Fringe benefits

Independent work beyond the individual (part 3/3)

For someone like DC, a 22 year old ethnographer in New York doing freelance research work, life as an independent is pretty good. Though it would be nice to make more, he pulls in enough money to enjoy life in the city and he uses the flexibility of independent work to his advantage, visiting museums at times when they’re not crowded and exploring the neighborhoods when he needs an afternoon break. Having gone to school here, he is socially connected in New York yet when it comes to work DC, feels lonely. He keeps in touch with mentors and peers from his hometown and elsewhere in the country. “They keep me aloft. It’s nice to hear compliments despite what your bank account or clients tell you.” When I interviewed him, DC’s independent work was paying his bills, but not meeting his needs. Shortly thereafter he took a full-time job.

In the previous essay I wrote about macro forces that are changing the context of work. Here, in the final installment, we extend this discussion beyond income to look at the role of employment more broadly, assembling a framework of nine needs related to humans and their work. The first five I refer to as the core.

The core

Effort, Flexibility, Responsibilities, Pay, Security

The basic contract between a full time employee and their employer is an exchange of one’s effort and control over their time, in trade for pay and security. Put another way, employees are paid for their effort, but they pay the company for security by committing to regular work hours and, in effect, giving up some degree of freedom.

Inside most (but not all) companies, full-time employees are given tasks and responsibilities through the management chain of command, which more or less ensures that everyone has something to do all or most of the time. This is the value proposition of employment: one commits their effort, applied against responsibilities, in exchange for pay and security.

Independents consider the ability to have more agency in their work as a resource that can be bargained with, which means they are more choosy about giving up flexibility in exchange for security. There’s also no automatic conveyor belt of responsibilities, so some of the flexibility that independents retain is spent on finding new work—a constant pressure identified by most of the people I interviewed.

We’re beginning to see relatively small innovations in this model. Websites such as Task Rabbit, oDesk/eLance, HourlyNerd, and WorkingNotWorking have all recognized that there’s opportunity in rethinking the way responsibilities are distributed by creating marketplaces that match up individuals with potential jobs. Some of these companies also hold payments in escrow, which theoretically lends a sense of security to independents and their clients, but leaves the worker beholden to the potential idiosyncrasies of the platform.

Otherwise, there’s very little experimentation in new ways to provide security—and that’s not a lament for a European social safety net (though I do happen to think it a good idea on balance). In a country as aggressively market-oriented as the US, it’s surprising that there aren’t more companies offering insurance and financial services targeted at independents. Predatory lending aimed at freelancers will be a marker that we’ve passed the tipping point towards the project economy!

The core, as defined above, describes the economic engine that has worked for companies for ages. But employers are economic units that create social (and sometimes environmental) effects, so if we imagine a world with fewer employers we need to think about replacing their whole set of roles, not just the economic functions. These further challenges for independent work have to do with finding new avenues for identity construction, community, professional development, and scale. My focus is on the role each of these play in helping humans live and work together efficiently and effectively.


Love it or hate it, one’s job in an economy of full-time employment usually played a strong role in an individual’s identity. Of course, you could choose to let another aspect of your life play a more defining role (such as being a parent or a sports fan), but “where do you work” has long been standard small talk, just after observations of the weather. This is changing, though.

Next time you’re at a conference, look at how the speakers describe themselves in the bios. Or have a look on Twitter. What you’re likely to find resembles the right side of this diagram:

Left: 20th century, Right: 21st century

Few people seems to be happy with doing one thing these days. Being ‘just’ an architect does not seem to be satisfying, so the bio becomes a description of interests or roles in an attempt to be more representative. Many people are doing multiple things to generate income, so the answer to “what do you do” is becoming more of a tongue-twister.

But the ‘slashification’ of self descriptions also speaks to a general anxiety about being pigeon-holed, as though omitting something from the list means that the individual somehow loses that ability. As the boundaries of industries, disciplines, and professions start to blur, its natural that the language we use to describe ourselves also gets fuzzy. As an individual choice this is benign, or even positive. People should be able to describe themselves with whatever words make them feel comfortable.

