Fruitful, Frustrating, or Futile? How 6 Freelance Writers Feel About PitchingBy Stephanie Walden May 6th, 2021
Love it or hate it, pitching brands and media outlets is part of every freelance writer’s career. Whether it’s a foot in the door to a dream publication or way to get work from Contently, pitching can lead to some lucrative opportunities.
Not all writers feel the same way about the process, however. To examine the spectrum of opinions, we spoke with six professional writers about how they brainstorm pitches, what they enjoy and dislike about it, and the work they’ve landed as a result.
What’s your area of focus?
Arestia Rosenberg: I’m a creative director with several retainer clients ranging from brands to agencies. I help my clients with storytelling, content strategy/creation, and ghostwriting, as well as the odd one-off editing job, article, or website copy gig.
Poornima Apte: I’m a trained engineer turned technology content marketing writer. My beats are mostly (but not limited to) AI, IoT, big data, robotics, SaaS, MarTech, and mechanical and civil engineering.
Martin Soto: I’m a freelance B2B technology writer with a degree in computer science. I’ve been working as a freelance writer for about a year.
Joey Held: I’m a writer and podcaster. I typically work in verticals like marketing/advertising, insurance, and sports.
Jasmine Gayle: I’m a writer who focuses on niche issues that regard the Black community and mental wellness.
How long does it typically take you to construct a freelance pitch?
Rosenberg: I get most of my business now by word of mouth, so I typically do a 30-minute intake call to get to the heart of [a client’s] problem. If I think I can help them, I’ll normally take up to an hour to come up with some recommendations. A bigger assignment might take an additional hour. On the flip side, sometimes a clear brief is enough for me to get going without a pitch.
Soto: On average, I would say it takes me 30-45 minutes to construct a pitch. Most of my time is spent coming up with an article to write based on whether the website has covered it or not, and finding the correct person to pitch it to, since some websites have multiple editors. I have my own template, so I save a lot of time with that.
Held: It depends on how much background info I already have, as well as my relationship with the editor. I like to do a little bit of research beforehand to make sure there’s a viable story, so in those cases, crafting a pitch may take 30-45 minutes. In other situations when I have an idea of what I want to do already, those pitches usually take 10-15 minutes.
Gayle: It usually takes me anywhere from 3-4 hours to construct a pitch. I do a lot of research on the company, their website and writing style, social media, etc. These are all basic steps if you want your pitch to be seriously considered. Writing the actual pitch takes about 15-20 minutes.
What do you dislike about pitching?
Rosenberg: I hate putting so much heart into my pitches and not getting [the work], or worse, not hearing at all. I often give people free advice with my pitches because I truly love problem solving, but it takes so much time that it sucks when it doesn’t pay off or you don’t even get a thank you.
Apte: Too often, it feels like you’re nailing Jell-O to a wall. Whether or not an editor says “yes” depends on so many factors: whether a similar story was just assigned, whether there’s room in the budget, shifting priorities, and on and on. So many of these factors are completely opaque to us writers. There are times when an idea goes into a black hole and you never hear back. It’s understandable, as editors are busy people. But for me, the return on time and energy invested to actual positive outcomes is too low.
Too often, it feels like you’re nailing Jell-O to a wall.
Soto: Pitching can be time-consuming, and there isn’t always a guaranteed result. You can spend a long time crafting the perfect story idea for a specific website, and then not even get a simple reply saying they’re not interested. It can crush your enthusiasm for pitching after the first few failures.
Umesi: The anxiety of putting myself and my ideas out there, the fear of rejection, and honestly, the time it takes. Unless you have no work and need to pitch, brainstorming and pitching can be tedious and feel almost like you’re wasting billable hours.
Held: I dislike when places have really strict guidelines about their pitching process. I understand those rules are likely in place to give structure to writers, but it feels restrictive. If I’m pitching someone for the first time, I can provide a couple paragraphs on the article and share a few links to show my writing quality, and that should be sufficient. Sometimes, though, the process almost feels like a full-time job application.
Gayle: Since I enjoy researching, I never really dislike pitching. However, the waiting game can be daunting. Some editors never respond—but most do.
What are some of the pros?
Apte: Early on in my career, I pitched a fair amount and worked on meaty features that highlighted my strengths and knowledge of technology. That established my credibility and pushed me up the rungs a bit. So pitching played a role when I was getting started. But even for a pitch to get accepted, you often need clips—so it’s a chicken-and-egg situation sometimes.
Soto: The most significant advantage about pitching is that ultimately, you can decide what you want to write about. You’re able to choose what you want to cover. Also, many popular, prestigious websites that most people would love to have bylines for typically aren’t reaching out to freelance writers.
