Really nice read. I'll add that it's effective to scope design docs up and down as needed, both in terms of how big your project is and how big your company is. A 50-person startup doesn't need a full design doc with multiple approvers. But a one-pager explaining what you're doing and having some documentation is really helpful even with an engineering team of 5. I'll also still write design docs for code changes that only touch a handful of files, if I feel it's important enough. The process of writing in a concise and precise way for other people to consume also has the positive side effect of making things more clear for yourself, too.

> Interfaces section

Only real criticism I have here, is I would not include any code in a design doc, unless it is really really vitally important. I've seen a lot of design docs (especially in the LLM age, written by more junior staff) which are effectively just an English summary of code. The point of a design doc is (generally) not to explain that you're going to have a WidgetManager and WidgetFactory class and what specific properties and methods they have, it's to explain how the widget creation workflow works and maybe you have the WidgetManager/WidgetFactory in an architecture diagram. As a general rule, if you're starting to include actual code, you've gone too low-level, IMO.

> Not all design decisions are equally important. Some choices are more permanent than others.

At AWS one of the corporate culture memes was calling a decision either a "one-way door" or "two-way door". Just asking yourself the question, if we had to walk this back, is it truly irreversible or just an inconvenience? Turns out most day-to-day decisions are two-way doors, particularly engineering ones. Even if the choice made is wrong and a bunch of work needs to be done to switch back, it's still preferable to what a lot of companies end up in, which is decision paralysis where every change needs approval from multiple committees, resulting in months or years before work can start. Note that this doesn't meaningfully increase the odds the decisions made are the right ones; it just delays the implementation and diffuses responsibility if the wrong decision was made.

> A from-scratch rewrite would never work, and even if you manage to write new code in Rails, you’re still maintaining code in two wildly different languages.

Orthogonal to the article, but this line of thinking (including the link to the classic 2000 "Things You Should Never Do, Part I" article[0]) may be worth reviewing in the post-LLM world; for all their flaws, LLMs are spectacular at language-to-language translation, and we already have one major project released[1] that shows porting a relatively large and mature project from one language to another is possible. Not to say that it's the best use of your time, or that you shouldn't do your due diligence and pick the right language up front, or even that the original 2000 article was about a language-to-language rewrite (the Netscape rewrite was an architectural redesign).

[0] https://www.joelonsoftware.com/2000/04/06/things-you-should-...

[1] https://bun.com/blog/bun-in-rust