I don't mind making mistakes. Obviously I'd avoid making them if I could, but sometimes that's not easy. I don't have solid ideas for not making mistakes the first time. I do, however, have some suggestions regarding the second time.
Now, you might reasonably be thinking "But surely nobody expects us to be perfect. And not making mistakes a second time sounds very hard, maybe impossible."
True as far as it goes. First I'm going to argue that when we care enough about reliably not making mistakes, we can get closer to perfection than you might have thought possible. Second, I'll explain why the marginal mistake prevention is often cheap at the cost.
The Federal Aviation Administration has my respect as one of the more competent organizations in America. Airplanes do not simply crash; each crash is investigated by the National Transportation Safety Board and the cause is ferreted out and then a fix is implemented. The FAA has not achieved perfection — you can read their list of failures at that Wikipedia link — but as a fraction of airplanes that lift off this is pretty impressive.
And of course there's medical operations. I'll go with deaths in childbirth; the mortality rate per live birth is around 25 per 100,000 live births. That is impressively low. And those deaths usually aren't because the obstetrician randomly goofed up an otherwise perfectly fine birth either.
"Sure," you might say, "but I'm not an airline pilot and I'm not a medical doctor. Why is catching my marginal mistakes that big a deal?"
I'd argue it's because it's easier than doing it the other way.
If I do the dishes but don't scrub them very well, then when the dish dries there's still foodstuff stuck to it. It's easier to double check the dish before moving it to the drying rack than to try and scrape off the dried stuck bits. It's not worth scrutinizing every dish under a microscope the way the FAA would, but it's worth a second check.
Once I went on a trip to another city, and forgot my laptop charger. That involved having to make two trips to electronics stores to find one that would work. These days I have a short checklist of items when I'm going on a trip, and I tap each object as I'm putting them in the bag.
Then of course there's my old job as a software engineer, which involved doing some devops work. Avoiding silly screwups becomes pretty nice when you consider the alternative is explaining to your boss why you broke the build.
First, make note of your mistakes.
I'm not being metaphorical. Write them down. Do it somewhere you'll be able to pull up later.
I have a habit in every project I work on, where as soon as I encounter my first problem I open up a document called "[Project] mid-mortem" and write down the problem. Then I go about solving the problem. Sometimes after the project — or during if I have time — I'll make notes on what the solution was. That later version is the post-mortem.
Then — and this is the key part — I reread those notes the next time I'm doing a project like the last one. Many problems are hard to solve day-of and easy to solve with a couple weeks foresight. I do pre-mortems, anticipating ways the project could go off the rails.
Someday I expect to write a review of The Checklist Manifesto. Today is not that day.
Today is the day I talk more about checklists. Surgeons use them for surgery, and those checklists contain things like 'you had twenty surgical clips when you started this operation. Count how many you have now that you're done.'
I use them for everything from monitoring software build releases to going for trips to preparing for a dinner party. See, when you copy a checklist from last time, and you make a mark when you accomplish something, then it gives you an extra chance to notice if you've forgotten your power cord again.
You can't fix your mistakes if you don't know about them. So make it easy for people to point them out to you.
After big events, I like running a feedback survey. When I'm in the middle of work, I try and be approachable so someone can come up to me and point out a mistake I'm making, and I try to make that a good experience for them instead of getting visible irritated at them. But I don't just hope for the happy circumstance where someone tells me they're having a problem; I try to proactively chat with people, asking how the event is going, and what the worst thing about the event so far is. (Hat tip to Saul Munn who I copied the habit of asking about the worst thing from.)
When I'm about to do something I can't easily undo, I stop, walk away for two minutes, then come back and look at it again.
This catches an amazing number of silly mistakes for a delay of two minutes. Now, it does obviously cost some time. That's not always worth it. But any time two minutes would be worth two minutes to avoid, say, not accidentally booking a big event for the wrong weekend, or sending an email to the wrong person, I consider the two minute pause.
See your work with fresh eyes, and read it from the top.
Once upon a time I ran a big gathering, and someone got drunk.
I didn't really know how to handle it well. They were fairly out of it. An acquaintance of mine asked me to help, and I basically failed to do anything useful until the acquaintance took it upon themselves to solve the problem.
Afterwards, I took notes. I cross checked those notes against what the internet suggested doing, and then again against what some people who had wilder college experiences than I did suggested. I made a short list of what to do to help someone who is drunk. I then made moderate efforts to memorize the list. The next time someone around me got very drunk, I knew what to do.[1]
I do this a lot, and it's a lesser, slow superpower. I can't learn everything, but I can keep track of the gaps I keep running into.
Why does all of this matter?
Partially I admit it's pride. I want tomorrow to be brighter than today, for my future to be better than my past.
Partially I admit it's dignity. When I sort Portland Oregon as though it were the city of Oregon in the state of Portland, well, mistakes happen. But doing it twice is embarrassing!
Mostly this is because it's the realistic, tractable way I know of to get better.
There is no replicable button for blasts of insight or sudden enlightenment. Not reading the Sequences, not being really smart and thinking super hard, not anything in the rationalist canon I know of. Sometimes people solve new problems nobody else has solved yet, sometimes it's even me, and yet this involves a bit of something clever that I can't transmit. But I can walk you through this, the art of making fewer mistakes, and that does hold pieces of the harder problems.
Step by step we ratchet towards perfection, and though we may slip along the way we'll get back up and try again — and hopefully not slip in the same place a second time.
My list of what to do if someone is very drunk: