Writing down ideas over breakfast
Business, The Journey

Pitch, Please! – Part I (19.35%)

I’m the type of person who much prefers to ask questions than be asked questions. That’s why, as part of #my500words challenge, I decided to invite friends, family, and perfect strangers to ask me [almost] anything.

Livin’ la vida outside my comfort zone, you guys.

Here’s one of the first questions I received:

“How’d you get your first writing gig and were you confident you could do it?”

I’ve decided to answer this over two instalments: first, I’ll share the story of my inaugural publication pitch, and then I’ll share a few tips on how to do what I did… only much, much better.

Alright – let’s do this.

The Swing

I had already been freelancing for about a year prior to launching Paper Plane Communications (a bumpy journey you can read more about here). Back then, I went by the moniker JR Writes Things. Despite dizzying spells of Imposter Syndrome – an issue I still struggle with today and one I plan to spend a lot more time talking about here on LWBW – I’d added myself to my alma mater’s “Editors for Hire” list at the University Learning Centre. Each week I’d edit my way through piles of English 110 papers and show up to tutoring appointments with an armful of resources I knew were likely destined for the recycling bin.

Though I did learn a lot during that first year, I knew something was missing: nearly all my time was devoted to words written by others, which left very little room for words of my own.

As it happened, I had recently discovered PINK Magazine, a free publication for women in my home province of Saskatchewan (Canada). I remember leafing through the latest issue and thinking to myself, “Hey, maybe I could do something like this.”

And so, in a demonstration of feeble conviction and youthful naivety, I reached out to the magazine… by Twitter. That’s right: I sent a Tweet asking if I could write for them.

Pause for slow clap.

Now, I know I said I’d hold off on sharing Tips and Tricks until tomorrow, but please heed these words: Twitter is not designed for pitches, because a pitch should never be 140 characters or less.

Much to my surprise and thanks to what I can only call Beginner’s Luck, a DM popped up shortly thereafter. I was invited to contact the magazine’s managing editor directly which, of course, I did.

The Miss

I suppose “The Miss” is a bit misleading, as those of you who know me know that I’ve been writing for PINK for the past three years. What you don’t know about, however, is The Embarrassing E-mail that followed The Embarrassing Tweet.

I had to dig deep into my e-mail history for this one, but here’s what 2013 Jessica (cringe) felt was an appropriate pitch:

Good evening,

This afternoon I was in conversation with someone from Pink Magazine via the magazine’s Twitter account about the potential of coming on as a writer. I was told to contact you directly to provide you with my resume. Please find attached my resume complete with contact information and publication history.

The link below will direct you to my blogging content for The Rooster, a lifestyles e-magazine powered by SpareParts. Because the target demographic for this magazine is 18-35, I adopt a fun, somewhat informal writing style. Rest assured, though, that I am a versatile writer and can cater to different demographics/parameters as required. This is supported by the list of academic publications included on my resume.


Please advise if you require any additional information or samples.

I look forward to hearing from you.



Oh, how the editor in me longs to assault this e-mail – and its wordy little author – with a red pen.

I must give special kudos to PINK’s editor, Moe, for the kind response I received the following morning and for, months later, bravely taking a chance on a Pitiful Pitcher.

Although I can’t explain why or how I eventually got the gig, what I can do is point out where I went wrong and what I’d do differently.

And I will…


Until then,



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