Here’s the cold, hard truth about how I’ve landed some of my most impressive bylines and my best freelance writing clients: I pitched. 

Cringe. Sigh. Groan.

I get it. It’s the news nobody wants to hear — especially since so many writers hate pitching. But I mean it when I tell you that learning how to write a pitch and getting over my fear of pitching  was a huge boost for my freelance writing business. 

8 common questions (and answers) about freelance writing pitches

Needless to say, I’m a big believer in the power of the pitch. Such a strong believer, in fact, that I created “Pitch Pack: 8 Pitch Templates for Freelance Writers.” It’s a collection of eight different email scripts to help you send pitches that get responses and results. 

I love templates for giving you a tried-and-true formula to follow, but I also recognize that they can leave some of your questions unanswered. So, I’m rounding up some of the most common questions I get about pitching as a freelance writer — along with some hard-won answers. 

1. What should I use as the subject line for my pitch?

Oh, subject lines. So few words, yet so much stress. Fortunately, writing your pitch subject line doesn’t need to be a nail-biter. I recommend freelance writers use the same subject line for every single pitch they send. It looks like this: 

“Freelance Pitch: [Proposed Article Headline]”

What makes this so effective? For starters, using the term “freelance pitch” at the front shows editors and content managers exactly what you’re getting in touch with them about. Listing “freelance pitch” as opposed to just “pitch” is helpful, as it separates you from any PR pitches that could be landing in their inbox. 

Next up is your proposed article headline. We all know that the most effective headlines should be attention-grabbing, making it a powerful thing to use in your email subject line. And bonus? It shows that you’ve thought carefully about the angle of the story you’re pitching. 

While I use this as my default subject line when sending pitches, I always make sure to check for instructions from the outlet I’m pitching. If they have posted submission guidelines, occasionally they’ll ask that you use a specific subject line so your email gets filtered correctly. It’s crucial that you follow those instructions! 

2. How long should my pitch be? 

Spoiler alert: short. 

I get that there’s a strong temptation to make friendly small talk, explain your background and share a dozen of your favorite writing samples, but an editor isn’t going to spend time scrolling through all of that. 

Instead, the bulk of your focus needs to remain on what really matters: your story idea. That means your pitch email should be no more than a handful of paragraphs and your story pitch itself should take up the most space.

While you’re at it, other email-writing best practices apply here to. Using short sentences and paragraphs and even things like bullet points make your email that much easier for an editor to read — and hopefully respond to. 

3. Are there good and bad days to send a pitch?

This is one of those things that I think freelancers have the tendency to assign a lot of importance to. Yet, I’ve heard from practically every editor I’ve ever worked with that they couldn’t care less about what day you pitch. 

In general, I’d avoid sending in a pitch on a day where something super newsworthy is happening (like an election or a major natural disaster), unless your pitch is related to that specific event. But otherwise, every other day of the week is fair game.

I know plenty of freelancers (myself included) who still have personal superstitions about when to hit “send” on their latest pitch. For example, I avoid Mondays and Fridays because I think editors are either swamped with emails or checking out of their inboxes for the weekend.

But again, all of that is pure conjecture on my part — there really isn’t a proven “best” day to submit your pitch. 

4. How long should I wait to hear back from an editor?

You submitted your pitch, and now you hear nothin’ but inbox crickets. Should you follow up? If so, when?

This will largely depend on your story. If you’re pitching something timely (i.e. something that needs to be written and published in the next couple of days) you might need to follow up within 24 hours. 

If you’re pitching something evergreen without a strict timeline attached to it, then waiting about a week is a reasonable timeline. Once that week has passed, you can check-in with a friendly nudge without seeming pesky or overeager.

Related to timing, there’s one more thing I started doing it after Tim Herrera, editor of The New York Times’ Smarter Living section, recommending it during a panel I participated in: including a deadline with my pitch.

I’ll jot a line that says, “If I don’t hear back from you by [date], I’ll assume you’re not interested and move forward with pitching this story elsewhere,” at the bottom of my pitch emails.

While you might think that seems pushy or demanding, I’ve found that editors actually appreciate it. It takes some pressure off of them, as they don’t have to respond if your pitch isn’t a fit for what they’re looking for.  

5. Can I pitch an editor who previously rejected me?

Absolutely! Rejection always feels personal, but it’s important to remember that your story idea was turned down — not you as an entire person.

If you come up with another idea you think could be a good match for that outlet or publication, you’re more than free to pitch again. I know from experience that sometimes it takes a few pitches before something sticks. 

When you do decide to pitch an editor who previously turned you down, resist the urge to explain or, even worse, apologize for the fact that you were rejected before. This might be the story idea that lands, and there’s no need to justify why you’re reaching out again. 

6. How do I know what writing samples to send with my pitch? 

When I submit a pitch, I also include links to a few writing samples in case that editor wants to get a better sense of my default style and what I’m capable of as a writer. I’ll also send a link to my full portfolio, but I prefer to hand-select some more targeted pieces for them too. 

How do I decide which ones to send? The most important thing I look for is relevance. If I have a sample that’s somewhat related to the article I’m pitching — whether in format, style or topic — I’ll include it (provided I feel it’s a solid piece). 

If I don’t have anything that’s relevant, then I’ll pull a few of my pieces that I think are the strongest. Take note that those aren’t necessarily the ones that are published by the biggest-name publications. Rather, I want the ones that showcase my abilities best. That should be your golden rule when selecting samples to send: You want samples you feel confident in. 

7. Can I pitch if I don’t have any writing samples?

Here’s the first question I’d ask you: Why don’t you have any writing samples? 

Sure, maybe you haven’t written any paid articles for clients or publications. I get it — everybody starts somewhere. But, there’s no reason why you can’t write something for your own website. Or publish a piece on LinkedIn. Or on Medium.

While it’s more than possible to pitch without including samples in your email (hey, a good story idea is a good story idea!),  it’s helpful to include a few links that show the editor that you’re capable of stringing some sentences together. If you don’t, it’s entirely possible that they could ask you for some samples. Then you’ll be stuck explaining that you don’t have any to share. 

Keep in mind that the editor will care way more about the quality of your samples than they will about where they’re published. So, ultimately, there’s no reason why you can’t send some clips (even ones you wrote and published for yourself!) along with your pitch. 

8. Should I pitch the same story to several outlets at once? 

In general, I’d refrain from doing this. What if more than one publication wants to run your story? How will you explain that? And more importantly, how will you decide who gets to run it? 

That’s why it’s better to pitch the story to one outlet at a time and include the deadline for a response that we talked about earlier. If you don’t hear anything by the date you listed, then you can move forward with pitching your idea to other outlets.

There’s one important exception here: If your story is urgent or timely. In those cases, you might want to pitch to several places at once so that you can run it in that tight timeframe. But, when you do so, consider including a note that you’ve pitched the story elsewhere. 

Ready to become pitch perfect? 

I get that pitching as a freelance writer is enough to inspire nail-biting and sweaty palms, but it doesn’t need to be nearly as intimidating as you’re making it out to be.

Need more help? My eight different pitch templates for freelance writers will get you on the right track. There are copy-and-paste templates for a variety of situations — from pitching an editor who previously rejected you to pitching when you don’t have many published clips. Plus, each template includes a completed sample, so you can see what that email looks like when it’s all filled in.  

You’ll be well on your way to sending pitches that get results. I’m rooting for you! 

Photo by Vlada Karpovich from Pexels

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Roland Millaner