Now that I’ve reached some small level of success as a freelance journalist I’ve had many budding writers reach out to ask about getting started in the biz. I want to be of service, as so many experienced journalists were when I began, so I’ve prepared this blog post just for them.

Let me just start by saying that it’s a painful, lengthy, harsh, soul-crushing, brutal process, and if you make out the other side in one piece it’s only because you believe that any amount of pain and suffering is worth the opportunity to be a journalist. If you have any trepidation, any reason to doubt that this is what you want to do with your life, you likely won’t make it.

If you’re serious about being a journalist, and I mean really serious about it, than I may be able to provide some advice:

I spent the first year of my career barely earning any money. Instead I was contributing to notable but still small publications without much of a freelance budget, not for the money but for the addition in my portfolio. My first bylines appeared in local publications like BlogTO ($0.00 at the time) VICE Canada ($75.00 for 1,800 words at the time) and Post City Magazines ($200 for 1,200 words at the time).

Once I had enough content in my portfolio from unpaid/barely paid work, it was time to start pitching bigger publications. You can start pitching bigger publications any time, but they probably won’t be responsive until you’ve got something substantial to show them. Even today I’m looking a few steps ahead, thinking about how a story in a local paper on financial technology, for example, might provide the credibility required to write a story on financial technology for a top-tier magazine down the line.

Before you pitch, research the publication as much as you can. Go back and read the last 2 or 3 editions, or spend an afternoon or two on their website. Identify their tone, the audience they seem to be trying to attract (often found in the section dedicated to advertisers) and the section(s) of that publication that you want to write for. Then go back and read even more from those sections. Get a sense of the length of those stories, overarching themes, their go-to writers, how they start and how they end, etc. Then identify the editor of that section and send them a pitch email.

Once you know the publication inside and out, send the editor of the section you’re targeting a confident email that isn’t begging for work, but explaining why THEY NEED YOU to write that story for them RIGHT NOW! Based on your research, your pitch letter should open with a little bit about the story and go on to explain why their audience needs to read about this subject right now. Remember, editors think in terms of headlines, and the first thing they think about when reading a pitch email is “what will the headline look like?” If you can feed them a story that has a compelling headline, your odds will skyrocket.

The basic structure should look something like this (using absolutely none of these exact words):

It is rare to get a response on your first email. Follow up no less than 48 hours later (no more than a week). If it’s breaking news that won’t be relevant in 48 hours, send the email, wait 2 hours, and give them a call to ask if they read your email (but be really apologetic about it, knowing they likely didn’t have time to read your email, but explaining how this story can’t wait for them to get around to it).

To be a freelance writer, you don’t just have to deal with rejection, you have to learn to love it. I do. If I’m not rejected 20 times a week, I’m simply not trying hard enough. You can’t take it personally, and you can always adjust stories and repurpose them for different publications if they fail the first time around. If the editor is kind enough they might give you a reason why they rejected the story and encourage you to try again. If they’re too busy you may never hear from them. Embrace it.

When Stephen King began writing he had a nail hanging above his bed that he tacked on every rejection slip he ever got. When the papers got too heavy and the nail fell out of the wall he replaced it with a railroad spike and kept on writing. They don’t send rejection slips by mail anymore, but if they did, I’d proudly have a full railroad spike (or two) hanging above my desk for inspiration.

Every editor I’ve spoken to tells me that they’re amazed by how many freelancers get to this point and disappear off the radar. The reason why I have a career at all in this business is because I submit all of my work ahead of deadline with minimal editing required (not always, but I try). I was getting assignments over people twice my elder when I began simply because of reliability. To an editor, headlines and reliability are the basis of their interactions with freelancers. Give them both and you’re on your way to a long lasting relationship.

That’s all for now. If you are an aspiring freelance writer/journalist and have any questions that aren’t covered above, feel free to shoot me an email. You may also want to take a look at this story I wrote recently on freelance journalism. Best of luck!