Month: August 2025

🎹 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.

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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.

🎹 Music for this post: https://www.youtube.com/watch?v=XOnqh7LplTs.

Thanks to Charles, Karl, Daniel, Frank, Reggie and Lori for all their input on this post along its journey. Please don’t miss the five-part thought exercise that leads to this piece.

Many decades ago when I was a boy, I found myself caught in a rip current on the Atlantic shore of Fire Island, in Robert Moses National Park.

Invisible hands softly took hold of my legs and dragged my body under. I resisted with panic energy, gaining enough control to catch a breath, only to be pulled under again. I shimmied in every productive way I could to escape the grasp. Another breath, another pull on my body, each time deeper into the churning salty olive murk. After a few cycles of this terrifying experience, a lifeguard caught hold of me and swam me to shore.

This was back at a time when we didn’t call people heroes for doing their jobs. The lifeguard accompanied my frazzled frame up the sand to reunite me with my father, who had dozed, sunning himself. As he reconnected us, I am sure there was nothing much more than a “thank you” and “you’re welcome” exchanged (I vaguely remember the word “undertow” used as part of the explanation, but we know today to use the term rip current), and all three of us went on with the day.

When recollecting this event, I find myself smiling about the lack of drama and sympathy that would accompany something like this today. More critically, though, I learned sometime afterward that my instinctual response almost killed me. Those who are better-educated than I was back then know this: when encountering a rip current, if you are a skilled and strong swimmer, you can swim parallel to shore to escape it. But if you are more of a wader, like I was, a “flip, float, follow” strategy will save your life: flip on your back, float, and follow wherever the water takes you. Even though you may wind up further away for a bit, you won’t drown, and you will save your precious energy until someone with skill can rescue you.

Float.

Always remember to float rather than fight.

Things that nearly kill us have a way of shaping our most primal principles.

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As a leader, whenever I hear people use words like “concerned” or “worried” in regard to things at work, I like to pause the conversation and note: those words should be best saved for people rather than things. We should be concerned or worried if a coworker or a customer has cancer, or if their loved one is in the hospital. We should be worried when someone is summoned to the emergency room to meet a loved one who was in a car accident.

But if a report is late or a deliverable is overdue, unless someone’s life, health or livelihood is at stake, “concerned” and “worried” should not be in our vocabulary. (If only your livelihood is at stake, but your customers livelihoods are not, that may be an sign of work-as-artifice.)

Before today, there were nine foundational values of The Progressive CIO:

• Exhibit vulnerability so that others feel more comfortable exploring their fears and weaknesses with you.
• Exhibit humility to remind others that we are all small creatures in a large universe.
• Spend as much time empathizing with those you serve so you can better understand them.
• Continually refine your skills with patience; good things take time, especially when it comes to developing people.
• Show compassion by actively stepping out of your own comfort zone to help others when they are down.
• Be truly curious; ask questions about everything, with the mind of a child.
• Endeavor to make only the commitments that you can keep; then keep them.
• You will struggle often, but develop a willingness to do the things that you know you need to do, even if you are uncomfortable doing them.
• Love is the most important thing in our lives. While co-workers might not love one another, we must do our best to honor the love that each of us has, and help one another tend to that love.

We should be vigilant about taking anything negative at work so seriously that it comes at the expense of any of the above. I call this buoyancy, and it is the tenth and final value in our arsenal.

Float.

Always remember to float rather than fight.

Buoyancy at Work

Here’s one of my favorite quotes, however dated in its “maleness”:

This is a man who understood the “game” part of life.

Here’s something I’ve seen many times throughout my career: a bunch of folks on our team have been stewing on a topic, and then eventually someone comes to me to, well, share this information in the hope I will commiserate. I say something to the effect of: “Why are you making such a big deal of this? Why does it really matter? Don’t waste your energy.” Or something like that.

That might seem dismissive, as if I don’t care (I might not, but that’s not always the case). I respect everyone’s need to have their unique feelings, yet I am incredibly sensitive to energy waste. Most of the time, I find complaining indulgent. I admit that I like to do it myself from time to time; it can feel good, and sometimes it helps us work through our fears. But I have found, more often than not, that once vocalizing our complaints has finished helping us work through those fears, excess complaining doesn’t accomplish much more than catharsis. The energy we have available to us at any given moment is limited. Doesn’t it make more sense to use that energy for things that can bring about positive change?

I hope that, after traveling this far together, you and I agree that work is not the point of life. If we do, then why do we allow our emotions about work to consume so much of our energy? Work winds up being important to most of us simply because it is the means through which we fund the rest of our lives. We understandably want to be sure that something that takes us away from the rest of our lives is not a drag. Our energy is well-spent figuring out a way to make work not a drag; stewing and complaining are not pathways to that.

This is why, when we teach leadership, we talk so much about emotional intelligence. Buoyancy is, to me, the most powerful distillate of the sap of the emotional intelligence tree. It reminds us to laugh at ourselves. It reminds us that people matter more than things. It reminds us that much of work is silly artifice, created without our input or control. It reminds us to be light of heart and to remember our shared humanity. Through buoyancy, we let go, to get to what really matters.

In that sense, buoyancy plus willingness equals agility. Which is to say: agility is when we combine an ability to flow and let go with an ability to work with our fear to try something new.

Float.

Always remember to float rather than fight.

Simply Put

There is a simple elegance to buoyancy:

• Learn to let things go, lest they drag you under.
• Try to have a sense of humor, and lighten your heart. It’s not always possible or appropriate, but with practice, you will be surprised at how often this becomes possible if you remember how much of our work is artificial.
• Keep perspective. People matter more than things and work.
• Ask yourself: what other values (Vulnerability • Humility • Empathy • Love • Patience • Compassion • Curiosity • Commitment • Willingness) can rescue you from the riptide?

Yes, the nine other foundational values we discuss here are tools to employ when your buoyancy needs a boost. But you cannot access the other nine values if you’re sinking. Buoyancy comes first.

Float.

Always remember to float rather than fight.