Have I found some sort of point that I can now articulate or am I about to start another cycle and wander off into the weeds?

It’s now late in the day, I’m running out of steam, and I don’t see any flashes of insight looming on the horizon. Back when I was building sets for the theater, we would sometimes encourage one another to “nail it before it rots.” Time to set the hammer down.

My wife and I spent fifteen months living in Nazaré, Portugal. We sold our house, sold our car, gave away our furniture, handed off our dog to our younger son, and embarked on what we are now describing as our “senior year abroad.” It was indeed an excellent adventure.

One of the principal reasons it became an adventure rather than a permanent relocation was my inability to acquire any meaningful facility with the Portuguese language nor demonstrate any likelihood of ever doing so.

I did study French in high school and, for a short while, in college. I never developed any real conversational facility there either. I thought I understood why that hadn’t worked well and I thought I was ready to do the necessary work to make a better run at Portuguese.

What I got instead was yet one more lesson that motivation is not the only relevant component in learning. For one, I don’t have a particularly good ear for language. I struggled to hear the distinctions my teachers and tutors were pointing out. I struggled even more to reproduce them. For another, my environment didn’t provide suitable forcing functions to block falling back on my English.

What I wished were true wasn’t enough. An essential reminder as I contemplate ways to improve my writing practice. I won’t solve the problem of better rhythm and cadence in my practice simply by wishing it so.

I need to design solutions that call for the least effort and least motivation possible. I need to be thinking in terms of designing paths of least resistance.

If you’re foolish enough to pursue a doctorate, expect to spend a substantial portion of your time reading. I can’t recall any reading list from my course work that wasn’t multiple pages worth of classic books and journal articles.

One of our core courses was labeled simply as “Doctoral Reading Seminar”. Each week a half dozen of us would meet with Professor McKenney who oversaw our program. One week one of us was whining about the workload (it’s possible I might have been the one whining). McKenney’s observation was that this time was a luxury we might want to contemplate appreciating rather than dreading. It was the last time for a long time when our only goal was to invest in building our base of intellectual capital. Eventually I learned that it was more fruitful to work out why McKenney was right rather than whether he was.

This all took place nearly forty years ago. The technological infrastructure of 1986 bore little resemblance to what we take for granted today. I offer that as a weak excuse for my failure to fully think through what McKenney was trying to knock into our heads.

The persistent mistake I made then and continue to wrestle with is to think that this base of intellectual capital is something that exists solely inside your head. What I observed was more experienced players (professors, students ahead of us in the program, my cohort of doctoral candidates) rattling off references and supporting arguments off the top of their heads. If there were tricks of the trade, they weren’t evident to me.

I still have most of my notes from those days. I even built a small system to help me track the bibliographic information about my reading (I couldn’t afford any of the handful of programs then available). But all my notes were handwritten. That was sufficient to what I understood the task to be. To get the knowledge into my head and to be ready to hand as I developed the deliverables I was expected to turn out (and turn in).

Life took me back into a consulting career after I finished by doctorate. I went back to a world of clients and deliverables. Ironically, I ended up responsible for knowledge management in my organization. But deliverables remained the driving construct in my thinking. While I’ve tried to argue for the importance of a certain degree of laziness in knowledge work, the reality is that when client deadlines loom I am more likely to “power through” than to worry about being clever or thinking about the long run.

But a collection of on time and on budget deliverables doesn’t add up to a body of work. Nor does a body of work equal an intellectual capital base. They are related but conceptually distinct. This is an aspect of the hype around notes and note-making I am only now beginning to grasp.

I know how to work backwards from an understanding of the end result. Understand the deliverable and you can lay out the path to travel to get there. Once you have a path, you can identify intermediate waystations.

Learning to walk the path as you create it is a different skill. One that it turns out I am still learning.

I’m continuing to examine how I write as a path to getting better at it. Today, I’m looking at my focus on deliverables as a driving force.

Producing deliverables is what I know (How better thinking about deliverables leads to better knowledge work results). I’m now wondering about the limitations of that bias. While working backwards is a fine strategy it can get in the way of smarter ways of working.

One way that I get blog posts finished is simply to decide that it’s past time to write one. At that point, more often than not, I will start a new bullet point in my daily note, note the time, and start freewriting about what’s on my mind that might be transformed into a blog post. This post started with asking myself whether I might try “some continuation of reverse engineering my writing process”. After two hundred words or so, I came up with the first version of the sentence that opened this paragraph.

At some point, if things are moving along, I will carve out my notes from my daily note and transfer them to a new individual note (a simple task courtesy of a plugin in Obsidian, my current writing environment of choice). I’ll continue to freewrite there. If I’m lucky or if things are flowing well, I’ll find myself to a lede and the beginnings of an overall flow. If not, I will set things aside and do something else for a while.

