Habitual Struggles

One of my bad habits is obsessing about my deficiency of good habits. I know that good habits are important because the nuns and monks were relentless in telling me so; decades later their ambivalence about my academic success without suitable discipline still lingers.

I’m not devoid of good habits. Lately, I’ve had some success with Jerry Seinfeld’s keep the streak going/don’t break the chain trick (Jerry Seinfeld’s Productivity Secret), although Friday’s NY Times Crossword stumped me, breaking a 355-day streak. Two and a quarter years ago, I managed to reboot a journaling habit by starting a Morning Pages effort. 

Habits are on my mind lately for several reasons. Back in March, I finished Wendy Wood‘s Good Habits, Bad Habits: The Science of Making Positive Changes That Stick and thought it worth processing my thoughts into a post here. A bit slower than I would like, but not unusually so. 

More recently, I came across an interesting blog post from Eleanor Konik, The Difficulties of Teaching Notetaking » Eleanor Konik. I’ve been chipping away at improving my own note-taking practices and was toying with how and whether to incorporate any of that into my teaching. Konik’s argument is that no one implements good techniques simply because they’re good techniques. We’re all adept at cost/benefit calculations and the payoff structures for most “good” habits are hugely dependent on how heavily you weight the suasion of authority figures. For most of us, most of the time, the payoff for following objectively good practices doesn’t rise to the effort. 

This is where the accumulating research on habit formation comes in. Converting an activity from an invocation of willpower to automatic pilot effectively eliminates the effort and energy part of the equation. This is why Alfred North Whitehead’s observation continues to show up in discussions of habit:

 Civilization advances by extending the number of important operations which we can perform without thinking about them. Operations of thought are like cavalry charges in a battle- they are strictly limited in number, they require fresh horses, and must only be made at decisive moments. 

We know that thinking is expensive. As knowledge workers, thinking is a definitional component of your work. One of the highest returns on IQ points is reducing the demand for IQ points wherever possible. 

Woods offers an observation that I’ll close with; 

we repeatedly do the things we love doing. But we also grow to love the things that we repeatedly do.

The task then is to be more intentional about the practices whose repetition will lay down the habits that will free up the capacity for better “operations of thought” when those decisive moments arrive.

Don’t ask what is best

Dad was an engineer by training and temperament. His handwriting was as neat and precise as mine is not. He worked hard to express his thoughts clearly. 

My processes look and are much messier than his ever were. One trait I did inherit, however, was to worry about using language precisely. And, I was fortunate to have mentors who cared equally about precision. It isn’t something that seems a high priority in many current settings. 

There’s a question form guaranteed to set me off; “what is the best way to…?” I’ll grant that such questions are generally well-intentioned but are weighted down with so many unidentified and unarticulated assumptions as to be devoid of meaning. 

While such questions come from a good place, pushing back on their fuzziness won’t win you many friends. I’ve learned to be very cautious and selective about raising them in public. What I have tried to do is become more aware of when I am asking those forms of questions for myself. With that comes more effort to be more precise about the question I am trying to answer and to search for those assumptions. 

This is the underlying driver for my skepticism about exploring productivity in the context of knowledge work. Productivity is anchored in comparisons of “better” and “best” and I’m not sure those terms carry as much meaning as we might think. Instead, I’ve been working to shift my thinking toward the notion of “effectiveness.” It’s still too slippery a term but it does encourage me to widen my perspective to find those assumptions, understand the context, and be more precise about what I am hoping to accomplish. 

PKM Isn’t About Apps

I characterized my most recent post (Putting Personal Knowledge Management in Context) as potentially a grumpy old man rant. The triggering event was a side-by-side software review, Obsidian vs. Roam: Which PKM App is Right For You? – The Sweet Setup. My instant reaction was “PKM isn’t about apps” and thinking that it was will get you in trouble. I thought it might be helpful to explore that reaction and see where it might lead.

The review itself is a very well done comparison between the two apps in question. But it is based on an implicit assumption that is also flawed. Because the assumption is implicit, people aren’t likely to catch it and wonder later why they become dissatisfied with whatever choice they make. There is a clue lurking in one of the opening paragraphs:

It’s impossible to say “just use this one” when it comes to picking the right connected note-taking app for you. On the surface they may seem similar, but there are several important differences that stem from fundamentally different approaches to how your notes are stored and managed.

