Question: Should I wait for a freelance callout to apply? Should I pursue the lead editor of specific publications regardless of a freelance call? Should I pursue maybe not the lead editor, but another member of the same company who may understand my vision best to try and get them to take my idea to the editor? What does a successful pitch actually look like? If I fail to make any traction at one of my target sites of application do I keep applying and tweaking the idea/keep applying and stand firm behind my initial vision/at some point give up and target other smaller publications? 

As usual, we begin with rapid fire answers and then break them down into something more nuanced. Here it goes! Do not wait for a freelance callout to pitch. Follow the guidelines. There are times where it’s appropriate to approach the lead editor directly but not as many as you may think so be careful not to overstep or annoy. Other people at the publication cannot pitch on your behalf. Don’t put them in a position where they have to tell you that. However, you can contact to ask who to send your pitch to (this is for cases when the site has no calls and no posted guidelines and no staff page and essentially no way of you knowing how to pitch them). A successful pitch is clear, concise, interesting, fits the site, explains how you’re gonna execute, and why you’re the best person for the job. If it’s an evergreen pitch and a larger publication doesn’t want it, try it elsewhere sure! You can tweak it as well. Maybe run it by peers for feedback if the editor didn’t give you any. Also shift your mindset on smaller publications in general.