The Future Of Work Is Five Different Conversations

The future of work can mean anything.  I’ve had many conversations and discussions around the idea of “future of work” where people talk past each other, often focused on different fundamental issues.  In an effort to make sense of this complexity and create some common ground for the many people having these conversations, I propose differentiating between five future of work conversations:

Conversation #1: Macro Trends (consultancies, journalists, politicians)

This conversation is typified by looking at trends and then working backward to see what the implications are for people.  Terms like “fourth industrial revolution,” “the end of work,” “post-work,” “artificial intelligence,” and “robots” are used prolifically.  McKinsey writes in a report on the future of work:

Automation, digital platforms, and other innovations are changing the fundamental nature of work.

…and Quartz:

Automation, advanced manufacturing, AI, and the shift to e-commerce are dramatically changing the number and nature of work.

…and finally, The Brookings Institute:

Robots, artificial intelligence, and driverless cars are no longer things of the distant future.

These trends are positioned as irreversible and having an impact on people rather than something we should question at a fundamental level. This conversation tends to center not around individuals but “the workforce.”  Think tanks and consultancies produce charts showing the numbers of jobs that will be eliminated by AI or show the types of jobs and skills needed in the future.

For example, The World Economic Forum writes:

Creativity will become one of the top three skills workers will need. With the avalanche of new products, new technologies and new ways of working, workers are going to have to become more creative in order to benefit from these changes.

While it is fun to talk about the future, this conversation often falls short of the reality that many current jobs that require creativity and other “human skills” (teachers, social workers, retail workers) are still undervalued in our economy.

This conversation often lends itself to identifying policies to either reduce suffering or reduce inequality in the workforce or economy as a whole.  It often highlights long-term trends that do not appear to be shifting such as the decreasing labor share of income and increasing rent-seeking as a percentage of our economy.  Thought leaders propose work-related policies such as minimum wages, unemployment protection, health benefits, portable benefits, paid leave and other similar policies. For example, The Aspen Institute has proposed a $25 million innovation fund to experiment with new approaches for portable benefits.

While these are great in theory, they often only end up helping the types of people who already have good jobs and benefits in the economy.  When one digs deep into some of these issues and starts asking “why?”, especially in the US around why so many benefits are tied to employment, they are likely to end up in conversation #5 (see below) questioning some of the sacred cows of the modern workforce.

While many of the issues in this conversation are important, they are a bit distant from the reality on the ground.  The articles get a lot of clicks and are great for panels at conferences but hard for most people to understand what changes they should make when they show up to work the next day.


Conversation #2: The Gig Economy (Journalists, Companies, Consulting Firms, Talent Platforms)

Given media bias towards writing that gets clicks, this conversation tends to be geared towards the worst parts of the gig economy and perhaps misses some of the people who are benefiting from the increased freedom and flexibility of the gig economy.  McKinsey’s report mentioned previously highlighted this fact, showing that even independent workers “by necessity” into it were “as satisfied” or more satisfied than comparable traditional workers, with the exception of income security and level of income.  While I agree with the fact that lower incomes are not a great thing, it does appear that the gig economy is somewhat of a release valve for people to prioritize things that do matter to them like flexibility and independence.

Companies making money from the gig economy also tap into this conversation with mixed results.  Some of the material is transparent content with little usefulness, while others have been thoughtful additions to the conversation.  Talent platforms have added the most useful content to this discussion.  UpWork’s Freelancing In America report and Catalant’s Reimagining Work reports are a bit optimistic, but provide unique insight into the people using their platforms.

Nonetheless, the gig economy highlights a continued optimization of the productive class.  What makes it different in the context of the gig economy is that a movement from full-time work to gig work often means a lack of a sense of security, good health care coverage, and a consistent wage.  While this is great for someone with high earning potential, it is a disaster for people with lower wages.  These challenges are often framed within the context of the current economic system (pay higher wages, give more benefits), but I believe the true opportunity for transformation will come from looking backward and questioning our current employment paradigm as Marco Torregrossa, leader of the “freelance revolution” in Europe, has done, “We shouldn’t complain that Uber drivers don’t receive full-time benefits; we should reconsider why benefits and security come attached only to full-time jobs.”

