A reader writes in with a classic conundrum that we’ve all faced. Say you’d like to profile Peter Moskos, the renowned author and thinker on policing issues, for Esquire Magazine, but you have no connection to either Moskos or Esquire. You may not want to pitch Esquire until you’re sure Moskos will cooperate and you’ve done a preliminary interview to get enough material to bait the hook. But at the same time, you don’t want to ask Moskos for his time until you’re sure you have the assignment from Esquire. Chicken, meet egg. The solution is staring you right in the face. It is, as it so often is, abject honesty.
Approach Moskos first. Tell him, “I am preparing a memo about you for the editors of Esquire in the hopes that they will assign me to write a profile of you. May I please have a preliminary interview to gather some material for that memo?” Note that you haven’t said that you have such an assignment. You haven’t implied that you’re a staff writer or that this is a sure thing. You’ve told the truth, the whole truth, and nothing but the truth: You’re preparing a memo for the editors of Esquire. That should be enough to get you that preliminary interview, during which you can ask Moskos whom else you should interview to write the memo. (His will be self-serving suggestions, but if he’s found himself on the opposite side of an issue with anyone, that name should come up in the preliminary interview, too, and you can decide whether he or she should be interviewed for the proposal.) Once you’ve done the preliminary interview with Moskos and anybody else that seems necessary, and you’ve gathered the documents you’ll need fully to understand Moskos, you can write the proposal, being careful, as discussed here, to write it in Esquire style.
This may seem like a lot of unpaid work with no guarantees. It is. Writing a successful magazine proposal can take as long as it takes to write the story itself. Once you get the assignment, writing the piece is easy because you’ve already done all the hard work — conceiving the story, deciding on a structure, finding the sources and the documents, even doing some interviews. This is how you make money and keep from going broke as a freelancer; you do this pre-proposal work quickly and with great concentration, and you write a truly stellar proposal. This is when you really work hard. Even though the assignment, once you get it, will come with a deadline, you can actually rest on your oars a little as the post-assignment research and writing begin. You’re over the big hurdle. As Hunter Thompson used to tell his impatient editors at Rolling Stone, “the piece is finished; all I have to do is write it down.”
Got a problem with any of this? Let me hear from you.