Listening Sesssion 2: Independent Workers

Reading Time: 5 minutes

The Gig Work Project hosted a facilitated gathering to explore the challenges and opportunities that independent workers face. The session was attended by 19 past, current, and aspiring independent workers, ranging from high school students in an entrepreneurship program to seasoned professionals.

In addition to offering time for participants to get to know each other formally and informally, the session included facilitated exploration of three main topics as follows.

Current Tools & Practices

We asked participants to list the tools, practices, and resources they find helpful for independent work. Themes that came up during our discussion of the most important tools available to independent workers centered on two main points:

  1. The importance of relationships for bringing in new business, including specifics like word of mouth referrals and actively making new connections for yourself and others.
  2. The importance of the “soft stuff” that we don’t always address when talking about business: health, wellness, inspiration, and connection.

When participants were asked to vote for the one tool or practice they felt was most important for them, the vast majority of people selected an item that reflected one of these two points.

You can see the full lists that were generated, including the votes for most important tool (denoted by the * icon) below.

Desired Tools & Solutions

Next, we facilitated conversation on another question: based on your biggest challenges, what do you wish there was a tool/program/solution for, but there isn’t currently? Participants were encouraged to share realistic solutions they could imagine being created, as well as magical tools for situations they don’t know how to address.

The ideas shared in this session reflected a much wider range of concerns. Some of the themes that emerged included:

  • Creating formal structures and organizations that enable independent workers
  • Ensuring everyone approaches work in helpful ways (ex. making decisions with input from the people affected or giving honest feedback)
  • Improving our own effectiveness (ex. giving us discipline or making us look deeper inside)
  • Addressing systemic issues (ex. changing how credit scores and felony records affect business prospects)

You can also see a full list of the ideas shared below.

Sales Assistance for Independents

Our final prompt reflected some of the themes we noticed in our other work. In our survey of local independent workers, “Sales” was the number one area for which respondents indicated they would like assistance. The importance of networks and direct relationships was also a recurring theme, making it hard to hire someone for direct sales assistance the way one might hire an accountant or administrative assistant. We wanted to learn more about what “sales assistance” could mean for independent workers in a network-driven landscape.

Participants emphasized how important it is for independent workers to articulate their value. The group converged on a process including:

  • Getting feedback from others about strengths
  • Developing a genuine story about an individual and what the individual has to offer
  • Being prepared to tell explain value in an elevator pitch type verbal format
  • Creating a video and/or other materials to share stories and value more broadly

While the group agreed that having an authentic story was important, some participants raised the point that showing may be more effective than telling. Context and audience were felt to be important in making this determination.


Many of the challenges identified through group discussion at this gathering present opportunities to better support independent workers. The varied degree to which participants utilized available tools reflects an opportunity for greater education around existing tools and practices that can support independent workers. There was also a clear consensus that training around the identification and articulation of one’s unique value would be helpful.

The importance of the kinds of self management skills identified in A New Skills Landscape came through in discussion, reflecting the fact that independent workers have both the opportunity to apply these skills for greater life satisfaction and the challenge of a harsher learning curve in these areas in order to be successful.

Some of the challenges participants shared don’t yet have clear solutions. There may be room for innovation in creating social and business structures that support independent workers and their clients, but such solutions would need to take into account the importance of direct relationships, the unique value propositions of individual workers, and the kind of self-direction that makes independent work appealing for many professionals in the first place.

Notes from the Facilitation

Tools currently in use:

Sales/Getting Work:

  • **Word of mouth
  • *Connecting others
  • *Referrals from existing clients
  • *Centers of influence
  • *Cross promotion
  • *Neighbors
  • Getting coffee
  • Linked-In connections
  • Social media
  • Promo codes
  • Sandler sales trainer
  • Media (broadcast)
  • Apps
  • Professionalism
  • Project events – good food & projects

Business Processes & Organization:

  • *Prioritization
  • Google Docs
  • YouTube / other internet
  • Organizing your emails
  • Mentors/advisors
  • Get out of office & go to public place
  • Facebook
  • Data visualization of connection of people and/or events/tools/items
  • Detailed proposals
  • Separate business email from social email
  • Todoist
  • Brand identity


  • QuickBooks Online
  • Excel
  • References from others
  • Save all receipts in a folder organized by month
  • Accountant
  • Keeping receipts
  • Tax write offs
  • Post expenses and income daily/regularly – don’t let it pile up

Time Management:

  • **“Eat that frog” – do the thing you’ve been avoiding first
  • *Toggl – online time tracking
  • Careful calendaring
  • Google Calendar
  • Google Drive
  • Templates
  • White board & post-its / time log
  • Set calendar appointments for to do tasks
  • If it takes less than 5 minutes – do it now!
  • Outlook Calendar on smart phone
  • Proprietary systems (made up system)
  • Self awareness – know how you work best
  • Scheduled disconnected times to focus exclusively on tasks/projects
  • Strive to not work on weekends
  • RescueTime (online tool)


  • Informal (free) advising
  • Sharing of templates with others and download/internet research
  • Legal Zoom
  • Copyright
  • Sharing contract templates
  • Don’t fuss until you’re making real money
  • Ownership
  • Business publishing