Umesi: Because I have a couple of clients on retainer, it’s easy to fall into a routine of doing the same kind of work all the time. Pitching keeps me on my toes and engages my creative side. It forces me to think outside the box, even if I don’t get the opportunity.
Pitching keeps me on my toes and engages my creative side.
Held: Whether you’re writing an article for a newspaper or doing content marketing for a brand, as a freelancer, you’re offering a perspective that the in-house [team] doesn’t have. When you pitch an idea and can feel excitement coming from the other side, you can’t help but smile.
Gayle: I enjoy researching, I really love getting a feel for each company, brand, and their unique style. It makes speaking to my clients easier. I feel like I’m already a part of the team.
What’s your ideal split between pitching work and receiving assigned work?
Rosenberg: Honestly, I would never pitch if I didn’t have to. I like to think my work or my previous clients’ recommendations speak for themselves.
Apte: I like to spend most of my time writing the actual article or case study or whitepaper, and my editors usually assign me work. I hardly ever pitch. It also helps that I enjoy writing everything, and I’m not picky—if an editor wants something done, they find me and we hit the ground running. I love that. No guessing games.
Soto: It makes sense to craft pitches if you want to be featured in niche publications. Being published on large [outlets] is another way of obtaining routine inbound leads. Many companies read articles on these niche publications and look at who writes them. It’s never a bad idea to have multiple ways of getting work.
Umesi: Ideally, 20 percent pitching, 80 percent working—but then again, not every week is ideal.
Held: Somewhere between 30-40 percent pitching and 60-70 percent assigned work. I like the flexibility of crafting a pitch, and sometimes when I’m doing that initial research, I’ll discover something that triggers another idea. The ideal situation is having a client that offers a steady stream of work but is open to pitches from you. It shows they value your input.
Gayle: When my work starts to meet my income goals, I just switch to a temporarily unavailable status [and stop submitting pitches].
Do you think pitching has gotten easier or harder over time? Why?
Rosenberg: Much harder, but mostly because everyone now says they are a “writer,” and there are way more pitches for an editor or client to wade through. It’s hard to break through and stand out.
Apte: I do like to pitch editors I work with somewhat regularly. In such a case, I already know what they’ll like, so it’s easier to get to a “yes.” In these specific instances, pitching has gotten easier. That said, a lot of it is still difficult, especially if it’s a new client with loosely defined content guidelines.
Soto: In my opinion, pitching has gotten harder over time. Editors are receiving more emails than ever, which has made it harder to stand out. On the other hand, pitching becomes easier the more you do it and the more successful results you get. You eventually learn what works for your niche.
Regardless of staff size, just about every place values a good story.
Umesi: Both. It’s easier in the sense that I understand the process better; I don’t feel as blind as I did at first. I also know what I like to write about, and I no longer pitch to just any outlet. At the same time, it’s harder to pitch because of time constraints.
Gayle: Definitely now with the pandemic, it’s a little harder. Companies’ budgets have fluctuated. However, you just have remain consistent with your pitches.
Held: Is it a cop-out to say both? I think it can be harder to break into some publications because editorial staffs are unfortunately shrinking and in-house writers are being asked to do more. But there are so many places producing content that you can find a nice niche to work in, no matter your areas of interest. And regardless of staff size, just about every place values a good story.
Describe a time you got to write an awesome story based on a pitch.
Apte: One I absolutely loved working on was the concept of “sponge cities” to prevent flooding. It was a story I pitched JSTOR Daily, and it was wildly successful. The neatest part was when my husband’s cousin randomly pinged me and said I was trending on some geek group he was part of.
Umesi: I pitched the BuzzFeed Books editor an idea I thought was very cool (middle-grade readalikes for popular young adult books). I like to think it was the first crossover post of its kind, and she loved the idea and the final result as much as I did.
Held: I’m a big fan of wordplay—some might even call me a word turbine—so when I learned about the O. Henry Pun-Off in Austin, I knew I had to check it out. It’s an annual competition where people write a monologue full of puns or participate in a back-and-forth Punslingers event… This story was one of the longest lead times I’ve ever had—I pitched it in the fall of 2015, attended the event in 2016, and the article ran in the spring of 2017. Even with all that waiting, I love how it turned out!
Rosenberg: I wanted to write about my favorite music festival, The Newport Folk Festival. I was working for The Daily Beast at the time, and they didn’t go for it. The next year, I tried again with a new angle, and they accepted and published it. It felt really good not only to get the win, but to write about something I love.
Responses have been edited for length and clarity.Image by Lilanakani