The 5 Biggest Mistakes I’ve Made While Pitching

When I began writing freelance, I’d already been writing for my blog for a few years. I knew there would be a learning curve because writing for yourself is completely different from writing for another publication. 

To prepare myself, I participated in a few workshops and was mostly interested in the lessons about the best ways to pitch, since I’d never done it before. After gaining as much insight as I thought was necessary, I set out on my endeavor as a freelance writer. 

I quickly realized trial and error were better teachers than any class. 

There were so many things I learned from actively pitching. In this post, I’ll share with you the five major mistakes I made, and how the experience helped me hone my skills. If you want to perfect your own pitching strategy, feel free to use my tips as a “cheat code” so you don’t make the same mistakes I did!

Not Realizing There Are Multiple Editors at a Publication

As a beginning freelance writer, I did not take into consideration that there is often a different editor for each topic covered—especially in some larger publications. I soon discovered you shouldn’t pitch to the first editor you come across. 

Instead, you must do your due diligence to make sure that the editor you pitch represents the area that your piece falls under. Otherwise, you run the risk of pitching to the wrong person and you waste your time and theirs.

Especially if you obtain the editor’s contact information from a source outside of the publication, always do a quick internet search for the masthead and the guidelines. This way, you make sure you’re pitching to the correct editor and you are following those ever-important submission rules. 

Being conscientious will save you time, unnecessary headaches, and the embarrassment of annoying a very busy editor who will likely have no interest in your pitch if it’s unrelated to what they cover.

Another risk is the editor may never respond to you and you misinterpret this lack of response as a rejection stemming from the quality of your pitch. In reality, you may have simply emailed the wrong editor. If you’d done your research, you could have sent your pitch to the appropriate editor and possibly gotten a green light. The mistake then becomes a missed opportunity. 

Luckily, when I committed this faux pas, the editor I pitched was nice enough to forward my email to the right editor. But not everyone will do so. 

Another time (yes, unfortunately, I did this more than once), the editor simply said they weren’t interested. I chalked it up to another rejection until I realized the person edited a different topic than what I had pitched. I felt really foolish. I surely didn’t make this mistake again, and neither should you.

Not Analyzing the Significance of Evergreen vs. Timely Pieces

An important thing to understand is the difference between evergreen and timely pitches. The difference may seem obvious, but implementing this understanding comes with strategy. 

Consider pitching evergreen pieces to publications that are bigger, that you haven’t worked with before, that take a long time to respond, or that don’t respond unless they like your pitch. The reason behind this approach is if you send a timely pitch to these publications, by the time they get to your pitch in their overflowing inboxes, the timeliness may have passed. 

This concept also relates to simultaneous pitches. If you have a timely piece, you should pitch it to several publications so that you can increase your chances of getting a response before the timeliness lapses. We’ll take a look at simultaneous pitches in more detail later in the post.

Once, I pitched a timely piece about a popular show. I assumed that because the show’s season was still running, the publication would be open to submissions about it. I failed to realize that publications often have their publishing calendars scheduled well in advance and many writers get early screeners of shows and can write a story before the show even premieres.

To the same point, if there is something huge going on in the news cycle, you should submit your timely pitches even if information is still developing. For example, when the Black Lives Matter protests made a resurgence, almost every publication wanted pitches from Black writers. 

At the tail end of the protest coverage, I tried to catch the wave and pitched to several publications. Some editors later responded that they were just getting to my pitch and would have accepted it had they received it earlier. 

Implementing a strategy including when, how, and where to pitch an evergreen pitch versus a timely pitch is another crucial way to save time.

Not Having a Strong Hook

This tip is probably the most important of them all. When I began my freelance career, I struggled to articulate my hooks. Not having a strong hook, burying it in the middle of your pitch, or tacking it onto the end of your pitch will result in your pitch being much less likely to grab the attention of an editor.  

Be Strategic

Crafting your hook takes practice, but it’s also another opportunity to use strategy. Sometimes, the effectiveness of a hook depends on how niche or mainstream the publication is. 

Niche publications tend to appreciate relatively broad, relatable hooks as long as they align with the type of content they publish. Readers turn to special-interest publications to learn things within that area, not necessarily to read a story from a unique point of view. These publications are more concerned with what a group of people have in common. 

On the other hand, publications that cover a variety of areas tend to be drawn to hooks that are specific and distinct. One reason they look for distinct hooks is that the broader, informative stories are usually written by staff writers (or uber-successful thought-leaders), not procured from freelancers. 

The other reason is publications that serve a wider population want a story that will interest the masses. What is more interesting than a truly unique story that no one has ever heard before?

To illustrate this broad versus distinct hook concept, here are two examples. A smaller yoga magazine would probably accept a freelance pitch about the best yoga poses for stress relief while a larger, more mainstream publication would not, even if you pitched to its wellness editor. 

The mainstream publication would more likely accept a freelance pitch about how a yoga class taught an interracial adoptee the importance of family and community. 

Moreover, note that the first example covers one topic, while the second example is a combination of topics, which tends to be more intriguing. You can get away with one-topic hooks with smaller niche publications, but not so much with larger mainstream publications. This method, of course, isn’t an exact science; there are always exceptions. 

Crafting Your Hook

Another tip is to brainstorm your hook before you start writing the pitch. This is another seemingly common-sense concept, but often when an idea comes to us we hit the ground running. It’s perfectly fine to start off, as they say, “pantsing” it, but make sure to do a rewrite that begins with your hook and continues in a clear and concise way.

More than a couple times, I wrote a pitch that I thought had a great hook. In reality, my pitch was convoluted because either the hook was not clear or my writing gave the impression that there were multiple hooks. It wasn’t until a few days later when I was making the same pitch to another publication that I realized what a mess it was. 

