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).
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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 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.
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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 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 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.
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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 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.

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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 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
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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 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.
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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.
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.
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@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.
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.
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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 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.
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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 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.
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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 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.
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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@infosec.exchange
Thanks, seems like great advice I can pass on to people who wanna switch -
@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.
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.
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@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.
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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 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
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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 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.
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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 this! Begin with firefox, then LibreOffice and whatever application you need.
Then when you switch to linux you already know the applications. -
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 I was technical lead for a customer Y2K migration to NT4.0 including over 900 applications.
It was a huge job but we managed it. It would have been way easier doing it as you suggest and without the impending time constraints that we had.
The rationale and stack are different, but I think the same principles apply.
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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 that's what the French gendarmerie did, took them 10 years, but they saved millions.
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@david_chisnall this! Begin with firefox, then LibreOffice and whatever application you need.
Then when you switch to linux you already know the applications.@david_chisnall for organisations, first install linux on an old extra computer (do this instead of throwing away 3 years old PC) so people can test it and familiarise themselves with it.