Espresso at Fuglen Asakusa in Tokyo

Rethinking work beyond the factory

What software developers teach us about the future of collaboration

I recently completed a two-week creative residence at Almost Perfect in Tokyo. I split my time on the trip between working on Booklet and exploring Japan.

The Almost Perfect residence runs continuously, with two residents at a time. Each residency concludes with a public gallery showcasing the resident’s work. Many residents are artists who present visual works crafted during their stay. For instance, my co-resident Stu presented illustrations inspired by his explorations of Tokyo.

I wasn’t sure what kind of gallery to host because I was an odd “technology” creative with no drawing skills. I considered ideas ranging from a wall-sized mind map to a prototyping workshop. I settled on presenting an “artist statement” about my work at Contraption Company.

The surrounding Kuramae neighborhood, a historic home to craftspeople in Japan, inspired this presentation. The tools craftspeople make for themselves can change the world - such as the printing press. This presentation explores work’s future through the lens of software makers.

Flyer for the presentation at Almost Perfect

I gave this talk on 3 February 2024 at Almost Perfect to a small crowd of artists and technologists. The presentation was not recorded, so this essay adapts it to a written format.

I also recorded this talk if you prefer to listen to it on the Contraption Company podcast, or watch it on YouTube.

Rethinking Work Beyond The Factory

In the era of the Internet, people create economic value by thinking. This “knowledge work” differs starkly from manual labor. Yet, the ways we organize digital work still resemble assembly lines.

Technology Solves Our Problems

Humans leverage technology to solve their problems.

As hunter-gatherers, humans had scarce food. Farming technology solved this problem, making food supplies more stable.

As farmers, scarce land resulted in fiefdoms and wars. The steam engine started industrial economies by enabling more efficient production and transportation.

As factory workers, labor was scarce. Making more cars required hiring more people. The Internet, computers, and robotics enabled humans to automate processes.

Today, we are in the Information Age. Cars drive themselves wherever we want to go, guided by satellites. We grow food in robotic warehouses. We can instantly communicate with anybody, anywhere in the world. Work happens with our minds instead of with our hands.

People today generally have food, shelter, and jobs. The new scarcity is attention. Netflix, YouTube, TikTok, and your job compete for a limited number of waking minutes daily.

Boredom is going extinct.

Industrialization introduced the work practices we recognize today

A standard job consists of commuting to a workplace for eight hours, five days a week, as an employee of a corporation. We hold this style of work as sacrosanct today. Yet, it is relatively new - Henry Ford standardized this model fewer than 100 years ago.

Before industrialization, work was different. As farmers, people mostly worked from home. They didn’t have the technology to commute. Their work wasn’t on a strict schedule, and its tasks varied by season.

The Internet made knowledge work mainsteam

Computers and the Internet changed the nature of work and transformed the economy. Collaboration has become globally real-time and instant. Knowledge workers create value by manipulating ideas and information. Robots are replacing humans in all manual labor - from factories to driving to warfighting.

Yet, how we work hasn't caught up

However, our labor practices haven’t yet adapted for the Information Age. We still live like factory workers - commuting to a workplace for a 40-hour work week in 9-5 shifts with repetitive work as an employee at a big corporation.

Industrial practices make knowledge work abstract, arbitrary, and bureaucratic. Software engineers are changing work to restore autonomy and craft.

Before Ford, craftspeople filled factories doing autonomous work. Workers hated it when Henry Ford introduced his assembly line and began quitting. Ford had to double wages to get people to stay.

Applying the factory model to knowledge work today continues to make us miserable. We hire based on abstract teamwork qualities, enforce arbitrary working hours, and deal with management bureaucracy.

We cannot measure the productivity of knowledge work the same way as a factory. Technology automates, so every workday brings different and new tasks. Different people solve the same problem in different ways. The maker’s personality comes through in their work.

Today, developers are rethinking their trade to restore craft and autonomy. Craft and autonomy enable developers to solve complex problems with uncertain solutions. Along the way, software engineers create tools to make their work more efficient. We will look at these tools and workflows today.

About me - Philip I. Thomas

My name is Philip, and I am here at Almost Perfect for a two-week creative residency.

I am unusual among the residents at Almost Perfect because I am a “technology” creative. I build software applications that help people work online.

I studied systems engineering at university and apply this “systems” lens to my work today. When considering a change, I analyze its second and third-order effects on the overall system. I draw inspiration from cities, infrastructure, and food around the world.

This trip is my first time in Japan. I spent the last two weeks exploring the country, keenly interested in work culture and urban planning. I spent most of my time wandering in Tokyo, with a brief excursion to Morioka.

In the past I founded Staffjoy and Moonlight, and now I run Contraption Company.

I founded three companies in the past, all focusing on rethinking work for the Internet age.

Staffjoy built scheduling software for app-based delivery workers. My senior project in university applied math to increase flexibility for hourly workers. Staffjoy commercialized these algorithms. The company raised venture capital, but failed to achieve mainstream adoption. Today, it lives on as an open-source project, which we will discuss later.

Moonlight sprung from my experiences building Staffjoy. It helps companies hire remote software developers. I built the company while traveling full-time around the world. The company became profitable, raised venture capital, and was acquired in 2020. It continues to operate today.

Contraption Company is my current business. I founded it almost two years ago.

The Contraption Company is a studio developing tools for online work.

The Contraption Company is a product studio developing tools for online work. There, I build three main products. Booklet is an asynchronous community app that is alternative to chat. Postcard lets anybody make a personal website in five minutes. And FRCTNL is a community for part-time technology workers.

We will talk more about some of these products later.

I'm building Contraption Company to promote craft and autonomy.

I’m building Contraption Company in a different way than my past startups. I structure the company in pursuit of craft and autonomy. I avoid time constraints when developing products. The company structure supports operating multiple long-term products. And, it is a one-person business - me - with occasional help from contractors.

My day-to-day work consists of coding in coffee shops around New York City. I write the code for Contraption Company products myself.

Trends we will look at today: Smaller, remote companies; less rigid work weeks; written, async collaboration.

This presentation will look at three trends among software developers that may become mainstream: Smaller, remote companies, less rigid work weeks, and written, asynchronous collaboration.

Change 1: Smaller, remote companies

The first trend we will discuss is smaller, remote companies.

Moonlight's history: Companies resisted remote, then it became the norm.

When I co-founded Moonlight in 2017, I believed remote work could help startups grow.

Remote work was a hard sell in 2017 - most companies insisted only on hiring on-site employees. A handful of companies believed in remote work and helped Moonlight grow. But, most companies told us they would adopt remote work in a decade or two.

As COVID lockdowns began in 2020, these companies adopted remote work overnight. They already had the necessary tools, so the transition was smooth. As lockdowns lifted, few companies returned to their offices. Momentum had been the only thing preventing the adoption of new, better practices. After a change in norms, momentum prevented a regression to offices.

At first, companies moved their old office routines online. Recently, they began to rethink work to be remote-first.

The way companies worked during COVID remained primitive by remote work standards. People’s routines stayed the same, sans a commute.

Now, companies are rethinking the first principles of work for a remote team.

Remote-native teams: Hire best person, anywhere in world; Pay based on abilities instead of location, local economy, or seniority; Flexibility in location and government

A “remote-native” team can hire the best person for a job, regardless of where they live. Today, most “remote” companies have not achieved this vision of transcending time zones. Once they do, it completely transforms the business, enabling them to operate 24/7.

In the past, companies based salaries on the local cost of living. An office in New York City paid more than one in Arkansas for the same work because living in New York costs more. Remote work is changing compensation from cost-based pay to value-based pay. Companies no longer pay a premium to live in an expensive place. Many workers increased their quality of life by relocating to cheaper areas.

