I had nothing to do.

It was sometime in early September in 2018. I had just moved across the globe to Taipei. I was technically a self-employed freelancer but didn’t have any clients. I was single and had declared to my friends a month earlier that I was going to embrace a life path as a “cool uncle.” I had one friend in town but he had a job and other things to do so he could only be my chaperone so many hours.

A year later I would be planning a tiny wedding with my girlfriend, figuring out what to do next with the accidental business I created, realizing that writing was an important part of my life, and most of all trying to make sense of a newer, deeper appreciation for life.

Don’t worry, I’ll answer some of your questions but first I want to talk about non-doing.

Non-Doing

To not do things can be scary.

Growing up in the US, we are constantly aware of the perception of others and that if we are not doing enough, we might get called lazy.

You always want to avoid being called lazy.

I’m not here to convince you that being lazy is worthwhile but instead to argue that our fears of being perceived as lazy keep us from experiencing a much different feeling which is better explained by a term from another culture, wu-wei or 無為 in Chinese.

In Chinese this literally means inaction or non-doing but does not necessarily mean “doing nothing.” The desire to “do nothing” often shows up for people as a reaction to spending a lot of time doing things you want to escape from.

Being in a state of non-doing, you are not escaping anything. Instead you are doing things that come naturally and with a spirit of light-hearted playfulness.

Walking around in Taipei was the first time I experienced this feeling. When I was living in New York or Boston in the previous ten years I might be wandering around the city doing very little but it was always in tension with the predominant culture that I should be doing something, that I might have forgotten something, or I might not have done enough.

In Taipei, that feeling evaporated. I didn’t yet know the cultural scripts or expectations around me. I was both in a state of not-knowing and non-doing. 

And I felt okay.

Picture yourself floating in the middle of an ocean and all you can see is the horizon all around you. You have no idea where you are.

Sounds terrifying right?

Now picture you are not worried about where you are. There is no where to go and deep down you know you will be okay. This is the feeling I’m talking about.

The best description I’ve seen of this is from the Tao Te Ching, written in China in the 6th Century BC:

In pursuit of knowledge, every day something is added. In the practice of the Tao, every day something is dropped. Less and less do you need to force things, until finally you arrive at non-action. When nothing is done, nothing is left undone. True mastery can be gained by letting things go their own way. It can’t be gained by interfering

Nothing to do and nothing left undone.

Non-Doing Puts You In Tension With Modern Reality

When I first experienced this feeling in Taiwan I was not transformed. Given enough time, feelings of guilt and shame appeared. In my head were voices shouting “you lazy bastard,” “you’ll go broke,” or “you can’t just do this forever!”

Yet guiding me was a line from from a Rebecca Solnit book I had read, “that thing the nature of which is totally unknown to you is usually what you need to find, and finding it is a matter of getting lost.”

Embracing a state of non-doing felt like being lost. So I kept leaning into it.

Over time this enabled me to have a little more comfort with the underlying uncertainty of life. While we can never fully overcome this it is more clear to me now that no amount of action will ever give us the sense of control we desire over life.

The hardest thing about this is the tension it creates with others. When you shift away from moving towards things, progressing towards extrinsic goals, or doing things in exchange for something else, it can raise alarms.

“Don’t you want _____?”

“Don’t you want to grow your audience?”

“What do you mean you aren’t focused on making more money?”

“How could you not want to go? Everyone’s going.”

…and this is the rub. The degree to which you can be content depends just as much on embracing a state of non-doing as the tension and distance between you and your environment.

Legible Goals are the Least Interesting

In my writing I’ve been exploring how non-doing overlaps with our current culture of work. The short answer is that it doesn’t.

Our current work culture and our global economic systems incentivize almost everyone to orient around the idea that more and bigger is better.

This has led to the bizarre scenario where profitable businesses are sometimes called “lifestyle businesses” while “serious” businesses can be losing billions of dollars a year.

In my past work life I was a successful worker in the prestigious world of strategy consulting. To break in and to succeed in this world requires a certain level of business insight, awareness of how to make money, and an ability to decode the paths of how to get there.

With this perspective, my rational brain is tuned to identify extrinsic goals that I know I could reach with a certain amount of discipline.

While these path are not certain they are more comfortable to pursue than embracing the unknown and thus can be nearly impossible to reject Yet as I’ve found when you do say no and create a space, more interesting things emerge.

Non-Doing Is The Space Where Interesting Things Might Happen

You are probably saying, “yes Paul, this is great, but how the hell did you end up married?!”

Great question.

When I tell the story of meeting my wife I tell people that we met at a time when I was wandering around Taipei and reading books in random parks. 

What I was really doing was embracing a feeling of non-doing and seeing where it took me.

I could whip out a bunch of cliches to summarize that story but I think that would hide the deeper truth that when we create space in our lives the things that matter to us seem to show up.

By saying no to the default goals that everyone else expects and accepts I’ve also stumbled upon the fact that I love writing. When I write it feels like something that fits into the flow of life. Something that matters to me. Very much in the spirit of non-doing.

I feel similarly when I am able to get up on a random day and go explore with my wife. Over the last two years we’ve gone on more explorations together and spent more time together than many married couples might in the first five years of their relationship.

Most people see the wisdom in pursuing these things but in practice, grappling with the insecurity of non-doing typically convinces people to opt-in to sub-optimal things and to spend time trading the present for future outcomes.

I spent most of my life in this mode and while other people seem to praise the outcomes of some of my efforts, I don’t think I became much wiser.

I’m a big fan of reading books with advice of people near the end of their life or who have gone through hell and lived to tell the tale. Almost all of these books seem to have the same advice:

Don’t sweat the small stuff. Don’t get caught up in extrinsic goals. Love the people that matter. Don’t put off bold risks. Have fun.

Embracing a state of non-doing gave me the clarity to see the things that matter and belief that its worth non-doing them now rather than some day down the road.

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post The Magic of Non-Doing appeared first on Boundless by Paul Millerd.

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In that essay, he makes a powerful point about how people think about possibilities of the future that are not as dependent on the way we have worked for a long time:

The projection that we’d waste our time with idling activities like Netflix and the beach neglects that most working class humans today are overworked and barely getting by. Current notions of how we spend our ‘leisure’ time are products of, and responses to, our life conditions.

Oshan sums up his worldview as:

We’re all going to die, but in the meantime, the world is far more mysterious, wonderful, and stimulating than human consciousness plagued by economic precarity can experience.

We explore the possibilities that might emerge if we can imagine a life beyond work. This is a bold task but Oshan’s research and contemplation on this topic have inspired me to keep going and I was excited to compare notes with him on this podcast.

• Oshan’s Work: Musing Mind

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Oshan Jarow: The Reality & Possibilities For Work appeared first on Boundless by Paul Millerd.

Modern work critics blame Frederick Taylor for the hyper-optimization of the modern workplace. The accepted narrative is that Taylor kicked off a movement that looked at work as something that could be optimized and managed and that his efforts kick-started a 100+ year movement of steadily increasing optimization.

Sounds good but its not true. Today’s hyper-optimized workplace would not exist except for the emergence of a new kind of worker: the career-driven knowledge worker.

Taylor was mostly concerned with the manufacturing world and he believed that an embrace of his principles would help not only managers, but production workers:

“The principal object of management should be to secure the maximum prosperity for the employer, coupled with the maximum prosperity for each employee.

Frederick Taylor, Principles of Scientific Management, 1911

He wrote in a time in which the kind of service and knowledge work that is common today barely existed. While his techniques did gain popularity in manufacturing, it would take another 30 to 40 years for analytical and measurement techniques to gain widespread adoption.

It took the emergence of a new kind of work.

The Career Path & The Need To Perform

After world-war II as the US repurposed its military workforce there was a boom in employment in the business world and for the first time. the goal of working for a big corporation became a common goal.

William Whyte famously called them “Organization Men” and wrote more than 400 pages making sense of this new type of worker that started to identify with a company above any other affiliation in their life:

The ones I am talking about belong to it as well. They are the ones of our middle class who have left home, spiritually as well as physically, to take the vows of organization life, and it is they who are the mind and soul of our great self-perpetuating institutions.

William Whyte, The Organization Man, 1956

This was a dramatic shift from the age-old conflict between labor and the owners of capital. Once that had existed from the earliest days of capitalism.

While the manufacturing workers of Taylor’s time had a strong “class consciousness,” these “white collar” workers in the 1950s were not sure who they were:

White-collar workers rarely knew where they were, whom they should identify with. It was an enduring dilemma, rooted in what might be called a class unconsciousness, that would characterize the world of the office worker until the present day.

