Planning and Flaking: Can We Do This Better?


I’m hosting a discussion on Jan 7 at The Embassy in San Francisco called “Planning and Flaking: Can We Do This Better?” Here are some thoughts to start the discussion:

The year is 1957. You’re sitting on the couch, eating a string bean casserole and finally getting around to reading the day’s paper, when the tele-phone rings. You race across the living room to answer it. “Hello, it’s me, George! (Oh hello George.) Would you like to have dinner to-morrow at six?” Of course, you say, penciling it in your datebook. And as Aziz Ansari puts it, if George doesn’t show up, your only fair assumption is that he must be dead.

It’s a no brainer that things have changed since then. Environmental factors have enabled a drastically different set of conditions: Cell phones allow us to change location and time or cancel at the last minute, blurring the line that used to demarcate flakiness. Facebook (and tools like it) has made us more likely to interact with casual acquaintances and more aware of their events — we have access to more social events each day, which are more likely to be public. Dinner plans (and even large scale events) can spawn, then mutate several times, at the very last minute.

I have several questions and several ideas. First, the questions:

  • Is the old scheduling paradigm dying? If so, what would a fully realized new model look like, with plans slipping and sliding?
  • What techniques or statements have people used which have been effective in mitigating planning-based issues.
  • Who wins and who loses?
    Some possible wins:

    • Greater choice of events
    • More interesting events (this model gives people the freedom to propose adventurous ideas and see who’s interested — when planning in advance people are more likely to just meet for dinner.)
    • Hyper-social / popular people have more choice
  • Some possible losses:
    • The ability to be intentional with relationships, because last-minute planning is more focused on what is immediate
    • Introverts and those with less friends or options
    • Do one-on-one plans get pushed out in favor of group events?
  • What other factors lead to and reinforce scheduling problems today?

And some ideas about what kinds of *constructive action* can be taken to make planning work better for everybody (these and more we’ll be discussing at The Embassy):

  • Clearer communication: “I’m going to this event” or (for some people) “I’ll see you at six” just doesn’t mean what it used to. If people were more explicit about what their actual plans were, others could plan better. Often this means admitting that an event isn’t your first priority, which is uncomfortable for some. But it’s far kinder than misrepresenting yourself, and I think we can work to become more honest to each other and ourselves on this.
  • More words (or, quantifying flakiness): Maybe we need new terminology which is designed to help us be explicit. Below are some things which are difficult to express yet common in today’s planning landscape. Can we think of ways to make these concepts easier to say?
    • I’d like us to really actually do the thing we’re talking about (I usually ask “Is this a Plan with a capital P?”)
    • Quantifying gradations from not going to going:
      • This is my backup plan if something else doesn’t pan out, which is {likely / not likely}
      • This is on my radar but I’m not 100% certain I will go, as opposed to “I’m definitely going.”
  • Norm setting. In discussing this with friends, several people told me that they just don’t make plans with flaky people. Setting norms about when and how it’s okay to change plans is one way to affect this trend, but where is the right place to set the line and what happens when each of us draws it in a different place?

As a quick aside, San Francisco has been known to be both the place where habits are predictive of global trends, and a privileged monoculture whose behavior can’t be extrapolated to predict the future of society. I suspect in this case we’re the former, but we may be the latter.

If you’re around in San Francisco, I hope you can join us in this discussion, but of course I’ll understand if you can’t make it. I might not even be there myself.