The author is acknowledging that they cannot, in fact, answer the question they have set before us. They then proceed to explore the question anyway because it’s an easy question to ask and answer and because we are accustomed to expecting questions to have neat answers. Worse, we only ask questions that we expect have answers. 

I expect this bothers me, in part, because the underlying topic is knowledge management. The underlying motivation for knowledge management, whether in organizations or for individuals, is dealing with questions that don’t have obvious answers. Or questions that provoke deeper questions. 

Asking questions has always been a high-risk behavior. Where will we end up if we continue to explore the PKM space as a practice for asking questions that don’t yet have answers?

Putting Personal Knowledge Management in Context

The notion of Personal Knowledge Management (PKM) is experiencing something of a renaissance. This rebirth is being driven by a combination of new apps, new ideas, and new thinkers promoting their wares. The apps, ideas, and thinkers are all worth paying attention to. At the same time. the brightness of shiny new things is obscuring important history and context.

At the risk of sounding like a grumpy old man yelling at people to get off of his lawn, I thought it would be helpful to look at some of that context in the hopes that it might make it less likely that we would repeat old mistakes. We should at least strive to make interesting new mistakes. 

If you set aside the notion that knowledge management could arguably be considered a synonym for library science, what we label knowledge management in organizations today was born in the late 1980s/early 1990s in the efforts of a number of knowledge intensive organizations (HP, IBM, Accenture, McKinsey, Toyota, etc.) to systematically leverage the things inside their workers’ heads. Chief Knowledge Officers were appointed (a hat I once wore), taxonomies were defined, religious debates were held over the relative merits of Lotus Notes and Microsoft Sharepoint. Today, knowledge management is a reasonably well-defined function within most large organizations. 

Enterprise knowledge management was built on the premise that the number of knowledge workers whose knowledge mattered enough to manage was a small and easily identified subset of the workforce as a whole. Knowledge management was a hedge against having the knowledge in those smart heads walk out the door. 

The knowledge management problem changes when the proportion of the workforce classified as knowledge workers represents a significant fraction of the workforce. When everyone is a knowledge worker, knowledge management becomes personal not organizational.

A classic enterprise knowledge management problem is that of persuading the knowledgeable to share their knowledge with the rest of the enterprise. The naive hypothesis was that knowledge workers hoarded knowledge to preserve and protect their organizational status and position. A slightly less cynical take was that knowledge workers needed help to unpack and externalize their expertise so that it could be shared. 

My take is that the average knowledge worker has no clue about what it would mean to manage their knowledge and no useful models to emulate. You see individual executives and knowledge workers using email as their primary knowledge storage structure. You see arguments that enterprise search engines will bring Google inside the organization and prove sufficient to find and reuse knowledge assets when the time comes. You see elaborate folder and directory structures trying to impose order on proliferating documents and deliverables. 

The rise of personal computing and the web encouraged some knowledge workers to experiment with better ideas. Wikis, blogs, and bookmark managers were pressed into service. Ideas that were ahead of the technology curve (Memex, Augmentation, Dynabook, Mundaneum, and, recently, Zettelkasten) have been dusted off and revisited. 

The latest round of innovation and experimentation holds great promise. As an individual knowledge worker, you have several choices. One is to do nothing and wait for the dust to settle. A second is to place your bet on one of the current players and hope your support contributes to that player becoming the winner. 

A third strategy—and the one I am pursuing—is to recall an observation Peter Drucker once made about the productivity gains made during the early years of the 20th Century;

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.

Peter Drucker

Those extraordinary gains flowed from examining tools and task and rethinking the combination in parallel. Changing tools without changing the task is a recipe for speeding up the mess. Changing tasks without rethinking tools will make the current mess a morass.

Personal knowledge management has to be one component of a personal quest to become a more effective knowledge worker.

Rebalancing Planning and Doing: Seeking Knowledge Work Effectiveness

When I was first learning to be a project manager one of the mantras drummed into me was “plan the work, work the plan.” Hidden in this advice was a distinction between planning and doing. Today, we are immersed in doing; managing has been pushed to the margins. “Plan the work, work the plan” has shrunk to “work, work.”

