Use cheap tools until they break
Adam Savage once said that as a hobbyist, you should buy the cheapest tools you can find and use them until they break. When they break — and they will — you'll know two things: you're serious about the craft, and you now know exactly what you need. Then you buy the best tools you can afford.
This translates beautifully to technical writing.
Start with what gets the docs out the door
If you're early in your career, or switching to docs-as-code, or just getting started with structured authoring — use whatever ships the docs. Paligo. FrameMaker. Zendesk. Confluence. A CCMS that lets you publish topics and structure content? Great. IntelliJ's visual Git interface so you don't have to memorize CLI commands on day one? Totally fine. I love that thing.
The point is: don't let tooling anxiety stop you from shipping.
The skills matter more than the stack. Structured authoring, simplified technical English, user experience, content architecture — these don't change because you switched from Confluence to a static site generator. The fundamentals are the fundamentals. Focus on the process, the knowledge, and the writing.
Learn how to interview a developer. Learn how to break down a feature into tasks a reader can actually follow. Learn how to say the same thing in half the words. None of that requires a terminal.
When the cheap tool breaks
You'll know when it happens.
The GUI can't handle your reuse model. The CMS chokes on your branching strategy. You need automation that doesn't exist yet. You're copy-pasting the same update across 40 files and thinking there has to be a better way.
There is. And you're ready for it — because you've hit the wall.
That's when you go all in. CLI. Scripting. Pipelines. You start single-sourcing your OpenAPI specs straight from the source code. You automate generation of the sneak preview and the release notes. You add linters and style guides that run in CI. You set up an AI assistant that catches issues before you even open the file.
And here's the thing. By this point? You're not guessing. You're not automating for the sake of automating. You know exactly which part of the workflow is broken because you lived in it. You used the cheap tools. You developed the essential skills. Now you're investing your time where it actually matters.
"Afford" doesn't mean money
In this context, "the best tools you can afford" means time.
If you can invest in Python and version control from day one, do it. But if you're unsure about the career, hard-pressed for time, or just overwhelmed — resolve your merge conflicts visually and move on. No shame.
The tools don't make the writer. The writer makes the tools worth using.