Delays, Losses and Freelance Writing Confidence

Interview Interrupted

Originally, I planned to use my weekly post here to share an interview with a search engine optimization manager for a digital media company who frequently purchases freelance content.  Schedules being schedules and time zones being time zones, we weren’t able to make everything fall into place.

Frank Deford and I Disappear

Then, I wrote what may have been The Single Best Thing I Will Ever Write.  It was a thoughtful, considerate, 1200 word post that managed to tie my appreciation for sportswriter Frank Deford to questions of writer motivation while addressing some uncomfortable truths about most freelancers and the lies they must tell about the effort they pour into their work.

You’ll need to take my word that it was beyond good because it’s now nothing more than memory and vapor thanks to an apparently defective flash drive and/or a sudden burst of flannel-inspired static.  That beautiful, rambling post that conjured up images of Joe Frazier, Kirk Gibson and you sitting in front of your monitor on a trying Tuesday afternoon is gone and lost forever.

The Con Game

So, here I am…  A day late (or at least later than usual) and a post short.

I’ve decided that it’s time to stop mourning the lost Deford piece and to address something else that’s been on my mind lately…  Confidence.

I wouldn’t be the first person to argue that a healthy ego and a sense of confidence are good for business.  When you know that you’re capable, it’s that much easier to pursue the opportunities you want–and to snag them.

That’s the business side of confidence, but there’s another benefit that derives from an unwavering ability in you–it creates openings for extremely good writing.

You can tell when people are writing scared.  They hold back.  There’s a tension.  It’s like the kid playing a solo in the middle school band who’s more afraid of screwing up than he is interested in rocking the house.  It’s not loud enough or bold enough.  It’s uncomfortably muted and hurried.

I’m not talking about writing in crazed bursts of passion sentence after sentence.  There’s room for nuance, but even that only really works when writing is backed by confidence.  The exceptions are happy accidents.

Confident writers produce better material.  Confident writers experience more business success.

This is the point where I should put on my self-help guru cap and share a series of suggestions about how you an develop more confidence as a writer.

Today is your lucky day.  I’m not going to offer any helpful hints.  That’s because I don’t really have much of an answer.  For better or for worse (and it has definitely worked in both directions throughout my life), I have a natural tendency toward confidence.

Maybe it stems from the years of listening to my mom tell me that “I could be whatever I wanted to be,” even though she never really believed that I’d hit right in front of Jime Rice in the Red Sox order.  Who knows?  All I can say is that overconfidence is more of an issue for me than a lack of confidence.

But I know that’s not the case with many people and I see some extremely talented writers who fail to really dive into the fray because of confidence deficits.

I’m guessing we’ll all agree that a belief in your talents is good stuff for a freelancer.  I’m wondering if any of you have some tips for those who’d like to develop more of that confidence.

Who’s willing to put on their self-guru cap to share a few ideas?


  1. Kris says

    This was a truly great post. I (and I think so many writers) find that sitting behind the computer is a secure place to be. Why? Because yes, we lack self confidence. So the very reason (at least in part) that we chose this profession may be the very reason we are not great writers.

    Thanks for this post. Definitely food for thought!

  2. says

    Mourning the loss of the Deford post but you hit a home run with this one too. :-) My confidence has definitely waxed and waned and sometimes sickeningly so in nauseating waves of I rock, I suck, I rock, I suck. However, one sure fire cure to boost the confidence is to write often and write from the gut. Whether you’re writing about widgets or existentialism there is a story that you can tell from your heart, your way. Shove the critic in the cellar and pour it out your way. Always time to go back and polish the passionate musings once the story is out there on paper.
    .-= Karen Swim´s last blog ..Trippy, Tragic, Triumphant =-.


  1. […] “Delays, Losses and Freelance Writing Confidence” is a post about the power of confidence to boost one’s success in terms of output quality and business operation.  It’s also a rumination on a piece I wrote and lost about Frank Deford.  I mention that just because I’m still a little miffed about the whole thing. […]

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