“You can’t be too careful.”

Or can you?

Does this mean there’s no amount of caution that would be excessive – that the stakes are too high for any risk-taking?

Or, alternatively, is this an admonition to avoid being too careful?

In creative arts, risk aversion gets in the way of innovation. Might it be best to abandon caution in order to see what develops? If so, then you can be too careful – and the statement that “you can’t” is literal good counsel when mentoring an aspiring artist.

So just what does “you can’t be too careful” mean?

Apparently, it means quite the opposite of itself depending on context.

Such linguistic somersaults apply to many qualities that are neither an absolute good nor an absolute bad – but require a prudent measure of balance.

“You can’t be too merciful” could mean there’s no amount of forgiveness that’s not a good thing. Conversely, if taken literally, it means you ought not be too merciful … if you are, you undermine a sense of fairness, justice and responsibility. Sometimes tough love is what’s required.

This is similar to the notion that you cannot be too kind, too supportive, too loving, or too fair, too candid, too helpful, too truthful…

Approaching this from a different angle, perhaps we should turn our focus toward the meaning of “can” (and its converse: “cannot”).

If “can” means the capability of being able to do something, then its negative (“cannot”) asserts that, no, you do not possess this capacity (i.e., you are unable to overdo that thing).

But if “can” (and “cannot”) are meant as normative statements, i.e.,guidance as to whether you should or should not do something, then they convey recommendations about preferred behaviors – advice and admonitions.

Okay then, perhaps it’d be more precise to use the conditional “could” (and “couldn’t”) in place of “can” (and “can’t”)?

But that would force us to confront “could” versus “could not.”

And at this point I’m assuming you could care less. Which of course means that, actually, you couldn’t care less. So I’ll spare you.

Thanks for your patience.