Wtf is a deadline? Showtime, missing the bus, time walls, check-ins, &+

If this blog post contains only this paragraph and bullet list, it’s because it was showtime and this was all I’d written. The post is about distinguishing different kinds of things that are often all called “deadlines”. I really like showtime, and I liked the idea of writing being like a kind of showtime, although in practice this is quite hard to do for anything except an exam. I may schedule a time to write this post in full, but for now (Oct 4th) I’m simply writing this and scheduling a time when it’ll be published: noon on Wednesday, October 7th. If you’re reading this text (and only this text) before then, there was a bug with my schedule publish feature 😂

• showtime – “however prepared we are, the audience is waiting”
• deadline time wall – go/no-go – “I miss the bus” is the extreme case
• check-in / estimate – may not be finished by this date, but I want to reorient
• experiment end – try a thing for a bit, and then reflect on it

(Written the following day, in my personal journal, and added, at the time: Man, I’m excited for the blogging showtime! Fascinating that it took me this long. This is just making it true that something of mine will get published every so often, but not with any sense of commitment or whatever. The consequences are just the quality of whatever’s published. And I guess in that sense it really is a showtime. Hm… yeah, feeling that.)

Okay, here I am, 3h 11mins before the publish date. This is my performance over the next 3h. I’m not going to do this every time, but in this case I think there’s a beauty to simply leaving the above paragraphs there and continuing from them, as they function as a kind of teaser for the topic of the post.

This is a model that has been percolating in my system for years, and it was animated by 2 main questions, that didn’t obviously have any thing to do with each other:

1. why, as a student, did I usually vastly prefer tests & exams over homework & projects?
2. what does it mean (in the context of designing the Complice goal-tracking system) to put a date on something you intend to do?

The model, like posts I’ve written about habits, expectations, commitments & accountability, distractions, and explanations, is a model that takes a word and says “you thought this was one thing? this is actually 2 things, and it’s worth knowing the difference.” In this case, there are at least 4, maybe more things. But let’s start with the difference between tests & homework.

Why, as a student, did I usually vastly prefer tests & exams over assignments & projects?

Of course, preparing for a test or exam can have an assignment-like quality to it. What makes them different?

With a test or exam, you prepare however much you do, and then you show up, and however prepared you are, you need to perform for some period of time, and then that performance is what you’re graded on. This means:

• You can’t get the test “done early”. No matter how much you prepare, you still need to show up. Both literally in the sense of walking into the room, and in the sense of arriving rested & ready. (“Ready” here being a mindset, not a quantity of prep.)
• Assuming you show up, you’ll get some grades. No matter how little you prepare, as long as you show up, you get the chance to perform and score what you can. Not sure what to write? Well, write something. Now’s the time. There’s no procrastination, just you and your performance.

I thus like to call tests and exams showtime, because it’s like doing a live performance of music of theatre, and however much you prepare, the audience is waiting. Since the audience is waiting, there’s no asking for an extension or saying “look, sorry, I just didn’t figure this out”. The audience is waiting, and they want to see your best work, now get out on stage and see what happens.

Now. Showtime has a nowness to it.

Contrast that with assignments, projects, or graduate theses. Neil Fiore, in his excellent book The Now Habit, describes a common challenge shared by the graduate students he was trying to help: they had a constant nagging feeling of “I should be working on my thesis.” The thesis is a huge project and has a nebulous and flexible due date, if at all. So the question of “is now the time to work on it?” doesn’t have an answer unless you give it one. Fiore recommends making an Unschedule: block out large chunks of your day when the answer is just always “no”, creating lots of space to chill with friends or learn to dance without feeling guilty. This then leaves you with some narrow windows where now is the time.

The standard term for how assignments work is “deadlines”, but there’s something importantly different from how school & work assignments usually work, compared to a real deadline. [[School is fake]], and the deadlines are arbitrary and bendable and you know it. The teacher isn’t actually going to look at your assignment for hours or days after you actually submit it. But, there’s a need to generate some sort of nowness, and fake deadlines or arbitrary self-imposed schedule constraints are how people usually do it.