– Cubed, A Secret History of the Workplace

Despite attempts throughout the 20th century for labor movements to include these workers, knowledge workers distanced themselves from organized blue-collar workers.  Instead of labor unions, they formed “associations” and increasingly saw themselves as aspiring business people who might one day become business owners.

Taylor wanted to close the divide between labor and capital. These workers had no interest in seeing that divide in the first place.

The knowledge worker was focused on managing a career, developing skills and acquiring achievements or as Merriam-Webster now defines it, “pursuit of consecutive progressive achievement.”

People saw themselves not as a part of an organization but as someone with a first-person account of achievements and contributions and over time, that narrative was something that could be (and eventually, needed to be) carried from employer to employer. 

And as the job morphed into a career, the worker shifted from someone merely doing their job to someone that needed to perform. 

Continuous Improvement & The “Theatre Of Work”

Before the 1960’s the idea of a “career path” was not a thing. Workers hoped to merely keep their jobs. Early uses of the term seem to have been aimed at two audiences: men joining the military and women joining the workforce.

Over time, the idea of a promising career path was connected to the end of a college education and over the 2nd half of the 20th century, it would become common knowledge that the whole point of going to college was to land a good job.

Whyte, writing in The Organization Man writes, “The union between the world of organization and the college has been so cemented that today’s seniors can see a continuity between the college and the life thereafter that we never did”

The idea that a young person was to orient around a good career became increasingly popular. It was not until the 1980s, however, that the analytical tools became central to such a career. This is when new “schools” of business thinking like Total Quality Management, Six Sigma and Lean entered the scene. 

These programs gave the career-driven person language and initiatives to “proof” they needed and guaranteed that career success and analytical measurement of that success would become inseparable.

Every aspirational leader attached their careers to these programs in the 1980’s, most notably Jack Welch.  In 1989, he gave an interview in which he detailed GE’s newly launched “work out” program:

We want 300,000 people with different career objectives, different family aspirations, different financial goals, to share directly in this company’s vision, the information, the decision-making process, and the rewards

For someone at GE, it was very clear that you would need to get involved in one of these programs if you hoped to progress at the company. By the end of the 1990’s every large company had similar programs and employees had figured out that to get ahead you needed to document your progress.

In today’s working world, the reality of work is that good work does not pay off. You also need to share that success in something consultant Tom Critchlow calls this the “theatre of work”:

Many people aspire to “silent success” at work – to do work that “speaks for itself”. Unfortunately this is the wrong move in the theatre of work. Instead we should aspire to the opposite – for knowledge work, the performance of the work is the work.

Continuous Improvement programs helped complete the shift of work into a performance and kept workers in a non-stop search for problems that need to be fixed.

A New Kind of Worker

The point of all of this is not really to decide whether or not Frederick Taylor is to blame for our hyper-analytical workplace.

It is to make you aware that a unique set of circumstances emerged in the second half of the 20th century that birthed a new type of worker: the knowledge worker.

Despite knowledge work still only being half of the workforce (estimates vary), these workers have a dominant hold on our current myths and stories about what it means to work and what is means to be a human in the modern age.

Consider the changes in our mindsets that resulted from this new type of worker:

• The point of college is to get a job
• One should always be growing and improving at work
• Finding deeper meaning and belonging at work is vital
• The most important battles of freedom are for increased labor right
• Doing good work is not enough, you also need to self-promote

There are many subtle shifts that have emerged in the last 50-70 years but what makes them remarkable is that we all seem to accept that this is the way things have always been. Modern criticism of capitalism often miss this point. They don’t realize that work and a career was not always so central to our existence. It is only when work is the center that blowing everything up seems logical.

The emergence of knowledge work and the wealth that is has enabled many to generate across the world has been a huge positive in terms of freeing many people from having to worry about putting food on the table each week.

Yet the shift in consciousness that arose around the emergence of this new kind of work has led us into many traps. We look for belonging and meaning at work but never seem to grasp it. We crave the deeper truths of life but our schools only teach practical skills to get you hired. We fight for freedom for more people to work but find ourselves lacking the deeper things that give our lives meaning like connection, community and relationships.

I don’t have a utopian vision of what new work beliefs should look like but I can sense that they are starting to emerge. The majority of knowledge workers around the world are now working from their homes. They are finding that our scripts about the role work is supposed to play in our lives are outdated but they don’t have a better answer.

Whyte was a keen observer of the dark side of this new side of work when he was writing in the 1950s. He saw that the draw of aligning oneself with an organization and a certain kind of work was appealing

In a world changing so fast, in a world in which he must forever be on the move, the individual desperately needs roots, and The Organization is a logical place to develop them.

We still need those roots but after 65 years its time to realize that work is not going to deliver them.

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post The Knowledge Worker Mind & The Birth Of Careerism appeared first on Boundless by Paul Millerd.

The biggest losers, we suggest, have been management students

This was the takeaway of three researchers who dug into the history of the invention of Maslow’s pyramid. We’ll get to that story but first let’s take a look at what has become one of the most sacred ideas in the management world, Maslow’s pyramid:

The conventional way of thinking about the pyramid is a series of steps that you progress through with the goal of eventually spending more time focusing on self-actualizing. It is often used when thinking about what motivates people at work and thinking about how to improve culture to drive more productive employees.

The problem? The pyramid is an interpretation of Maslow’s research from the 1940s which he spent the next thirty years second-guessing and adding more nuance. By the end of his life, his investigations were well beyond any sort of neat and tidy pyramid that I had trouble trying to even describe and understand what Maslow thought about human motivation at all.

Let’s dive in.

A hierarchy, but not a pyramid

Maslow’s early research, presented in A Theory of Human Motivation (1943) presents something that feels familiar to someone who has seen the pyramid:

• The ‘physiological’ needs: The bodily drives for homeostasis included warmth, coolness, and hunger
• Safety Needs: Protection from danger and harm such as crime, violence, wars, etc… Some experience this as a lack of money as well.
• Love Needs: People have the desire to belong and be part of something
• Esteem Needs: The desire to be respected by others and by yourself
• Self-Actualization Needs: People that have satisfied their other needs and can spend time fulfilling their “potential”

In writing about self-actualization, this is where he says that being self-actualization is about meeting the other basic needs first but then goes on to share that he doesn’t really know much about how this is done:

The clear emergence of these needs rests upon prior satisfaction of the physiological, safety, love and esteem needs. We shall call people who are satisfied in these needs, basically satisfied people, and it is from these that we may expect the fullest (and healthiest) creativeness. Since, in our society, basically satisfied people are the exception, we do not know much about self-actualization, either experimentally or clinically. It remains a challenging problem for research.

This is the question that would shape his future research.

Maslow’s research quickly evolved beyond the basic “hierarchy of needs”

He moved even further away from a clear upward trajectory and embraced more nuance around human needs. He thought that for most people, the natural state was that many people were satisfied and dissatisfied at the same time:

In actual fact, most members of our society, who are normal, are partially satisfied in all their basic needs and partially unsatisfied in all their basic needs at the same time. 

Kyle Kowalski has a great deep dive on all of this and details what an updated pyramid of Maslow’s pyramid should actually look like:

In Motivation and Personality, he outlines his research on the people who are actually thriving in life. He called “Peakers”

Peakers seem also to live in the realm of Being, of poetry; esthetics; symbols; transcendence; “religion” of the mystical, personal noninstitutional sort and of end-experiences.

He differentiated these peakers from non-peaking self-actualizers, which seemed to be what we might call a highly effective “normie” today. He described these people as tending “to be practical, effective people, mesomorphs living in the world and doing very well in it.”

Here is his prediction in 1954:

My prediction is that this will turn out to be one of the crucial characterological “class differences,” crucial especially for social life because it looks as though the “merely healthy” non-peaking self- actualizers seem likely to be the social world improvers, the politicians, the workers in society, the reformers, the crusaders, whereas the transcending peakers are more apt to write the poetry, the music, the philosophies, and the religions.

Perhaps this is why so many people who seem to be so successful still feel like something is missing?

D-Psychology & B-Psychology

In the late 1950’s he started to see that certain kinds of people (the peakers) were living in a different reality from everyone else. He became obsessed with people who were able to spend a lot of time achieving what he came to call “full-humanness” or more simply, people that were in states of being unmotivated by their deficiencies.

He started to see the field of psychology as two domains – b-psychology and d-psychology. One with a focus on being and a focus on deficiency. He felt that psychology, especially as it increased its use of data, was too focused on what people lacked and wished the field would embrace more of the mystical and unknown side of life.

I think Maslow would be pleased to see how broadly those terms like “being” have been embraced and more awareness of eastern practices that emphasize states of being but likely a bit disappointed by the field of psychology and its continued obsessions with experimental data.

By the time Maslow wrote Towards a Psychology of Being in 1968, Maslow had all but abandoned the rigid hierarchy of his basic needs from 20+ years earlier and started to add dashes to almost everything using the b- and d- to signify that he was talking about two different perspectives of psychology – being and deficiency.

This is also when his ideas become a bit hard to follow. We’ll get to that but first…

Wait, So Where Did The Pyramid Come From and What Did Maslow Think?

Todd Bridgman, Stephen Cummings, and John Ballard wrote a fascinating paper trying to find out where the pyramid came from.

What they found was that the pyramid emerged in a number of steps of other people’s interpretations of the pyramid. The first was Douglas McGregor of Theory X and Y fame who found Maslow’s ideas useful for his writings on human relations.

This was the jump from the psychology world in Waltham, MA to the business world down the road in Cambridge, MA. However, the first use of anything resembling a pyramid was in Keith Davis’ writing on human management. Here is the first time the hierarchy was visualized:

From there it showed up three years later in an article titled How Money Motivates Men by a “consulting psychologist” named Charles McDermid writing in Business Horizons:

What was the takeaway of the article? That you could use this pyramid and the theories of Maslow to meet employee’s needs through means other than money:

For management the important conclusion to be drawn from the whole theory is that no one incentive is the only answer to motivating men on the job. Money is powerful, but its power is limited. Aiding group activities, creating opportunities, recognizing worth, encouraging growth, and fostering individual expression can also promote employee effort, in some cases more effectively than money.

All of you underpaid startup employees have this guy to thank!

Maslow’s Big Question & Meandering Ideas

It’s worth pausing here before going deeper into Maslow’s ideas to reflect on Maslow the person.

In his later writing, I have the dual sense of thinking he is a genius and a bit off his rocker. He shifts between the deep truth of a poet and a more tenuous grip on reality reminiscent of a new age seeker who just watched The Secret.

This starts to make sense if you read his writing on how he was thinking about the stakes of the day. This is from 1968, two years before his death:

We are now in the middle of such a change in the conception of man’s capacities, potentialities and goals. A new vision is emerging of the possibilities of man and of his destiny, and its implications are many, not only for our conceptions of education, but also for science, politics, literature, economics, religion, and even our conceptions of the non-human world.

There’s no question that Maslow found something to work on that mattered to him but it seems he may have been frustrated by the rest of his profession not approaching it with the same sense of urgency and you can see in his writings later in life that he had a flurry of ideas that never quite connected.

Yet as his orientation shifted toward thinking about being and transcendence, why was he so willing to go along with an older 1943 version of his thinking?

It seems that his own love and belonging needs were lacking.

As Bridgeman writes:

By the time the (hierarchy of needs) was beginning to be celebrated by McGregor, Davis, McDermid and others aspects of Maslow’s professional life were unraveling. He felt underappreciated in psychology, whose journals had been taken over by experimental studies, which depressed Maslow for their lack of creativity and insight. He also had more pragmatic concerns, suffering periods of ill health and financial difficulties. Maslow found personal and professional redemption in his acceptance in the management community and financial gain through speaking engagements and consulting. He welcomed the new field showing an interest in his ideas and offering the potential for personal benefit.

The rest of the exploration is quite harsh on the pyramid and attempts to understand how a theory that Maslow didn’t fully accept came to be adopted almost completely in the business world. They argue it is one of the most viral memes in the business world:

But Maslow’s (hierachy of needs) may be the only management theory that has “gone viral” and become a meme, and it is doubtful that this would have happened if it did not comepackaged in a pyramid with five clear categorical levels.

The lesson for the business world? Make it pretty, worry about facts later.

Later Research: D-Needs and The B-Realm

Despite the emergent popularity of the pyramid in management thinking, Maslow’s remained dedicated to the evolution of his thinking.

His later research still referenced needs but in a much more complex way than his simple hierarchy published in 1943. He defined them as d-needs or deficiency-needs. These are the things we are motivated to solve so we do not feel lacking – lack of safety, lack of love, lack of food, and so on. These are the closest things to his early hierarchy.

The other side of that was b-needs which are about our desire to grow, to become, or to embody certain human values. He called these b-values or being values:

B-Values: wholeness, perfection, completion, justice, aliveness, richness, simplicity, beauty, goodness, uniqueness, effortlessness playfulness, truth, self-sufficiency

This list likely gives us a glimpse of why he was so frustrated with his field of psychology. All of these concepts are so deeply human that it requires a much different orientation towards life to appreciate and accept them and what I mean is a mostly non-academic, non-scientific orientation towards life.

It seems he had more in common in his day with his contemporaries Ram Dass and Alan Watts and his description of what he called the b-realm might have had more uptake in the emerging “turn-on, tune-in, drop-out” late 60s crowd:

“Deals with ends; with end-states, end-experiences (intrinsic satisfactions and en­joyments); with persons insofar as they are ends-in-themselves (sacred, unique, non-comparable, equally valuable with every other person rather than as instruments or means to ends)”

It’s sad then, that Maslow passed in 1970. You can imagine the excitement he may have found trying to make sense of the human potential movement and having a bit more time to come up with something as coherent as the pyramid.

Despite his writings being a bit all over the place, I got the sense in revisiting his major works this week that Maslow really just wanted people to see how beautiful life was, despite his own struggles with that own journey.

So I might propose a simple framework for his later ideas. Not as catchy as the pyramid, but simply two bubbles of two different worlds:

Maslow doesn’t give a lot of prescriptions for how to move from the d-realm to the b-realm but talked a lot about having an attitude that the b-realm was possible.

That’s what I try to show above. That despite most of us spending almost all our time trying to satisfy our d-needs – acquiring more things, attention, approval, or money – we are missing the fact that there is a b-realm close by that offers a different and more interesting lens on life.

A world where we can just “B”

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Maslow’s Imaginary Pyramid: Who really invented the pyramid? appeared first on Boundless by Paul Millerd.

A hustle trap is something that we fall into without asking “why?”  Many of the traps exist because of outdated work beliefs or behaviors we have carried forward from full-time employment.  Many people only realize they have fallen into a trap when they find themselves burned out and noticing that they have created another job for themselves.

Wasn’t the point of becoming self-employed to avoid such a fate?

Let’s dive into ten of the most common traps I’ve seen in my conversations with people on the self-employment journey from around the world.

Hustle Trap (noun): A mental model built on legacy ideas of how one should work and live that leads to burnout, anxiety or the sense of being trapped. Often obvious in retrospect.

#1 The dopamine bomb of internet fame

Creating content on the web is still a relatively new thing and because of this, If you are able to consistently create content, explore topics you are genuinely interested in and develop some way to improve as you go, you will inevitably get some version of 15 minutes of fame. This could come from a famous person promoting your content, getting published in a mainstream publication, economic success or or some piece of content going semi-viral for a few days.

To the self-employed creator that dances in daily uncertainty and self-doubt, this can unleash a satisfying dopamine bomb of approval. It can be so exciting that it can reshape everything you claim to care about.  This effect is so powerful that even some of the most successful media organizations have gone the way of chasing clicks rather than focusing on the content they claim to care about.

I got a dose of this when I posted a Twitter thread exploring the “40% of Americans can’t afford a $400 emergency bill” meme. If you read the report and the data, you’d be doing some serious mental gymnastics to land on such a takeaway. However, I was looking at it from the perspective of a former consultant who is skeptical of how data is represented and didn’t realize I was walking into a political talking point. This exploration earned me the applause of right wing trolls and a twitter follow from Ann Coulter.

That wasn’t a path I wanted to keep exploring.

#2 Copying the tactics of a guru who isn’t you

It has become a norm for successful entrepreneurs and creators to share their approaches for how they got to where they are.  This includes things like writing and audience building strategies, pricing tactics, content creation approaches and so on. The depth of information available to people who want to follow certain paths is more honest and useful than before.

However, many people mistake the tactics for the journey and overlook the unique psychology, motivations, and financial situation of the person they are following, not to mention the role of luck and timing. Eleanor Roosevelt highlights the risks of this path:

When you adopt the standards and the values of someone else or a community or a pressure group, you surrender your own integrity. You become, to the extent of your surrender, less of a human being.

The only sustainable path over the long-term is to find your own way. Robert Greene spent years exploring how some of the most successful people in history did this, resulting in his book Mastery.  He found that people progress through three stages – the passive, practice and active modes:

1. Passive Mode: Learning the rules of the game (often working for someone else over a series of years)
2. Practice Mode: When someone start taking action on their own, taking ownership of what they are creating and actively building a set of skills
3. Active mode: The person goes out on their own, creating under their own name, or starting their own venture.

As Greene says, shifting from the practice to the active mode is often the hardest thing:

most people wait too long to take this step, generally out of fear…you must force yourself to initiate such actions or experiments before you think you are ready

Similarly, people often follow gurus and take courses from others much longer than they should.  Most people would be better off by hitting publish on their own creations despite them not feeling like they are perfect.

#3 The productivity trap / Streak trap

Growing up in the US and many other countries these days is to be convinced that your purpose in life is to continuously be doing things. To rest is to be lazy.

It can be useful when you first start creating to commit to some type of rhythm, such as posting once a week, because this can help you overcome a lot of the self-doubt and friction that emerges when you first start sharing online.  However, this can quickly become a trap as you mistake the streak for the thing that you want to be doing.  

Anne-Laure Le Cunff, who has written a lot about the traps of productivity, argues this is a way to avoid the questions that matter:

We are scared of idleness because stopping would mean having to really consider what we want out of life and what we currently have. Sometimes, the gap feels so wide, we’d rather stay on the hamster wheel.

To build a sustainable path, work has to be downstream from life and at least some of what you work on needs to be something you actually want to create. When you are self-employed you definitely need to find some way to motivate yourself, but often people mistake the insecurity of not feeling productive for the thing that keeps them going.

When you create deadlines that stress you out, remember that you are the one tuning self-employment into a job and isn’t the whole point of self-employment to avoid having a boss telling us what to do?

So I give you permission to take a week off. If anyone gets mad, blame it on me.

#4 The desire to prove yourself, especially to your parents

In my conversations with people around the globe, the secret anxiety that many share in a  deeper conversation is that they fear what others think of them, especially their parents.  

The fear of parental disapproval can keep a lot self-employed working on things they hate or keep them from taking bolder risks.  Being self-employed in the digital world is a life that is illegible to many people over the age of 40 and I’ve seen many people not ever give working for themselves a fair shake before returning to full-time employment.  

It’s easier to default into socially accepted roles than to try to carve your own path and for that reason there needs to be something deeper driving you than winning approval from others. 

Stephen Warley, who has become a friend and mentor, has been self-employed for almost the last twenty years, but says it took years before his mother accepted his path. Once he came to terms with the fact that the approval may not come, he was able to move forward.

4 years in, I was struggling and I was talking to my mom one day and she asked if I would ever consider getting a job.

I told her absolutely not and I haven’t struggled since!

The hard truth is that acceptance may never come.  As someone taking a path that is outside the norm, people are always going to be a bit uncomfortable with what you are doing.  The only way 

#5 Chasing “audience” over people you actually want to engage with

At some point someone will say to you, “you need to be on ______ to be taken seriously.”  Insert the medium of the moment:  a blog, a personal website, a medium, instagram, snapchat, patron, tinyletter, podcast, substack, twitter, YouTube.  You get the point.  

Engaging with other people online is one of the biggest challenges modern creators and entrepreneurs face.  The insecurity and FOMO of not being on a certain platform plus the algorithmic nudges towards engaging in ways that get the most attention are a double whammy of anxiety.

My approach has been to pay attention to what platforms result in meaningful conversations, both online and in-person.  In choosing where I engage, I ask myself the question “How do I build an audience in a way that might align with the life I want to live?”  

For me, more connection = happier Paul.

Through experimentation, my answer has been writing weekly on substack, posting longer pieces on my blog, recording podcasts when I find people I’m excited to interview, posting the random video to YouTube with no set schedule, and light twitter engagement.  I don’t really spend any time on any other platforms except for personal reasons.

I know many people that have built sizeable audiences, but have done so through sharing things they aren’t all that excited by.  They let the algorithm decide.  

Spend a month in Bali and you’ll inevitably meet an instagrammer with a massive following but feels trapped by what they are doing.  They’ve created a job for themselves, decoding what an algorithm wants rather than figuring out what smaller group of people might make their life better.

#6 Chasing status to calm your insecurities

Khe Hy left his job as an investment banker in 2015.  His initial plan was to take 18 months for some time off with his family and then to start a venture-backed tech company.  Where did he come up with this idea?  

As he details on the ZigZag podcast:

My plan was initially…to become a venture-backed entrepreneur.  I wanted to go and raise money and do the thing that Fast Company writes about….it sounds so lame but to me a big portion of success was other people thinking I was successful and what better way to do that is to do the thing that was actually even harder than what I was doing on Wall Street.

However, a few months into his break from his job.

I had had just enough separation from my old life that was like I don’t think I really want to do this.

He had realized that his desire of others to see him as successful was driving him to create trade one identity for another, which would have just delayed his inevitable leap into a more unknown, but more rewarding path.  Instead of trying to quiet that insecurity of not being seen as “successful,” he took the path towards more freedom and uncertainty while also grappling with it in public through his writing, which is a treasure trove for other self-employed creators trying to avoid hustle traps.

One of the most common insecurities is one’s relationship with money.  After years of a steady paycheck, a couple months without an income is the ultimate test for your ego.

Similar to Khe’s initial plan, the easiest way to calm this insecurity would be to make a ton of money.  While practically this can make sense immediately after your leap, over time you’ll just end up creating another full-time job for yourself instead of creating the space for new opportunities and your creative energy to emerge.

#7 Not Changing Your Environment Or Making New Friends

There’s a saying that goes “if you want to change yourself, change your environment.”  

I would offer a similar but slightly different claim: if you are making a big change in your life, your current environment may feel a bit lacking on the other side.

The number one recommendation I make to anyone making a major work change in their life is to make at least one new friend who is on the path ahead of you.

When I became self-employed, I was living in New York City and the majority of my friends and family operated their lives around full-time employment.  While those people are fantastic, I didn’t have many people in my life that understood what it felt like to go months without an income or try to design a life around working independently.

This led me to put myself in circumstances where I could meet more people who were working and living outside of the default path.  Joining a coworking space, attending conferences like the World Domination Summit, and living abroad and meeting people in global nomad communities helped me make new friends who I could lean on when the question “what the hell am I doing?” emerged,

I’ve had a number of weekly, biweekly, or monthly virtual or in-person conversations with these friends.  Beyond sharing our experiments and catching up, they are often deep contemplations on the deeper questions of life.

This kind of friendship, or what William Deresewiecz called “the deep friendship of intimate conversation” is a way of helping me feel at home when I am feeling lost and feeling connected when I am living in a new place around the world.

#8 Not Taking Time Off

Spend long enough in full-time employment and your sense of reality shifts to think about life as mostly work interrupted by two to four weeks of vacation per year (or more if you are lucky enough to live in Europe!).  

When you first graduate college this seems terrible but over time as all of your friends start to march to the same schedule, it just seems like what is.  At first many who become self-employed gravitate towards a similar schedule, working Monday through Friday, but find themselves burned out much quicker than they might in a full-time job.

This is because the amount of motivation needed to do work on your own is much higher than it might be in a full-time job.  When you are working for someone else, it may be painful to do something you don’t want to, but you find a way.  I tell people that when they are working on their own, if you aren’t at least “8 out of 10” excited about doing something, it’s going to feel like pushing a boulder through quicksand,

Even when you find work that you are motivated to do, it can be hard to step back and figure out a broader strategy for your life and work.  In full-time employment, job changes and promotions help you shift your focus, but in self-employment, the best way is usually to take an extended break.   This can be scary for many of the above reasons, but is often pivotal in figuring out what kind of work you are truly drawn to.

#9 An income goal as the metric of success

Nothing will force you to compromise quicker than lofty income goals for your self-employed life. In my first year of self-employment I used my freelance target income calculator and figured out that if I’m living in the US, I could pay for a life I really liked for about $35,000-40,000 in earnings per year.

This required a year of testing my limits after living in a high-end apartment in New York City, but it also helped me to be able to say no to many paid projects in that first year. Instead of those paid projects I developed things like Boundless, the Reimagine Work podcast and my future of work mindset assessment.

While these things haven’t led to any financial success, they help bring me alive.  If I only optimized around reaching an income goal of something like $100,000 a year, I would not have pursued any of these experiments.

Money is important but most people tend to overvalue the importance of money as they start their self-employed journey and undervalue the unexpected upsides of more flexibility, space for creativity and leaving time for unknown opportunities to emerge.

#10 The “I am a x” identity trap

You used to have an easy answer to the “what do you do?” question. Now you find yourself mumbling random lines about making friends on the internet and writing 25 blog posts about an obscure topic you’re fascinated by and you get hit with blank stares.

This can make a lot of people desperate to have an easier to understand label.

