Why Freelance Writers Need To Fail

by Anne Wayman

In comments, Philippa Willitts admitted to being such a perfectionist she set a goal to “Make more mistakes.”

I love it! Here’s why:

When you start any endeavor, including freelance writing, you’ll never start if you don’t write and submit. My first two submissions, one to Family Circle and the other to Woman’s Day were rejected with the standard form rejection.

But I’d broken through my own fear of failure and actually completed the process from writing through submission to, in that case rejection. The fact of doing that was way more important than the fact of rejection.

The very same thing is true if you want to bring in clients – you’ve got to find ways to market yourself and if you don’t try something, even if it doesn’t work the first or fifth time, you won’t have clients respond.

It’s hard to get worse at something you practice. Think about it – the only way you’ll get better at writing and better at selling your writing is if you write and market, over and over again. When I look at some of my early published writing I’m a bit embarrassed. It isn’t awful, but it sure could have been better, except it couldn’t. It was the best I could do at the time.


When I look back at some of my early marketing efforts it’s the same thing. While practice certainly hasn’t made my marketing perfect, it sure has made it better.

If you’re not failing at least some of the time you’re probably not expanding. Cathy Miller has a great post she calls Solid Business Writing Lessons From Ice Road Truckers. Take a look, both at the message and how she gets there – two lessons for freelance writers.


The blog, Fail Your Way To Success, has some interesting statistics that they got from from the Sales & Marketing Management Institute:

  • 87% of all leads are never pursued
  • 48% of all sales leads that are pursued are dropped after the first call/meeting
  • AND YET… 80% of all sales close after the fifth contact/meeting

Translating that to freelance writing it means that:

  • You’ve got a ton of potential markets out there you’ve never tried – how many have you skipped because you were afraid to fail and not trying meant you didn’t fail?
  • You’ve allowed a single rejection to stop you from trying that market or the failure of a particular marketing method kept you from ever again – probably because you’re unwilling to fail a second time.
  • You probably shouldn’t stop trying with a particular market or marketing method until you’ve tried at least five times.

In a very real sense a failure really is an opportunity to learn. Sure it doesn’t feel that way but you’ll never ever know what you can achieve if you aren’t willing to risk making mistakes, getting egg all over your face (although that is usually your perception, not the world’s) and failing.

What risk, what mistake are you willing to allow yourself today?

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Image: Attribution Some rights reserved by fireflythegreat


{ 18 comments… read them below or add one }

HP van Duuren April 17, 2012 at 3:16 am

It’s my experience that…..,

‘From Frustration
comes Inspiration…!’ :)

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Brandi April 11, 2012 at 9:48 pm

Thank you Anne and Cathy for your posts that I really needed to read today. Sometimes as freelance writers it’s so easy to get down on yourself and to equate rejection as permanent failure. It’s difficult to be a writer, but I know I didn’t get into this field because it was glamorous or easy. When rejection after rejection gets to me, I also remember that the only time a rejection means a failure is if I give up. And I’m definitely not doing that. Thanks ladies!

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annew April 12, 2012 at 8:21 am

Hang in there Brandi, and notice how brave you are.

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Andrew Kardon April 11, 2012 at 8:00 am

Great post, Anne! It’s like anything else in life… failure is a great learning tool. You can’t ride a bike without falling. The best way to learn how to stand, is to fall down and pull yourself up.
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Sharon Hurley Hall April 10, 2012 at 2:31 pm

Great post, Anne. I remember getting my first piece of journalism back from the editor – it was covered in red marks. It took a few months, but I felt a real sense of achievement the first time he passed something for publication without ripping it to shreds. :)
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annew April 11, 2012 at 6:50 am

Sometime after I’d gotten published a bit and had even won one award, but before I could make a living at it, I worked for a tiny newspaper in Idlwild, CA. L.J. Hunsaker was the editor and he’d yell at me and the other 3 writers and mark up our copy like mad. I hated it and I remember the day I wrote a long cut line about, of all things, standing eggs on end at the equinox. He must have read it four times before he hrumphed and said, “Not bad.” Was like, I suspect, winning the Pulitzer!

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Sharon Hurley Hall April 11, 2012 at 10:12 am

Yes! That first grudging acceptance is like hitting the jackpot.
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Amelia Ramstead April 10, 2012 at 12:35 pm

Yes! I felt like a real writer, holding that first rejection in my hands (yes, it was a physical letter. I felt so honored!).
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annew April 11, 2012 at 6:47 am

A very sweet moment indeed.

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Sarah Reece April 10, 2012 at 12:57 am

What a superb piece Anne… I have worked into various jobs all my life from Sales to Marketing to Technology (Being a Computer Engineer) to writing, but I must say that most leads do not get converted into Sales not just because of a fear of failure but also lack of discipline. I have always found myself torn apart into doing multiple things & not completing them all.

P.S.: Great Blog.. would hang around more often..
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annew April 11, 2012 at 11:21 am

Glad you’re here.

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Amandah April 9, 2012 at 11:00 am

I always feared failure because my dad expected perfection (he served in the U.S. Army). I grew up hearing, “If it’s not perfect, it’s not right.” Another favorite was, “If you do things right the first time, you won’t have to go back and redo them.” He meant well.

It wasn’t until I read the following quotes by Albert Einstein that I shifted my thoughts around failure and being perfect. Einstein said, “A person who never made a mistake never tried anything new.” And, “Insanity: doing the same thing over and over again and expecting different results.”

I’ve submitted numerous queries and pitches that have been rejected. It happens. Maybe it’s timing. Maybe it’ my angles. I’ll keep trying. It’s not a big deal, anymore.
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annew April 10, 2012 at 8:05 am

Wonder how your father identified perfection Amandah? I never could. Love those quotes… glad you’re submitting – keep it up.

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Cathy Miller April 9, 2012 at 10:15 am

Thanks for the shout-out, Anne, and what a great topic for a post. We do need to fail to learn. It’s like the toddler learning to walk. Imagine if they quit after the first time they fell down.

I like to put it in the perspective of what’s the worse thing that can happen? They say no? So what? You are no further behind than when you started and you often learn something from the experience. Like you said, Anne, if nothing else, it’s good practice.

Great post, Anne..
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annew April 9, 2012 at 10:51 am

I didn’t include it in the post ’cause it’s a bit trite, but I kept thinking of how we learn to walk ;)

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Cathy Miller April 9, 2012 at 3:55 pm

Great trite mins think alike. ;-)
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Cathy Miller April 9, 2012 at 3:59 pm

P.S. I just noticed I put worse when I meant worst. I’m claiming lack of caffeine when I wrote it. That’s my story & I’m sticking to it. :-)
Cathy Miller recently posted..Solid Business Writing Lessons From Ice Road TruckersMy Profile

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annew April 10, 2012 at 8:08 am

Cathy, as you probably know, I mostly ignore typos or as I say, typos allowed here… coffee driven or not.

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