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 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.
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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 actually very sound advice. Haven’t heard it being given before actually. Also sounds very logical.
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@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.
Especially if you've got some centralised login system and file server (or cloudy equivalents), where you can get your desktop from different computers. You can set up the Linux machine to allow access to the same files and, mostly, the same apps.
The danger of using an old machine for this is that people are likely to think Linux is slow because they're using Windows on this year's machines and Linux on the old ones (three years is optimistic: I think the last time I saw a company doing three-year rolling upgrades was over 20 years ago, most places seem to have moved to seven-year or 'when it wears out' policies).
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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
Our workplace decided to free themselves from Microsoft licenses and rolled out openoffice across the board. Except they never updated it to assure interoperability with MS Office users. Then they made exceptions for folk who needed excel because of macros, then people who had to send a lot of docs to other places then people who complained because him at the next desk had "real" office. Eventually the whole initiative just fell apart. -
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 good advice! I switched to Libre Office. I'm not yet as proficient with it as I was with ms office, but I'm getting there, and I like it.
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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 my experience, not migrating the OS first is too much of a tentation to go back to your "usual" tools at the first friction.
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@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 -
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 Oh absolutely!

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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.)
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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 good advice! Is there a "quitting smoking" parallel somewhere in there?
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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 Yup, worked for me. The only thing I miss is Notepad++, but KWrite is a good enough replacement. It fortunately also worked for my wife. Even on Windows, she already used LibreOffice, Audacity and MuseScore. The only last-minute change was swapping Chrome for Firefox, but thet went pretty smoothly too. So now we are a completely Windows-free household.
