Keeping to Regular Deadlines

I have up at BeTheStory.com a blog conversation with Kevin Cummings, humorist and author of the new book Happily Domesticated. We talk about his history as a writer, his writing process, and (of course) his book. He does most of the talking.

One of the things that I admire about him is that he keeps to a regular deadline, and has been successfully doing so with his blogcast for almost 3 years. I’ve never been able to keep to regular deadlines for any length of time. For me, deadlines go something like this:

1. There’s always more stuff to do than you have time to do it in.
2. “Well, I’ll do the best I can.”
3. Crash. Burn.

So for me, the issue is prioritization and effectiveness. Schedule only the most important things, in small chunks, in order to get them done by the deadline. And I actually did that successfully during my last “normal” job, and then carried some of those practices into my consulting work, and even for limited stints in my own work. For example, that’s how I completed the first Abe’s Turn book, by publishing regular episodes.

But long-term, regular deadlines have eluded me. The pattern seems to go something like:

1. Commit to complete each episode a week before it’s actually scheduled to go live.
2. Actually do it for the first few episodes.
3. Something goes wrong.
4. My email is backing up!
5. “Hey, Tim! Can you take care of this?” (And “that.” And “the other thing.”)
6. I have plenty of slack in the schedule.
7. Now, episodes are getting done the day before they’re due.
8. Something else goes wrong.
9. All-nighters, working into the morning the episode is supposed to be posted.
10. Episodes are being posted late.
11. Get back on schedule! Damn it!
12. Give up.

Sigh.

So that’s why posts on most all of my blogs have been irregular and hit and miss.

But I truly believe I need to establish a regular schedule in order to succeed as a writer, at least for certain sites and posts. So I’m trying it again, but with some tweaks. (And I promise this is the last list in this blog post.)

• I’m measuring how long it takes for me to write posts, stories, and chapters. From this, I’ll estimate my velocity and use that estimate to set a sustainable pace.

• I’ve set a schedule for all my sites, prioritized which weekly and bi-weekly pieces are most important, and scheduled them.

• Major posts will be complete by the end of the day the Friday before they go live. This is because the weekend always resets my mental state. So it’s easiest if the following Monday, I can begin thinking about the next post, rather than continuing to work on the last one.

• Other pieces (like this one) I’ll continue to post ad-hoc.

Major pieces I’ve scheduled include a “Friday Fun” post for this blog (the first scheduled one will run next Friday), a weekly Gilmore Girls post for Gilmore-ism.com, a weekly post for BeTheStory.com, and a weekly short fiction piece. That’s actually very little, a nice slow start, if I can stick with it.

Wish me luck!

-TimK