I agree with the premise that you put forth on an individual level, but I don't think it scales and I believe that is dangerous not to mention.
On a systematic level, this idea could easily lead to unreasonable deadlines that force employees that literally cannot afford to get fired to stay overtime and sacrifice their personal lives.
What I'm worried about here is that you've made this concept very digestible/salient, and CEOs and other company leaders could use this idea as a justification for over-working people. At the very least I think it's worth adding a footnote or something about this.
I feel like I learn a lot of things by doing a project while feeling enough slack to explore a possible better way to do it (but with more of a learning curve), and wind up learning something new and important that I can use going forward. Or just go down a rabbit’s hole trying to understand something related to what I’m doing. If I was always doing things in a rush for my whole life, I feel like I would know many fewer things and have many fewer skills, even if I would have done more projects.
I understand that different roles have different tradeoffs (and different people are different) but I’m wondering if you’ve noticed anything like that.
I like this and feel it is useful, though an important corollary of this heuristic is that you have to know how much time you will need for the task. This year I at one point had to get a serious deadline moved at (or actually, slightly after) the last minute as I was unable to meet it. I have a tendency to work as you propose but since returning to work after my maternity leave, my internal clock for when to start work pre-deadline was way off. My previous 'last minute' was based on an expectation that I could use my downtime to meet a deadline, whereas now with a baby my downtime is inflexible. My estimates of how long something will take me are improving (after a brief overcorrection).
Feynman describes the importance of unfettered roving attention - of watching dishes hurled in a jocular cafeteria brawl oscillating in mid-air, and being triggered towards the solution of a festering problem, as I recall; where the moral seemed to be that planning is lethal to creativity, and that the primed mind must be allowed to simply wander. Of course proper procedure is vocation dependent; I want my bus driver to defer creative pursuits to off-hours.
Parkinson's Law states that work expands to fit the space allotted. The idea being, if you give someone a month to write a report, they'll take a month, but if you give them a week, they'll take a week, and then they'll have three weeks to do three other reports! The one-week and four-week reports won't be identical; but in my experience it is surprisingly often nearly as useful as the four-week version, and you get strictly more work out of people.
(I, myself, am a special case of "people".)
This is common knowledge, and the implied practical advice can be found in its dual:
A related question we might ask is: when is working on the task even worth it? It's famously the case that most work gets done just before a deadline. If we model the work getting compressed to the end with a pareto curve, the last 20% of the time produces 80% of the value.
It's often taken as inspiration, that one can be so productive, and productive-hackers try to make all of their time this productive. But one man's modus ponens is another man's modus tollens, and in fact, I think most of the marginal effort spent before a deadline is sufficiently not worth it as to be better spent just chilling out. This leads me to a more practical heuristic.
It’s counterintuitive, but the only time that I ever clear my email inbox, is when I don’t quite have enough time to. During a week where I have a lot to do and am getting a lot of emails, I start getting through them fast. But if I have tons of free time, I spend tons of time thinking about and replying to individual emails. It's only when I barely have enough time that I prioritize appropriately.
The fortnight before LessOnline is the time in the year that I make the highest density of improvements to the Lighthaven campus. The few days before I launch events are when I do the majority of the design work on their respective websites. This is true even if I've known about them for months. It's counterproductive for me to get more time on it, because it's time I could use to rush productively at something else just in time to meet a deadline. I just did almost all the organization of LessOnline in one month, whereas other years I did it in three months, because this time a different project I had ended a month before LessOnline.[1]
It's bad to give me work without a deadline. I will waste time and effort. Instead, I have learned to figure out the first deadline, and either work on something else until it is coming up, or make the first deadline come sooner[2]. I hereby name this Parkinson's Heuristic.
Every time I ship a website for an event, I am under the impression that it
—all while making questionable calls about what the event will be like. In the moment I launch, I confidently expect I'll need to make many major changes. It's just good enough, but no more.