Multiplied across society, however, this diversity of language translates to a cognitive tax paid every time someone takes pause to make sense of the unique way an individual presents themselves. We’re collectively spending more time making sense of each other, and that leaves less time for working together. In the industrial era, the short, universally-understood descriptions we had were actually quite useful as a way of helping people sort through large pools of potential collaborators, clients, or new hires.

In the independent economy more people are making assessments of potential collaborators more often — on a project by project basis rather than a job by job basis. In this context slashified titles are a source of friction that slows things down.

This is an opportunity: what tools, or even shorthand language, can we proliferate to make it easier to grok someone and their work so we don’t have to rely on outdated or unfit titles and role descriptors? What can augment or replace the CV and the portfolio as tools to assess someone else quickly? How might platforms allow for idiosyncratic representations of self, without losing the ability to provide aggregate views that help people navigate options more effectively?


Coworkers form an immediate community of peers, possible mentors, and potential collaborators. This has direct benefits to the work being done inside a company, because it means less time spent searching for and forming professional relationships and more time dedicated to getting on with the work.

The benefits are emotional too. Even if one is driven nuts by the annoying person two desks down, the sense of belonging that comes from working inside a company is clearly missed by a lot of independents. It’s one of the things they try to recreate by “working alone, together” in coworking spaces.

This is relevant at a broader geographic scale as well. Work-related community has been useful for a populace as mobile as ours. Along with religion and sports, meeting people at work is a low-barrier way to begin knitting oneself into a new place. As the ranks of independents rise, we can expect to see communities of interest (such as Meetups and private clubs) and communities of intent (such as coworking) playing the role that the community of circumstance inside a company played for employees in the past.

I think we probably want to perpetuate these three community ‘side effects’ even if companies are not the thing generating them. How will independents recreate or reimagine community?

Photo of San Francisco’s Embarcadero Skyway, which separated the city from its waterfront for forty years. Photo by GeraldPHawkins on Wikimedia Commons.

In the industrial era cities and regions thrived based on their throughput of goods. This motivated decisions that seem crazy in retrospect—only someone maniacally concerned with getting things and people from one place to another could justify building a highway between a city and its waterfront! But developments in the technology of physical connectivity were the basis of competitive advantage then, and so these absurd acts were rationalized.

Once connectivity is ubiquitous or nearly so, as it is now, connections become a more important competitive advantage. When you’re focused on connectivity, you worry about how easily people (and things) can come and go, but when connections take primacy the focus shifts to how easy it is for people (and their ideas) to stay. The question is not how many flights your airport can boast about, or how many containers your port can process, but how many of the people flowing through your city want to stay? Connectivity is won with quantities, connections are won on qualities.

We see this online and off at the moment. The investors backing today’s social networks are not fooled by basic user counts; they value engagement. Who’s staying, and why? Coworking spaces similarly thrive when there’s a relatively steady community of peers that show up regularly. Connectivity helps new ideas spark, but deeper connections are what develop those glimmers into new projects and companies. And connections, like the trust that fuels them, take time to develop.

We cannot confuse reputation with trust. In a fantastic paper called the Structure of Trust, Toshio Yamagishi ponders a paradox that helps reveal the difference. Why is it that companies from Japan, which is considered a high-trust society, are more hesitant to do business with unknown partners than companies from the US, a place considered to have relatively low trust? The answer, he argues, is that in a tightly-knit, homogenous society one is kept in check by the risk of upsetting peers.

This implies that what might appear to be a high degree of trust in Japanese society is actually motivated by a mechanism of ‘assurance:’ step out of line and you’re going to get it! That’s like asking everyone catching the participant of a trust fall to sign a contract. It doesn’t have the same effect when there are explicit penalties for noncompliance. Trust and risk go hand in hand.

