Mac? Windows? Arch Linux. Choosing an OS for a business built on open source + AI

When the new notebook landed on my desk, the first decision was not “which password manager” or “which folder structure”. It was the most fundamental one: which operating system carries a working life where an AI agent does half the work?

The answer became Omarchy — an opinionated, beautifully styled Arch Linux with the Hyprland window manager. Here is the honest trade-off, because the usual suspects had good arguments.

The requirement that sorts everything

My yardstick was not “prettiest system” or “most familiar system”, but:

The agent must be able to operate the whole machine — files, configuration, services, windows, everything. Whatever it cannot reach via terminal or API does not exist for it.

That sounds technical, but it is the core question of this whole series: I am building a working life where routine work goes to an agent. Every corner of the system that is only reachable by mouse becomes a manual-labour reservation.

Why not macOS?

The honest answer first: macOS would have worked. Excellent hardware, Unix under the hood, the agent tooling runs well there. Three things tipped the scale:

• The system is only half mine. System settings, updates, signing requirements, an app ecosystem behind Gatekeeper — much of it is deliberately removed from automation. A feature for consumers; a cage for my goal.
• The cost logic. A business that tells customers “open source instead of licence lock-in” is more credible when it works that way itself.
• Configuration as code. On Arch, everything is a text file in a repo. My entire desktop setup — windows, shortcuts, theme in the company design — is versioned and reproduced on a new device in minutes.

Why not Windows + WSL?

Because I had exactly that for years — my old workstation still runs it today. It works. But it is two worlds with a seam: the agent lives in the Linux part, real life (browser, Outlook, files) in the Windows part, and the seam chafes daily — paths, permissions, networking, two clipboards, two update worlds. An agent that is supposed to organize your whole life needs a system without a seam.

And yes: the elephant is called Outlook. The Exchange exit is the hardest part of this migration and will get posts of its own — the short version: mail, calendar and contacts move to self-hosted, open services, step by step and without data loss.

The honest cost of the decision

So this doesn’t read like a brochure — there were moments where, after 25 years in IT, I felt like a first-year apprentice:

• I wanted to edit a file and discovered: no vi, no vim — and in nvim I didn’t even know how to copy properly. (“I still have to learn Omarchy!” is a literal quote from my history.)
• Passkeys with the built-in fingerprint reader: on Linux that is a research project of its own, not a given. The research became its own decision document.
• There is no vendor support. There are wikis, forums — and an AI agent that explains patiently.

That last point is the real game changer: the learning curve that used to make Arch steep is now absorbed by the agent. It knows my system, explains the shortcuts, writes the config — and documents it so I can do it myself the second time. The old truth “Linux costs time” no longer holds like it used to.

What this means for companies

The private OS choice is a miniature of a company question: not “Mac or Windows”, but “how much of our stack can we automate — and how much do we actually own?” Anyone who wants their business AI-ready will have to measure every system against that — from the notebook to the ERP. Which is exactly what the next part is about: the hardest criterion in every software decision.

Questions, objections, experiences of your own? Write me — I answer personally.