This article could also perhaps be called "How to Better Manage People's Expectations." It's been a little bit of a cranky week: I've done articles on the power of telling people no and also how people are getting more and more distrustful. But I think this is a point worth making, especially since I run into it a lot in the freelance writing world.
Even if you're a lone gun, you want to please the people you work with. No one wants to disappoint anyone, and this is totally out of whack with the fact that we're all doing way too much. We work too many hours for too little pay, don't want to let anyone down and are not willing to let the ball drop anywhere – even though, inevitably, it does, somewhere. Whether we're aware of it or not.
Something that surprises me, though, is that a lot of people I know, when given the opportunity to set their own deadlines, set themselves up for failure. How? By promising something too early and then waiting until the last minute to even start. If you're their boss and are lucky, they'll let you know, shoot, they just won't be able to make it. More often, though, in my experience as an editor, people will try to duck you. Not only does that breed friction between a manager and their employee, freelancer or what-have-you, but it's just downright rude and completely transparent. It's like when you had a huge paper due at school and you stay home that day, thinking you'll be able to avoid the pendulum of due dates. Deadlines are called deadlines for a reason.
So, rather than set yourself up for failure, and if you're given a choice, artificially inflate your deadline. I do it all the time and almost always deliver the article, pitch, whatever early. That's more of a win-win situation than a lose-lose, and while I realize it isn't always possible, it's apparently something that isn't quite common sense. It should be, but you really can't make assumptions about anything anywhere anymore.
In short: If you want to please someone, set their expectations a little lower (ask for more time) and then surpass them (turn stuff in early).
David Wolinsky is a freelance writer and a lifelong Chicagoan. In addition to currently serving as an interviewer-writer for Adult Swim, he's also a comedy-writing instructor for Second City. He was the Chicago city editor for The Onion A.V. Club where he provided in-depth daily coverage of this city's bustling arts/entertainment scene for half a decade. When not playing video games for work he's thinking of dashing out to Chicago Diner, Pizano's, or Yummy Yummy. His first career aspirations were to be a game-show host.