We’re in the home straight of the 5x5 Pitch Challenge!
If you’re reading this, you should feel proud of yourself for dedicating this much time and energy to improving your pitching technique. Pitching is a gruelling and often thankless task. It’s the freelance writer’s white whale.
The good news, though, is that it can be conquered! It just needs to be tackled head-on. Developing a solid habit of pitching regularly is a sure-fire way to figure out where your strengths lie and what needs improving. By this point in the challenge, you might be thinking about stepping your pitching game at bit.
Here are some advanced pitching tips to think about this week.
Pitch the simple idea
Rory Gilmore’s life could have taken a very different turn had she just taken that assignment on lines more seriously…
You might be thinking, hang on, if this is advanced pitching, why are we talking about simplicity. Here’s the thing, though, a brilliant idea doesn’t have to be complicated. In fact, some of the most compelling writing brings the mundane to life (hello, Guardian long read on sandwiches).
And as the sandwich feature also shows, a simple idea can be the basis for an ambitious project. When you break it down, the premise for that 5,000-word story is a really straightforward question: how did sandwiches become so popular?
Questioning the mundane is a great place from which to mine good stories. We don’t often stop to ask too many questions about the things that are right in front of us. But when you do, you tap into something that speaks to so many people.
If you’ve been struggling with idea generation, going back to basics can yield some interesting results. What’s something that you do, see, eat or think about every day? What bigger story does it tell? Ask simple questions, like why and how. Why do people do that? How did that happen? See where a simple idea can take you.
Pitch over the phone
If you have an existing relationship with an editor, the next time you want to pitch them try asking for a call rather than doing it over email. It’s always good to try and speak to clients you work with regularly on the phone because it puts a voice to the email, but it also can give you a better sense of how they like to work.
If you like talking on the phone anyway, you may find that pitching like this actually works better for you. But even if you hate talking on the phone, having to say your idea out loud will force you to articulate it in a punchy sell.
The other benefit of talking to an editor on a phone is that you get a chance to get some real feedback. If you get them on the phone, they can’t ignore you like they can an email. And if they do turn down the idea, they’ll have to give you a reason for doing so.
Kill two birds with one idea
If you’ve got to a point where you’re comfortable turning ideas into pitches, level up by multiplying them. There’s no one way to tell a story; from one idea, a series of stories can spring.
As you’re developing your idea, think about what the best way to execute it might be. Can you spin out a feature, profile and op-ed from one idea? If one of the issues you’re having when fleshing out your pitch is deciding on which angle to take, separate out all the angles into different pitches.
Related to this, if you’re struggling with idea generation, consider some follow-ups. Have you written about something in the past that has since developed? You can either pitch it as a follow-up to the same place, or just pitch the idea fresh to a new outlet.
Pitch American publications
If you’ve been writing for the same places for a while, or if you’re just looking for new outlets in general, try pitching to American ones.
Check out my bumper list of publications to pitch to for ideas of where to send pitches.
Generally speaking, there are just more American publications. So if you’re struggling to find a home for your pitch, particularly if it’s for a niche idea, trying looking across the pond. American outlets also tend to pay higher rates and are also more open to longer features.
Pitch out of your comfort zone
Just like anything else, we can get stuck in freelance ruts. If this has happened to you, think about pitching outside of your comfort zone.
Start by identifying what your comfort zone is and where you’d like to be instead. Are you an op-ed writer but would like to try your hand at features? Or maybe you want to write profiles or longer-form features?
Once you’re clear on what your ambitious pitching aims are, try taking them to an editor you’ve worked with before. Tell them straight up that you’re looking to start writing about XYZ and pitch them something new.
Negotiate your rates
And lastly, the ultimate way to take your pitching to the next level is simply by asking for more money!