Many, many years ago I and a friend wanted to do something that quite frankly would be utterly not allowed these days. (It was questionable then, too). So I had my first encounter with the phrase, “Better to ask forgiveness than permission because some asshole will always say no.” We went ahead and didn’t encounter an issue, but that was another of those “youthful indiscretions” that could have easily gone awry. (The details aren’t important) A recent local situation brought this memory to mind along with a common misconception about this phrase.
I have heard others cavalierly toss this out when faced with the sudden realization forgiveness might not be granted. People have a tendency to think their “initiative” or “boldness” will count more heavily in their favor. It very often does, particularly if the action results in something good. Even so, though, it can also lead to friction within a group as not everyone may be in the “forgiving” mode. The point though is it doesn’t always. At those few times I’ve witnessed the reaction of the one “not forgiven” the common reaction is one of disbelief followed by an emotional response of anger and/or pleading for reconsideration. (More about that below)
A boss of mine later expanded on the idea with his three “rules”. First, make sure what you want to do is legal. Second, think it through carefully and be able to explain your reasoning. Third, accept the consequences if things don’t go as planned. To reinforce the above paragraph, that meant prepare myself if the action/decision didn’t work out correctly or forgiveness was not in the mix. This is one of those life lessons that served me well and I passed it on to numerous subordinates during my career.