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I have been thinking along the following lines in the run-up to the New Rules Symposium:

It can be difficult to keep up with the evolving etiquette of smiley faces, exclamation points, or appropriate 21st-century saluations and signoffs — something might not have been acceptable a year ago but is commonplace today. I would propose however, that there are two rules that always remain relevant, rules that will point any writer in the right direction whether in 1807 or 2007. Those are: clarity and correct perception of context. Is my meaning transparent? Is what I am writing likely to distract or offend the reader?

If those are the questions we ask each time we hit “send” then we will tend to phrase our writing conservatively, which is a good thing. No boss who receives your memo is going to care if you’re the very last person to employ emoticons, but he sure might if you’ve chosen to be part of the emoticon avant garde. This of course does not mean conservative thinking. The idea is only to decrease the chance that your style distracts from the thought you wish to convey.