Remote work affects developing economies dramatically. There, one software salary can create secondary jobs. A high-earning worker may hire a cook, cleaner, and nanny. But, local startups now compete with high-paying American corporations for employees, which hurts local innovation.

Remote work creates flexibility in location and local government. I spent two years as a digital nomad, working and living around the world with only a backpack and suitcase. Governments are adapting to attract high-earning remote workers. Japan just announced a digital nomad visa. Applicants must have almost twice the salary of the average Japanese worker. Many other countries have similar schemes.

Location flexibility among workers is changing government. In the past, people could only change their government with votes or revolutions. Now, governments compete for residents. In the USA, remote work triggered an exodus from San Francisco to Austin for lower taxes and cheaper housing. People may also choose a government based on the policies they want. Surrogacy laws, public transportation infrastructure, and welfare programs become differentiators.

Remote work gets rid of boring commutes. But it also flattens the global labor market, creating competition between governments.

Big teams used to be how factories made more money. Now, big teams mean beaurocracy and high costs. Small teams are more profitable.

For an industrial-era factory to make twice as many cars, it had to hire twice as many people. Capital was leverage for the business.

When Elon Musk bought Twitter, he decreased the size of the team by 90%. While Twitter has problems, the site generally still works. Decreasing the team size by 90% without a significant outage is remarkable. That would have never worked in a factory.

Elon’s changes triggered other tech companies to confront problems of bureaucracy and over-hiring. Investors now encourage companies to keep teams small because efficiency drives profit.

Software scales infinitely. Instagram had 13 employees when it sold for $1b. Whatsapp had 55 employees when it sold for $19b. Who will make the first one-person $1b company?

Before my presentation, I talked to Luis about his favorite illustration software, Procreate. A lifetime license costs only $12.99. Procreate’s model works because software scales infinitely. After developing the code, selling one extra license costs the company nothing. Software is like a book - the product work is all upfront.

Software’s scalability means that a small team can have a disproportionate impact. WhatsApp had 55 employees when it sold for $19 billion. Instagram had 13 employees when it sold for $1 billion. And people soon expect a billion-dollar, one-person business to emerge.

With software, you don’t need to hire a big team to be successful. Small teams can serve infinite customers.

Middle management is going away. One person can do the work of an entire team. AI is accelerating this.

Industrial career paths involve a ladder from individual contributor to manager to executive. Technological advancements are reshaping this model.

Since Elon’s downsizing trend, many middle managers have returned to individual contributor roles. Recruiting and hiring used to be a core task of technology managers. With a trend toward smaller teams, there’s less recruiting work. Improvements in communication enable executives to talk directly to employees instead of relying on managers.

Technology advances continue to make workers more productive. A single individual can now manage tasks that previously required a whole team. Amazon Web Services enables a solo developer to spin up a data center of servers and databases in a few minutes. Figma allows a designer to prototype a clickable application in an afternoon. Mailchimp enables a marketer to contact millions of customers in minutes.

Demo of using AI to write code in Cursor

Artificial intelligence is further accelerating these productivity gains. I talked with many people in Japan about how AI could affect their industry in the future. For software developers, AI isn’t a future trend. It’s already a tool they use every day.

This video shows how I used AI today to help build a Booklet feature. I provide some natural language directions, and then OpenAI writes code. And it writes quality code.

In the past, a senior engineer would manage a team of junior developers. Now, that senior engineer can manage AI instead and get as much done. These AI-enabled senior engineers, sometimes called “centaurs,” are wildly productive and efficient.

AI tools make me more productive, enabling me to work alone instead of hiring a team. AI is driving a new wave of creative output by enabling solo creators.

New problems are emerging: Decoupling of work and social; Isolation and loneliness; Changing cities; Hard for new graduates to learn.

With remote work and smaller teams, new problems are emerging.

The decoupling of work and social results in loneliness and isolation. Offices anchored many people’s social lives. They would see the same coworkers daily, have social lunches, and chat at the water cooler. People met friends and even spouses at work.

