Almost 25 years ago, I wrote a blog post with the title ‘jumping ship slowly’ about leaving Windows (XP was awful, it was mind boggling to me that Vista managed to make people nostalgic for XP). My advice remains the same:

Don’t try switching OS first. The OS is the most easily replaceable bit in the stack. Switch applications first. Most ‘Linux’ apps are cross platform. They’ll run on Windows, and the few that don’t will run in WSL2. You can switch out apps one at a time, and take the time to get comfortable with the alternatives.

Once you’re comfortable not using any Windows-only apps, changing the OS but using all of the same applications is very easy to do. Changing OS and application stack at the same time is an enormous obstacle.

I believe this is also why a lot of corporate and government Linux migrations fail: they try to change everything at the same time and that’s too steep a learning curve.

@david_chisnall
After 2k Pro, XP was not a fond experience for me.

I multibooted OS/2 and Linux until I got early access to test Vista, and it was a revelation (once NVIDIA straightened up their drivers for the new WDDM).

I slowly adopted open data formats, then programs, then finally switched to Alpine Linux for myself and my family.

A long road, but as you noted, it need not be terribly difficult (in many cases).

@Brett_E_Carlock

The need for an Internet connection to register and the linking of the license to a motherboard were the deal breakers. My 2K machine had gone through four motherboard upgrades by that point and was often updated somewhere where the Internet was flaky to nonexistent. The tellytubby UI was awful.

@david_chisnall
Yeah, my 2k box had a _very_ long life, but I eventually needed dynamic CPU freq/volt scaling, and 2k couldn't do it.

I made my peace with Luna (XP's skin engine) by making and using my own skin and icon pack while I had to use it.

Fun fact: My eMachines 633ids, made for Win98 (my win2k box above), booted every Windows up until early Windows 10 on unmodified ISOs. Still have it, still works, haha

@david_chisnall

Yes, that was what finally got me to leave Windows, too. I'd been using #Linux full-time at work since mid-2000, which helped a lot.

It must be twenty years since I last owned a machine running #Windows. (The work laptop doesn't count.) If it hadn't been for #Microsoft's intrusive anti-piracy measures, I might be running Windows even now.

@Brett_E_Carlock

@CppGuy
There is a ton of good things about that OS family, but they went way too far and I needed to step away.

#Linux #Windows #Microsoft

@Brett_E_Carlock @david_chisnall I've been giving similar advice. Start by installing Libre Office and learning to use that. Get Firefox or another browser. Many of the major FLOSS programs provide Windows versions. (as you note)

@bluetea @Brett_E_Carlock

I cheated a bit back then by having a second computer (a dual-CPU P3 that I got very cheaply on eBay because the listing advertised a 'duel processor' machine and not many people knew to search for that typo) that ran FreeBSD and using a remote X11 to run the apps that didn't work on Windows. That was back before x86 supported virtualisation (and Windows on Xen was painful), but now it's very easy to boot a VM and run the few things that don't work (or are painful to install, which is more common) on Windows, and WSL2 makes it trivial.

@david_chisnall
WSL2 was my gateway to Alpine, which convinced me to switch off Windows after 20 years of multiboot/VM Linux usage.

@bluetea

@david_chisnall @bluetea @Brett_E_Carlock on power up the two CPU's fight to be the first to get the electricity and the victor runs the pc until next power cycle when they are destined to duel again

@mekhos
Shitpost or real?

Things were wild at the edge of computing back then, I could believe it was basically roulette that picked the main device by what responded first, and the second was marshalled by the first.

@Brett_E_Carlock Shitpost. I'm not very knowledgeable, was just going for cyber western vibe ;)
@Brett_E_Carlock I agree things were loose so its possible. Totally worthy of a screenplay if true

@bluetea

I'm at the beginning of the transition using Libre, Vivaldi and Firefox, Proton email and slowly migrating to their calendar (missing important stuff like tasks), but struggling to figure out what to use to replace Outlook.
As much as I hate Microsoft, Outlook's functionality still seems head and shoulders above alternatives (especially with Proton Mail Bridge not handling 3rd party calendar access).

@Brett_E_Carlock @david_chisnall

@joeinwynnewood
I hate to even say this, but after three years of using Proton, my honest recommendation is don't.