There’s a subtle difference between adopting labels to increase legibility to potential clients and seeing that label as who you are. It makes sense to tell potential clients you are a freelance consultant, but if you start seeing the world through the eyes of what a freelance consultant might do and looking at others freelance consultants for what kind of work to do, this might be a trap.

You are a human playing the role of a freelance consultant. Always remember that and your game will be a little more fun.

The anti-hustle path forward doesn’t come with a how-to guide

When I started sharing publicly online a few years ago, the dominant narrative for online creators was a hustle narrative. Do as much as possible, as productively as possible. This works for some people but is a trap for most and in some cases, people start to mistake the productivity hacks for the work itself.

I tend to agree with Anne-Laure that a lot of this comes from fear:

…Consuming too much productivity porn can sometimes be a symptom of lack of confidence. The process of learning from supposedly more productive people is akin to asking for permission to start working on an ambitious project

The only way to gain confidence in self-employment is through the discomfort, finding things you want to create and people you want to engage with. It doesn’t make sense to create 100 podcast episodes if you hate podcasting.  Find a better medium or take a break and see where your energy goes.

When you first become self-employed, it’s easy to let legacy work beliefs dominate how we think about our time:

“I need to make a lot of money”

“I need to have a lot of followers”

“I need to work all the time”

“I must scale”

“I need to prove to others I am successful”

It’s great to have some direction and despite trying to do so, I’ve failed to find a good map that gives people a lot of confidence about what comes next.  When successful individuals recount their stories, there are often more surprises and moments of inspiration than well-thought out plans.

At the beginning of my journey I felt a huge relief when I read this line from David Whyte.

…it can be a release then, to think, that when we first come across the idea of a pathless path, by definition, we are not meant to understand what it means”

I’m still on a journey and where I’m headed? I’m not sure.

I’m just trying to take it a bit slow and avoid falling into the many hustle traps along the way.  Hopefully I can help you navigate the path with a little more care as well…

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Hustle Traps: Ten Guaranteed Paths To Burnout For The Self-Employed Creator appeared first on Boundless by Paul Millerd.

Our imagination about what happens in the business world has become disconnected with reality and it all starts with an accepted narrative about the unstoppable power of Fredrick Taylor’s ideas

The narrative goes like this: Fredrick Taylor introduced managers to analytical methods and tools that helped them to dramatically improve productivity; however these efforts also kick-started a non-stop line of efforts that led to the inevitable over-optimization of human labor.

This over-simplification of Taylor is part of a narrative that has become entrenched and feeds a broad movement that says organizations are broken. The story says that organizations might be efficient, but at enormous cost – they destroy autonomy, stifle creativity and at worst, are systems that enable widespread verbal and physical abuse. All starting with Taylor of course.

Yet, as I’ll show you, this story is wrong, misses the context of Taylor’s time and ignores that a hyper-optimized mindset towards work did not take hold until the emergence of the “career path” in the 1960s. This coincided with the rise of “knowledge work” and this shift turned work into a performance, distracting many from the real mission of any organization: survival.

Instead of seeing organizations as broken, a more accurate starting point is to think of them as complex systems and instead of broken, as fragile. As the scale of business gets bigger, the hidden fragility of many organizations puts employees, customers and society at risk.

To address this fragility, I want to look at organizations as “complex adaptive systems”, an idea that emerged from a field called Chaos Theory in the 1970s and 1980s. I want to push for a broader adoption of these principles and encourage a new generation of “chaos managers” to become interested in the survival and success of our institutions.  

I first learned about chaos theory 13 years ago and have been thinking about it ever since.  During the ten years I spent in the corporate world and as a management consultant, I couldn’t escape the feeling that something was missing.  This is my first attempt to fill that gap and to give many other frustrated managers and leaders an additional lens to help them think about helping their organizations thrive.  

This essay will explore the following:

• What we got wrong about Taylor
• How the idea of the “career path” turned workers into performers
• How organizations subsequently became complicated, not complex
• Why chaos theory does not lead to anarchy
• The implications of chaos theory on leadership
• An actionable five-part guide for the modern “chaos manager”

Taylor’s Promise & How Workers Become Performers

If you dig into Fredrick Taylor, you find a number of surprising things and I’m not talking about his 1881 US Open Doubles Tennis championship.  What I’m talking about is the historical context of his famous contribution, Scientific Management. 

Taylor saw his approach to business not as a set of tools, but as a paradigm shift away from the harsh worker versus manager divisions that were common at the time. His ambitions were quite profound as he felt that his approach would lead to “elimination of almost all causes for dispute and disagreement between them” and unlock “prosperity for the employee, coupled with prosperity for the employer.”

This is overlooked when modern work critics blame Taylor for the hyper-optimization of the modern workplace. They miss the fact that Taylor’s focus was on production workers and the union of workers and management as well as the adoption of his tools did not become widespread until the emergence of the knowledge worker.

These knowledge workers emerged 30 years after Taylors time after World War II and were distinct from production workers. While those who worked in manufacturing had a strong “class consciousness,” the new class of “white collar” workers were not really sure who they were:

White-collar workers rarely knew where they were, whom they should identify with. It was an enduring dilemma, rooted in what might be called a class unconsciousness, that would characterize the world of the office worker until the present day.

Despite attempts throughout the 20th century for labor movements to include these workers, knowledge workers were distinct because of their desire to distance themselves from organized blue-collar workers.  Instead of labor unions, they formed “associations” and increasingly saw themselves as aspiring business people rather than at tension with the owners of capital and leaders of organizations.  

The knowledge worker was not concerned with bargaining for rights.  Instead, they focused on managing a career, developing skills and acquiring achievements or “pursuit of consecutive progressive achievement” as Merriam-Webster puts it. It was only time before they became part of the elite.  

People saw themselves not as a part of an organization but as someone with a first-person account of achievements and contributions that could be carried from employer to employer. 

As the job morphed into a career, the worker shifted from someone merely doing their job to someone that needed to perform. 

Continuous Improvement & The “Theatre Of Work”

In the 1980s, new “schools” of business thinking like Total Quality Management, Six Sigma and Lean entered the scene.  The accepted narrative of this shift is that US companies needed new approaches to compete with Japanese companies.  There is some truth to that story, but it ignores the fact that these programs would not have been adopted with such enthusiasm without the fuel of career aspirations.  

Every aspirational leader attached their careers to these programs in the 1980’s, most notably Jack Welch.  In 1989, he gave an interview in which he detailed GE’s newly launched “work out” program:

We want 300,000 people with different career objectives, different family aspirations, different financial goals, to share directly in this company’s vision, the information, the decision-making process, and the rewards

For someone at GE, it was very clear that you would need to get involved in one of these programs if you hoped to progress at the company. By the end of the 1990’s every large company had similar programs and employees had figured out that to get ahead you needed to document your progress.

I got my first taste of this game in my first internship.  I spent the entire summer creating a proposal and then purchasing a foam board which helped our group organize some inventory we kept in a file cabinet.  While it didn’t appear that the parts were too hard to find in the file cabinet in the first place, by the end of the summer the project helped the group earn the next “level” in the company’s continuous improvement program.

Consultant and writer Tom Critchlow would argue that I was operating in the “theatre of work”:

Many people aspire to “silent success” at work – to do work that “speaks for itself”. Unfortunately this is the wrong move in the theatre of work. Instead we should aspire to the opposite – for knowledge work, the performance of the work is the work.

Continuous Improvement programs helped complete the shift of work into a performance and kept workers in a non-stop search for problems that need to be fixed.

The Organization, It’s Complicated

A Taylorist revolution this was not.  Instead of real productivity improvements there was an explosion of paperwork, reports and well-intended initiatives, many of which drove increasing complicatedness.

Today’s business leader sees almost every issue and activity through a complicated lens.  This lens sees all commercial issues and behavior as things that can be understood, measured and then documented or fixed in a process.  

Anyone who has worked in a large company has run into the complicated approach when they have to deal with their expenses.  Typically any expense above a certain amount must be approved and then you need to go through a formal process for reimbursement.  While this approach eliminates the chance that an employee will spend recklessly, it adds additional work for every single person in the company and may unnecessarily limit useful expenses.  However, when this kind of approach is implemented, it will also help the project leader show quantified savings that they can point to at their next performance review.  

In contrast, a complex lens would admit that cause and effect is not easily understood, there may be many solutions to a problem, and that even if you “fix” something, the process and related human behavior will continue to evolve and adapt. 

A good example of a complex lens is how Trader Joe’s thinks about customer service.  If you walk into a Trader Joe’s and ask an employee if you can try one of the items, they will take a box, open it, and let you try some, no questions asked.  This creates complexity and uncertain outcomes, but the employees also get a lot of interesting feedback that they can pass along to the people that buy products for the company.  