To make work-from-home sustainable, people need to leave their homes. But many people don’t have a place to go. Car culture and suburbanization created sparse landscapes of isolation.

Remote work changed cities. Business districts feel empty, and their restaurants are suffering. But, walkable city neighborhoods are attracting remote workers seeking connection.

I live in New York City, which used to cater to commuters who drove from suburbs to downtown offices. While a massive 23% of New York offices are vacant, a low 1.4% of apartments remain empty. New congestion charges further discourage commuter car traffic into the city.

Cities are not dying - they’re shifting to be more residential.

Finally, it’s a weird time to be entering the workforce. Companies used to spend months training new hires in anticipation of a long career. With work becoming more transactional and efficient, new hires have to produce immediate value. Exam-focused education ill-prepares graduates for ambiguous, project-based knowledge work.

Change 2: Less rigid work weeks

Next, we’ll discuss the second trend: less rigid work weeks.

With remote, nobody sees how long you sit at your desk. People are judged based on their output.

Before the Industrial Revolution, only the wealthy had access to clocks. Assembly lines required people to be at their stations at the right time for the factory to operate. So, workers had to start caring about punctuality.

In remote teams, nobody sees how long you are sitting at your desk. Instead, you’re judged primarily on your work output. Performative acts of “looking busy” no longer matter.

In a factory, output was determined time input. In knowledge work, output is determined by both time and intensity input.

In a factory, productivity was generally a factor of time worked. People had to stand on an assembly line to manufacture cars. Working twice as many hours could produce twice as many cars. We standardized pay based on time.

With knowledge work, work output is no longer a pure function of time but also the intensity of focus. This change means that the value somebody creates per hour may be inconsistent.

4 hours of intense focus outperforms 8 hours of moderate focus.

In knowledge work, four hours of intense focus produces more than eight hours of moderate focus. The ability to control attention and focus is a rare skill among modern workers.

Companies have begun to adapt to incentivize focus. New “Results-Only Work Environments” measure only work output, not hours. Working faster lets you finish earlier.

Fractional work trend: Experienced engineers are choosing shorter workdays instead of higher pay.

One of the trends I’m interested in right now is fractional work. Fractional work is a midway point between freelance and employment. It typically is a half-time job with a company, paid weekly or monthly. This arrangement has more stability than freelance and more autonomy than employment.

Fractional roles allow experienced workers to choose shorter workdays over higher pay. In the age of scarce attention, they free up valuable time for various pursuits. Fractional roles enable raising children, pursuing hobbies, and starting companies. Some even work multiple fractional roles to diversify their income.

FRCTNL is a community for fractional workers I build, and is growing quickly.

On a whim last year, I started FRCTNL as a community for part-time technology workers. Since then, the community has been doubling in size every month. Its members are technologists pursuing part-time work.

Businesses say that a fractional senior engineer costs less and produces more than a full-time junior engineer. New part-time work tools rethink the fundamentals of recruiting and payroll.

Fractional work feels like a new frontier.

Fractional brings new problmes: Shared ownership made Silicon Valley culture; Work becomes transactional; Less social support, such as healthcare; People not spending free time in high-quality ways.

Fractional work signals a rethinking of the traditional 40-hour work week. But, a move toward fewer working hours comes with challenges we need to address.

A core Silicon Valley innovation was making every employee a co-owner in the business. A typical technology job includes a mix of cash and stock - sometimes half and half. Stock incentives align everybody to care about the company’s success.

Fractional work typically includes only cash compensation, not equity. Removing equity compensation decreases the alignment between workers and the company in the long term. Cash compensation makes work more transactional and gives workers less upside.

Stock-based compensation made many workers rich. However, the recent downturn wiped out the value of many workers’ stock, leading to resentment of the model. A generational shift could replace stock-based compensation with more time for personal “side hustles.”

