technology

Maybe get them interested in some useful/simple automation/shortcuts stuff?

Bookmarklets? Easy to start.

I think the best option would be finding their uses/needs and tailoring the approach to that.

If they use excel/Libreoffice, maybe the Record macro option would be good? Or mail merge?
Teach them.about the quick access bar and some new shortcuts that would help them?

I think helping them with backing up settings and data would be a good thing too.
It'll be a good start, to get them to know the need and importance of backups. Backups could also make them more confident in trying out stuff. Like, knowing that they can come back to the backup if things go wrong.

I would recommend having them install Linux on an old laptop. That’s covers a lot of ground.

Getting them set up with a Python development environment and a few tutorials is a good start. Have them try and script up something simple that's related to something they like.

This is something I have been thinking about since I was a small child so I have a lot of ideas. And I will always take a chance to try to learn this stuff so it's based on various experiences. Life is better when not being abused by technology, which is of course a proxy for the capitalists who use it as a way to subjugate people.

Socially, of course you have to be patient and very focused on their goal and not your own. I make some examples below from common software that I hope doesn't need background explaining too much. But just showing those to anyone would be of zero assistance if they're not interested.

I don't have any experience with the ideas you suggest but from my non-gaming experience, they seem like things that might just be a matter of following instructions. As long as everything is perfect. As long as nothing unusual happens, the environment is exactly as expected, and no knowledge is wrongly assumed, nothing is misunderstood, the documentation is perfectly up to date, no bugs introduced from upstream, updates are handled perfectly or never needed. Any deviation could be a big trouble.

For example I wanted to install custom firmware on my wifi router. I read on the firmware website that my model of wifi router was supported. I kept trying to install it... I would spend a few hours on it, give up, put it away, then weeks later talk myself into trying again thinking "this should work" and start again. Making sure I downloaded the correct file, checksumed it, formatted the SD card... Doing all kinds of what turned out to be irrelevant troubleshooting. Someone on a forum says their SD card was shitty and it works when you buy a new brand name SD card. Someone says it works when they flash from windows but not from linux. It was just unsolvable. What I didn't know was the same model number came in different versions, which you could only find out about by looking at some very small, almost hidden text on the bottom of the device. Different models = different chips. only some of the chips are supported. So I was following the instructions properly. It's just whoever wrote them happened to have a supported chip so they didn't realize one of the steps was to consult an obscure spec document and compare it to some other document having to do with driver development to determine if installation would be possible.

All that is to say I wouldn't assign someone a project like this to get started. I barely got through it after decades of nerding around under my belt.

To get to the point where I wanted to install custom router firmware, I already had to have a foundation of a) knowing what a wifi router is, b) knowing which model I have, c) knowing what firmware is d) having a preference about firmware. Flashing firmware router sounds like an awful waste of time to >99% of people, why would they want to learn that?? This

There is one philosophical thing I think you should keep in mind, which explains the whole wifi router question and broader project.

To a non-nerd, the device/application is either "working" or "not working". To a nerd, it's an uneven gradient that extends farther in both directions.

"it's working fine the way it is"

not

When it's "working" people just look at the part of the interface they know they need to use and ignore the rest. One of the simple things I have always done since I was a little kid, is that in every application I look through every menu and dialogue I can find. Expand every collapsed item. Open the Preferences. Enable "Advanced" options. Right click on things to see what submenu comes up. Even when I don't know what everything is for, just to peruse how things are set up. You see words that don't mean anything but as you start to use it then you think of a phrase in a menu and think "Oh I wonder if that would be helpful" and it may or may not be.

Like I can do a lot of basic spreadsheet stuff only because I noticed e.g. there was a button labeled "Sort" and thought "I wonder if this would sort the spreadsheet"; even though I didn't originally know that you could sort a spreadsheet. I can tell you so many examples of times when people didn't realize they could do things that were plainly available in the main interface because they only looked at the exact thing they were doing.

Then you see something and you aren't sure what it does so you maybe search the phrase and you can learn a concept you didn't know before. And sometimes you encounter an error but it reminds you of a similar phrase you saw somewhere else in the interface.... and maybe you solve it.

