Figuring Out What Works: Hard Deadlines with Something at Stake

Deadline is a scary word.

I’ve struggled with completing large projects for many years. And the truth is, until recently, I tried everything BUT deadlines. Why? Because, like I said, deadlines are scary. It has the word “dead” right in it, after all. So, in my mind, deadlines were an absolute last resort.

I never wanted to be dependent on deadlines. They suck! I wanted to work without them … until I absolutely had to work with them. Like someday, in the far future. If ever.

Deadlines, deadlines, deadlines. They constantly get in the way of an ideal lazy life. For example, I have to go to work each day and fulfill scheduled promises and contractual obligations in order to keep my job, and I have to pay my bills on time. None of this is fun, but it must be done. There’s a lot at stake, such as the well-being of my family. We are a one-income family, so the pressure’s on. And so, I have no choice but to keep meeting my deadlines.

I was still in college until very recently, and every homework assignment had a deadline with something at stake. For a very long time, I was (somehow) maintaining a 4.0 GPA. It was a heck of a motivator to make sure I turned in every assignment on time, because it had become something important to me, and it was constantly at risk.

Somewhere down the road, I ran into two particularly difficult professors who managed to chip me down, and I recovered to a 3.9. But by then, I’d gotten so in the habit of turning in all my assignments–ensuring they were well-polished and on-time–that maintaining such a high GPA became easier than I ever thought possible. It became a ritual. It became habit.

Now, if only I could finish writing a novel.

…I guess the writing’s on the wall, huh?

I’ve even got rock-solid proof that hard deadlines works. A professional editor friend of mine who has done a fair bit of ghostwriting–along with developmental and copy edits for books you’ve likely heard of–promised that he would do a full service edit of Chio Pino for free if I could finish the manuscript and have it on his desk in two months.

Of course, it all clicked into place. I found myself working hard, understanding how much I was capable of completing each day and how quickly I could complete my goal. I knew this free edit would normally cost me around $10,000 and that this guy is usually far too busy to handle things on the side like this, so something was very much at stake. Now, I’m not such a bad editor myself, but it can never hurt to have a second pair of eyes on a manuscript, especially eyes of that pedigree.

Lo-and-behold, I managed to complete and polish up my story just in time.

Which brings me to part B of this blog post: Self-imposed deadlines don’t work. At least, they don’t work for me. I can deny myself something, sure, promising to give it back to myself if I meet such-and-such a deadline. But trouble is, I’m an adult. And as Jerry Seinfeld once famously put it: “If I want a cookie, I have a cookie.”

Some people can just write down a deadline on a calendar and abide by it because it’s their schedule. That’s awesome, but that’s not me.

I’m not one of those people who can reliably make promises to myself and fulfill or deny them. Now, if it’s for someone else, I can be very reliable. I can hold someone else to a deadline and even deny a reward, especially if it’s for their own good. But holding myself accountable is a really tough thing to do, and it seems to combat human nature. It’s a bit like expecting a criminal to stay in their jail cell … after hiring them to be their own guard and handing them the key.

Yes, I just compared writing to being locked in a jail cell. As much as I love writing, I also hate it. But when there’s a story burning inside you, one you HAVE to get out, it can feel a bit like being a prisoner with a life sentence. And there’s only a few ways out of your self-imposed jail cell.

1. You finish your story, which makes the freedom taste all the sweeter.
2. You die in there, having never finished your story.
3. You escape (or get released early) by convincing yourself that the story wasn’t worth writing in the first place, or that you were never cut out to be a writer and are ready to move on, or other such excuses.

I’m pretty dead-set on #1. It’s seeming more and more likely that avoiding #2 will require the use of deadlines and/or something at stake in some capacity. But nothing is at stake for me right now (besides my reputation with this pen name, and dying some unknown day, but what’s new?), and I have no one imposing a deadline upon me.

It seems like I need an accountability partner, someone who can promise to reward me something special if I meet a certain deadline, or at least reward me if I complete a manuscript. I realize this sounds a tad selfish, but if it works, it works. Now, I just need to define “reward”. I highly doubt that editor will ever approach me again with another free offer, but he did provide me a valuable service by showing me that I am capable of completing longer manuscripts and meeting hard deadlines.

And maybe I’m not giving myself enough credit. After all, I’m meeting my self-imposed goal of posting here everyday except Sunday. There’s nothing at stake if I don’t meet this goal. No one who reads here even knew that I’ve self-imposed this goal until this very moment. But blogging here feels more like part of writing every day than meeting a deadline.

My brain’s funny like that: If I have two or more purposes for doing something, I’m far more likely to do it. For example, if a friend of mine writes a story, I’m guaranteed to read that story in a timely manner if I’m also helping them edit.

This is a lot for me to contemplate. I feel like all the needed puzzle pieces are here, but I’m not quite sure how to fit them all together.

• Hard deadline, or maybe even a soft deadline (such as completing a manuscript), check.
• A carrot dangling before me, only rewarded if I complete said deadline, check.

That should be it, really. I guess I just have to choose a goal and figure out what my “carrot” is. Something that only someone else can give me, something that would be motivational. I’m open to suggestions.