As for a client, closest I found to Outlook is GNOME Evolution, and it even beats it, IMO.

Bridge is a persistent nightmare, yes.

@Brett_E_Carlock

Appreciate the info.

Re: Proton
Both email and calendar or just calendar?

@joeinwynnewood
Anything from them, honestly.

Their corpotate politics rub me the wrong way, their whole platform is very funnel-shaped, and leaving is more friction than it ought to be.

Outbound delivery is good for email, I will give them that.

But their mail product makes it clear nobody working on it reads/writes email for a living, and that pattern holds for all other products, IMO. Drive? Oof.

Everything is, IMO, at best serviceable. Not great when branded as premium services.

@joeinwynnewood
Unhelpfully, I do not really have an alternative I can enthusiastically recommend.

I have nextcloud+dovecot/roundcube on a VPS.

My outbound delivery is miserable.

Otherwise, all my data is easily accessible and movable, and usable everywhere because standards-based.

You are doing the right stuff, so I do not mean to take the wind out of your sails, but we started with Proton at work for the same reasons and three years on... we are looking to move, again.

@Brett_E_Carlock

Yeah, not fun without a serviceable suite that effectively handles all of the basics.
I'm going to have to muddle through with Proton for now. Changing email addresses alone is a major hassle with dozens of accounts to deal with on top of all the personal contacts and mail clients "helpfully" remembering my old email for them...
Moving 60GB of data on top of that and the time sink grows and grows.
Thanks again for your input.

@Brett_E_Carlock Got any advice or resources you particularly like for Alpine? I'm starting to play with it to replace several things, and I feel like I'm having to relearn a lot of fundamental stuff.

@noodle
I am always availble to help as I can.

I would say the Gentoo and Arch wikis are great, as Alpine tends to do things mostly like Gentoo, and Arch wiki usually always has gotchas documented.

Alpine Wiki is great, but can be outdated.

Main advice: backup /etc/apk/world to versioned backups. I do post-install, post-setup-desktop, post-personal packages, and post-work packages.

Move or copy the backup over world, doas apk fix, software state restored.

Try the default/alpinic way first

@Brett_E_Carlock Do you use autoconfig scripts or similar? For my purposes I'd prefer to rebuild rather than restore when things break. I keep very little data in the first systems I'm replacing.
@noodle this machine has been alpine for 7 years and it's still going. if you're using it as a desktop, i don't think you need to rebuild when something goes wrong, because the sorts of things that go wrong should be easy to repair.
@dysfun
@noodle
Yeah, alpine is pretty bullet-proof, especially when tracking latest-stable.

@noodle
No, I run it for family personal computing, not infra.

The Alpine cloud-init script might be a good base to poke at, as well as the setup-alpine answerfile.

What do you mainly want to use it for?

@Brett_E_Carlock @noodle I've been moving to Alpine from Debian, and the documentation could definitely use improvement. For example, the documentation for apk gives some example commands and says that tags are explained further below, but then tags aren't mentioned at all.

I'm thinking of trying to write a more definitive packaging guide, it's a bit fragmented at the moment.

@mathew
@noodle
Yeah, like almost any volunteer-driven OSS project, docs can fall behind.

I keep telling myself I will step up soon, but time has not been kind.

I am certain they would appreciate any new or fixed up docs/wiki entries.

@noodle
For me, it was _very_ unlike the Debian-deriveds I used, so same lack of familiarity, but I found the cognitive load of using it much lower once I got over that unfamiliarity.
@david_chisnall This is such great advice. I think that's how the French police managed it in the early 2000's. They first switched users to LibreOffice. It's also what made me switch. I first got into the command line on macOS, then felt comfortable to make the switch.
@TimothyRoes
Not the police but the Gendarmerie, but the difference is not relevant here.
400.000 users migrated and millions of public money saved.
And other administrations start or plan to do the same.
Thank you Trump !
@david_chisnall

@david_chisnall

Couldn't agree more. That's exactly what I did and in Linux FOSS apps are better because they all autoupdate unlike on windows so when you switch you even feel an improvement right off the bat!

@david_chisnall This. So. Damn. Much.

