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