In the USA, social systems do not support self-employment. Corporations mostly organize healthcare, parental leave, and retirement, not the government. Navigating these systems as a small business takes a lot of work.

Finally, fractional workers have to contend with what to do with spare attention. Many will spend newfound time on low-quality leisure, such as TikTok or YouTube. Encouraging high-quality leisure that promotes creativity and happiness will be a societal challenge.

Change 3: Written, async collaboration

The final trend we will discuss is written, asynchronous collaboration.

As communication got easier, we started communicating more. Memos, then emails, then chats. Now, average knowledge workers check email and chat every 6 minutes.

Technology has enabled progressively easier communication - from books to email to SMS. The reality is that the easier we make communication, the more people communicate. When IBM first switched from paper memos to email, within days, they saw communications increase by five to six times.

As businesses embrace chat products such as Slack, communication volume further increases. The overhead of monitoring communications now overwhelms knowledge workers. Most knowledge workers now check chat or email every six minutes. Over-communication disrupts the work we’re so busy talking about.

I analogize business chat apps to Facebook’s newsfeed. We know that social media feeds present a never-ending supply of low-quality leisure. Now, chat distracts workers with a never-ending stream of new, low-quality messages to read at work.

Over-communication harms concentration and productivity.

You’re tired from physical work at the end of a factory workday.

You’re tired from intense focus and context shifting at the end of a knowledge workday.

Over-communication hurts concentration and productivity by introducing constant context shifts. A rule of thumb for online groups is a single message gets read one hundred times. By making it easier to send, we’ve burdened readers with decoding sloppy messages. This constant multi-tasking destroys work intensity and leads to mental strain.

Over-reliance on chat reveals a deeper disfunction in the structure of knowledge work. Workers chat to seek consensus on unclear work tasks and assignments. Remote-first work environments need a more structured way to organize and assign work.

Open-source software powers the world. People work, for free, on free software. But, open-source has no meetings. It's entirely asynchronous.

To learn how software engineers self-organize their work, I want to discuss open-source software.

Open-source is a culture of software developers working for free on free software. Open-source software permeates the world, powering every device, application, and business. iPhones use an open-source operating system called FreeBSD. Most web applications use an open-source SQL database. Almost half of websites use WordPress, which is open-source software. And almost every programming language anybody learns to code on is itself open-source.

Open-source software powers the world, but it has no meetings, no Zoom calls, and rarely has chat. It’s entirely asynchronous.

Next, I want to highlight two open-source tools engineers have collectively built.

Git is the collaboration tool that software engineers built for themselves. It allows people to work asynchronously, and additional software such as Github builds on Git to allow review and merging of work in an asynchronous manner.

The first tool is Git, an open-source collaboration tool for code. Almost every software engineer uses Git, through Github, to submit and review work.

Software work is typically organized into Issues. Developers get assigned an Issue or pick an unassigned one to work on. The developer writes code and then submits it for review. Github assigns reviewers who leave comments and either approve or reject the code. Reviews often include automated tests, which enforce expected functionality and style. Accepted code can get merged and deployed, marking the motivating Issue as closed. Git maintains a log of who did what work and when.

This workflow is explicit and unambiguous. After submitting code for review, coders don’t wait for feedback - they move on to the next Issue. Instead of constant context shifts, coders batch their attention to work on one thing at a time. Every step has a clear owner - from tasks to reviews to revisions.

Even Bitcoin was invented to enable more asynchronous work - its protocol allows value to be moved without waiting for a central bank or authority to release it.

The second tool I want to highlight is Bitcoin. Bitcoin is an open-source software whose origins are in enabling asynchronous payments. I know that the cryptocurrency industry has had drama. But, the underlying technology allows people to move money without waiting. Banks are a synchronous technology - you can only withdraw money if they are open. Bitcoin addresses the limitations and processes that slow down commerce.

Waiting on others is a leading cause of systemic slowness. Developers pursue asynchronous, non-blocking systems like Bitcoin to make systems more efficient.