I got my dad off from XP that way as well. Switched him to OpenOffice, TuxGuitar, etc.

Themed his taskbar grey.

And then one day he had Xfce instead of XP, he almost didn't notice that differences.

Now he is back to Windows because he moved in with his new gf and she couldn't get his printer to work... that is, they didn't try because she instantly loaded the driver CD and then spent hours figuring out to install wine and install those programs, instead of just plugging the printer in. She gave up and they bought a new one, declaring it's too complicated.

When I stopped around a month later, I plugged the printer in and it just worked™. But she still insists "You must install the driver CD!!"

Oh, also this new system was much faster than his old Linux. Well, yeah, if you replace a old Pentium(!) with 4GBs memory some i7 with 16GBs... . I doubt it's the Windows that's making your PC faster, ffs.

@david_chisnall There's a tangent here to be had about good cross-platform apps that look roughly the same on all systems. Unfortunately that seems to have died.

@ljrk

Good cross-platform apps integrate with the platform's native behaviour and UI models. That's why they're so hard to write.

Switching between Windows and most open-source environments is fairly easy because the native apps are inconsistent anyway. Last time I daily drove such a thing, I counted four different sets of keyboard shortcuts for navigating within a text box in the apps I was using regularly. That's improved a bit due to consolidation on GTK and Qt, but using apps from GNOME on KDE or vice versa is still not ideal and big things like LibreOffice and Firefox do their own things. On Windows, they've decided on a new shiny GUI toolkit every few years since .NET launched and you get a mix of these and of things where people have given up and gone with Electron, Qt, or something else to avoid dealing with Microsoft's mess.

Moving from macOS is harder, but Apple's push to mess everything up with Catalyst and SwiftUI is helping a lot.

@david_chisnall Yup, I wholly understand the difficulty of the problem (and I'm glad I'm not working in that part of the industry), but as you say: There's been both some good consolidation as well as some really unnecessary moves that make shifting/adjusting harder.
@david_chisnall From looking at a financial services firm, the ship-jumping mainly affects the non-IT parts of the firm.
Here's what runs on NIXes: core banking stack (client accounts, payment processing etc.), trading systems, the grids for risk simulations, online banking, settlement systems, reporting engines, data lakes etc.
Here's what runs Win: laptops.
On these laptops: a browser running cloud services like the GUIs for the above-mentioned services, also Jira but also sharepoint (Which I guess can run on Linux?).
And here's the big one: MS Office, incl. Teams.
That's it. That's the one big thing that keeps Linux off these laptops.
I do not like MS Office, but I have to admit that no Libre Office or Thunderbird comes near it when it comes to the office workflow.
However, I wonder if Copilot and Co do not reduce the switching hurdle. If I e.g. ask Copilot to compare two Excel tables and highlight the differences, I no longer mind if it's doing it in Excel or Calc or Sheets or Lotus 1-2-3.
@david_chisnall I installed Slackware, decided it was too much for me, did "rm -rf /" because that sounded pretty cool, and forgot that /dosc was automatically mounted. That's how I ended up switching. ;-)
@amenonsen @david_chisnall Damn, you reinvented suicidelinux !
https://qntm.org/suicide
Suicide Linux @ Things Of Interest

@david_chisnall Great point. I think this idea of migrating one's applications first and *then* the OS also applies to many hardware platforms. For example, degoogled android OS for mobile telephones. I've seen many people who tried to migrate OS first complain their apps didn't work, but those who had been gradually transitioning toward more privacy-respecting open-source apps before switching OS seemed to have a grand old time.

#grapheneOS #degoogle #defenestrate #FOSS #software #operatingSystem

@doboprobodyne I’m actually doing this for iPhone and windows pc simultaneously and it makes the two work better together with each shift as well.

@doboprobodyne @david_chisnall

For example, degoogled android OS for mobile telephones.

However, Android has added a desktop UI.

Android's potential likely out-classes anything from the "Desktop Linux" realm. The latter doesn't even really exist, IMO, as its a loose collection of things that confuse non-technical users.

We must stop trying to lure the general population to Unix culture. They will keep spitting it out.