So first of all the concept of "working" can be expanded. Sure it works now but but keeping your eyes open you realize it can be better. Then you start to have expectations beyond "I hope it doesn't crash!" and "Trying not to break anything here" which is how a lot of people feel. They are basically in a tense truce with their technology. Worried that if they ask too much the technology will lash out like an abusive partner, so they settle for an appeasing strategy. Once you start to raise your expectations, that's when things like modding, customizing etc will start to become attractive. You realize you don't need to settle for absolute bare minimum. Start thinking "what else can it do?".

And as you do this across software you start to have transferable ideas from one use to the next. Like I know a lot of software having to do with text will have a "Find" feature. If I am using a different PDF reader than usual, I expect it will have "Find". A lot of people do not know about "Find" generally and they will just scroll through data like trying to call a tree doctor from the 1981 yellow pages. So naturally the experience of navigating any sizeable data on a device is torture as they plod along hoping their eyeballs to land on something meaningful. Their feeling of the experience is "it's so hard and slow reading stuff on the computer... I am so bad at computers". And they will try to just avoid the situation. Having looked through thousands of menus, I have the confidence to know a PDF reader without "Find" SUCKS and I am not to blame. I don't feel it is due to some inherent deficit in my tech wizardry. I also let the misery roll of my back because this bad experience will not be universal.

The same principal applies to other scenarios:

• look at all buttons, ports, connections on a physical device
• what are all those files and directories you don't use on your computer?

Making a habit of looking around is the basic reason I have always been "comfortable with computers".

"It's broken/crashed"

So once someone knows what they want but can't get it.

Whatever the problem, help them out but only in the most minimal way so they have to struggle through the problems. Have them guess at how to do something, and try it out. Talk out the problem. The person might try reading what it says on the screen out loud (even if you can also read it) and explain it. What's going on here? What were they doing, trying to do etc? What was expected, what happened?

Go back 1 step, or start at the beginning, and see if the problem happens again. Is it exactly the same problem? Getting handy with screen shot software can help you to remember the exact steps you took and the results.

Obviously stop them if they are going to make some sort of horrible mistake and cause a major disaster. :)

If frustration is building or they are going down a totally fruitless path, give the most minimal hints. Like sometimes there's a vocabulary being used that they don't know, so sometimes you can clarify that without fully giving away the solution. Ask some questions that are a bit leading in the right direction. Or pretend you don't already know the answer and think about what your first step to solve it would be. And go through it together, in a naive way. Like we know about searching for errors on the web, but sometimes the error window has multiple components, or only part of it is relevant, or you have to find the error elsewhere in the interface. So forget everything you know and struggle through it how they will have to when you aren't there to hand hold.

They need to learn to isolate the problem. I found writing up support and issue requests really helped me to sharpen this. Sometimes there are multiple things going on and you really need to narrow down the problem by removing complexities. For example I have remote storage mounted on my computer and over time I realized that when my network gets flakey it causes strange and seemingly unrelated problems. So to avoid going up the garden path, I make sure I am operating on a local file for any troubleshooting. Sometimes I totally unmount all remote storage even if I am not directly using it because it causes certain applications to misbehave.

Other ways of doing this for different situations: private browser window, alternative browser, disconnect from the internet, connect via ethernet not wireless, turn off bluetooth, disconnect peripherals, use default not custom configurations, make a new system user, fresh install in a different location, work on a fresh new file, try a different USB cable. And the classic: reboot device. Only do one thing at a time.

UNLESS the required information is really some piece of trivia that it will be impossible to figure out. Like my example about the router model version. Suffering thru that didn't benefit me.

With anything that might have to do with hardware, there is a magic #1 trick to just memorize. Solves way more problems than you would think. This should always, always be the first thing. You need to check both of these things, every single time, even if you already know the answer. You need to physically check with your hands:

1. Is it plugged in?
2. Is it turned on?

Literally there are many people who think I'm some sort of tech genius due to rigorous application of the above.