Cal Newport, in his most recent book A World Without Email: Reimagining Work in an Age of Communication Overload, argues the case that email is the culprit. More specifically, the work style promoted and encouraged by email and other forms of instant communications. He labels this the Hyperactive Hive Mind, 

A workflow centered around ongoing conversation fueled by unstructured and unscheduled messages delivered through digital communication tools like email and instant messenger services.

Tom Davenport has often quipped that the default management strategy for knowledge workers is to “hire smart people and leave them alone.” This strategy can work if most knowledge work is independent; if your model of knowledge work is the individual data scientist, college professor, or computer programmer. 

Organizations, however, don’t exist to tackle problems that individuals can handle. They exist for problems whose scale and complexity exceed the capacity of any individual. We understand that for problems like churning out automobiles, breakfast cereals, or insurance policies. For those problems, organizations have learned to spend time to design processes that work at scale, spend time to deploy those processes, and then run those processes at scale. Running those processes at scale requires designing in the instrumentation and measurement to monitor and maintain compliance with the process. There is planning followed by doing.

Newport’s thesis is that email (and other channels of instant communication) disrupts this balance of planning and doing. The immediacy of message and response rewards one set of behaviors while concealing important costs.

This is where Newport’s and Davenport’s perspectives intersect. While we were deploying email and its cousins throughout the organization, we were also leaving all those smart people alone to figure things out on their own. We amped up the doing and left each knowledge worker to their own devices to do whatever planning seemed appropriate. 

While Newport is an academic computer scientist, he does manage to find his way to Peter Drucker’s work. Newport, Davenport, Drucker, and pretty much anyone else who’s thought about it, identify knowledge worker productivity as the problem to solve for modern organizations. Newport, however, does miss this observation from Drucker;

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

Email may not be thousands of years old, but it is the wrong tool for many tasks. At least in the way it is typically used in most organizations. 

The second half of Newport’s book works through several good approaches for attacking the problems he lays out so well. While some of his strategies can be applied unilaterally, most are premised on no longer leaving smart people alone. 

To achieve better overall outcomes, organizations need to rebalance planning and doing with respect to knowledge work. This is no longer a task that can be left to the individual knowledge worker. That leaves us trapped in a world of productivity hacks and the search for the magic shiny tool. We’ve all seen that that doesn’t work. Newport adds stronger evidence for why that approach can’t work and pointers on where to go next. The first step is to elevate the conversation to the organizational level; to put the topic on the agenda of those with the power to drive change. 

Planning to be Creative

When I was a very junior consultant, we were coached that there was one client question you were neither expected or allowed to answer, “how much is this going to cost?” A few years later, in the midst of getting my MBA, the one question you were trained to ask and answer was “how much is this going to cost?” Lately, I’ve been thinking about how much of my career has been spent caught between these two pieces of conflicting advice.

Nailing down answers to that question is a matter of nailing down assumptions. What materials from what suppliers? How many customers in each market? What’s the going rate for good sales reps? All reasonable questions; they all depend on knowing what you are doing. 

They are also generally impossible to answer when you don’t. Pretending to more knowledge or foresight than you have isn’t a recommended approach. As an individual manager, what do you do when faced with this dilemma? You’re being asked for answers to questions you are still trying to formulate. How do you work at articulating outcomes to drive planning when your fuzzy view of outcomes is what you are trying to address?

Too often, the default answer is to accept the brashest claim to knowledge in the meeting. “I have the answer” wins out over “let’s explore and see what we can learn.” We need to replace that default with approaches more likely to surface answers that we couldn’t know beforehand but outstrip the obvious, safe, and, ultimately, disappointing answers limited by what we already know.

You still have a project management task; organizations do not have unlimited resources even when the questions are open-ended. You are not simply executing, you’re also doing field research. The project management task is to thread a needle between systematically managing effort, tasks, and resources and what the phenomena in the field are revealing about how to adjust and redirect those resources and tasks. 

This marriage of exploration and execution is what agile methods are seeking in the realm of systems development. But the strategy extends to any setting where the destination has to be discovered or invented. With apologies to Gene Kranz, failure is always an option. It just shouldn’t be the only one.

