My Failed Attempt to Ditch Microsoft

As a CTO, my job is to make my products cheaper, faster, and better.

My daily life is an uneven amalgamation of coding, training AI, delegating, meetings, research, and emails.

I ditched Microsoft on my primary workstation years ago for Ubuntu, and I have never been happier. Yes, there are occasions where NVIDIA causes my monitors to go black after Ubuntu updates, but nothing a few hours of maintenance cannot fix.

I still have Windows 11 and Windows 10 on two of my other PCs and in a VM, so I do spend a few hours every week on them.

I hate those hours.

I used to love Windows. I was part of the developer program for over a decade. But recently, even “despising” is an understatement for accurately describing my emotions.

So I entered 2026 with a goal: make my company ditch Windows altogether.

It was bleeding us out financially and mentally:

• Software updates that broke machines.
• Borderline data theft.
• Aggressively pushing AI into everything.
• The feeling that tools were making my colleagues dumber instead of helping them think better.

As someone who designs AI for a living, watching my colleagues consider Copilot and other AI slop as a glorified mystic creature — when it is often nothing more than a cheap party trick used to drain my budget — used to make my blood boil with disgust and anger.

So I convinced my CEO to give me a few months to make the switch to a software stack that was free, owned, and heaps and bounds better in terms of privacy and general productivity.

We switched our operations to open source alternatives, including Nextcloud.

And then my dreams came crashing down within a few weeks.

Some context about the company

We are a small, but over 14-year-old, tech company that makes safety and environment related AI software for energy and heavy industries in Norway.

We take pride in our ability to save lives.

Our CEO and board of directors are almost exclusively made of people who have personally suffered life-changing injuries or have lost someone to negligence.

Our CEO is pushing 60. He is clever, intelligent, and bold — and looks like Vin Diesel from Temu. I like him and respect him. True Viking.

But when it comes to tech, I do have my differences with him.

What happened after the switch

Here is what happened in the few weeks we were on the open source stack:

• A freakout when mail stopped working for a few hours during the transfer process.
• Huge FOMO because meeting URLs were not “Teams” links.
• Internal complaints about looking “unprofessional”, when it absolutely didn’t make sense to me.
• A feeling of “nakedness” and imposter syndrome among my colleagues.
• Everything that went wrong — or even felt like it went wrong — in operations seemed to originate from the change.

As a result, we had to switch back to Microsoft within a month.

It was a win for marketing and a huge loss for tech, data privacy, and ownership.

Did I feel bad switching back?

No, I did not.

I value my colleagues’ opinions, and I want them to have a stress-free tech experience.

Are my colleagues too old for such drastic changes? Yes.

And not only that, most of our clients have upper management and decision makers in the same age demographic. I don’t have filters, can’t do anything about it 🤷🏼‍♂️.

Is Microsoft reaping past crops? Also yes.

The harsh truth I had to swallow

Microsoft is not winning because their software is superior.

They are winning because they are a generational comfort blanket.

For an organization whose leadership team is forged in the high-stakes, safety-critical world of heavy industry, cognitive load is a finite resource.

When our CEO looks at a screen, his brain should be entirely focused on risk mitigation and strategic scale, not wondering why a Nextcloud calendar invite looks slightly different than what he is used to.

By stripping away the familiar, bloated Microsoft UI, I inadvertently stripped away their operational confidence.

Infrastructure means different things to different people

We tech purists often forget that to a non-technical executive, infrastructure is not about data sovereignty or code transparency.

It is about predictability.

A broken email script during a migration does not just mean “a few hours of downtime” to them. It reads as a systemic failure that threatens a 14-year-old reputation.

The “unprofessional” critique was not really about the actual utility of open source tools.

It was the psychological terror of stepping outside the corporate monoculture.

If you are not sending a Teams link, the unspoken, irrational fear is that you are running a garage operation. And that sentiment is silently echoed by our aging enterprise client base.

The incompatible human stack

This experiment taught me that forcing an ideal tech stack onto an incompatible human stack is a recipe for operational rejection.

I still despise:

• The telemetry.
• The forced AI wrappers.
• The financial bleeding of the Redmond tax.
• The way Microsoft has turned familiarity into a moat.

But as a CTO, my ultimate mandate is to make our products cheaper, faster, and better.

I cannot do that if the team building them is paralyzed by the very tools meant to empower them.

Closing thoughts

We are back in the Microsoft ecosystem, paying the premium and tolerating the slop.

It was a tactical retreat that wounded my engineering pride but saved our collective sanity.

The battle for data privacy and software ownership is noble, but it cannot be won by staging a sudden coup against human habit.

For now, I will keep my Ubuntu workstation as an isolated island of sanity, accept that my colleagues need their familiar safety nets to save lives in the real world, and wait for the day when open source finally learns to design for the user, not just the architect.

References

• Uploaded screenshot: Microsoft and open source illustration