A couple of days ago I was part of a private email thread about the popular Grace Hopper quote "It's easier to ask forgiveness than it is to get permission." and the somewhat related blog post by Kate Losse (please go and read it first, it's really good). I got a helpful and friendly nudge to put the response I wrote on here, so here it is in a slightly edited version to fit the format:
I have so many opinions on that and I hope the following brain dump makes sense/helps.
I should start off with the disclaimer that I think there is something to that quote but it's been completely repurposed to serve as a backwards justification for a lot of things. I think the variant "If it's a good idea, go ahead and do it. It is much easier to apologize than it is to get permission." is a much better version (although still problematic) of this quote. But I highly dislike the often quoted form together with its corollary "move fast and break things" which basically has the vast majority of the same problems.
So why do I dislike it? First and for all because it's arrogant and disrespectful. It has the implication that rules don't apply for some (for a certain value of some) people and that it is in their judgement to decide what applies to them. It also implicitly means, because (usually though not always) rules are made to protect/help people, that what you want to do is more important than protecting/helping. I'm probably extremely biased because I work in infrastructure where a large part of work is maintenance. But in computering what following this rule most likely means is hack something together that works and then figure out how to maintain it and who. And in that regard it often comes down to upholding the romantic VC notion of a 10X engineer/lone wolf programmer who is so genius that you have to get everything out of their way because they can change the game in an instant. That they don't have to communicate, follow rules, or workflows, because their beautiful mind justifies everything. Another thing I highly dislike.
The next problem I have with this statement is that it is so ambivalent that it doesn't really mean anything. And as so often, can only be verified in hindsight. The article you linked really pin pointed one of the major problems there. In order to be granted forgiveness, you are betting on "the authority" (this could be your manager, execs or tech leads, or even the police) to turn a blind eye on something you did or even praise you for breaking the "law" for making things better. This usually is only the case if you are a member of the same race, culture, class, group as those you will have to ask for forgiveness. Which doesn't work well for everybody. It's also important here, that - if I'm not mistaken - the quote comes from a time where Grace Hopper was almost retired and already an accomplished Rear Admiral. The power and influence that comes with such a rank shouldn't be neglected. And I highly doubt that the same thing worked when she was a Sea(wo)man or Petty Officer.
That being said there is something to that quote. But as I said in the beginning, I see it more in the context of the variant quote. And more importantly in the context of efficiency thoroughness trade-off. A lot of times you can't ask everyone for permission to do something because it takes too much time and doesn't make sense. Especially when it comes to computering there is often a lot of merit in trying to get a prototype in place so there is a concrete thing to talk about. It's also often worth it to only bounce ideas off of a handful of people before trying it out instead of getting a formal review and the exec's agreement to do it. But with all of this the impact if it's a bad idea has to be taken into account. If everybody runs off doing their weird ideas, we likely would have chaos. At the same time if everybody spends their day with getting permissions about work, there won't be any work getting done. Ideally we trust our colleagues that they know what is needed to bring things forward. That is why there are always tendencies to reduce bureaucracy and empower individuals. But I don't think this means you should do things where you have to ask for forgiveness. Because if you have to, you likely made someone else's day pretty miserable.
I hope this was a somewhat coherent write up and answers at least some of the questions you had. Also I'm super happy to be proven wrong here since this is very likely a pretty narrow view on things.