@david_chisnall Interesting observation. As someone who's been using both Windows and Linux (different DEs and WMs) for over 20 years my main problem with my (first, current) work Mac has absolutely been window management and keyboard layout, applications have absolutely not been  problem - but I guess as a dual (or tripe OS) user I've been relatively flexible in my choice of tools and alternatives anyway.

But I don't disagree, my main PC at home is still on Windows unfortunately, because of some small things I couldn't get configured (or running) as I'd like, despite preferring Linux anyway.

@wink @david_chisnall I think it depends on the individual too though. Sometimes you gotta actually prevent yourself from using the other stuff or you'll just keep going back to it. Part of my transition to Linux was a second old PC and a crossover ethernet cable because I couldn't get the wifi working and I had to find a way to make it feasible :)

(That was also about 20 years ago when that sort of compatibility was a bigger issue!)

@david_chisnall

I mainly maintain my Windows (game) computers because of the games / steam currently runs best on Windows, if Steam and NVidia (and perhaps AMD) get their act together I would be happy to change tack, for everything else (besides work) I use the Linux already.

@hnapel @david_chisnall What games do you play? Is any of them broken on Linux if you check ProtonDB? Nvidia for the most parts works fine already on Linux. (I run Pop OS with RTX 2070 Super and I've had no problems so far.)

@Razemix @david_chisnall

Picking berries in Horizon Zero Dawn mostly.

@hnapel @david_chisnall My daughter has been on Bazzite Linux for a while because she did not want to use Windows 11.

There's been some minor issues but most games work fine.

@david_chisnall Looking back, that's pretty much what I did. Moved to OSS apps that were cross platform, so the final jump wasn't too long.

@david_chisnall My main issue was - and still is - the OS layer.

I used MacOS (Yes! Capital "M") for 25 years. Some things are engrained in muscle memory.

I tried using linux for a few years but there were some parts that didn't go away and still slowed me down even after several years.

And investing several days to dig into the depths of driver configuration and libraries on linux to just get the trackpad-behaviour right didn'T pay off.

In the end I went back to macOS.

@heiglandreas

Yup, the transition from macOS is harder because OS X was consistent and tightly integrated, from the command-line up through the GUI.

When we were doing Étoilé, I joked that F/OSS DEs would pass OS X usability in 20 years even if the F/OSS people didn't change anything, just due to the rate at which OS X was getting worse. I think Apple's been doing their best to make that prediction true in the last couple of releases.

@david_chisnall @heiglandreas I recently started using Linux in parallel to macOS and I prefer KDE Plasma DE over Apple's desktop. But when switching between different apps, mac apps are so much morer consistent in keyboard shortcuts!
Anyway: great advice in your original post!

@david_chisnall I like your point about corp/org migrations. Another advantage to transitioning programs first is, once that happens it becomes possible for others in the org to use another OS and still engage with others without needing all sorts of workarounds.

It is also the easier migration to do in my experience. The hard migration is usually IT & Security, who are quick to throw out words like: "No", and "Impossible", and also happen to usually be in a position to more or less veto such initiatives. In a Windows-entrenched environment, IT probably does not know how to deploy Linux across the org, much less support it. They also often have a lot of networking tools, telemetry, management engines etc that are Windows-specific, and depending on how hard they lean into corpo-spyware mess there may be no viable Linux alternative.

But by going applications-first, one by-steps all the fights with IT & Security. At worst, they just have to white-list a few more apps.

@david_chisnall Thanks, seems like great advice I can pass on to people who wanna switch
@david_chisnall this is really, really good advice. I guess I'd also suggest checking compatibility with your existing hardware too. you buy some peripheral that only supports Windows and that doesn't seem at all like a problem until it's time to switch and you're kinda stuck
@david_chisnall i loved xp and 7 but 8 and up i hated. when i was forced to buy a new machine and go from 7 to 10, i full switched to linux and never looked back. i hated not having control over my machine anymore.
@makeitmythic great point. working with legal teams in education I’m realizing how much everyone (who is paying attention) hates not having control over their machines! as one example- constantly having to dodge ai and “smart” features when working with student information is exhausting people.
@surfsup31 its v frustrating and disheartening trying to find a medical provider who doesnt use ai, as well.