Designing a Freelance Life Part 1: The Brief

April 24, 2013 — 10 Comments


A recent article on the freelance workplace refers to an Intuit study that predicts 40% of the workforce will be freelance by 2020. To many, this is an exciting idea where talented and creative individuals get to leverage their skills free from the tyranny of the “boss.” To others, it is a scary proposition where individuals work crazy long hours with none of the traditional perks and protections of employment. What interests me is: How might we be intentional about the design of a freelance life such that we get more of the former and less of the latter?

What are the tools that we need to manage freelance careers? What are the new behaviors amongst individuals and corporations that might make freelancing sustainable? How might our social structures and education systems have to change to accommodate this shift in work style?

I would love to come back to this topic from time to time. What are the questions we should really be asking? Where might we look for insights and inspiration?

How have you designed your freelance life?

(Posted also on my LinkedIn Thought Leader blog)

Tim Brown


10 responses to Designing a Freelance Life Part 1: The Brief

  1. Freelancers need cooperatives. I can’t do everything myself, not well. I can’t be the accountant and do the marketing and install new device drivers and set up an MS Access database and do the job I’m good at. Payment for services is a problem because is you are, for example, a freelance writer/editor, the computer guy doesn’t my services so barter or even a local exchange trading currency doesn’t seem to be the answer.

  2. I think exploring the notion of free agency opportunities that allow one to be a specialist compared to those (most?) that demand one becomes a generalist would be good. I suspect the value creation and rewards are skewed toward specialists. It may be that the economic drag of becoming a generalist is not worth moving from specialist employment.

  3. Heather Parker April 29, 2013 at 5:27 am

    Design thinking is, really user-centred thinking. So designing a freelance life, is about designing a life that suits you best. I’ve been successfully freelancing for years, and have some thoughts that may be worth tossing into the discussion:
    1. Like business, know when to outsource. I have a financial manager, and a tax guy – both low retainers, both worth their weight in goal. I outsource technical stuff (site design etc). Everything else, I can and do undertake myself, as I am my own business, and am best placed for to market and deliver in my own niche.
    2. Design balance. I find a spreadsheet handy: it helps me track what I’ve done for who for billing purposes later; but it also has lines for “exercise”, “people”, “fun”. Your social capital and your health are non-negotiable, but often neglected. If I’m getting less then three checks against any of those in any one week, I know I’m heading for trouble.
    3. Design boundaries. For freelancers, the law of diminishing returns kicks in quickly. Know when to call it a day, and when to say no.

  4. Andrew Arehart April 29, 2013 at 7:33 am

    I appreciate Terry and Heather’s comments on subbing out/networking certain tasks. I think the perception of freelancing can be inaccurately solitary. It can, however tend towards siloing…doing things your way without being aware of other modes.

    Tim, your question about how the educational system relates to this is pertinent. The general system in place now is said to have been built with an industrial mindset to produce suitable workers for the industrial age. This is more evidence that our society will function more effectively if our systems are growing in tandem, which I believe is possible. A step in this direction is broader recognition of our evolving education and employment needs by the people and our government. People at all levels are motivated by the bottom line.

  5. Definitely a timely question – something which would address a mashup of Rifkin’s The End of Work and Friedman’s The World is Flat.

    The motivation is there, in startups like Grind who are redefining work collaboration. What’s maybe missing is a framework which allows freelance flexbility but safeguards confidential information flow at the same time. For example, how do I work in a commercial function, but also work freelance?

  6. Nick Stocking May 1, 2013 at 7:42 pm

    Tim- Great post, enjoyed the links too. I’m deeply involved in this question of developing an intentional solution to the freelance conundrum. Since 2011 I’ve run a freelance collective in Chicago (Design Cloud) which provides a platform of resources to help designers across disciplines work better and feel, simply, happier.

    We’re working better in that we take full advantage of our specializations economically and share resources, which benefit our clients and brings real value… value we capitalize on.

    But more importantly, we’ve been very focused and intentional on developing a culture which helps build confidence, trust, and creative risk taking…leading to greater happiness w/ our team. Happy designers=happy clients…that’s great, but really there’s nothing more rewarding than doing what you love, on your terms. It starts there.

    I’ve done a lot of lean start-up style research on freelance designers locally in Chicago, along with reading up on the larger demographic trends which is very exciting. Would be happy to share my knowledge and experience. Email me, thx.

  7. Freelancing is the great concept which will reduce the overall cost to the corporations, great example is the Onforce.

  8. Dan Soltzberg May 9, 2013 at 9:42 am

    In his book, Makers, Cory Doctorow lays out a fascinating and very plausibly described future in which corporations just sponsor individuals to freelance innovate–it’s a great provocation around the corporate business model and the future of freelancing.

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