My Two Big Pitch Mistakes (and What You Can Learn From Them)

by hollyj on February 8, 2010

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My Two Big Pitch Mistakes (And What You Can Learn From Them)

If you’re anything like me, the idea of pitching to a really big client, blog, or magazine makes you feel like you’re about to have a heart attack. Pitching is one of the great fears of the freelance writer. I think in part this is because we get so attached to our writing, the idea of sending it out into the world is both fascinating and frightening.  All of the sudden, we have someone who really matters (usually more than we do) judging our words and our skills.  This anxiety only ramps up when you’re pitching to famous people who you really respect, and whose opinion matters.  To make you feel better, today I’m going to tell you some terribly embarrassing stories about my first two months as a freelance writer, and some lessons that are worth taking away from them.

No One Is Pounding On The Door Of The Famous People:

Due to the phenomenally wonderful tool that is the internet, our world is getting smaller and smaller.  Tools like Twitter bring us all closer together, and equalize the writing community in astounding ways.  The second week in January, I was happily finishing up a project one night while Twittering away in the background.  I saw a Twitter name I vaguely recognized posit the theory that guest bloggers never pitched to him because they were scared of his stature in the blogging community.  Well, I’ve never been one for common sense or to resist a challenge, so I automatically responded back. “I’ll do it!”, I cockily volunteered, not really reading the name or doing any research. I was then very sweetly invited to send my piece over to Michael Martine so he could take a look at it for his blog.

There are several lessons to take away from my story, which hopefully you never repeat. Lesson one is obvious: make sure you know who you’re networking with so you aren’t surprised and have to get yourself together on the fly. The real lesson of this story is larger though: sometimes, even the dumbest things can yield incredible opportunities. After I nearly had a heart attack, I sat down, and wrote the scariest piece I’d ever written in my entire life. Even scarier, I made it personal. I figured that I’d never be in this position again, and so I needed to go for broke. My piece made it, and my business grew by leaps and bounds as a result.

I learned a big lesson that week. Whether it’s on the internet or in print, the big movers and shakers aren’t faced with a pitch from an unknown very often.  By making yourself the unknown with the guts to go for it and put yourself out there, you may very well be pulling ahead of the rest of the competition without knowing it. Once you know this, the writing world becomes a much more accessible place.

Sometimes You Just Need To Ask

Two weeks after the first incident, Naomi Dunford called me.  Now, before you think that I’d done something spectacular, it had absolutely nothing to do with me.  I had called her the week before to thank her for her online business school, and been too scared to even leave a message.  Well, the call was recent enough that she had sat on her phone at the hairdresser, and managed return my call accidentally. This isn’t an auspicious beginning to the story, I realize, and following so close on the heels of the first pitch incident, you’d think I would have dealt with this gracefully.  Well, I didn’t.  In retrospect, I probably most closely resembled a 13 year old girl at a rock concert.  I gushed, I told her how amazing she was, and I vaguely remember using the words, “I’d like to be you when I grow up.”  This is lesson one: when faced with your idol, take a deep breath, get your head together, and try not to say anything to imply that they are old.

In the back of my head, I still had my interactions with Michael Martine , who had been a wonderfully kind and helpful person two weeks before. When I finally managed to breathe and recover myself, I remembered the lesson I had learned with the last pitch.  I took a deep breath, dug my nails into my leg, and told her I’d love to write for her blog.  To my surprise, she said she’d be happy to look at a pitch.

This is another really important lesson.  We spend a lot of time forging connections and doing research and carefully crafting opportunities to pitch to people who we idolize and can make us rich, but very rarely do we simply go out and ask nicely.  In many cases, no matter how well known someone is, politeness and sincere interest is enough. While I certainly wasn’t smooth or calculated on the phone, she could hardly doubt my sincerity. In addition, the fact that I asked seemed to be enough for her to at least look.  While I still can’t tell you the outcome of this story, I can say that it gave me the confidence to pitch to several other people whose sites I enjoyed.  After all, once you’ve hit rock bottom in terms of fear and panic, everything else seems easy.

When you start looking at the really big blogs, magazines, and websites, take a deep breath and try to remember that no matter how they come across, we’re all just humans.  We have the same concerns, and most importantly, the same fears. The very busy and important person that you’re pitching to also remembers their days when they were scared and starting out. If you are polite, sincere, and take your opportunities when they grab you, you can probably pitch successfully despite your fears and hang-ups. And when in doubt, remember that at least you didn’t make them feel old or network absentmindedly:  you’re already two steps ahead of me.

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