Real deadlines and fake deadlines

To my knowledge, I've set three concrete goals for myself about how much effort I am going to put into this blog:

1. In A promise to myself, I made an (implicit) promise to write a blog post every month, in perpetuity.
2. In Writing begets writing, I explicitly promised that I would write at least ten thousand words between work and the blog in November 2025.
3. Some time in January, I set a goal for myself that I would write at least twice a month.¹

I've only stuck with the first one.

The funny thing is, when I set both of the latter goals, I already sorta knew that I was not going to follow through. In some sense, both the second and third goals had "fake deadlines." They sounded nice on paper, but I was not willing to put in the effort to accomplish either goal.

To a rough approximation, I think a deadline is more or less "real" based on how much pain one is willing to bear to achieve it within the parameters set. Writing a monthly blog post is quite a "real" goal for me in this sense: I've stayed up late on weeknights trying to get a post out by the end of the month.² The 10,000 word goal was "fake" because I even willing to put in the effort to scope out a publishing schedule. But whether a "deadline" is real or not is always a matter of degree, not kind. If I had a family tragedy, I'd feel okay missing my blog deadline, for instance. Different deadlines have different thresholds.

One way to get a goal done is to make a deadline more "real." The easiest way to do that is to add social proof, of course. I hit deadlines at work I could not with this blog because I want to do the things I've told my editor that I will do.

There are other ways to make deadlines more real. The one I lean on the most is the fear that missing a deadline will make it harder to respect deadlines in the future. Being able to set and hit deadlines is an essential skill. So if I ever break a deadline I took seriously, I make it harder to motivate myself to keep deadlines in the future.³

But I think there's a second way to get more stuff done: reduce the amount of pain it takes to hit a deadline. If it's easy to complete a task, then one doesn't need a strong deadline for it.

Finding ways to make it easier to do the things I want to do has been one of the main themes of this blog. I make accountability measures joyful. I give myself the grace to return to activities I've let lapse. I set intentionally set small sub-goals which are easy to achieve.⁴

Both making deadlines realer and barriers realer are useful skills. But there's a secret third way to hit more deadlines: only set deadlines for things one has an honest shot of succeeding at.

It's failing at this last strategy which makes me a bit sheepish for my failed blogging goals. I don't think I've done much harm to my ability to set "real" deadlines, but I'd still rather avoid feeling disappointed in myself.

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Notes