Power of (to?) the deadline

An ode to the professional writer's most important accountability tool

I'm inspired to discuss shifting deadlines because it's the second week that I've moved mine from Friday evening to Saturday morning for this newsletter. My intention is to make this a weekend read to help those who are either busy freelancing during the week to think about these big picture issues, or newcomers to freelancing who need inspiration for their weekend side hustle. Either way the timeline between Friday night and Saturday morning doesn't matter as much as making it pre-weekend. I aim for Fridays so that Saturdays are a fallback. Because other than this flexible one, deadlines are one of my most significant professional values.

What I’m saying is that I actually love deadlines. And not in the way of that famous Douglas Adams quote: "I love deadlines. I like the whooshing sound they make as they fly by." As a writer my life is mostly built around deadlines, and I'm always surprised when I hear another writer casually comment about being relaxed on deadlines, or dismissing their importance. Whether it's a publication or a client, I think one of the best fulfilments you can make is to produce what you said you would in the timeframe you agreed on.

I will stay up late and break many of my other boundary rules (i.e., don't work before 9 or after 5 without good reason) to meet a deadline. That said, one of the challenges of this work is juggling many deadlines. Your other clients likely don't know that you have five other projects due that week (or that day) but really, that's not their problem.

I tell my students that if you are going to miss a deadline, and you've tried bending your own boundaries, then try to give your client (or your professor) as much notice as possible. In business, it's one of the challenges of freelancing to decide how much work to take on so that you can fit things in comfortably, or to decide to be a bit uncomfortable when the feast is on to account for any famine later. I actually get most antsy when an editor tells me their deadline is flexible (“just get it into me the next month or so”) because I want to be held accountable to a date. I often set myself an internal deadline anyway just so I have a target to shoot for. With a work life that’s really flexible, I find that I need deadlines the way a toddler needs a bedtime in order to feel productive and in control of my week.

What's your relationship with deadlines?

Any tips or tricks you use to stick to them?