The best assessment of the creeping complicatedness in organizations is from Boston Consulting Group who studied the internal operations of more than 100 companies.  They found that the “amount of procedures, vertical layers, interface structures, coordination bodies, and decision approvals within organizations had increased by anywhere from 50% to 350% over a 15-year period.”  And in the top 20% most complicated organizations?  The managers in those organizations “spend 40% of their time writing reports and 30% to 60% of it in coordination meetings.”

The experience of sitting in “coordination” meetings is one of the most painful experiences for the modern worker and as many come to realize, is the stage of the theatre of work, where the most powerful people battle it out for having the most compelling narrative of what is really happening, complicatedness be damned.

The Early Excitement Of Chaos Theory

But what if this creeping complicatedness of our organizations increases the fragility of the organization? 

That is the conclusion of researchers who think organizations should be understood as “complex adaptive systems.”

In the 1970’s and 80’s a new field of research began to emerge called Chaos Theory. Scientists were looking at complex dynamic systems and trying to understand how they emerge and evolve. They drew inspiration from the natural world, looking at phenomena like how organisms grow in the wild, and how weather evolves. Eventually, they began applying the lessons to fields such as finance, biology, economics and eventually, organizations.

One of the fundamental implications of chaos theory is that small changes have the potential to have big effects within the system, whereas large changes are less likely to shift the underlying order of the system. This is because the organization is seen as a complex system rather than a fixed body. The individual behaviors and reactions of people within a complex system are unpredictable, but they are linked to one another. The feedback from each of those unpredictable actions will give feedback to others in the organizations and influence their subsequent decisions and reactions.

In the 1990s there was a lot of excitement around these ideas.  In 1999, Richard Pascale, a former management consultant and author, wrote about chaos theory in the MIT Sloan Management review, predicting that “the next point of inflection is about to unfold”.

However, Chaos Theory Has No Star

Alas, a new era did not unfold. The increased use of computers and connectivity coincided with globalization and growth of large businesses that paired well with change management frameworks like John Kotter’s 8-step “change management” approach. 

I first stumbled upon Pascale’s writing on chaos theory while leading research at BCG where I helped revamp their thinking on organizational change in the mid 2010s.  I thought that the Partners I was working with would share my excitement.

However, I quickly realized the problem.  Kotter’s approach puts the senior executive at the center of the story and the leader’s task is to force a change on a resistant organization.  To him, the business leader “defines what the future should look like, aligns people with that vision, and inspires them to make it happen despite the obstacles”

Chaos theory, in contrast, removes the senior executive from the center of the story and puts the system at the center.  That is exciting for people who enjoy thinking about complex systems, but isn’t likely to be profitable to a consulting firm which sells projects to senior executives.

I don’t deny that many of the people at senior levels of organizations do have useful experience and are probably better than most at figuring out the direction of the company.  However, it is worth considering why that seems to be the only way we believe modern organizations can be run.

Former CEO Luke Kanies gives us a rare glimpse into the awkward implications of large organizations.  He had the experience of growing up on a commune and then building a 500+ person company and really struggled with the tension between the belief in a free market and the reality of running a company as a top-down operation.  

We still live in a free market economy, but it’s not one Adam Smith would recognize. Instead of individual or small operators, ours is composed almost entirely of corporations. Really big corporations. And these companies use the same kind of central planning that we so despise in communist systems.

…We could see no way to have a system where the people doing the work built a plan for the organization. Even thinking about it now, my reaction is, “How would they know what my goals are?” That’s the kind of question you can only ask in an authoritarian state, not in a free market economy.

My goals became my company’s goals, and the only real way to ensure people worked toward them was for me to provide a plan.

We have no other playbooks for running large companies.  Top-down and complicated is the only way we know how to do it and this fact is worth acknowledging more openly.  Many corporations engage in culture PR, telling employees that they will be given the Dan Pink sandwich of autonomy, mastery, and purpose when the day-to-day reality is far from it. 

A first step towards adding new models to the toolbox like Chaos Theory has to be an admission that creating dynamic large organizations remains elusive, and the very few examples we have means that there is very little expertise on how to behave in new ways.  

Chaos Theory Is A New Lens On Business

It’s an open secret in modern organizations that most change efforts fail.  Kotter estimated in his book that upwards of 70% of change efforts fail and this has become one of the most repeated facts from consulting firms who unironically share this in the front of pitch decks which then go on to sell another top-down change program.

The best argument to immediately increase awareness of Chaos Theory is that it gives managers a way of understanding the reasons why these change programs fail.  

With a deeper understanding, managers can then use it as a lens to re-frame many of the activities which are traditionally seen as bad practices such as redundant activities and lack of processes.  While many of the implications of chaos theory are counterintuitive, Pascale offers four basic principles of “complex adaptive systems”:

1. They consist of many agents acting in parallel and are not hierarchically controlled
2. They continuously shuffle these building blocks and generate multiple levels of organization and structure 
3. They are subject to the second law of thermodynamics, exhibiting entropy and winding down over time unless replenished with energy. In this sense, complex adaptive systems are vulnerable to death. 
4. They have a capacity for pattern recognition and employ this to anticipate the future and learn to recognize the anticipation of seasonal change

Chaos theory posits that this is a natural state that emerges without central control.  Instead of letting things emerge, we do the exact opposite, we try to control organizations as much as possible.

This approach makes a lot of sense because organizations are run by humans who have a natural desire for control.  But consider the implications of operating in an organization which is a truly complex adaptive system, suggested by Professor Gary Grobman:

Complexity theory suggests that organizational managers promote bringing their organizations to the “edge of chaos” rather than troubleshooting, to trust workers to self-organize to solve problems, to encourage rather than banish informal communication networks, to “go with the flow” rather than script procedures, to build in some redundancy and slack resources and to induce a healthy level of tension and anxiety in the organization to promote creativity and maximize organizational effectiveness

This is terrifying for most managers and helping them grapple with inevitable insecurity and emotional challenges of embracing these methods is just as important as an understanding of the principles themselves.

“Eyes On, Hands-Off”: Chaos Does Not Mean Anarchy

“You can’t just let people do whatever they want.”  This is the most common pushback to the idea of chaos theory.  People mistake chaos theory as the first step on the road to anarchy.  Yet in the highest stakes arena, the military, they openly embrace many of the principles of chaos theory.  

A publication from the US Marine Corps published in 1996 titled “Command and Control” offers a view of a seemingly traditional view of leadership through a complex lens: “command and control is not the exclusive province of senior commanders and staff: effective command and control is the responsibility of all Marines.”  It goes on to detail command and control as “a complex system characterized by reciprocal action and feedback” that “provides the means to adapt to changing conditions.”

Here is General Stanley Mchrystal writing in his book “Team of Teams” which details how the military had to come up with a better approach to counteract the more “chaotic” and emergent activity of the terrorists they were fighting in the early 2000s:

The temptation to lead as a chess master, controlling each move of the organization, must give way to an approach as a gardener, enabling rather than directing. A gardening approach to leadership is anything but passive. The leader acts as an “Eyes-On, Hands-Off” enabler who creates and maintains an ecosystem in which the organization operates.

Notice how similar this is to Grobman’s conception of a chaos theory manager and how antithetical this is to Kotter’s definition of a leader.  This goes against the caricature of military organizations as top-down rigid hierarchies.  Unlike many companies today, military organizations have people who plan to have much longer tenures within the organization and are personally at risk if the organization becomes too fragile and complicated.

The Five Roles Of The Chaos Manager

A good way to think about chaos theory would be by thinking about how Jazz relates to most other music.  As Louis Armstrong said, “If you have to ask what jazz is, you’ll never know.”  Chaos Theory is similar.  It can’t be easily boiled down to easily understood scientific laws, great business book narratives, credentials or 8-step plans.  Similar to jazz, it is improvisational in nature.

Many people in the business world are hungry for a different way of thinking about change in modern organizations but don’t buy into the idea that organizations are “broken.”  They also don’t think that the solution to these problems is another complicated continuous improvement program or consulting firm transformation program.

Chaos theory can be the improvisational permission that leaders need to explore ways of leading and managing beyond simply what has been done for the last fifty years.  This can help to inspire a new generation of “chaos managers” that want to treat organizations as they are: living, dynamic systems.  

