The 500 Pitches Project and why I can’t stop trying to make it as a journalist, even if I’m deluded

Yellow typewriter with white paper sticking out of it saying "Hire me, pls" in red type, next to "x 500" in turquoise text, all on a dark grey background.As you might have heard, journalism’s in the crapper. I’m not just talking about its reputation in the wake of phone hacking and the New York Post’s irresponsible “who cares if we’re right as long as we’re first” reporting on the Boston Marathon attacks.

Turns out, during a recession, magazines and newspapers are luxury items — as are most of the brands that advertise in them. Ad rates have dropped, publications have folded, requests to write for free have soared, and even writers with years of experience are flogging their services on job-bidding sites while weeping into a vat of Value gin.

So now is the perfect time for me to decide that I’m going to make a success of a career in freelance journalism once and for all. (What can I say? I’m a womanprenuer!) I know this may not be the best business decision, but I don’t have any other options.

I don’t have experience in another field, and thanks to a disabling illness or three, I can only work part-time, from home, preferably while wearing a ratty old dressing gown. I can’t take on side gigs like temping or cleaning toilets to survive, much as I might want be willing to. Oh, and I’ve wanted to be a writer my whole life. (Photographic proof.)

After having some bits and pieces published and co-editing a books site, I went as close to full-time as I could manage back in 2008, breaking into glossy magazines and newspaper sections and contributing to several blogs for actual money.

Then in 2009, I tried to go back to university, relapsed badly, spent almost a year fighting to get Employment and Support Allowance, was kicked off it after another year and realised that scratching out a living as a writer while trying to recover physically was literally all I could do. That or lie in bed weeping, which I also experimented with.

In 2012, I had a couple of small contracts and some one-off assignments, but it wasn’t a banner year, partly for health reasons. In 2013, I finished those contracts and have brought in just two new commissions so far. Eek.

I know it takes a while to build momentum. When I jumped into freelancing with both feet back in 2008, it took me seven weeks to get my first pitch accepted. Then, the day after I’d been crying to my mum that no one would ever want me to write for them again, I got seven commissions in 24 hours, like a sign from the universe saying CALM DOWN, I WAS JUST KIDDING.

Still, every time I have a phase of un(der)employment, I assume it will last forever. The thought that I’m the only one who can dig myself out of this situation is terrifying.

It’s also kind of exciting.

About three weeks ago, after a lot of “no thank you”s in a row, I was feeling like a failure and started to slide into a slough of despond. But then I stopped. Something inside me snapped. And I thought, what if I decided to just never give up?

I grabbed a notebook, turned to a fresh page, and wrote:


I decided I was going to send out 500 pitches, and I wasn’t allowed to feel disappointed or think about becoming a beggar until I’d finished. If I hadn’t got a single commission after that, I told myself, I’d do 500 more. If that didn’t work, I’d lie face down on the carpet and cry for a week. Then I’d do 500 more. This way, every rejection isn’t so much a devastating blow as another step closer to success. (Or something.)

So what counts as a pitch? I’ll often send the same idea to a few different places before an editor bites (or I give it up as a bad job). I’m counting those emails as separate pitches because I do a significant rewrite for each market. It’s a marathon, not a sprint, so I’m not rushing to get the numbers up, but I am aiming to send out five (well-researched, well-written) pitches every week.

I get that there are lots of talented writers out there, and that no one owes me a media career. But I need one. And I wonder what would happen if I really went for it, without letting failure be an option. I don’t think I’ve ever done that before.

There isn’t as much work as there used to be, but there are still pages of print and swathes of the internet that need to be filled. And I think part of the reason I’m not filling as much of them as I’d like is a lack of confidence. It’s a vicious circle: you feel unworthy, have ideas rejected, and then become convinced you are unworthy. Not to get too Secret-y, but it’s hard for good things to happen when you’re in such a negative headspace.

Plus, there’s a genuine downside for women writers who succeed: if you write the kind of pieces that mean your photo is published, there are always people who’ll rip you apart. If you say something overtly feminist in a mainstream publication, you risk the kind of brutal rape and death threats that have become routine. That’s justifiably scary.

But I can’t let my own psyche or strange people on the internet hold me back.

My experience of writing and and of life in general is that everything is more difficult and takes longer than you hope or expect. But you can always work harder, do more, and find new things to try. So that’s what I’m going to do. When it comes to building a career in journalism, I AM JUST NOT WILLING TO GIVE UP. Times 500. Times a million.

Image: Vintage Typewriter Isolated by Just2shutter via Free Digital Photos (+ a little light Photoshop Elements).

After words:: When I need a boost to keep going with freelancing, or writing in general, I always turn to Only As Good As Your Word (the spine has fallen apart on mine) because Susan Shapiro is the ultimate writer who just wouldn’t quit, and she has loads of insight.

  • Good on you Diane. It seems to be that there are vast numbers of people who say they want to be writers but do nothing about it, other than overusing the hashtag #amwriting. The fact that you are taking action, and a lot of it, immediately puts you ahead of the field. I wish you fantastic success.

    • Thanks, Joanne! I really appreciate that, although I do reserve the right to *also* overuse that hashtag 😉

  • Vicky

    This is a great idea! Like you, I’m in the early days of my freelance career, and so far there have been many, many more nos than yeses. It’s very disheartening, but I’m going to take your approach: every rejection is just a step closer to the next acceptance! Good luck.

    • Thank you, and good luck to you, too! I think there will probably always be more nos than yeses, but expecting that takes a little of the sting out of it. Also, I now never send out a pitch without having another one in the wings, and I always think of a few places each one might work, so it’s just like, “OK, on to the next.”

  • MallyMum

    Never lose sight of the fact that some of your yeses have been from very prestigious publications. And not just in the UK either. You CAN do it and you certainly will!! 🙂 xxx ♥

  • Hattie

    Any form of self employment has the same sort of self-doubt and down times when nothing much is happening and these financially difficult times make it soooo much harder for us all in the ‘luxury’ markets. I’m sure things will get better and at the end of the day raw talent, which you have is spades, will always win.

  • cal

    so encouraging … thank you