Where Freelancing Meets Independence

People who work for themselves often cite independence as the most appealing element of their work lives. They praise the flexible schedule, the lack of a boss, and the ability to select the work they do. I certainly value those concrete benefits, but what matters to me more is the freedom to assess quality as I see it, without the burden of internal politics or the sometimes senseless rules, both written and unwritten, of organizational culture. Despite not being bound by those strictures, some freelancers censor themselves, fearing to tread into territory that might displease a client. But that usually diminishes the value of their own work and denies them the sense of satisfaction that only calling things on the merits can provide.

Merits are relative, to be sure, especially in the worlds of editing and writing, where I spend about half my work life. But people with keen, analytical minds who try to honestly assess everything they encounter usually end up agreeing quite a lot with one another about what the merits are — even if it takes a lot of debate and deliberation, not all of it pleasant, to get there. Some organizations have managed to make room for this kind of honesty internally, but they are relatively rare.

Much more often, I have found, work environments function in one of two ways: a moaning and groaning culture, in which people routinely make things more burdensome than they need to be, or an “everything’s great” culture, in which people are pathologically positive and reflexively ignore flaws in the interest of preserving equanimity. Of course, most workplaces have a mix of those characteristics, in part because of the diversity of personalities, work styles, and subcultures in any one institution. But I must say that I have very rarely encountered a workplace climate that simultaneously (1) challenged chronic complainers directly on the substance of their exaggerations and (2) unmasked the type of self-censoring, Stepford Wives–style optimism that, by tacit agreement, keeps everyone creepily content and uncritical. Fear, self-interest, and willful ignorance are usually what entrench these mind-sets, but brute force is not the way to break their strangleholds. Dispassionate leadership-by-example does a much better job, though that can be hard to execute when you’re on the outside.

If you happen to be pretty good at influencing insiders, the outside perspective that freelancing enables still does not entitle you to preside like a robed judge over poor petitioners who seek your counsel, even if you’re explicitly being paid as a consultant. Loftiness is not what this freedom is about. Quite the contrary, it’s about allowing yourself to explore and question with the enthusiasm of a curious scientist, then negotiate the practical value of what you find with the deftness of a skilled diplomat. It’s, in short, the thrill of discovery and the craft of persuasion all wrapped into one. But plainspoken critique is sometimes required, and, yes, that could cause you to lose a client.

In my work life, an independent point of view is what I’ve always valued more than anything else, whether that perspective is mine or that of the people with whom I collaborate. Freelancing has allowed me a bit more breathing room as I try to do the best job of this that I can. And, frankly, it has given me the wherewithal to do some of my own writing, this blog included. Finding time for such independent expression still remains a huge challenge, especially for someone like me who struggles with saying no to people. But independence of mind is, after all, more about space than it is about time. And there’s more of that on the outside than there is within one institution’s four walls.

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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.

3 Responses to Where Freelancing Meets Independence

  1. Leah says:

    People in so many workplaces are afraid to critique each others’ work collegially. Your Stepford Wives comment is very apt, and it made me laugh out loud. Fun to click over to the film clip, too. Thanks for another great post.

  2. rachel says:

    Thanks for all the great posts that deal with living the life of a consultant. How ironic that right as we “met” (in cyberspace) – I also transitioned from full time industry slave to full time consultant. Reading your posts makes me realize that all of the weirdness that I experience in my new day to day life are normal, andyour articles/blogs also alerts me to experiences that i have not yet encountered, but probably will soon! Thanks for all the great advice!

  3. Daniel Silverthorne says:

    I quit my so called sucessful mind numbing job making X dollars which was supposed to satisfy, yet only frustrated my internal sense of wanting to be free. I stumbled on to low paying jobs which eventually satisfied me once I got into the right company of people with like mindsets. A mindset of caring loving and looking after one another than trying to bite each other’s head off. Now money doesn’t matter to me anymore and I did find a rather well paying job doing what I love with a God given purpose. Without a God given destiny…..what is life, but a bunch of coping skills learned from circumstances rather than contenment with love and purpose. If my creator gave me gifts that I don’t use why bother having them. Why struggle through mediocrity trying to be a jack of all trades, rather than what I was meant to do, and fall into apathy….why not do what is meant to be the fit for myself which is what I do. When I succeed at this, I tend to grow faster into other occupations and freedom of expression and self discovery and grow. Apathetic stagnation sucks. I lived in that desert too long. Ultimately I’m here for the benefit of others and removal of self. Galations 2:20 I have been crucified with Christ, and It is I who no longer live. The life I live I live by faith in the Son of God who died and gave himself for me. That brings me meaning even in the most dire circumstances. God bless you Steve and may your travels and this journey called life bring you home to your creator, as I can see you know who you are, and what you are good at. May it lead you to the one who loved you so much, that he died and gave His life for you, so you can live it to the fullest and in abundance, being diligent to please him with an attitude of gratitude for everything He has done for you. God bless u and your
    family. Daniel

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