Unfortunately, in relation to writing, as I’ll discuss a bit later, it’s hard to have a realistic showtime where you can’t actually do the writing beforehand (which would make it not a true showtime). School tests and exams are also arbitrarily scheduled, and constrained like sports games, intended to produce fair competition (by giving everyone the same amount of time) and avoid cheating (by not allowing people to use text that existed at the start of the exam), which doesn’t create a natural environment for actually creating your best work.

Contrast this with the purest simplest deadline: missing the bus to the airport. The bus is going to leave at a particular time, and if you want to be on it, you’ve got to actually be on it. There’s no showing up half-ready and being half on it, unless you count “running out the door having forgotten to pack a few important things.”

Anyway, so it looks like we’ve got 2 types of time boundaries: showtimes and deadlines.

However, people often use the term “deadline” when they actually in practice mean something more like “check in date” or “date to start feeling bad if I haven’t done it”. This dilutes the power of a real deadline. Aside from externally imposed constraints like the bus schedule, planting season, or someone else needing something at a time, most deadlines are at least somewhat arbitrary, but they can at least be honored as a real boundary if that’s what they’re supposed to be.

Fixed time, variable scope

This is a principle the Basecamp folks use, documented in their book Shape Up, particularly in ch 3. Set Boundaries. When most companies (or individuals) designate a period of a few weeks to do something, they might talk about a deadline but they don’t usually expect that by the end of those weeks the entire project will be completed. They hope it will, but if it’s not, well, give it another week, or two, or three, or whatever it needs. Knowing implicitly that time budgets are flexible, people take on all sorts of work that doesn’t need to happen, and leave lots of loose ends to tie up later.

Basecamp doesn’t. Instead of a time estimate, that can constantly get pushed back, they have a time wall: whatever we have ready by the end of that wall is what ships, and work on the project stops. This absoluteness has the same power as a showtime. There are last-minute tweaks (having performed in a number of musicals, these are indeed numerous, stressful, and sometimes hilarious) but there’s no chance to redeem yourself the day after.

sdf

The difference between an “estimate” and a “wall” is so important.

With an estimate, you can be wrong and just keep going. (Spending more and more $$).

With a wall, you have to stop when you hit it. This changes the way you think about everything.

— Ryan Singer (@rjs) June 29, 2020

It’s probably too late to redeem the word deadline so that it clearly means the thing where you actually stop, which is unfortunately because it has a pretty evocative etymology. But you can at least avoid using it and use something clearer. Deadlines are dead, as a concept.

So, a heuristic: if you plan to completely leave the project in whatever state it’s in, call that deadline a “time wall” like Basecamp does. Otherwise it’s a check-in (or estimate).

Check-ins can be quite valuable, themselves—the important part is being clear on what actually happens when the moment comes?

Commitment contracts & making no-lose situations

It occurs to me while writing this that this is a different lens on a topic I covered 5 years ago in a guest post on the Beeminder blog, called Hard Commitments and Soft Commitments. By “soft commitments”, I was mostly referring to essentially “committing to checking in—not just letting the moment pass without reflecting on whether you did the thing and what comes next”. By “hard commitments” I was referring to the commitment contract approach, where you put money on the line for doing a thing, whether one-off (“I’ll publish my book by this date”) or ongoing like Beeminder (“I’ll do 5 minutes of meditation a day”).

Interestingly, commitment contracts are not actually intrinsically any of “showtime, time wall, check-in”! Is it a 4th thing? Well, there’s a consequence at a date based on whether or not something is done. That is a kind of deadline.