This conversation also highlights a third way, if you will, showing the success that companies like Managed by Q and Hello Alfred are having by choosing not to use gig workers, investing in their people and culture instead and unlocking a value by using technology in all places except the optimization of their labor force.


Conversation #3: Evolving Organizational Ecosystem (Companies, Consulting Firms, Authors, Entrepreneurs)

Within the past ten years, the corporate world has stumbled upon the belief that “millennials” needed to be catered to.  While this makes sense as Millennials have become the largest percentage of our workforce, investing in people is not anything new.  Many companies have been screaming from the rooftop about how investing in people leads to higher returns for decades (see basecamp, Southwest, Atlassian, Trader Joe’s, Costco, Toyota).

I believe what has changed, however, is that social media has made it almost impossible to hide a bad culture and gives many an outlet to share the most egregious elements in public (LinkedIn, Facebook, Glassdoor, etc…).

While I was pretty optimistic at first, I am less optimistic now.  Companies are changing policies, launching new initiatives and creating new values, but are failing to take a deeper look at the underlying behaviors, beliefs, and assumptions of the organization.  What I have seen in my experience talking to leaders and working as a strategy consultant, was that many of these initiatives increase complexity and increase attention on bad elements of culture. It is often not much more than “Culture PR.”

One welcome addition to this conversation has been the tech industry’s willingness to invest in culture.  My cynical hypothesis of why this has happened is that software businesses lend themselves to high margins and high levels of automation.  This leaves many thoughtful educated people a lot of time to think about how to spend that cash to keep people motivated.  Google, basecamp, and Netflix have arguably done the most to advance this conversation, sharing their counterintuitive culture practices (self-nomination for promotions, maximum 32-hour work weeks, get rid of jobs that are not needed anymore.  Others like Gravity Payments have gained attention by raising minimum salaries to $70,000 a year.  Regardless of the impetus, all of these experiments are needed and a net benefit to workers.

There has also been an emerging conversation in the corporate world around corporate purpose.  This can get muddled very quickly if you start talking about individual purpose within the same context.  However, there has been a lot of evidence showing that purpose-driven organizations dramatically outperform other organizations.  However, outside of a few organizations with dramatic and clear long-term visions, it is often hard to find organizations that operate around a set of values beyond profitability.

Frederic Laloux wrote perhaps one of the most provocative elements of this discussion with his book Reinventing Organizations. In it he calls out this the hollowness of many corporate mission statements:

Executives, at least in my experience, don’t pause in a heated debate to turn to the company’s mission statement for guidance, asking, “What does our purpose require us to do?

He highlights organizations that have built companies around their people, rather than traditional ideas of how a company should be run.  In it, he talks about how these companies have something called an “evolutionary purpose”:

The evolutionary purpose is not the same as a vision statement. A vision statement usually reflects the ego-driven state of consciousness of the management team, who decide what they want the organization to be. The evolutionary purpose…reflects the deeper reason the organization exists

He gives examples of Buurtzorg (“Helping home-based patients become healthy and autonomous), Patagonia (“Use business to inspire and implement solutions to the environmental crisis”), or FAVI (“Two fundamental purposes: the first is to provide meaningful work in the area of Hallencourt, a rural area in northern France where good work is rare; the second is to give and receive love from clients”)

His book, if read in the context of many of the current practices of the business world, is revolutionary.  Hopefully one day it is just seen as business as usual.


Conversation #4: Personal Transformation (Freelancers, Entrepreneurs, Educators)

This conversation is about the individual.  Not just the person as “worker,” but the person as a person.  This conversation is founded on rebellion and the loudest voice in this space is probably Seth Godin, who urges people to “make a ruckus.”