  • ***Music
  • *Seeking outside (not invested) counsel from people who love/trust you
  • *Making sure you’re mentally/physically healthy
  • *Read! Stay up to date any way possible. Learn.
  • *Wandering
  • Meditation
  • Prayer
  • Exercise
  • Talking with people
  • Yoga
  • Unpaid, fund versions of work-like projects
  • Eating at the same time every day
  • Work/Life Balance
  • Staying away from “vampires” (people who drain energy)
  • Listen to anxiety

Tools We Want:

  • Remove differentiation between W2 employees and 1099 contractors
  • Critique of entrepreneurship as “the way out” for poor (minority) populations
  • Alarm or shock collar for people making decisions about others not in the room
  • Tool that differentiates between urgent and important
  • Work-Life Balance tool/alarm
  • Tool or list to see what work is available: marketplace / flea market for projects
  • Business structure or “stable” can plug into as an independent worker
  • Upon delivery of a project-end report, automatically get honest feedback
  • Get rid of credit scores – make loan decisions by judging the business
  • Simple way to know when something is coming up for clients
  • Well-respected community of independent workers where everyone does get work and you can vouch for each other
  • Training on how to market what you’re really good at
  • Tool that allows you to see future value (if you use support from person x, you know it will be valuable)
  • Business plan success predictor
  • Tool to make you look deeper inside
  • Tool that gives you discipline
  • Non-BS calendar: shared view of all activity in a sector
  • Project concierge: people who hustle for you, so you can just produce
  • Place to drop in and bounce ideas around
  • Felonies don’t limit job options
  • Networker – pulls up people you need, keeps in touch
  • App for youth with ideas to share: feel supported, other young entrepreneurs
  • Dumpster full of cash

A New Skills Landscape

Reading Time: 7 minutes

Many employers and commentators acknowledge the need for baseline, non industry specific skills in all workers. This has been discussed here previously in the Collage Career1 post. Demand for skills like problem-solving, leadership, communication, organizational skills, and computer skills all point to the changing nature of work: highly networked, fast-changing, less stable, and more creative.
These high level skill sets are frequently being sought without attention to their basic building blocks. Leadership and creativity, for example, require time and space for reflection. Yet few companies that want leadership or problem-solving skills in their workers create structures for this time and space, and few educational programs teach individuals how to do so for themselves.

The model that follows provides one perspective on how we might think about the core building blocks needed to develop highly skilled workers. We need to relate deeply with self, with others, and with information.

Screen Shot 2016-07-10 at 4.00.38 PM

Self Management Skills

Self management refers to all aspects of how we relate to our own experience, including our thoughts, feelings, and behavior. An often under appreciated skill set in the working world, imagine the implications of being strong or weak in these areas:

  • Motivation and self discipline
  • Ability to focus and direct attention
  • Self knowledge, including awareness of strengths & weaknesses
  • Intersection of self perception & behavior (ex. confidence)
  • Working with emotions
  • Self care and personal health
  • Tolerance for change & uncertainty

Many of these skills greatly influence worker productivity and engagement. Weaknesses like flying off the handle when upset, volunteering for projects better suited to a colleague, or failing to motivate oneself to finish tasks can have radical effects on a workplace. Independent workers often have more freedom to develop these skills, but also more room to flounder if they haven’t mastered them.

While we don’t often think of these areas as “skills,” they are just that. Tools and frameworks for improving in these areas abound, from personality2 and strengths3 assessments to mindfulness practices that are proven to improve focus4 and reduce emotional reactivity.5 As these tools are becoming popular in workplaces, we need to guard against the tendency for a “one and done” mentality with the expectation of miracle results. Developing self management is a complex process. What works for one person may not be effective for the next. A big part of developing self management skills is allowing space for regular reflection and exploration.

Social Skills

Modern workplaces also require us to work with others in a meaningful way, making social skills like cultural literacy important. Without awareness of the cultural norms within different groups, collaboration and communication are often riddled with assumptions, misunderstandings, and distrust. Similarly, understanding social power structures within organizations makes a real difference in our ability to navigate our work environment and get things done.


Few will deny communication is a necessary skill in the workplace, yet “communication skills” are often oversimplified. Courses that teach professional communication skills often emphasize just one or two aspects while ignoring others. For example, learning to present ourselves clearly and confidently, including verbal and nonverbal cues, can be helpful. But if we ignore the importance of building authentic relationships or how to express emotions in a productive way, communication will remain shallow and ineffective. The best communicators combine knowledge of social dynamics with self management skills.

Similar to self management, social skills and communication are messy. While frameworks like Non-Violent Communication6 and Crucial Conversations7 give us tools to create more systematic and useful approaches, part of the skill we need to cultivate is the self management ability to tolerate a degree of uncertainty in our interactions with people.

Organization Skills

Modern work experiences require us to manage ever increasing amounts of information. Organization skills, which help us track and organize that information for maximum usefulness, are critical.

Much of this fact results from the technologically-driven, networked nature of contemporary work. As a result, the ability to use software, either on computers or phones, is also important.