I’m trying to capture the essential messiness of this practice. That’s mostly for my own benefit as I hope to gradually build a better one, It’s also to acknowledge the realities of creative work. I feel that too many of the accounts I’ve seen over the years mask this messiness to everyone’s detriment. There are the occasional comic moments of crumpled sheets of paper tossed into or near wastebaskets, but they conceal as much as they reveal. Bless Anne Lamott for encouraging “shitty first drafts”. But she’s less forthcoming about how many drafts might follow..

I should note that my thinking here is about how I generate a deliverable more from a desire to get something done and less from having a particular thing to say. I essentially create an assignment for myself and work to finish the assignment. I work through the process until I find my way to a point. Sometimes that happens quickly and smoothly. Other times, things might need to cook for a while.

At some point, a draft will cross the threshold of “good enough”. Along the way, I will tweak things from elements of wording and phrasing to overall flow. I’m long past seeking perfection. I don’t know that I ever fell prey to that temptation. That’s the upside of thinking in terms of deliverables. The goal is “done.”

The downside is that I haven’t given enough attention to the potential benefits of system and process. I’ve been successful enough with my hacking approach that it’s taken a long time to turn my attention to the opportunities in more discipline.

I’ve hinted that I find my writing process less than transparent. I’ve demonstrated that I can get from idea to finished product time after time. That doesn’t mean that I have a clear understanding of how I do so.

Being unhappy with that lack of understanding isn’t a sufficient basis to start laying down a new and improved practice. How would I judge whether an idea was either new or improved?

So, I need to invest some thought into understanding how I get to a product that I am comfortable declaring done and worthy of sharing. I need to reverse engineer a process out of whatever clues I can dig out from the artifacts that I can find.

My inclination is to beat myself up because I know how thin and inscrutable these artifacts and clues are likely to be. I know that I am a sprinter at heart. “Powering through” is as central to my writing practice as it was to my race strategy.

Let’s see what we can discern by some powering through on this individual piece. At this point it is about 190 words sitting at the tail end of over 3,000 words of a draft note that I’ve been tinkering with for the last three weeks. That long note has already spawned two previous blog posts (one of 405 words (Claiming identity as a writer), the other 487 (Beginning to think about my writing practice systemically). This will be the third blog post spawned.

Today’s gurus of note-making would chastise me for not already carving that large note into suitably crafted “atomic” or “evergreen” notes. They’ve got a point and I’ve been working on that problem since I first encountered Sonke Ahrens’ How to Take Smart Notes in 2019. But the battle between old habits and new ideas remains secondary to getting to the next finish line. I continue to prioritize the deliverable over the process.

What I am usually looking for in an individual blog post is a lede or a working title. If I can identify that and rough out some bullet points for where I think I want to go from that start, I will usually find a way to cross the finish line. More often than not, I won’t know where I am going to end up until I get there. I’m very much in the “I don’t know what I think until I see what I say” camp. That path to a finish may include a temporary diversion through a handful of additional bullet points to see if I can reach a satisfactory end. Other pieces reveal themselves as temporary waystations on the way to a more distant destination. This piece appears to be a waystation. What remains less clear is what the next stop on the path might be. I’ll declare victory here and we’ll see what comes next another day.

In my previous post I noted

What and how I wrote once flowed from the work. The structure of the work and roles drove the writing. My writing practices grew organically from that over the years. That’s a consulting term of art for “it’s a disorganized mess of spaghetti.”

Claiming identity as a writer

In all those settings the writing was driven by deadlines and deliverables. Set those two and everything else pretty much falls into place. The responsibility for setting those constraints fell to someone else; a boss, an editor, a client.

That responsibility now falls to me. Which ought to feel like a liberating moment.

I’m reminded of a story from earlier in my career. I had been recruited to a startup to set up the IT function. Our CEO had come out of IBM where he had been a product manager and was ruminating on the gulf between operating with IBM’s resources and the realities of a start up. At IBM, whenever he identified a task to be addressed he could turn around and hand the task off to someone waiting to pick up the load. In our start up environment, there was never anyone to turn things over to. Even if you hired someone to hand a task off to, you then had the task of working out what needed to be done now.

I’m feeling less liberated than on the edge of overwhelmed.

The thing about deadlines and deliverables is that they make sense in the context of a larger process. That feeling of being on the edge is a tell that I need to shift focus to that larger context.

It’s a context that I now need to design for myself rather than conforming to some external process of someone else’s design. Complaining about the rhythm and pace of my writing outputs is a rearguard attempt to make that someone else’s problem instead of taking ownership.

When I was teaching various aspects of systems design, a consistent mistake my students made was to start proposing solutions before they had invested enough time to understand the problem at hand. They would find it amusing to watch me falling into the same error.

Like many design problems, I am not starting from a clean sheet of paper. I have multiple intuitions about things I would like to fix or improve. Like any client, I’m impatient to get on with implementing answers before I’ve got a solid handle on the questions.

This is going to take longer than I’d like.