Godin describes his life as a series of “projects” and has been carving his own path for decades.  He sees his role as helping to “shift the culture” and has helped people develop new mental models through his books, writing, podcasts, and courses.  In his book Linchpin, he boldly challenges our modern conception of work, “The educated, hardworking masses are still doing what they’re told, but they’re no longer getting what they deserve.

It also includes people like Tiago Forte, who writes about the opportunities that highly-skilled freelancers have in this economy by diversifying their activity and depending on different revenue sources. He argues that “full-stack freelancers” often have the ability to capture a lot of the value previously captured by institutions:

Full-Stack Freelancers respond to technology as an opportunity, not a threat. They leverage software-as-a-service and online platforms to vertically integrate a “full stack” of capabilities, instead of focusing on one narrow function. This allows them to capture a much greater percentage of the value they create, instead of giving it away to gatekeepers and distribution bottlenecks.

This conversation also includes “The Future Of Learning,” which is a broad discussion ranging from MOOCs, alternative education institutions to boot camps and academies that are reacting to the needs of people that need to continually reinvent themselves in the world.  Godin’s altMBA is a prime example of this.  In a 30-day program, he helps people “level up” their skills and mindset through a hands-on action and intensive feedback and support from a committed community.  Future of work thought leader Heather McGowan captures the mindset shift that people taking advantage of Godin’s altMBA have already embraced: “we need to stop thinking of the professional you want to be (end state) and focus on the skills you want to acquire (continuous). Instead of focusing on learning as something that happens in the first 22 years of your life, it is instead something that never ends.

Forte also writes about the emergence of “Short Tiny Exclusive Virtual Experiences” (STEVEs) with he sees at the next (an improved) iteration of the MOOC and online course platforms.  Essentially “bootcamps as personality-driven brands.”  Or put more simply, on-demand learning from people you want to learn from.  Better tools such as Zoom and slack recently enabled me to pilot my first digital learning experience (Solopreneur Shift) and the future looks promising, especially with tools such as VR and AR that will continue to eliminate barriers and threaten the current learning establishment.

This conversation also includes people that are creating new ways of living, including digital nomads, remote workers, the FIRE (financially independent, retire early) community, vagabonds, and the work by professors at Stanford around “designing your life” with design principles. While people living alternative lifestyles have always existed, I would argue that social media has lowered the walls to seeing inside different ways of life.  Part of why I became a digital nomad myself was realizing that it seemed pretty achievable based on the many people I saw embracing the model online.

Digital nomads are perhaps the ultimate expression of the “personal transformation” conversation.  They often combine the opportunities of the gig economy and technology with the ability to learn and grow while traveling.  Companies like Remote Year have popped up to tap into this market (and countless similar companies such as Hacker Paradise, Wifi Tribe and more).  These companies are offering realistic alternatives to a “traditional path” through their networks of remote job opportunities and offering their own curriculums and communities.

Which leads us to conversation #5…


Conversation #5: Fundamental Questions (Philosophers, Academics, Freelancers)

In contrast to conversation #1, this conversation looks deeper and questions our fundamental assumptions about work and life and challenges our belief that we need to have a “future of work” that is more or less similar to what we have now.  This conversation can be framed beautifully by a set of questions offered by long-time self-employed entrepreneur Nita Baum:

  1. Why do we work today?
  2. Given that the goods and utilities we need to survive and thrive are abundant, what is the purpose of work?
  3. What does this say about how our resources are and could be distributed more equitably?
  4. Could the purpose of work be to make us more individually and collectively whole- in material ways, in well-being and in a way that is conscious of the individual and the collective to the exclusion of neither?
  5. If so, how would this shift our patterns of consumption and production?

These are tough questions, but luckily ones philosophers have been grappling with for a long time.