This is commonly framed or experienced as a punishment, but doesn’t have to be—a neutral articulation might be that what commitment contracts do is:

• create clarity about a timeline
• pre-emptively shift story/identity
• and, particularly: tip the balance of your priorities
  ↳ You can tell if this worked because now:
  • the choice to eg exercise or wake up now just feels obvious, rather than conflicted (more on this in my article on self-referential motivation)
  • if you find that what you’re doing isn’t working, obviously the answer is to go meta and learn how to do it differently
  • you find your creativity going towards solving the problem rather than making excuses or undermining your progress

In the intended world, the existence of this deadline+consequence causes the thing to happen, which could be in line with a time wall although that requires you to make sure that you don’t just do the bare minimum and leave a lot of clean-up work for later.

In the unintended world, Beeminder says “hey we just charged you $30” which certainly could prompt you to check in and reorient, but doesn’t necessarily do so.

For years, my Beeminder blogging system was what kept me writing and publishing blog posts. A few years ago, trying to get more in touch with intrinsic motivation, I turned it off, and, well, I have published very few blog posts since then and mostly when some other external time constraint arose, such as the fact that uhh… I want my yearly review posts to go out sometime around New Years’.

For awhile, I sort of felt embarrassed about this, but there was some sort of integrity to it and I’m glad I’ve stuck with it, because I have a new strategy now that seems like a total pareto improvement over my old Beeminder system. With the old Beeminder system, I was trying to construct a counterfactual world in which I would pay money, to convince myself to avoid that counterfactual world by writing & publishing a blog post. That’s awfully convoluted, and sometimes resulted in me paying money and still having no blog post—now two problems, instead of one.

My new approach is that I’ve simply decided that the malcolmocean.com live concert tour is going to perform here every week or two (I’ll probably settle on a default rhythm / time of week) and, as your host, Malcolm Ocean, I will show up and give you my best. Or I won’t! But if I don’t show up to write a full post, then my readers will still get a few paragraphs, an outline, or a rough unedited tweetstorm, that I pasted into the blog post draft when I hit the Schedule button.

Isn’t that fucking cool!? I feel like a genius coming up with that. Instead of spending effort trying to avoid the counterfactual, I just made it actually impossible—something will get published. There’s no way to lose now! Nothing is behind.

Importantly, I’m not considering “my readers get a half-written draft” to be an unwanted outcome I’m trying to avoid. I’m playing this game in such a way that I strictly prefer this outcome over the situation where they get nothing.* There’s no bluffing, no bad outcome. I woke up this morning with a clear intention to write this full post because I wanted to spend the time so you get to read it, not to avoid some bad outcome where you see only the first two paragraphs. That would have been cool if that had happened! I wrote the paragraphs with that in mind.

(*hell, people who tell me that I’m too verbose might actually find it a relief to just get a little outline or whatever)

I actually had this idea months ago on the phone with my friend when I rambled to her about why I liked exams and didn’t like assignments. At the time, I thought it would be really cool to actually build out a little app that would work like this. Basically a newsletter system, and every week you get a textbox and whatever is in that textbox at the end of the week goes out to your readers. If it’s completely empty, they get a random tweet of yours and an encouragement to ask you a question that you can answer for next week’s newsletter.

Alas, perfection is the enemy of completion on the meta-level as well; for wont of the app, I didn’t think to just set up an prototype using my existing toolkit. I suspect this might actually be a similar case to the Beeminder counterfactual thing above. I think I was implicitly slightly trying to pressure myself into creating the app by stacking all the good things together {I blog regularly, I have made this app} and the bad things {I don’t blog regularly, this app doesn’t exist}. I think this sort of pressure can sometimes work, but usually it’s better to just make something happen, like I’m doing right now. Honestly, I think that my creating a prototype with the blog schedule feature makes it more likely that this app will come into existence, via me iterating or via someone else being inspired to make it. (If you are so inspired, hmu; would love to advise you on design & business models.)

(And if I forget to schedule? I have a few systems for that, so I’m not too worried, and you can also help by pinging me on twitter (@Malcolm_Ocean) and saying “hey, can you queue up a blogpost showtime to elaborate on this tweet/thread of yours?”)

