A Thought Exercise, Part V – The Progressive CIO

🎹 Music for this post: https://www.youtube.com/watch?v=a01QQZyl-_I.

Preface

This is the fifth and final part of a thought exercise that leads to the introduction of The Progressive CIO’s tenth foundational value, whose formal introduction will occur in my next post. Little did I know what a tease this all would be when I promised to unveil value number ten back in December of 2024. What follows was incredibly difficult to write; I’ve been working on it for a year. The 8-bit computing detour I recently took, thanks to John Gruber (1, 2, 3), provided precisely the distraction I needed to get the rest of it all to snap into place.

This fifth part happens to stand on its own, but I suspect you will enjoy it even more if you read it in the context of its predecessors, starting with Part I.

A hearty thank-you to Charles for his constant support and always-inspiring insights, to Karl for his contributions to this piece’s final refinement, and to both of them for confirming that what was once only in my head actually makes sense in this form.

Let’s explore the notion that the bulk of what we call “work” today — the work that involves the formality of commerce, companies, positions, titles, interviews — is artificial. That is, it’s not part of the natural order of things; it’s an artifice, something made by humanity itself, an artifact of human development.

Other animals work, but how is their work different from ours? Through our limited vision, the work that non-human animals do distills down to finding and retrieving sustenance, avoiding harm, and reproducing. Let’s look at the daily work of a deer:

Early morning:

Grazes on grass, leaves, or shrubs
Senses for danger while chewing thoughtfully

Mid-morning:

Wanders to a shadier spot
Stares into the distance, wondering things unknown to us

Afternoon:

Lies down in tall grass, digesting food
Occasionally flicks an ear at a fly

Evening:

Grazes some more
Cautiously visits a water source

Night:

Sleeps lightly, ears twitching at most every sound, moving around now and then to feed in the safety of the dark

The life of a deer — and many other animals we can think of — resembles the life of a retiree more than the life of a worker.

There are other creatures — many species of ants and bees come to mind — who, by all appearances, have a distinct and full-time work culture that does not at all resemble a retiree’s life. It’s curious that human work life more or less mimics the work life of creatures we often consider lower forms of life.

Is the life of a worker a requirement of the human condition? There are human societies whose lives more closely resemble those of deer, so the answer cannot be a simple “yes.” Many major religions, however, believe that work is an essential duty of the human experience (e.g., the Calvinist work ethic, or Laborem Exercens in the Roman Catholic church). With a great deal of work philosophy rooted in religion, this is no simple issue. There have been many others who have offered counterpoint to that notion; here are a few good starting points if you are interested:

Henry David Thoreau, “Life Without Principle”
Bertrand Russell, “In Praise of Idleness and Other Essays”
Bob Black, “The Abolition of Work and Other Essays” (There’s also a thought-provoking video where he shares his perspective.)
David Graeber, “Bullshit Jobs: A Theory”

I happen to enjoy thinking like this very much, but I am not here to try to convince you to drink from this cup. What I think is more reasonable is to acknowledge that many of us have decided to work — or feel we must work — and it’s helpful to identify what’s important and not-so-important about that work. Through work-as-we-know it, we sacrifice certain aspects of life to gain something in return. If I could distill what we think we have obtained through this sacrifice, it might be:

A feeling of stability or predictability
A feeling of progress in our control over nature, increasing our comfort and safety
Status

Yet:

As for stability and predictability: when we compare ourselves to deer, how do we appear to be doing?
As for our control over nature and our comfort and safety: aren’t we still subject to nature and disease, as well as the dangers of violence, automobile accidents, and many other similar things?
As for status: arguably all other animals have status hierarchies — are ours all that different, or are their particulars just more familiar to us through experience, exposure, and habit?

If you could be born as anything other than a human, you would not have commerce, or job interviews, or currency systems, or all the trappings of the work world as we know it today. You would simply live, as simply as one could. Your life would be quite a bit like the life of a retiree, for your whole life. Of course, you would have no medicine, no television, or many other things. You would eat simple things, shelter yourself, and largely live — until you don’t. I’d wager that many people would say this sounds unproductive, and that might fall at odds with those for whom work is a key part of their belief system, religious or otherwise.

But is that truly unproductive? If I were to propose that “productive” means something resulting from our actions that can be used to bring benefits to ourselves or others, deer are productive, aren’t they? Would it be terrible if our productivity were limited to benefiting ourselves and our families and nearest neighbors? Things were certainly more like this in the pre-industrial era. Ponder pre-industrial farming: we tend to think of working from home as a new concept, but working from an office is a far newer concept. In other words, somewhere between the pre-industrial era and today, there was a significant change in our human notion of productivity. That should help us see that what we have today is a result and not a requirement. This is why I think it’s helpful for us to consider our work — as we know it today — as something artificial.

Let’s take a further look at how silly all this begins to look when we take a deeper look at today’s workplace:

All who work share one experience: a divide between what is considered work, and what is not. We are programmed to believe that the height of work — productive work — is time spent working directly with some artifacts, developing solutions to problems.

For a moment, I’d like you to create two lists: one that contains examples of things you do or encounter at work that you consider productive, and another that contains examples of things you do or encounter at work that you consider unproductive.