One of the best examples of this conversation is the one Andrew Taggart has brought to life.  He is a Practical Philosopher who argues that “There may be no greater vexation in our time than the question of how to make a living in a manner that accords with leading a good life”   He has brought back to life a discussion “Total Work,” an idea first proposed by Josef Pieper in 1948 in his work, “Leisure: The Basis Of Culture.”  Taggart argues that total work is stronger than ever and “eradicates the forms of playful contemplation concerned with our asking, pondering and answering the most basic questions of existence.“ He pushes us further and argues that we make a dangerous mistake when we put “making a living” ahead of the question of “what is a life worth living” (see podcast for full discussion).

When Pieper published Leisure he argued that work was consuming life and threatened philosophical traditions of contemplation and a certain type of leisure.  He argues that because work is becoming central in our lives, we fail to imagine any type of leisure beyond anything that is beyond a break from work.

In 1951, Alan Watts argued in The Wisdom Of Insecurity that our working world turns us into cogs in a machine:

Thus the working inhabitants of a modern city are people who live inside a machine to be batted around by its wheels. They spend their days in activities which largely boil down to counting and measuring, living in a world of rationalized abstraction which has little relation to or harmony with the great biological rhythms and processes.

More recently there are philosophers like Andre Gorz, who in Reclaiming Work (written in 1999), challenges us with the line “real work is no longer what we do when at work”  by showing that when a parent decides to stay at home with children, they are deciding “not to work,” yet what is taking care of children, if not work?  He says this comes from a limiting mindset around how we define work:

it has to be a job, a profession: that is to say, the deployment of institutionally certified skills according to approved procedures.

There is a long tradition of questioning the fundamental questions around work, labor and how to live.  It may be a mistake to think this time is different.  In 1964, a report on the “Triple Revolution” was put forward to President Johnson as a way to figure out what to do when all the jobs disappeared.  More than fifty years later, the jobs are still here and we still have an economy that fundamentally assumes that one should work to earn a living.  However, given the transparency of how bad this situation is for most people (see the fact that only 37% of Americans are employed in full-time jobs), we may in fact, be ready for a new conversation.

Professor David Graeber has said that those jobs should have disappeared and that a range of different political, cultural and historical factors have meant that we have created scores of “Bullshit Jobs” to make the economy look like it is still operating as designed.  He first proposed this idea in a viral essay in 2013 that turned into a recerntly published book.  He defines a “bullshit job” as:

A bullshit job is a form of paid employment that is so completely pointless, unnecessary, or pernicious that even the employee cannot justify its existence even though, as part of the conditions of employment, the employee feels obliged that this is not the case.

Graeber estimates that almost 50% of our economy is “bullshit” and explores how this came to be from a systemic lens, looking at things such as how time became something that could be transacted (“the idea that one person’s time can belong to someone else is actually quite peculiar”), how we value some labor over others (“typically involve work that needs to be done and is clearly of benefit to society; its just that the workers who do them are paid and treated badly”), and how the labor theory of value once ascribed to by Lincoln (“labor is prior to and independent of capital”) was demolished by Carnegie’s “gospel of wealth” and the shareholder value movement of the 1970’s.

We may be in a situation where many people, as Jean-Paul Sartre would say, are operating in “bad faith.”  That is, they have adopted a set of values they don’t really believe in as a way to deny their own freedom.  When I was in business school, there was a general belief that the system was rigged and that shareholder value probably wasn’t the best idea.  “But what are you going to do about it?” people would say.  Philosophers would urge us to reconcile this gap in our beliefs and our actions and to find pursuits that are more in consonance with who we are.

Some of these ideas are being talked about, but they are often dismissed as “the way things are.”  Some people are putting skin in the game, such as Scott Santens, who has crowdsourced his own basic income while also being an ardent supporter of the idea.  He advances this conversation by using his own experience and research to bring alive some of the fundamental flaws of how we think about work, money and survival and how we think our connection to each other and place in the world.


About Paul Millerd

Paul is a writer, creator, and curious human that is passionate about how people can reimagine their relationship with work to do things that matter. He published The Pathless Path in 2022.

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