Yet after shipping, I never look back. I move on to solving other problems. I change the website if a new problem demands it (e.g. I must add some way to book hotel rooms, or I must add a new sponsor who has come on board). But it turns out, the website is sufficient and works. One of the things I've learned from getting a lot of work done before a deadline, is that most of what I thought I was supposed to do, can be cut. At some point I just cut it to the absolute bare-bones and get that together as fast as I can, and it turns out to be pretty good.
My whole work is seeking out these moments. I am constantly asking "What can I move towards, what can I ship, that will force me to get all my other ducks in a row?"
This rhymes with a core part of the working culture at Amazon. In the book Working Backwards, two senior Amazon executives explain that all projects at Amazon start first with a written press release that announces the launch of the product they're proposing to build. It describes what it does, what problems it solves, how it does that, and includes an FAQ on the product. It's called a "PR/FAQ".[3] This is also how we start many projects at Lightcone. It's about getting as fast as you can to the point where you actually are forced to make the key decisions.
It also helps me not burn myself out. I often don't stretch myself by thinking I'm supposed to be doing work, if a deadline is not near. I relax. I go home early. I will simply get to it when I have to, and no earlier. This is strictly superior to being anxious and doing various related pieces of work right now, only to realize I was basically going to do all the critical stuff in the last two days anyway.
I can do it earlier if I want to. If I have to write a report in a week, and I want to do work on it before the last possible minute, then I set a deadline to send a full copy of the report to 5 friends by the end of the day. Now I have a new deadline. I tell my colleagues about this deadline, and sometimes (when I feel like I won't treat it as real) I commit to burn $1,000 if I don't meet it (by donating it to a random charity).
So Parkinson's heuristic is to find a way to minimize the time that you can spend on a task. The other prong of the heuristic is to not burn yourself out spending time on something that doesn't have a deadline. You'll look back and realize it was spent wastefully.
This is all well and good for work. But what about leisure? What about free time?
I manage to waste my weekends and evenings regularly. I try to be kind to myself and not force myself to do anything, and as a result I flop around like a fish. Right now I'm on vacation and I'm actively concerned it will just be a few weeks of dead time.
One wish I have is that this could be time where I bring the energy I bring to my work, to my own life. I'll fix all the problems I've not had time for, relating to physical health, immigration, taxes, home decor, and more, with some time left over for new artistic and restful experiences.
Late last night while drunk with a friend, I decided that any deadline would be worthwhile. And the main hole in my soul for the last few years has been writing. So, in a place all my friends were able to read, I wrote down a commitment to publish a blogpost daily for the coming week, and if I failed then I'd burn $2,000.
I have hope that this will get a lot of things on track. Now, when I'm thinking on some other small question in my life, to do with health or finance or what-have-you, I won't be able to sit on it all day. At some point I'll have to start seriously prioritizing. Do I have enough time to do this and then get to writing my post for the day? What is the minimum work required to move the ball forward on this, that I can do before I get to writing?
I am starting to feel some confidence that I will not look back on my vacation, and think it was a waste of time. On reflection, getting into a regular writing habit, plus losing a lot of weight on GLP-1s, would be sufficient for me to feel good about the time, and everything on top of that will be bonus. So I'm pretty close.
Today I had grand ideas: returning to a story I published a while back and adding a new chapter, and returning to a draft essay I've struggled with for two years in which I plumb the depths of how to live an ethical life. Yet only when 9pm came around did I finally sit down to write—when I knew I had to. And now I find myself having written this essay instead. Did I produce something valuable in the last ~10% of my day? This is a question I will leave to the reader.
This is simplifying it a bit too much. It was still crucial to announce LessOnlien about 3 months before-hand, and two of my colleagues did that work.
Also, the one piece of work I told my boss that I couldn't do in one month was to build a conference app, and he assigned someone else to work on that. They ended up spending ~2 months working on it, which sounds like it adds up to 3 months again, but the conference app went far over and above what we did the previous to years, so it's not an apples to apples comparison.
What matters is that, other than making and announcing the conference website, I did most of the work that I did each of the last two years in a third of the time.
Or just chill out. Read a book. Go for a walk with a colleague I've not caught up with personally for a while. Go home early.
Quoting the book: