Where Freelancers Fear to Tread

Avoidable inefficiency gnaws at me. I hate to see time and money wasted, even if it’s not mine — and even if I’m the one getting the check. To some who work for themselves, that seems like fool’s logic. Call me a fool. A fool who freelances.

I’ve met some freelancers who happily thrive on inefficiency, milking every last drop of pay from the udders of their hirers’ cows and adopting an “it’s their problem, not mine” attitude. Most, however, prefer to take the high road and do the best they can in the time they’re paid to work. Instead of exploiting inefficiency to earn a few extra bucks, they simply tolerate it and smile, streamlining things at the margins where they can but usually saying little about it. It’s all perfectly sensible, above-board, and low-risk.

Maybe I’m reckless, but I prefer to tell the people who hire me — point blank, though in as constructive and polite a way as I can — where their systems are not serving them well. Clearly, only some of those systems are in my purview, and I try to be careful to limit my comments to areas where I can actually see the big picture, making all the necessary caveats. But saying nothing is, to me, a travesty.

To be sure, before you make any critiques as a freelancer, you need to be honest with yourself and distinguish between what inconveniences you personally and what actually compromises overall efficiency for the hirer. If only the former is at issue, just drop it. However, when it comes to the latter, insiders often listen to well-reasoned suggestions with open minds, particularly if your feedback reflects that you’ve accounted for many of the contingencies that they have to confront. And if change would happen to also make your life easier, admit that openly, specifying how the situation is a win-win for both them and you. A powerfully persuasive argument is that their money would be better spent if a greater percentage of your time were dedicated to the core job than to clearing unnecessary hurdles. And, while you’re at it, mention in very specific terms what is genuinely working well.

Even if you have an “on the merits” approach to feedback that includes positive comments, insiders can bristle at point-blank suggestions that challenge their ways. You may be perceived as whiny, or a know-it-all, or just plain irritating. Insiders often assume that the picture of the whole that you’re seeing isn’t quite big enough to account for all the variables. And that certainly can be true. But having been an insider who worked with freelancers for much longer than I’ve been an outsider working as a freelancer, I can tell you that the insider’s tunnel vision is usually much more profound than the outsider’s ignorance. That tunnel is an old friend of mine — warm and cozy, but narrow and dim.

Of course, you can’t compromise your living in the name of shining light into the darkness. Being straightforward as an outsider has potential costs, even as high as losing future work or never getting a job in the first place. You obviously shouldn’t tromp and stomp like a jack-booted thug, but treading too lightly does nothing to stimulate the soil. I’ve decided to let my shoes, even my feet, get a little dirty rather than walk on pristine eggshells. And I must say, a heel to the earth strengthens the spine.

(For specifics about how freelancers can give and receive feedback, see my posts “Your Freelancer Can Be a Low-Cost Consultant” and How to Give Feedback to Contractors.”)

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About Steven DeMaio
Steven DeMaio teaches English and math at the Community Learning Center in Cambridge, Massachusetts, and the Somerville Center for Adult Learning Experiences in Somerville, Massachusetts. He also works as a freelance editor and writer. This is a continuation of his blog that ran for 10 months in 2009 on HBR.org.

2 Responses to Where Freelancers Fear to Tread

  1. Well said as always, Steven. And I don’t think you’re foolish or reckless. After all, higher efficiency for one client means you can get to work for another sooner and/or spend more time delegating. It’s good economic logic.

  2. Josette says:

    Love your extended metaphor in the last graf, Steve! Keep ’em coming!

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