I thought it might make sense to ask this question to ChatGPT, which is at its best when summarizing things that are statistically ordinary. Here’s the response I got:

Sure! Stepping into the shoes of an average office worker—let’s say someone in a mid-level role at a typical company—here’s how I might think about productivity on a daily basis:

Productive things I do or encounter at work:

Knocking out a clear to-do list

Finishing a presentation ahead of a deadline

Solving a problem for a client or teammate

Having a focused, decision-making meeting

Getting uninterrupted time to work on a project

Learning a new skill that helps me work faster or better

Collaborating with someone and making real progress

Automating a repetitive task that used to eat up time

Unproductive things I do or encounter at work:

Sitting through meetings that don’t lead to action

Answering endless reply-all email chains

Re-explaining the same process over and over

Waiting on approvals that stall my progress

Searching for information in a cluttered system

Fixing someone else’s sloppy or rushed work

Responding to Slack messages that derail my focus every 5 minutes

Doing work that gets scrapped or ignored

Let’s take a look at a few curious statements I’ve heard many times throughout my life, as I am sure you have as well:

“I was busy with my work, but then she came in to ask me a question.”

Why is it that people distinguish their inward work from the notion of being interrupted by others? Isn’t that just as much work as anything else we do? Is this supposed to mean that answering questions isn’t part of our work?

“I had to stop my work so that I could attend a meeting.”

Why is it that meetings are set apart from inward work as if one is inherently more important than the other? People hate meetings that are “unfocused.” But the work we do at our desks can be just as unfocused. Is our hatred for meetings really just a hatred of accommodating others’ present needs that are different than our own?

‌“Let’s stop talking, and get to work.”

Why is it that hallway and “water cooler” conversations are considered a waste of time? Is connecting with humans on a human level truly a waste of time?

Now, let’s look at our assumptions from a different viewpoint:

Has every great thing you’ve ever done started life on a to-do list?
Have all the best moments of your presentations been planned in advance?
Have you ever found value in a meeting that didn’t have a plan or agenda?
Would you say that interruptions are universally bad? What value do they bring for the interruptor?
Have you found that fast work is generally better work?
Have you ever learned anything from repeating a task multiple times?
Have you ever seen a benefit come from re-explaining — or even re-asking — things?
Have you ever found value in the fact that you’ve had to wait for an approval on something?
Have you ever found unexpected benefits from going down ratholes when doing research?
Have you ever learned anything valuable when you’ve had to fix the work of others? Has the other person found value from it?
Have you ever found value from producing work that you’ve had to scrap?

If your answers to any — or like me, all — of these questions fall at odds with prescriptive productivity, then what on earth drives us so hard to avoid and even actively resist these things? I think the answer is: expectations (meaning: premeditated resentments, a.k.a. “goals” or “deadlines”) your employer — and its customers — have that make it feel like a luxury to look at the world in such an inverted way. But if this inverted world helps us produce something better for those customers, then what’s wrong with that?

If your answer is, “My bosses don’t view it this way,” then you’ve just identified the root cause. Good bosses understand that people are more important than mere work. If productivity means something resulting from our actions that can be used to bring benefits to ourselves or others, then how can it be any other way?

Because there aren’t as many good bosses as we all need.

Is that natural? Well, it’s certainly real.

Given the state of things – that work-as-many-of-us-experience-it is FUBAR…er…artificial…a useful approach is to think if it a little more like a board game: less seriously.

If you compare work to a board game, you might find many similarities: each has a set of rules (that I suggest are identically artificial) and players (who I suggest are identically natural) and stated goals. The only difference — unless you are a professional board game player — is in financial compensation. But why do we make money on one and not the other? Because the one that makes money is the one that isn’t merely “fun” or “easy.” If it were those things, we wouldn’t get paid. Work is very much like a game that happens to be hard enough to make people pay us to play it. What makes it hard is that some aspect of it has to have enough value so that customers pay for it.

Other than that, there is no difference between work and a board game.

None.

You may think I am making light of the most serious occupations, such as surgery. Surgery is a wonderful achievement. Despite its status as something valuable and profound, though, it cannot be considered a peer necessity of things like food and respiration. Surgery is an artificial luxury, a privilege to receive, and certainly not natural. It did not even exist as a successful practice for humans until fairly recently, and it’s not something other animals provide for themselves at all. But it is not the vocation that I am suggesting might do well to be taken less seriously. It is the workplace scaffolding around the vocation: the titles, the politics, the lawsuits, the insurance and all the tortured levels of commerce that contributes to the occupation’s status as something more of a game than the elegant dignity of the vocation itself.

Perhaps right now you are beginning to see why I think work as we know it is artificial.

Why does this matter?

When we can absorb the fact that work-as-we-know it does not, by any laws of nature, have to look like it does today, we stand to gain perspective on how and when we allocate our energies to it.

If we live like earlier versions of ourselves, we lose advancement and privilege, but we gain simplicity and time to behold the world around and within us that is natural.

The notion of work-as-we-know it is a choice made by human beings in the distant past. It might appear that we have only two personal approaches to that choice:

Hop on for the ride and live like those around you, doing exactly what they do, lemming-like.
Run screaming from the work world and try to live more like a wild animal, “off the grid.”

But there is at least one — interesting — third choice:

Hop on for the ride, with an ability to laugh about the silliness that exists within.

We take things that do not have to exist as rote, and we spend a lot — of time, effort, and resources — on those things. We take our work selves too seriously — our person selves, not seriously enough.

I have an antidote for that.