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Brendan O’Brien

Winning in the Freelance Game

Symbol of success, winning, championship. Gold cup in hand. Trophy.
Anastasiia Nevestenko ©

Being a freelancer is hard. When clients don’t have work for you, you cease to exist for them even though your livelihood depends on them or on people like them. You need to be a team player, but often you will be dropped from the team abruptly when a project ends. This demands resilience.

Here are a few thoughts on flexing your resilience muscles by being proactive — boxing clever, if you like. (Some sporting metaphors are thrown in, because I like sport.)

Paint pictures

We freelance editors can partly create our own world through the questions we ask and the initiatives we take while editing. A phrase that is used in sport these days — especially rugby — is “painting pictures.” The idea is that players try to influence the referee’s attitude towards them by being seen to do the right thing, in a manner that may be stylized and borderline exaggerated: they paint favourable pictures of themselves and of situations.

Similarly, freelancers can paint pictures for clients. You can portray yourself as being especially helpful and efficient, for example — a problem-solver, an obviator of headaches. Put yourself in the other person’s shoes and consider whether the picture they’re seeing is the best possible one. As well as doing the right thing, be seen to be doing the right thing. Consider what they want (an easy life, basically). Don’t sit back and allow them to paint their own pictures (which, for all you know, might be grotesque caricatures).

Retaliate first

Another adage from rugby is “Get your retaliation in first.” Visualize and pre-empt problems. Sometimes explain your thinking in comments to the author, even if that is not strictly necessary, to give an impression of efficiency and knowing the score. Copy the client in emails to the author as appropriate. Email the client with updates. If there are problems, these should be perceived as occurring despite you rather than because of you.

Be a team player

A client rang me recently about a book that was at the printer’s. There had been some glitch with the typesetter’s file; the client wanted me to go through a few pages of the printer’s PDF thoroughly, as a spot check. I had already been paid for the job; the client knew that I wouldn’t charge for this extra work. It’s good to be a “team player” even when you’re not on the team — that way you remain in the client’s squad, and it becomes more likely that you’ll be picked for the next game.

Polish your trophies

As well as making our own world, we influence the world around us. When you walk into a bookshop, you may not see many of the publications you have worked on, but they are out there, somewhere. They are better for your work, and this means that the world is better, too. The human need for clear communication has been served; you have made a difference. Your trophy cabinet is dispersed, but no less real for that. It’s a reflection of your work ethic and expertise and a harbinger of your future successes. Bear it in mind.


Previous post from Brendan O’Brien: Is It All About the Author?

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6 Comments on “Winning in the Freelance Game”

  • Anita Jenkins


    Thank you for writing about this most interesting topic (freelancing, not rugby!). And thank you for using the term «freelance.» I think it is a lovely word, and that it describes a marvelous lifestyle.

    I understand that members of the Edmonton Twig were recently chatting about how this term doesn’t give the right impression. That it is better to call yourself a consultant or contractor. Say it isn’t so.

    Or we could say we are «gig employees.» I read that in an article claiming that one in three American workers are what we would call freelance. It’s a trend in the workforce, and one that can be embraced for many reasons. For examples, as the farmers say, «They are free to work whenever they want, as long as it is 20 hours a day.»

    • Brendan O'Brien


      Thanks for this, Anita. Yes, I have sometimes seen discussions on whether we should call ourselves independent contractors or similar, but I very soon forgot all about them and continued with «freelance». It seems to serve well enough.

      Those of us who have been freelance for a long time, and survived, perhaps have an advantage over the unfortunates who are entering the «gig economy» at this time.

  • Larisa Sarenac


    I love being a «freelancer». I am still just a student in terms of editing (SFU, Certificate in Editing, 2018–ongoing), but I used to work as a freelance translator, and I still pick up a project or two. Self-discipline is important when freelancing.
    Thank you for the article!

    • Brendan O'Brien


      Thanks, Larisa. I’m glad you like it.

  • Rosemary Shipton


    If you look at the economics of freelancing with a gimlet eye, the trick is to fill every hour of your day with productive work – just as you would if you were on staff. The problem comes with managing the flow of work from multiple clients. This problem is particularly severe if you are the first of the team in line – the only editor or the substantive editor on the project – because you’re at the mercy of the client or the writer sending you the text on the promised date.

    It’s tempting to overbook – to assume that there will be slippage, as there usually is. If you book only one project at a time, you’re doomed to days on end where you won’t be working. But overbooking also leads to work crunches, where your precious work-life balance flies out the window.

    And so we make our choices – to under work or to overwork. Just one of the myriad decisions we make as freelancers.

    • Brendan O'Brien


      This is true, Rosemary. I have been guilty of overbooking, including for most of this year, and my work–like balance has suffered. Right now, though, I’m in phase of needing to market myself and find some new clients.

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