The Promise of the Middle: Improving Knowledge Work Practices

Two years ago, I stumbled across Sonke Ahrens’ slim volume, How to Take Smart Notes: One Simple Technique to Boost Writing, Learning and Thinking – for Students, Academics and Nonfiction Book Writers. As a matter of practice, I am always on the lookout for potentially useful new ideas. The price of a book is a trivial cost and I only invest my time for as long as I’m learning something useful. I posted my review in March of 2019 [Unexpected Aha Moments \- Review \- How to Take Smart Notes \- McGee’s Musings). This is a bit of an interim progress report, although it feels more like a lament on just how hard change continues to be. Andy Matuschak’s recent observation that Note\-writing practices are generally ineffective hits way too close to home. 

Carving out an approach

Advice is always forward looking. The pretense is that you are starting from scratch. The reality for most of us is that we start somewhere in the middle. The problems of dealing with your existing bad habits and your existing body of work are left as an exercise for the reader.

One option is to pretend that you are starting from scratch. Ignore whatever artifacts and work in progress you’ve created to this point as well as whatever practices you’ve adopted. Start fresh with whatever your next project happens to be. Follow the proffered advice, practice new techniques, create new work products.

A second option—one that turns out to be a trap—is to believe that you need to fix or repair your history before you can move forward. It’s a trap I’ve fallen into. 

A middle approach that has evolved over time is to think of a knowledge work environment as a property that needs regular maintenance and remodeling plus occasional renovation. You do prefer to work with the materials already at hand, introducing new materials as needed. It’s also an environment that must support routine work; historic preservation is not the goal. 

Artifacts and Activities

My training and experience push me in the direction of organizing around projects and deliverables. I’ve begun reconsidering that (e.g., Deliverables and the downside of working backwards \- McGee’s Musings) and working toward a more nuanced view of knowledge work products.

There are some additional degrees of freedom to be found by shifting to more neutral terminology. I’ve started to think about what might be gained, besides alliteration,  if I start thinking in terms of “artifacts” and “activities.” 

Artifact encompasses deliverables but also extends to intermediate working papers. Anything that gets thinking outside of your head and into a representation that you can inspect and manipulate is worth considering. 

Some sequences of activity may be worth treating as discrete projects. But other sequences and patterns of activity may be worth incorporating into your repertoire and pairing with appropriate artifacts. 

Artifacts plus Activities Become Practices

The notion of “practice” has been floating around in my head for some time now. It isn’t something so structured as a process. Nor does it rise to the level of a project to be managed. But it does seem worthwhile to stay alert for stable patterns of artifacts and activities that yield insight. 

One implication here is that you should be attuned to two levels of thought. There is the ongoing work itself. And, there is a parallel level of the work of managing the work.In routine work environments, work and management are typically carried out by different players. In knowledge work, work and the management of work falls to the knowledge worker. I find it helpful to try to keep the two levels separate in my thinking. 

You never start from a blank sheet of paper

This train of thought appropriately brings me back to a piece I wrote some six months ago—Embrace the mess if you want to do better knowledge work. The trope about writing and writer’s block is the threat of the empty page or the empty screen. Unless you are at the absolute beginning of the path, this is an illusion. None of our work begins in the void; we’re always in the middle of one journey or another. Take advantage of wherever you are and start there.

Aspiring to Knowledge Work Professionalism

WorkstationIn April, 2003, the late Doug Engelbart gave the Keynote Address at the World Library Summit in Singapore; “Improving Our Ability to Improve.” The talk is an excellent entry point to one of his most powerful ideas. He also raises a specific question that I suspect wormed its way into my thinking back when I first encountered it. 

As an aside, I wish I could reconstruct the concatenation of events that led me to revisit the talk yesterday. I’m confident it was a revisit because I’ve been following Engelbart’s work for a long time and this piece was already in my systems. My note-taking and reading management systems are not so well-constructed, however, that I could do more than recall the essence of the piece. On the other hand, returning to old source materials can  pay dividends. The source may not change but my perspectives evolve.

Engelbart’s career was dedicated to exploring how information technology could augment human intelligence rather than displace it. He was especially interested in how that partnership could attack big, complex, problems. 

Shovels and bulldozers, to borrow and extend Engelbart’s analogy, both move dirt. If you have a lot of dirt to  move, a single shovel isn’t your best choice. If no one has managed to invent a bulldozer yet, you might be limited to shovels but you aren’t limited to a single shovel. 