Without risk, there is no trust, and without trust there are no relationships. Yamagishi found the culture of the US to be more willing to give a strangers the benefit of the doubt, and to contend with the increased risk by constantly recalibrating their assessment as needed. Contracts are used, of course, but every eventuality cannot be committed to an explicit legal document, and strong relationships reduce the risk of these gray areas.

As the ranks of independents rise, so do the number of connections between them, and between independents and their clients. Assurance-based reputation systems are fine for adding intelligence to transactional decisions, but they are a poor way to evaluate relationships, including working relationships. How can platforms and places go beyond mere connectivity to encourage meaningful connections? Trust is a phenomena that cannot be magically scaled with technology, but perhaps we can use technology to help us accelerate the formation of trust bonds.

Flickr and Github, two websites that have (or had) strong communities are useful examples. Both turn the native work product of their users into objects of discussion. Without any additional effort spent on documentation or packaging, the things that their users are already doing anyways become the starting point for deeper connection.

These “social objects”, to use a phrase coined by Jyri Engeström—photos with accessible EXIF data in the case of Flickr, visible code repositories in the case of Github—make it easier for strangers to get to know and make sense of someone else through their work. It’s important that these sites revolve around acts of production. A stranger can poke around and, in doing so, find the traces of how things are made, which exposes the soul of the other in unique ways.

How might the same notions be transferred to professions without such easily encapsulated work products, such as accounting or coaching?

There is a critical urban dimension to this question as well, particularly for the US, which has all but given up on public spaces. Can we reformulate our cities to endorse lingering and inquisitive inquiry around acts of production with the same enthusiasm we’ve done around acts of consumption?


Developing staff pays mutual benefits to the employer and employee, so companies have traditionally made some attempt, be it retaining talent through the availability of internal career paths, mentoring, or subsidized training. How will independents obtain the same opportunities in their own professional development without the larger infrastructure of a company?

Because independents have a number of projects instead of a single job, they’re better positioned to make a measured transition from one line of work to another. An independent workforce will reformulate the notion of professional development from the assisted movement vertically up a ladder (of titles, ability, responsibilities) to ease of exploration, horizontally, across new possibilities.

We live in a fantastic time for learning, with a profusion of online options from MOOCs offering university level content, to sites that focus on more discrete skills, akin to trade schools. Independents are well positioned to take advantage of this due to their ability to blend work and courses as needed. This is one example of how independents reap the benefits of the flexibility they retain.

Broadcast learning opportunities have seen a substantial amount of innovation recently, but situations where the emphasis is on peer to peer transfer of knowledge and experience has not enjoyed the same focused re-imagination. Independent work is zero-sum: any hour spent on professional development is not used to make money, so mentorship and other ways to learn on the job have a heightened importance.

There have been promising developments in the technology sectors with numerous accelerator programs designed to link up aspiring learners with willing mentors. In sectors that do not have similarly large potential pay offs, however, there is less evidence of this approach being attempted. The food sector is one notable exception, where programs like La Cocina in San Francisco and Kitchenette in London provide development pathways designed specifically to assist people in bootstrapping themselves into a complicated and difficult business.

Making experimentation easier for more people is positive because it means the cost of trying something else is lower, and that makes it more plausible for people to risk acting on their hunches (and being able to recover if they stumble). The physical and bureaucratic character of our cities are critical here, should we want to realize the benefits of a population who are more actively experimenting.

Having access to libraries, educational facilities, workshops, and the like are all important, but cannot remain at the entry level. For instance, a city that is tolerant of pop-up restaurants but makes it exceedingly difficult to open a permanent food business is a city that’s missing the opportunity of pop-ups. Places of low friction experimentation (pop-ups, maker spaces, coworking spaces) are ‘cool’ on their own, but they’re part of a broader transformation when they are part of an ecosystem designed to accommodate different stages of growth.


