Looking for the Write Road

photo credit: onewaystock.com

photo credit: onewaystock.com

Following up on yesterday’s post, I feel the need to take my bearings on something I merely touched on there: how to go about securing enough freelance writing and editing work to pay the bills while building up CASE, my Sudbury schooling nonprofit.

I suppose this may simply be one more take on the ancient “day job” dilemma. My Sudbury passion doesn’t currently support me, so I look to other work—namely, wordsmithing, another of my passions—to fill in the gap. Yes, I could (and may have to) look for non-passion-driven work, anything that will generate income while leaving me enough time and energy to do what I love. But after all, the whole point of this blog, of my quest, is to find a path that doesn’t require excessive compromise; to prove that one can make a decent living pursuing one’s passions.

That’s all well and good, yet here I sit, enjoying the challenge of crafting words for which I am not being paid—which, for all I know, will never lead to a paying job or any other source of funding. Or might these verbal games actually lead somewhere? Such is the siren call of my current lifestyle: never knowing whether what I’m doing at any moment is a waste of time or an investment in a future of viable creativity.

So how do I solve this puzzle? Lately I’ve begun falling back on what proved reasonably lucrative in a previous lifetime: combing the Craigslist ads of various cities (thank you, telecommuting!) for promising opportunities. In the past week or so I’ve sent off cover letters and writing-sample-rich resumes in response to perhaps fifteen different ads. So far I’m pursuing leads with a content-writing wholesaler (i.e., an outfit that matches freelance writers with web content jobs) and a resume-building business.

Will this be enough, though? I’m not sure there’s any way of knowing. Meanwhile I’m also, of course, competing against the clock which is my dwindling savings. How long can I wait for the trickle of possible work to turn into a reliable income stream? Should I tap into my various networks, personal and social, with pleas for paying wordsmithing work? Should I create and post flyers where I live, should I actually pay attention to the LinkedIn profile I’ve had who knows how long?

What am I overlooking here? Rather than eking out a pittance writing things I don’t believe in, and which I have to force myself to complete, should I instead go all-in and write only things I want to write (such as this blog). Should I spend time figuring out how to get my children’s books published, and the balance of my waking hours promoting CASE and my quest to support myself while supporting the Sudbury schools I love?

Do any of you have any ideas or suggestions on how to blend my passions for Sudbury and for wordsmithing into a viable workload that doesn’t require selling out or surrendering so much time and energy that I have almost nothing left over for myself?

I ask for your help because I honestly have no idea what I’m doing. I ask because the two things I do know are, first, I cannot abide work in which I don’t believe. Also, the longer I spend in limbo, the more appealing an all-or-nothing approach becomes—and the “nothing” side of that equation scares me more than a little.

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4 Comments

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4 responses to “Looking for the Write Road

  1. MC Persiko

    A few thoughts:

    1) Have you considered applying your wordsmithing passion into grant-writing for CASE?

    2) I have read that regular LinkedIn users spend an average of 30 minutes per day on LinkedIn. It is not merely for “job hunting”: it hosts innovative forms of finding connections, becoming a “thought leader” in some area of passion (education, I assume, in your case,) and some other features (some of which might be pay-to-play.)

    3) What do you think about distance-learning and online course presentation? Could teaching/developing courseware provide bridge income while pursuing your larger goals with wordsmithing?

  2. Hey, thanks for the thoughtful reply! I’ll respond by the numbers…

    1. Absolutely! Grant-writing is a natural fit for CASE, though I wonder how much of a foundation (no pun intended) I need to have in place before going down this road. Also, grant-writing for Sudbury schools is tricky, as we don’t believe in evaluating students.

    2. The more time goes by, the more I think it’s all about networking. Yet with time being finite, I want to spend mine networking in the places most likely to yield results. How do I determine whether LinkedIn fits the bill for me (other than, of course, trying it)?

    3. I’m open to all sorts of things that would pay the bills while letting me play with words and/or talk about things I love. What I need help with is finding people willing to pay me for these sorts of things, and cultivating the imagination to be proactive and efficient in making this kind of work happen.

  3. Melanie G.

    Check out this fellow in Seattle who used Kickstarter to self-publish a book about a trip to Tokyo with his six year old daughter to explore Japanese food and restaurants: http://blogs.seattletimes.com/allyoucaneat/2013/06/21/seattle-food-lover-writes-a-pretty-good-tokyo-tour/

    I wonder if you could, for example, fund a trip to Sudbury and other alternative schools and write a book for educators and parents?

  4. Pingback: Write Road P.S. | Write Learning

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