Is This Freelancer a Fake?

I call myself a freelancer, but I might be an impostor. First of all, I spend half my time working as a teacher in adult education. It’s a position I very much enjoy, but it’s not freelancing. Four days a week, I go to a school, where I run a classroom (several in fact), interact with colleagues, share an office, and comfortably inhabit the workplace culture. When I’m not teaching, I do editing and writing that might be more traditionally called “freelance.” But, frankly, it doesn’t feel especially entrepreneurial, since I’m not really building a business — and I’m quite happy with that.

You see, I do my best work when other people are depending on me, expecting me to produce. They might be students in a classroom, editors who need me to help them meet deadlines, or writers who are (by their own admission) swimming in their own verbiage without a guiding hand. But what so many freelancers tell me they love about independent work life is the ability to build your own little enterprise — in effect, to own your own labor.

I’m not much of an owner, though. Don’t get me wrong, I like the partial control I now have over my schedule. But I still get much more of my energy from fulfilling others’ needs than from cultivating my own. Knowing that another, specific person is waiting for my work — even at the other end of a cyber-connection — is what motivates me to deliver and to excel.

My freelance life, satisfying as it is, is pretty much devoid of self-advancement goals, beyond the basic earning of a living. That doesn’t mean that I’m not exceedingly busy, or that I’m not motivated by excellence. Anyone who has ever worked with me would tell you I’m a stickler for quality — and a discerning critic of how quality is defined. But the rewards I get are not quite “mine”; they’re the benefits that direct recipients of my work derive.

Take, for example, the blog I wrote for Harvard Business until last December. The editors wanted something from me every week, and I was chock full of ideas, and often five or six weeks ahead of schedule. The writing came easily to me, as I imagined delivering the best possible product to an editor on the other end. Furthermore, that editor needed my work on time — and often benefited from my early delivery of it. Sure, the whole thing felt sort of self-indulgent, given that it was a blog about my own career transition. But the fact that someone was waiting for me to deliver my drivel made it feel less like drool and more like lip-smacking food I was cooking up in the kitchen for someone else — someone I know — to taste.

Nowadays, my blog posts don’t get “received” by anyone whose face I would recognize on the street, beyond a few friends and colleagues. I put them online at will, and anonymous readers (not very many) wander in and out. Some offer lovely comments that I deeply appreciate.

But I have to tell you it’s not the same. I’m not terribly motivated to write posts without being able to feel a direct need from a person with whom I have a professional tie. And here you are reading my blog. And here I am disrespecting you by saying that that’s not enough, not enough to write about “freelancing” for an audience (of freelancers?) whose hands I cannot touch.

Is that irony or hypocrisy — or just downright boring? Can you even relate, fellow freelancer, fellow reader of drivel about a stranger’s career transition? Set me straight.

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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.

7 Responses to Is This Freelancer a Fake?

  1. WDF says:

    “The writing came easily to me, as I imagined delivering the best possible product to an editor on the other end. Furthermore, that editor needed my work on time — and often benefited from my early delivery of it. Sure, the whole thing felt sort of self-indulgent, given that it was a blog about my own career transition. But the fact that someone was waiting for me to deliver my drivel made it feel less like drool and more like lip-smacking food I was cooking up in the kitchen for someone else — someone I know — to taste.”

    Framed another way nothing has changed. You just need to imagine me, instead of the HB editors, eagerly waiting beside my RSS machine for your timely post. What has changed is that you can no longer use Harvard as your target and you have to choose the loose confederation of readers such as we are as your market. A period of redefining and tightening your delivery. I think maybe it takes a different discipline than you might have been used to before. A tweak perhaps.

    Best of luck in the transition and by all means keep on writing. I enjoy your posts.

  2. Lilith Fondulas says:

    I feel exactly the same way about my work. I do best when I have a defined task, a set deadline, and someone waiting expectantly for the product. And if I get feedback–especially shortly after delivery–that’s gravy. I don’t think that’s unusual, particularly in our line of work. As freelance editors, we are disciplined, detail-oriented, and focused on best communicating our authors’ vision to his or her targeted readers. And we usually find out, whether for good or ill, how well we’ve done the job.
    But when the author is us and the audience is amorphous, the game changes entirely. Even great editors need an editor, and how can you tailor your speech to a web cloud? What’s more, I’m guessing your feedback on your own work doesn’t highlight all the wonderful aspects of it. (All of which explains precisely why, in fact, I’ve never been able to keep a diary or journal.) So I’d suggest three things: pick a specific readership to whom you feel you have something to say, find a colleague to help put on that final coat of polish, and get a trusted friend to give you feedback. Your audience awaits.

  3. Josette says:

    Steve, this is just to let you know that I’m reading, and not just as a friend and colleague. I respect your writing and look forward to your posts. Writing is much harder than editing or teaching (hard as those two are!), and I’d put it in a different category. I’ve kept a diary since I was 8, and I write it in regularly, and with purpose, and I’ve published a few poems. But I have never gotten up the nerve to start a blog. It’s either a self-indulgent joke or it’s a serious piece of writing that you’ve spent time on and are proud of. You seem to still be putting effort into your blog posts and are not just spouting drivel. So keep it up, and an audience will shape itself. Or it won’t, because sometimes art is unrewarded. Good luck, my friend! -Josette

  4. Karen Dyck says:

    Steve,
    I am reading this post for at least the third time and feel compelled to let you know that I will likely keep it “unread” and return to it until I am notified of your next post.
    I left my job this past fall and discovered your blog on the WSJ around the same time. It provided comfort to me to know that someone else had walked a similar road. I am a “fake freelancer” too – I left my job to work on 2 secure contracts that take up as much of my work time as I want to fill – and find I usually identify closely with your tales and comments. So, please keep on sharing your experiences with me and the rest of your audience.

  5. Svet says:

    I know that feeling well, and I don’t feel disrespected in the slightest. Keep writing.

  6. i just discovered you and your HBS columns and, as a former WSJ reporter, was struck by your frank, genial tone and your deep insights. As a fake freelancer too, with a modicum of security like you (speaking engagements, booked ahead + 3 retainer clients) I really resonated with this, from you:

    You see, I do my best work when other people are depending on me, expecting me to produce. They might be students in a classroom, editors who need me to help them meet deadlines, or writers who are (by their own admission) swimming in their own verbiage without a guiding hand.
    ~ another fan

  7. SM says:

    Steve,

    I just found your blog by Googling “is quitting your job and starting over a smart idea?” I am comforted by knowing there is at least someone else that has had my grandiose illusions of having the world finally recognize my greatness, if only I QUIT MY CORPORATE JOB! I am enjoying reading and learning of your journey, not so much as I identify with your passion of writing/teaching.. but with your passion, period. I am deemed “very successful” at my current job, but know its not my calling. I laughed at your note about vacation time in the corporate world..my sentiments exactly..and yet, feeling no need for the typical vacation in your new fake freelance life, has me intrigued for that same sense of “relief” So… through the long and short of it all.. would you recommend the same path of quitting, for someone who KNOWS they are not being their authentic selves, yet feels the “responsibility” to stay in a well regarded high paying position??
    ~ nearly off the fence :)

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