I think this advice is pretty apt for small to medium sized companies. We're all invested in the company succeeding, but you don't want to become known as the person that always says "no".

At large companies, I've rarely found a reason to speak out on a project. Unless it has a considerable effect on my team/work (read: peace of mind), it just doesn't make sense to be the person casting doubt. There's not much ROI for being "right".

If you manage to kill the project before it starts, no one will ever know how bad of a disaster you prevented. If the project succeeds despite your objections, you look like an idiot. And if it fails - as the author notes, that doesn't get remembered either.

As a senior IC, the only real ROI I've found in these situations is when you can have a solution handy if things fail. People love a fixer. Even if you only manage to pull this off once or twice, your perception in the org/company gets a massive boost. "Wow, so-and-so is always thinking ahead."

A basic example I saw at my last company was automated E2E testing in production. My teammate had suggested this to improve our ability to detect regressions, but it was ultimately shot down as not being worth the investment over other features.

A few months later, we had seen multiple instances of users hitting significant issues before we could catch them. My teammate was able to whip out the test framework they had been building on the side, and was immediately showered with praise/organizational support (and I'm sure a great review as well).