Expressing a complicated idea in too few words is where misunderstanding can enter in. Tweets, though, tend to be very simple ideas, so it is generally not an issue.

In any case, it depends on the reader making it all the way through the text. A short message gives up detail in exchange for greater odds of the person reading it all. Longer text does the opposite.

Again, though, I think this applies mostly to complexity.

True, occasionally, I don’t get one. Usually that’s because I’m missing context (e.g. I don’t get tweet replies to people I don’t follow.)

As a technical writer by profession, I’ve more often found that shorter is more preferable to a lot of people. The longer something is, the more my readers complain that they don’t have time to read it. And when they don’t finish, they miss a lot.

I don’t think the length, per se, is really the issue. I think it’s what’s being said. To pull out an old chestnut (and add to it) – does the medium fit the message? And do the medium and message fit the audience?

While all writing has to deal with this, I think it does get harder from medium to medium.

Sure, but I don’t see how you can draw a straight line where misunderstanding descreases and you go from shorter to longer. In fact, in my head, I associate brevity with more clarity.

Different mediums might be more or less clear, but that’s going to vary by what medium the content is most suited to, the teller’s skills/preferences, the hearer’s skills/preferences, etc.

If you go read the post that kicked off my project, you’ll see it very clearly lays out the plan. Still, I had dozens of people thinking that each blog that commented would get a visit.

It just happens–you can’t control it, as you say, but you can improve the odds or worsen the odds. That all depends on what your goal is.

While all writing has to deal with this, I think it does get harder from medium to medium.

The key is just taking one small idea and saying it rather than explaining an entire line of thinking. That’s the whole crux of this being misunderstood issue, too.