Given a collection of shovels (and shovelers), you can organize the problem of moving dirt into a process. Process is an amplifier. With a layer of process in place, you can get further amplification by looking for ways to improve the process. Engelbart identifies one additional amplifier; improving how we do improvement. Engelbart labels these three amplifiers as A-activity, B-activity, and C-activity. It’s a simple enough model, but simple models can be very powerful. 

At the base (“A-activity” in Engelbart’s terminology), you have the realm of process; the monthly billing cycle, managing trouble-tickets at the help desk, the assembly line turning out Toyotas. The economy is built on transforming ad hoc practices into standard operating procedures and repeatable processes.

Repeatable processes that produce repeatable outputs open up the possibility of systematic improvement. What changes can you make to the process while holding the outputs constant? Process improvement (the “B-activity” in Engelbart’s model) is the realm of quality management, business process re-engineering, and continuous improvement. It’s an amplifier of benefits flowing from repeatable processes.

As an organization accumulates more experience with process improvement and more opportunities for process improvement surface, there’s another level of leverage in investigating how you can get better at those improvement processes (“C-activity”).

What Engelbart is doing here is employing a classic computer science problem solving strategy; adding a new layer of indirection or abstraction. Rather than attack a problem head on, step back from the immediate features and adopt a new perspective. Engelbart explores this three-tier model in more depth in Toward High\-Performance Organizations: A Strategic Role for Groupware \- 1992 \(AUGMENT,132811,\) \- Doug Engelbart Institute.

Returning to the keynote address, Engelbart launches into a bit of a rant about “ease of use” and letting the market decide what features and functions should be available. He isn’t a fan. As I was nodding along, Engelbart posed a question that grabbed my attention; 

Doesn’t anyone ever aspire to serious amateur or pro status in knowledge work?

If your answer is yes, then you have a problem in the context of the current information technology market and the purchasing preferences of most organizations. Those forces favor tools and services targeted toward beginner and intermediate levels of expertise. Think of the standard software installed on the typical corporate workstation. What training is provided on how to take full advantage of even those tools?

Reaching expert level performance in any field doesn’t happen by accident or by the simple accumulation of experience. It requires deliberate practice and a commitment to operate across multiple levels of perspective.

Muddling through as smart strategy

There’s a certain subset of academic articles that are as, or more, famous for their titles as they are for their insights. Charles Lindblom’s “The Science of Muddling Through” has to be on that list. Lindblom’s field was public policy but his insights are more broadly applicable. 

He starts with a simple enough observation; administrators don’t behave the way that theory says they should. Textbook decision processes of carefully articulating objectives, developing options, and selecting solutions that optimally meet objectives don’t show up in the wild. Real managers “muddle through,” making incremental changes and nudging complex systems in directions they hope will prove “better.” 

Lindblom’s insightful question was to wonder whether administrators weren’t as dumb as they looked. Theorists have the luxury of pretending that history doesn’t exist; real managers always start from Ken Boulding’s observation that “things are the way they are because they got that way.” The real world always imposes real constraints. 

The simplifying assumptions that economists and model builders must use to make their work tractable can be acceptable for simple enough problems. It’s dangerous to believe that the techniques that work for suitably constrained problems scale. Problems up the ladder aren’t simply bigger, they are more complex. That complexity transforms tractable problems into wicked problems.

“Muddling through” is what actually works; the primary metric for practicing managers. 

Buying Time

Review: Time Smart: How to Reclaim Your Time and Live a Happier Life

I think my father made decent money, although I don’t have any concrete numbers. But, if you have seven children to feed, clothe, and educate stretching every dollar is sound practice. My mother did this with sometimes frightening skill. She would drive out of her way to save a few pennies per gallon on gasoline or milk, both of which we consumed in prodigious quantities. Frugal was a badge of honor. Mom lived “time is money” more than any business school professor I ever met. It was a source of friction between us from time to time.

Ashley Whillans is a Harvard Business School professor whose research makes the case that we have that mantra inverted; “money is time.” But, unlike a mathematical inversion, the direction you adopt makes a difference. Whillans research investigates the trouble we get into by accepting the conventional wisdom. That leads to solid advice on how to shift your perspective to prioritizing time over money in spite of the pressures to do the opposite. Appropriately enough, Whillans manages to compress all of the argument and advice into a compact package respectful of and worth your time.