Fundamentally, the chaos manager thinks about five roles:

1. Emergence Architect: Increase the opportunity for changes that have large positive effects by engaging in more small experiments
2. Authority Aligner: Increasing the credibility of top-down leadership by focusing on personal authority in addition to positional authority.
3. Reality Sensemaker: Shift from the illusion of top-down control to better control though improved sensemaking, better feedback & making appropriate decisions at lower levels of the organization
4. Chaos Injector: Ensures that the organization is not stagnant and looks for ways to inject “energy” throughout the company
5. Survival Guide: Can increase the perceived credibility among employees, customers, society and shareholders by shifting organization’s mission to survival 

Role #1: Emergence Architect

The canonical example of chaos theory is the Butterfly effect. Far away in China, a butterfly flaps its wings. The tiny change in pressure it causes has cascading effects, causing whorls of wind, which in turn cause pressure disturbances of their own. These spirals of wind feedback further on themselves in a relentless positive cycle. Far away, a hurricane forms. The butterfly, oblivious, flies on.

The Butterfly effect occurs in all systems of sufficient complexity. It is characterised by two features:

1. Nonlinearity. Small changes in input (flap of wings in China) have big effects on outcomes (wind in the US)
2. Unpredictability. Because we can never know the precise nature of all inputs, and small changes in inputs lead to big changes in outcomes, we cannot forecast outcomes.

Both of these things are the enemy of the modern manager.  The modern manager spends their time convincing others that the future is both predictable and can be dictated by well-designed programs and initiatives. Yet over time this desire for predictability only ends in the inevitable path of stagnation.  

Yet not every company operates like this.  Amazon is a company both obsessed with long-term survival and a deep understanding that survival requires designing for complexity.  Here are three lesser known ways they design this:

#1 Designing for emergence of skills. From Bezos 2009 shareholder letter:

“Working backwards”  from customer needs can be contrasted with a “skills-forward” approach where existing skills and competencies are used to drive business opportunities. The skills-forward approach says, “We are really good at X. What else can we do with X?” That’s a useful and rewarding business approach. However, if used exclusively, the company employing it will never be driven to develop fresh skills.

#2 Accepting a stance of not knowing: From Bezos 2016 shareholder letter:

One area where I think we are especially distinctive is failure. I believe we are the best place in the world to fail (we have plenty of practice!), and failure and invention are inseparable twins. To invent you have to experiment, and if you know in advance that it’s going to work, it’s not an experiment.

#3 Making reversible decisions at the lowest level:

Amazon pushes teams to escalate one-way door decisions – those that can’t be reversed and may have long-term consequences.  However, with “two-way” decisions, managers are coached to make these decisions themselves.  Here is how one manager at Amazon describes it:

Decision-making processes are evaluated for speed more than control. It’s not an excuse for poor decisions, but rather a reflection that the search for perfect information is normally fruitless and slow. Delegation of these decisions enables better rigor and time to be spent on fewer, more critical decisions…If teams escalate two-way door decisions due to a perceived lack of empowerment, use the escalations as opportunities to coach the teams

Bezos has noted that most large organizations default to seeing every decision as a one-way door that results in “slowness, unthoughtful risk aversion, failure to experiment sufficiently, and consequently diminished invention.”  Making quick decisions increases the chances of mistakes, but it also helps the company continue to operate as a complex “invention machine,” as he calls it, rather than another fragile, large company.

Role #2: Authority Aligner

Done well, command and control adds to our strength. Done poorly, it invites disaster, even against a weaker enemy – US Marines, “Command and Control”

Many organizations are not in fact the command and control hierarchies that they are portrayed to be. While there may be a clear formal hierarchy and a well-designed org chart of the people in the organization, anyone with more than a week’s experience in a modern organization knows that informal networks control how things actually get done and that improvisational behavior is part of most work.

The chaos manager is concerned with the credibility of the organization and ensures that positional authority is aligned with personal authority.  That the people in leadership are the ones people want to follow.  While the Marine Corps has a clear position hierarchy, they have a deep understanding of this idea. 

Companies undermine their credibility in two ways: 

1. Official authority doesn’t have associated responsibility for its actions
2. Personal authority doesn’t get recognized and integrated over time

The first condition results when there is a lack of “skin in the game.”  When people within the organization see that senior leaders pay no costs for mistakes and carry no responsibility for their decisions, the organization fills with a creeping nihilism rather than ideas and creativity.

The second condition exists in most companies because positional authority is so salient and easy to understand.  Personal authority is the credibility that people carry within the organization regardless of their rank within the company.  While these people often command the respect of their peers, they often grow disgruntled because their skills are not a perfect fit for climbing the corporate ladder or are overlooked by senior leaders.

Bridgewater Associates is one company that takes finding the people with personal authority seriously.  As Ray Dalio says,

In typical organizations, most decisions are made either autocratically, by a top-down leader, or democratically, where everyone shares their opinions and those opinions that have the most support are implemented. Both systems produce inferior decision making. That’s because the best decisions are made by an idea meritocracy

To cultivate an idea meritocracy, they developed an app called a “dot collector” which enables all employees to rate each other along many different dimensions, ranging from “knowledgeability” to communication style. Over time, the app builds up a picture of each employee’s “believability” on different issues. This enables Bridgewater to understand where expertise lies within the company in addition to the hierarchical authority easily understood on an org chart.

Role #3: Reality Sensemaker

In a complex system, what is the role of the leader? General McChrystal says leaders become “gardeners” and Professor Grobman suggests leaders learn how to “go with the flow.”  We might have a general sense of what they mean, but what should a leader do on a day to day basis?

The chaos manager engages in a continuous search for truth about the reality within the organization and sees the organization not as a stable system, but an adaptive network with dynamic relationships, interactions and rules.  Today’s reality is not tomorrow’s.

Edgar Schein helped popularize the idea of assessing corporate culture in the 1980’s.  While many people gravitate to his three-tiered culture framework, he saw the understanding of culture not as a top-down reality shaping initiative but as a deep inquiry into the “nature of humanity, human relationships, time, space, and the nature of reality and truth itself.”  

The chaos manager takes this search for truth seriously and knows that the fine balance of command and control can only be reached if they have an accurate map of reality.  The chaos manager does not have authority because of their position, but because of their ability to learn, listen and integrate.  The best leaders have the best map of reality.  

One of the best accounts we have of embracing this model is from Steve Miller, who became a “chaos manager” later in his career at Shell:

The scariest part is letting go. You don’t have the same kind of control that traditional leadership is used to. What you don’t realize until you do it is that you may, in fact, have more controls but in a different fashion. You get more feedback than before, you learn more than before, you know more through your own people about what’s going on in the marketplace and with customers than before. But you still have to let go of the old sense of control.

Role #4: Chaos Injector

In the forestry world, a “controlled burn” is an accepted practice of lowering the risk of fragility.  A “controlled burn” is a fire purposefully set with the goal of lowering the risk of more uncontrolled wildfires that put people and communities at risk.

The chaos manager knows that organizations are at risk if they become stagnant and similarly look for ways to unleash controlled burns within their organization.  These are often small and subtle design decisions that may lead to unexpected positive outcomes.  Three simple examples include:

1. Unplanned Interactions: Steve Jobs had this in mind when he designed Apple’s headquarters: their corridors were deliberately small so you had to bump into colleagues you didn’t directly work with. Increasing connectivity between key nodes in the organizational network allows for both ideas and people to collide.
2. Human Judgement Over Rules: At Ritz Carlton, where employees are given a budget to spend on making customers happy, no questions asked. This is inherently unpredictable — each guest is different, so management may not know what money is being spent on. But as customer demands change, the company does not have to develop 
3. Aligning Career Incentives: Many individuals do not have any incentive to think about the health of an entire organization.  One way to do this is to increase the connections between groups, such as making an engineering team responsible for the customer service demands for their product after launch.  This can shift teams out of their default modes of approaching and solving problems and work in new ways.

The chaos manager is always listening and looking for teams that are stuck within rigid rules and individuals with limited autonomy.  The chaos manager knows that they need to inject chaos to ignite the literal creative energy of individuals throughout the organization.

Role #5: Survival Guide

In Chaos Theory, the mission is clear: survival.

Right now many organizations have operated for decades in a simulated reality that is itself fragile and where plans don’t have to make sense, competition doesn’t matter and second-order effects can be safely ignored.  Before the Covid-19 pandemic, the US and UK were rated the top two countries in preparedness.  Why? Because they had done extensive planning and even run simulations.  They had plans.

But their plans were overly optimistic and focused on keeping morale high and the economy running.  Anchored to these plans, people were more interested in trying to make them happen rather than taking a more adaptive response.  The deeper problem is the absolute faith in plans in the first place.  If you think everything can be modeled on a spreadsheet, you start to lose touch with reality and stop orienting towards survival. In this case, human survival was at stake too.