Most white collar jobs require workers to manage the following types of information:

  • Tasks
  • Files
  • Contacts
  • Emails and other communications

Software abounds to manage this information. As software becomes more varied, it’s no longer enough even to have strong skills in a specific software suite. We need to be skilled at learning new systems.

And even more important than being skilled at learning the technical requirements of new systems, is being flexible enough to change behavior to mesh with those systems. Being organized requires behavioral shifts like batching tasks and doing certain things at certain times.

Even though technical skill requirements vary according to the work, the general ability to systematize and organize information is important for everyone. For example, if we call instead of email, we need to have a system to make sure we call people back. And regardless of job type, finding and applying for work requires keeping track of information.

Group Process

“Collaboration” is a skill often quoted by employers as important for their workforce. Collaboration is essentially another name for group process, which combines the ability to communicate with the ability to organize work so people can accomplish things together. I use the phrase “group process” to highlight the importance of specific structures and processes for working together. Collaboration is often referenced in an amorphous way, referencing the overall fact of working together as much as a defined set of skills. The field of group process, on the other hand, includes tools like decision-making models8 and facilitation methods.9 We can maximize the rewards of collaboration—smarter decisions, greater productivity, and more engaged workers—by using structures that are designed to support collaboration.

Time Management

Time management marries organization skills and self management skills because time can and should be managed in more than one way:

  1. As an objective resource with discrete bits of information about when we are doing certain things – ie. calendaring.
  2. As a subjective reality that we experience in a personal way moment to moment, and that carries with it personal realities like moods and energy levels.

While time management skills have long been important for all kinds of workers, it becomes more so as the workforce shifts toward greater complexity, flexibility, and autonomy. Contingent workers often make their own choices about when to work on what, while many employers are waking up to the need for options like flex time for traditional employees.

Providing workers of all kinds with more flexibility in their schedules provides the opportunity for them to care for themselves better and feel a sense of autonomy, leading to greater worker satisfaction and productivity. Doing this effectively requires self management: knowing enough about personal energy cycles to establish an optimal sleep schedule, to schedule high-focus work at a time of day when we feel most focused, and to reserve time at the right moments to refresh and re-focus when we feel drained.

Greater flexibility can be fundamentally helpful to both workers and companies, to the extent that workers learn how to understand their needs (self management skills) structure work around them (organization skills), and set expectations with other workers accordingly (communications skills).

Relationship Management: Network

The degree to which we succeed as workers is most often a result of our network. We know the adage that “it’s not just what you know, it’s who you know,” but more to the point, it’s what those people are willing to say about us. In a world where jobs are less stable and individuals are more likely to be contingent or self-employed at some point, no one can afford to ignore their ability to obtain work. That ability often boils down to whether people are willing to recommend us. Referrals become even more important as employers and clients realize that industry-specific experience can be less important than attitude and the types of overarching skills identified in this post.

Many of the most highly desired workers have all the skills described in this post. Organization skills form the backbone of our ability to get the right things done and be productive. Knowing ourselves, managing our energy, and communicating fluidly are mandatory in a highly connected, complex economy.

We don’t have to look at complex work to understand why these basic units are so important. Imagine a “people person” who makes a great impression at first, but whose lack of organization skills causes them to lose your phone number and forget to call you back. Or a highly organized person who can’t manage their emotions and is unpleasant to work with. Or a really insightful person who struggles to communicate and collaborate. Would you recommend any of these people to a close friend or colleague who is seeking a new worker? Certainly they wouldn’t be able to negotiate the best compensation or get the best contracts. At the end of the day, we are unable to build trusting professional relationships and expand our network of allies without skills in the Self, Others, and Information spheres.


While these skills are important for all workers, they are especially important for independent, project-based workers. Independents rely more deeply on their networks since they seek new work more often. Additionally, self-management, social, and organizational skills give us the adaptability to work effectively when we encounter new team members, technology platforms, and organizational structures at the start of a new project. In fact, working as an independent can be a form of trial by fire for developing these skills, making us more ready to tackle changes even within a traditional full-time job.

The changing world of work asks a lot of us. While it behooves us to know and play to our strengths, the model proposed here suggests that we all need core skills—self management, social, and organization skills—that are often described as being separate or mutually exclusive. This separation of strengths is often encouraged by current personality models. Most people have higher natural competence in one area, and may feel uncertain about their ability to become more socially fluent, computer savvy, or organized if that isn’t a current strength.

Developing and integrating skills in all these areas would radically change our experience of work for the better. There are frameworks, tools, and models for learning every one of them. And yet the percentage of time spent on teaching them, whether in schools or professional development circles, is limited. More troubling, access to this kind of development is generally a privilege for people who already have a leg up. These skills largely determine work success, which in turn increases the availability of time or money to invest in further development: a classic example of the “success to the successful” systems trap.10 In order for companies and workers to succeed in our dynamic economy, we need to incorporate the development of these core skills in educational and work experiences—for everyone.

Questions for further consideration:

  • 8.1 What should be the baseline minimum skill level in these areas, regardless of industry or role?
  • 8.2 How can we integrate learning in these core areas into companies and educational settings?

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