For all the popularity of hive analogies and imagery associated with independent work, there is a lack of available models for individuals to retain autonomy while tackling problems larger than the capacity of any single person. This emerged when discussing the future with successful independents like GW in Detroit. “I’ve hit a glass ceiling and how to solve that is on my radar. I would rather be able to double or triple [my income] but there’s something about being the primary person that becomes the barrier because I can only do so much.”

It’s clear that a growing number of people dislike the trappings of organizing at scale, but we are still required to find ways to act at scale. The challenge before us is to design new tools, platforms, and arrangements that reliably enable collaboration and autonomy simultaneously. The technology sector is a useful example.

The ecosystem that technology companies participate in has been proactively redesigned, between the first web bubble of the late 1990s and today, to remove friction at all points. The impressive growth in this sector is not solely tied to historical improvements in digital technology. It’s also the result of very conscious efforts at the meta-level, such as the development and uptake of the lean startup methodology, a profusion of APIs and code libraries that make it quicker to build products, and the standardization around iterative pitch decks in place of formal, static business plans.

By making the basics of business into an open and shared concern, the technology community has been able to leverage collaborative efforts, therefore allowing founders of new companies to pour competitive energies into whatever is specific to their proposition.

In its own very (very) focused way, the tech sector has essentially figured out how to conflate tool-building for personal benefit with a pro-bono contribution to the community. Social mores among software developers (and those aspiring to join their ranks) applaud giving-back in the form of publishing code libraries, sharing experiences, and clever hacks that can be re-used by others.

Websites like Stack Overflow, a question and answer site for code quandaries, allow groups to swarm around programming roadblocks and hash out solutions. Whatever answers emerge are retained as part of the public record, making it easier for the next person with a similar issue.

No single individual (or company) could do everything on their own, and yet no single entity is in control. Collaborate on the general, compete on the specific. It’s a virtuous cycle.

There’s much to learn from the successes in this particular industry, but as an example it is flawed in a fundamental way: the accelerated experimentation here has been largely funded by venture capital, which was in turn attracted by the potential of big returns. Barring substantial market corrections, this trick will not work in sectors without the lingering potential of similar stratospheric payouts.

Redesigning the ecosystem of main street, of small business, and of sectors that employ people other than the highest of the highly-educated is a ground-up challenge.

This series began by saying goodbye to Busytown and the quaint simplicity of our industrial economy, and recognizing that the lack of data about today’s conditions point to the fact that deep changes are in motion.

We looked at the motivations behind the Leading Edge and discovered that they are not anti-establishment or anti-structure, but using creative means to give themselves high-quality work experiences in an economy where those opportunities are dwindling.

In Market Realities and Network Dreams we looked at why companies have been effective vehicles for human collaboration during the industrial era, and then examined the intertwined technological and managerial changes that offer new ways to work independently with similar (though not yet equal) efficiency.

All of this came together above, in an exploration of what employers have provided to humans in the past, including positive side effects in terms of identity, community, development, and scalar ability. For each, we were focused on the effect they have on finding, assessing and working with others collaboratively.

Despite the bluster that has previously been used to promote varieties of independent work as a glossy future—from the mobile warrior and paperless office dreams of the late 1990s to today’s so-called ‘sharing economy’—there has been much more erosion of inherited assumptions than the creation of new ones. To an extent this is good news, as it implies that we’re only at the midpoint of Schumpeter’s gale, when destruction of the old is more evident and construction of the new is yet to come.

Although the basic exchange of effort and flexibility for pay and security is unlikely to disappear any time soon, there are ample opportunities to reimagine the construction of identity, role of community, means of professional development, and the manner in which we act at scale. These last four elements are the ones that have the broadest social consequences, as they are each beyond the individual, and it is their specific character that helps create a productive context for collaboration, or discourages it. In that sense perhaps we do retain some aspect of Busytown: there’s a role for everyone in this transformation. The future of independent work depends on all of us.

Researched and written with the support of the John S. and James L. Knight Foundation. All opinions are my own.