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! 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.
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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 on one hand this makes lot of sense, on the other this makes the app switch worse. many apps that work on windows work there slightly differently and often are actually harder to use... which can be a deal breaker for people who are not sure about the entire thing (those who really want to make the switch will find the way one way or the other). as an example try to use something like darktable on windows.
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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.
2025 Schleswig-Holstein switched to Open Xchange, Thunderbird, LibreOffice and Nextcloud
2026 Schleswig-Holstein started to switch from windows to Linux
#SchleswigHolstein #openxchange #Thunderbird #LibreOffice #linux
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@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)
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). -
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 then some drone in Finance comes to you with some subscription Excel vbs macro + application that requires so many old Windows dependencies that you want to cry, and of course you can't port that. And that team gets to keep Windows and Office. Then everyone else wants it, too, because they don't want to adapt to anything new, ever.
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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 exactly what made my Linux transition smooth - ever since Windows 11 came out (a bit before, even), I've been making an effort to slowly switch my Windows-only apps for open source or at least Linux-compatible alternatives - RawTherapee replaced Adobe Lightroom, Davinci Resolve replaced Adobe Premiere, stuff like that.
So, when a few months ago Windows 11 pissd me off so much that I finally decided I was done with it, switching to Linux felt like a breeze - all my apps still worked, but the OS also worked.
It definitely was not seamless (I would describe the experience as seamful, in fact) - but not needing to replace all my applications at the same time made it 10x smoother
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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 the logic behind this, but at the same time, I noticed that LibreOffice and GIMP take much more time to open on Windows and macOS. That can discourage some users, so it's probably better to communicate this with them in advance.