Remote work is changing to require lower attention: Clear work tasks, organized in a tracker; Asynchronous communication; Work submitted and reviewed centrally.

Git and Bitcoin signal the future of collaboration, with clear ownership and no unnecessary waiting.

Structured processes enable open source to build massive projects with little coordination.

'I stopped pushing decision-making down. I pulled it in.' - Brian Chesky, CEO of Airbnb, on their organizational changes.

Communication is closely tied to how organizations make decisions. Airbnb is pioneering a shift toward structured, centralized decision-making in technology companies.

During the pandemic, Airbnb almost died because nobody was booking vacation rentals. Its CEO, Brian Chesky, used the abrupt change as a time to rethink core processes. Airbnb used to work as a consensus culture, where Chesky set high-level goals, and individual teams separately generated plans to achieve them. Now, Chesky centrally decides what the entire company does. He calls it “micro-managing,” but it’s created agency for the CEO to make changes. He no longer fights against momentum to get things done.

Historically, knowledge workers had freedom in what to work on. This led to over-communication as they sought consensus on decisions.

Airbnb’s style shifted to freedom of how to work. With clear objectives and decisions, teams can focus on implementation.

Top-down mandates shift the role of managers from coordinators to operators. Succeeding in this environment requires a deep technical understanding of the team’s work.

Changing how Airbnb makes decisions helped the company emerge stronger from the pandemic.

Chat is a tool for urgent communication. We need a new tool for important communication.

When you look at the communication patterns within Airbnb, chat doesn’t suffice. The CEO can’t share a company roadmap or product spec in a text message-length chat to the entire company. Chat isn’t built for long-form communication. The message could get missed or lost. An instant message from the CEO causes the whole company to stop working and shift contexts.

Chat is a tool for urgent, real-time communication. But, non-urgent information gets lost in it.

We need a new tool for important communication - announcements, decisions, and reports. These types of communications may take thirty minutes to read and understand.

Knowledge workers should plan dedicated communication time every day instead of messaging constantly.

Booklet is the communication software I build to make communication more asynchronous.

Booklet is the software I’m building to make communication more calm. It is an asynchronous community app that is an alternative to chat. It looks like a modernized email group software. I launched it three months ago and continue to work on it daily.

Slow, long-form communication is the core of Booklet. It batches all new posts and conversations into one email summary per day. Booklet keeps everybody informed, without bothering them.

Booklet’s first customers started hobbyist groups. Over time, more professional organizations use it. For instance, investment firms use Booklet to build founder networks. Companies are using it to communicate between offices in different time zones.

Every creative project starts with an insight. Since launching Booklet, I’ve been building features responding to customer requests. I used my residence at Almost Perfect as a time to return to the original insights behind Booklet and build features I wanted. I added progressive web app support, OpenAI-powered search, and more.


In conclusion, today’s work practices are relatively new, and are undergoing a significant shift.

Industrialization introduced the work practices we recognize today: Commuting to the workplace; 40-hour work weeks with shifts; Repetitive work in a corporation

Industrialization introduced the work practices we recognize today: commuting to the workplace, 40-hour work weeks with shifts, and repetitive work as an employee of a corporation.

Trends in software engineering signal the future: Smaller, remote teams; Less rigid work weeks; Written, async collaboration.

In this presentation, we looked at trends in software engineering that signal the future of knowledge work: Smaller, remote teams, less rigid work weeks, and written, async collaboration.

We have new problems to address: Loneliness and isolation; Low-quality leisure; Disorganized communication

But there are still new problems to address. These changes create issues such as loneliness and isolation, more time on low-quality leisure, and disorganized collaboration.

Thanks for joining my presentation, Rethinking Work Beyond the Factory, by Contraption Company.

Thanks for joining my presentation, Rethinking Work Beyond the Factory, by Contraption Company. Learn more about my work and products at, and subscribe to my essays to get more thoughts about the future of knowledge work.

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