(Btw: if you’re reading this and you’re a Complice user, I’ve been experimenting with a new Complice feature that lets you put money on the line for completing one of your intentions by a particular time later in the day. It complements Beeminder, which is all about the long-term. Let me know if you wanna be one of the first people to test it.)

What does it mean to put a date on something you intend to do?

As I indicated at the start of the post, this question arose for me in the context of designing the Top Priority feature for Complice. It’s got a date that is explicitly framed as a “check-in”, because I understand the importance of [[metaphor]] design and knew that it was not any kind of deadline. But I thought about adding a few different modes, most of which you’ve heard about already by this point in the post. So here’s a list that might act as a kind of summary.

1. this definitely has to be done in full, ideally by this date (fixed scope, variable time)
   • as long as the completion can be pushed back, all you can say about this date is that it’s a check-in or estimate
   • the check-in might be “do I want to keep working on this? revise scope” or it could be as simple as just tracking the accuracy of your estimates, on any timescale (I have a spreadsheet I sometimes use for this for 5-60 minute tasks)
2. something definitely has to be ready by this date and no later (fixed time, variable scope)
   • this is Basecamp’s time wall though I didn’t know the term at the time
   • this is also what you’d also use for preparing for a showtime
   • and missing the bus to the airport is sort of an extreme case of this
3. on this date, some phase ends
   • I typically call this an experiment because the idea is that you try something (a new habit, an internship, whatever) for a period of time, and then that period ends. Maybe the habit sticks, maybe the internship leads to a job offer, but there isn’t a particular deliverable.
   • On a tiny scale, pomodoros have this structure: whether you’re done or not, after 25 minutes of working, you take a 5 minute break. This might be called window of action
4. this date is the first/best chance to do something
   • I’d call this an opportunity. It’s pretty rarely used in practice except for things like Burning Man ticket sales (where the window of opportunity is so narrow it might as well be a missing the bus) because constraints like this aren’t common plus most people aren’t used to orienting to opportunities.
   • I sometimes use this a little bit by snoozing tabs until a moment I think will be a better time to act on them. It’s not like I have to do the thing at that time, but I know now is not the time and that future moment might be, so he gets to decide.
   • This could also be called a reminder, broadly speaking, and technically is what’s going on when you use a Spaced Repetition System to learn something.

Anyway, there are a bunch of ideas here, and I haven’t even elaborated on the last 3 in this post. The important thing is that whenever you schedule something, whether it’s snoozing an email or staking out a project completion time, to be clear on wtf your deadline actually means.

If you like this post, you might also like this 1988 paper by Phil Agre and David Chapman, What are plans for? which distinguishes “plan as communication” from the more common frame of “plan as program”.

Closing thoughts: this post itself

As I was falling asleep last night, I pondered what image I might use for this blog post, and I realized that it would be a great opportunity to create one of the beautiful graphics that I’ve made for other posts when I want to illustrate a model. I also realized that that would take me at least an hour to do at all, and a few hours to do well (and it’s the sort of thing I refuse to do not-well) and so I realized that it was not going to happen prior to the publication moment. However, I’m not strictly time-walling the project of writing this post—the point is simply that the post goes live at noon in whatever state it’s in, and then it exists. Will I create such an image later? I think there’s a decent chance I will—the moment I go to share the post on Twitter this afternoon I’ll wish to have such an image.

(Edit the next morning: I didn’t end up making a graphic to illustrate the different types of deadlines, mostly because the model ended up feeling hairy & nebulous and I didn’t want to reify it too much in its current form. But I took 15 minutes and made a share image that does evoke something that I like)

To what extent did this end up feeling like showtime? Honestly, it was pretty good. I went to bed last night with obvious clarity about what I would be doing this morning. Showtime is a little weird without a live audience but there is something real about writing words that I know hundreds of people will read very soon, versus even a draft on my public roamblog intertwingled.blog. It has a kind of liveness to it. (To be clear, I don’t actually want people watching me while I’m writing; unlike with playing live music, it would be distracting.)

I feel deeply thrilled about this: it feels like the renaissance of my blog.

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