If you’re having issues writing a pitch with a strong hook, write a rough draft and then sleep on it. You won’t have to employ this process with every pitch or even every time you pitch, but it’s good practice when you’re a beginner or if you have a multi-layered story to tell. As with regular writing, some time away from your words gives your brain a chance to process your pitch with new eyes when you return to it. 

Editors love a well-crafted and appropriately placed hook because it allows them to immediately tell where you’re going with your story and if they are interested. Most editors don’t have time to ask you clarifying questions about what you are trying to say, and you don’t want to be the one who tempts them to do so. 

Writing Pitches That Are Too Long

I can be a very verbose writer, so it’s sometimes hard for me to draft a pitch that stays within the desired word count. It didn’t take much time for me to learn that a pitch that’s too long, especially one that takes forever to get to the point, will make an editor quickly lose interest. 

Usually, I get excited about a topic and I start writing feverishly to get all of my ideas down. When I first started pitching, I believed that if I didn’t include all of my thoughts, the editor wouldn’t get the full picture of what I was trying to say. This way of thinking is definitely misguided. 

It takes skill to get your point across with as few words as possible. It’s OK to initially write your heart out in as many words as you like. But then you must go back and edit until you have a pitch that’s just the right length and shows that you can express yourself succinctly. 

If you accomplish this task, the editor will see how competent you are and, as long as the content of your pitch is suitable and interesting, they will want nothing more than to give you a byline. 

Whittling down your pitch to the most significant points can be challenging. But if you have enough confidence in yourself, your writing ability, and your ideas, the task will be that much easier and you will be well on your way to publishing success.

Not Pitching Simultaneously

When I first started pitching, I thought of a new pitch idea for each publication. I learned that unless the pitch is unique to the publication or the publication doesn’t allow simultaneous pitches, this tactic isn’t always the best idea.  

Not pitching simultaneously can create obstacles in your pitching process. Some editors do not respond to pitches at all unless they accept them. So, you risk wasting a story idea that another publication may be interested in while you’re waiting for a reply that is never coming. 

Cast many lines so you have a better chance of getting a bite. Of course, depending on the story, the pay, and the publication, pitching to multiple outlets at the same time is not right for every situation and it requires strategy. 

If you think your story is a good fit for more than one publication, and the guidelines allow it, pitch your story widely. If these publications have vastly different pay rates, pitch to the higher-paying ones first, and then stagger the rest. This way, you’re still prioritizing the well-paying publications, but you aren’t reducing your chances of publishing your story. 

Focusing on the goal of getting published does not mean you should pitch somewhere that does not pay well just to get a byline. Always do a costs-benefits analysis and use your best judgment.

Once, I really wanted to get published in a publication that was probably out of my league at the time. If I’d realized the pitching game is similar to applying to colleges, I would have pitched to other places too. 

Instead, I waited to hear back from this dream publication. After waiting in vain for a response, I understood I had to pitch my story elsewhere. Despite this setback, I ended up getting my story published in another publication and was very happy with it. If I hadn’t pitched simultaneously, my story wouldn’t have been published at all.

Bonus Tips 

Now that I’ve shared my five biggest mistakes and what I learned from them, let’s also take a look at some bonus tips that you can use to perfect your pitching strategy.

Join a Group or Listserv for Freelance Writers 

Joining a group will help you network, build a community, and acquire tons of support, information, and advice. I am a part of a group called Study Hall and, although it does cost, there are inexpensive package options. A subscription comes with a plethora of resources, like a weekly list of calls for submissions and writing jobs, and connections to thousands of writers. 

Having a community keeps you abreast of industry developments and allows you to discover that all freelance writers, no matter their experience level, go through similar challenges. 

Look at the Bylines of Other Writers

Have you ever wondered how a particular writer earned a byline in, say, the New York Times? Visit their website and check out all the places they wrote for before they scored their NYT piece. Scoping out another writer’s work will help you to find more places to pitch, especially if this writer works in your niche. 

Freelancing is a career you learn by doing and by observing how other freelancers navigate the landscape. You’d be surprised how much you can uncover by following a fellow writer’s trajectory. Of course, the key is not to follow the path precisely. But just seeing how it can be done is great encouragement to get where you want to be in your own career.

Pitch in Your Own Lane

Not everyone is a reporter or a journalist, although some of those skills can be learned through practice. I didn’t go to journalism school, and even though I’m pretty good at research and have conducted interviews for my blog, that doesn’t mean I can do research-based reporting or pitch a feature interview. 

I’ve happily realized that I’m not a reporter, but a freelance writer who specializes in personal essays and op-eds. I used to be intimidated by the thought of writing reported stories, but now that I know I don’t even have to think about doing that, I feel more comfortable perfecting the skills I already have.

In the same way, not everyone can tell every story. You may have to pass a story along to someone else or, if you get a rejection, remind yourself that maybe the story isn’t meant for you to write. However, if you’re passionate about the story and are up to the challenge, send out that pitch. If your piece is published, you have a new skill or niche to put on your resume. 

Practice Makes Perfect

As a new freelance writer, it’s hard not to feel overwhelmed by the idea of pitching. It’s also hard not to get discouraged by rejection. You may start to think there is something wrong with your writing and may even consider quitting. Yes, there are always ways you can improve, but that doesn’t mean you aren’t a good writer. Improvement may be as simple as shortening your pitches or being more strategic. 

The bottom line is, just as in writing, the practice of pitching is the only way you’ll learn to perfect your skills. I made many mistakes, but the experience helped me gain the skills I have now. Because of that, I can now pass these tips on to you.

If you build a community of fellow freelancers, learn what similar writers are doing and proudly own what your specific skill set is; you will be more likely to succeed. You will feel better about your writing career knowing that you are armed with the right tools, and you’ll have the confidence to keep pitching.