Many people have given up on institutions.  Chaos theory is a lens that can help us escape this nihilistic view.  Yuval Levin has chronicled the role of institutions in our lives and believes “We lose faith in an institution when we no longer believe that it plays this ethical or formative role of teaching the people within it to be trustworthy.” 

As I have outlined, almost every incentive within modern organizations is conspiring to shift people’s attention away from the organization’s credibility and survival.  Company starts struggling? Just get another job.  Your initiative doesn’t really matter? So what, it looks good on a resume.  Employees suffer under the current paradigm?  Sorry buddy, it’s always been that way.

Levin suggests that we need to start asking “Given my role here, how should I behave?”  This is a nice sentiment, but I’m not sure most people are there yet.

Instead, Chaos Theory can integrate with the current paradigm and give current leaders the feeling that they are still doing something while we discover what works.  To the many business leaders and managers who are frustrated with the accepted reality of organizations, it gives them a framework to play and experiment to potentially find a way out.

I might be a bit crazy, but similar to Taylor’s belief that Scientific Management could help transcend the divide between workers and owners, I believe that an earnest attempt at applying the lessons of Chaos Theory can help to soften some of the broad disillusionment across the corporate world that any real change is possible and help people take pride in their roles, institutions and our systems.

Special thanks to Thomas Hollands who partnered with me on the many initial drafts and helped me shape the overall theme of this essay and Jeremy Finch, who created the illustrations. Also to Vinay Debrou, Michael Kueker, Greg Doctor, Mike Tannenbaum, and Tom Critchlow for reading drafts and helping to make it a lot better.

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Integrating Chaos: Building Resilient Organizations with Chaos Theory appeared first on Boundless by Paul Millerd.

Remote work is poorly understood and for good reason. What most people have experienced is merely being “allowed” to work remotely on occasion, having to stay home with someone sick in the family, logging in while traveling or waiting for the cable guy to install internet.

While I am a fan of remote working I am not sure that most companies realize that experimenting with remote work until the end of the covid-19 crisis is a free strategy option. I’ll detail more of what I mean at the end, but first its worth helping you reframe how you think about remote work.

Over the last ten years many “remote-first” companies have been rethinking how work should get done and have discovered that to truly thrive as a distributed, remote organization there is an inevitable learning curve that one must progress.

Matt Mullenweg has been one of the biggest proponents of this way of working and is the CEO of Automattic, which employs more than 1,000 people “in 75 countries speaking 93 different language.”

In a podcast with Sam Harris he outlined his “five levels of remote work” which I thought was the best explanation of some of the subtle differences of remote work I’ve head.

Remote Work 101

Most people are familiar with the experience of level 1 or level 2 remote work. During the covid-19 crisis many employees are finding themselves in a “copy the office” experience of remote work still being available during the same hours they would in an office.

Level 1 – Emergency

Working from home is not easy, but possible. If you have to.

• Basics: Have internet, cell phone, some way to access email
• Work if possible: Usually can put things off until back in office because that’s how most people work
• Mindset: “we don’t know what employees are doing” therefore you want to minimize the ability for people to work remotely or flexibly as much as possible

Level 2 – Copy The Office

In level two, companies have better tools and access to working remotely, but it is still mostly for people who have an excuse. In this scenario, the company is still designed to operate around an in-person dynamic and people who are working remotely are expected to follow similar hours and procedures as everyone else. At this level if someone starts working remotely full-time it is often with the understanding that the person will be harming their long-term career prospects.

• Language: outdated terms like “telecommute”
• Requirements: Need to be able to access things from the office
• Default mode: synchronous; Copying “office hours” 8am-5pm; factory model for knowledge work
• Pitfalls: More tracking, screenshots of screens
• Challenges for workers: removing some freedom & agency, may end up being even less productive

Transition

The Covid-19 crisis forced many companies to adopt remote work quickly.

While many companies are “level-three ready” they have not spent much time operating in a truly remote fashion. However, the last three years saw many companies adopt a new stack of tools such as slack, teams, gsuite, zoom, and other live collaboration tools that have made it much easier to work remotely and in new ways.

Despite this, most companies that decide to start working remotely will do an awkward dance between levels 2 and 3, using new tools but making them morph into the office-first company culture.

Level 3 – Virtual Tools

In this phase people start adjusting to working remotely for more than a couple days. They typically upgrade their equipment, create a space at home for working, have a basic familiarity with the video and collaboration apps, but still mostly work in similar ways as if they are in the office.

This is copy the office with a bit more experimentation:

• Technology: Share screens quickly (desktop & mobile). People start to invest in better equipment: microphones, lighting, screens, ergonomics
• Unlocked modes: Collaborative work via video calls; live note taking for shared understanding
• New Skills: Companies start to realize that writing is vital. They start investing and recruiting for written communication – clarity, quality & skill becomes more and more valuable

This transition stage also surfaces a lot of challenges. People who are used to working in the “old way” reject many of the new approaches and declare remote working a failure. They may push for abandoning the experiment because its easier than than feeling uncomfortable.

Teams also find that doing things the “old way” just doesn’t work. The more capable teams start working in new ways, rethinking meeting, using video when appropriate and defaulting to longform over quick IMs.

Real Remote Work

Once companies get use to working remotely and the kinks are worked out they can start shifting to unleashing the power of remote work.

This is when things start getting interesting. As Amir Salihefendic, CEO of Doist, has said:

“Remote first isn’t the same as remote friendly or ability to work from home. Remote first is a whole new way to organize companies.

Level 4 – “Asynch”

This means new ways of decision making, communicating, developing trust, leadership, and recruiting and to do this with 4,000 people during an economic crisis carries a certain amount of risk. However, I think the alternative is more certain and caps any possibility. This is why I think going-remote will remain a “free strategy move” for the coming months.

This is why people are so excited about remote work. If companies are going to stay at level 3 there is not a ton of value in long-term remote working other than flexibility.

• Realization: You can’t track when people work so you shift to judging on what they produce. This makes people assess meetings and realize that “most meetings are terrible.” Eliminate many status updates meetings.
• Requirements: Need to develop capacity for handoffs, especially between time zones. Quality of handoffs should be valued over speed.
• Unlocked: Can start hiring & operating globally and do work at all hours
• Challenges: Use of writing and multiple time zones makes decision making harder and longer, but often results in better decisions.
• Space for New Types Of Workers: Introverted and non-neuroptypical types become more valuable for remote companies and they can hire great people that in-office companies don’t value. space for introverts, people that like space for thinking

Letting People Design Their Lives

The real magic of remote work is when you can start working asynchronously and give more autonomy to workers to let them decide when to work and how to operate within their teams. This takes a tremendous amount of trust but often creates a better relationship with work for not only junior level employees, but the senior level employees as well.

Level 5 – Nirvana

This is more of a “true north” than day-to-day reality, but Mullenwieg sees this as one of the great things about working remotely – its ability to unlock more freedom for employees

• Employees can design day around health, wellness, well-being. Able to operate around peak creativity, daycare, parenting, health, gym etc..
• Challenges: People often struggle with unlimited freedom and often end up overworking
• Goals: Striving for an “idea meritocracy,” where best ideas, projects and contributions are elevated throughout the company

As Gumroad’s Sahil Lavingia has discovered in his own company:

People build their work around their life, not the other way around. This is especially great for new parents, but everyone benefits from being able to structure their days to maximize their happiness and productivity.

Developing A Capacity For Remote Work Is The Greatest Strategic Advantage

Right now there is a huge opportunity for forward-looking companies. Because most companies are struggling, making bold bets doesn’t carry the potential downsides it might in regular times.

Going remote is a strong strategic play because it removes the guaranteed uncertainty of navigating the ever-changing guidelines and information on “returning to work.” Companies have two options:

• Option A: Follow everyone else and have guaranteed uncertainty of “returning to work”
• Option B: Go remote, remove the guaranteed uncertainty of “returning to work” and build a capability that will enable you to attract new talent and build a gap between you and your competitors. This move is inherently uncertain, but in the positive direction.

We’ve been operating companies for the past ten years as if the internet does not exist. 

In the last five years the tools we have are more than good enough and there are no good excuses for using remote work to build more agile and adaptive capacity within your organization. Business leaders are often worried about their own careers and getting fired if things go wrong. Right now, that may happen anyway, and going remote in the next six months is a lot more fun from a business challenge standpoint than navigating the guaranteed uncertainty of this pandemic.

If six months down the road, it looks like it won’t work with your company? You can get back in the same boat with everyone else.

41k+ Sold! (Top 1% Book) The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here

The post Matt Mullenweg’s & Automattic’s Five Levels Of Remote Work appeared first on Boundless by Paul Millerd.