Prioritizing So Hard It Hurts

“I’m prioritizing so hard it hurts.”

I first heard BJ Fogg, a Stanford professor who studies and teacher persuasion, utter this expression a year ago. As I listened to his interview (again and again — check it out here) I tried wrapping my mind around that idea. I didn’t get it, until a recent Saturday afternoon (which I’ll get to it below). The circumstances in which prioritization can inflict pain and cause ache suddenly emerged into focus.

The Progression of My Understanding

First the easy part: awareness  at the macro level, all the things you want to accomplish with your life. This is the long list of projects gathered and standing idly on your life’s to-do list, looking sophisticatedly bored, with “Hello, My Name is” tags like Learn French, Become a Working Actor, and Run a Marathon.

My list at the moment looks like: Build a Personal Finance Blog for Young Hollywood Professionals, Work for a Best Selling Author, Shoot Another Web Series.

The Granular Level

Next is the micro view, breaking these projects into actions, and understanding the next step at the granular level. The macro is understanding our year (or 3 years or 5). The micro is how we’ll spend the week or day. When I say granular, I mean, knowing precisely what you’re going to do for the next hour, in five-minute increments. That’s the exactness required.

Yes, it’s exhausting. Accomplishing life goals should be.

For me, that means when I wake up, if the plan is “Work On The Blog,” then I know which post and where I left off (annotated with “MING YOU ARE HERE”). If I’m studying a development course, in my notes I’ve marked where I’ve left off (e.g., Module 3, Video 2, 12:38). When I get to work, if I’m in the middle of an Option Agreement, it’s opened on my computer, a document next to it where I’m making my comments.

This is what granular looks like (gaps typically mean I’m at work, where I keep a different calendar). The idea of using Google Calendar to borrowed from Scott Dinsmore:


The third component of prioritization is understanding how much time everything takes. At the granular level. Not, “just start now” or “if I work at this for ten years, I’ll be successful.” Not that it’s not true, but it’s difficult to take any action at such a high level. What this looks like: “okay, this blog post will take me 1 hour to write. After that, it’s going to take me another 30 minutes to post because the formatting screws up after adding headlines and images. So really, I should  budget an extra 45 minutes. That’s how long the last few took.”

I accommodate this time into my schedule. Then I come to the all too human conclusion that there aren’t enough hours in the day. However, I understand why I’m doing something , what I’m doing, and how long it’ll take, so there’s this huge fundamental shift in how I look at time. The cliché, “not enough hours in the day” transforms to “I need to find a one-hour block to fit in this research but the only time I can give up is time allotted for drinks with John. Which is more important?” The first time I made that transition, I finally understood B.J. Fogg’s words, “you have to prioritize so hard it hurts.”

Cal Newport explained it a different and fantastic way: when you master the skill of manipulating your time, it’s like seeing the Matrix.” You see how all the pieces fit together. If you need to free up a chunk of time you can move this piece here and make room for it.” Seeing the Matrix is a skill you develop, through judicious practice, and an understanding of exactly how you work.

Personally, solid chunks of uninterrupted alone time (1 to 4 hours) are precious. Ask any assistant how often they have enough uninterrupted alone time to write an email, never mind string together 500 coherent words — it’s like unicorn hunting. Which is why to me, my mornings are sacred. Especially Saturday mornings, which I try reserving just for writing.

Prioritizing So Hard It Hurts

But one particular Saturday a few weeks ago, I scheduled a lunch, not giving much thought to it at the time. I tried squeezing in work before it, but it takes me 30 minutes to an hour to even get into the right headspace, and by the time all the engines were firing, it was time to make a 45-minute drive over the hill. (Neil Strauss says that’s why he keeps all appointments tentative: if you get going, don’t stop — you don’t know when it’ll come back.) The lunch was amazing and productive and will hopefully lead to an amazing partnership, but I was still berating myself for not defending my creative time more judiciously.

Amy didn’t quite understand why I was so upset with myself. “It’s only one afternoon,” she said. She was right: it was only one Saturday afternoon, with many more to come. I couldn’t really explain the feeling, until now: I was upset because the circumstances were completely within my control — this was a lunch I scheduled. I could have chosen another date, but I didn’t, so I let that determine my day.

I prioritized poorly. It hurt.

Photos Credit: JSN Skeet

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