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The map image in the masthead confused me when I found LW, and might reduce the probability that casual Web-browsing would-be-rationalists would take the time to understand what LW actually is before moving on.
I'm new to the community; this post may not be structured like the ones you're used to. Bear with me.
If LW is anything like the few sites whose analytics numbers I've seen, a significant portion of traffic comes from Web searches (I would wildly guess 10-30% of their pageviews). According to the analytics I've seen on my own site, out of those landings from Google et. al., many are likely to stay only for a few seconds, presumably trying to see if they've found what they're looking for.
[In my opinion] the name, small grey welcome box for new readers, and the tagline under the logo collectively do a good job of explaining what LW is, even for people who aren't familiar with any related terminology or concepts. The image of a map in the background, [in my opinion], does not. When I first arrived I thought for a few moments it was a site about maps. I ended up reading enough to stick around, but I wonder if some don't.
I would like to ask people who didn't understand what the site was about and didn't return to LW if the image was the reason... but we'll never hear from them. So instead, I invite people here to chime in about whether or not the image deterred them at first, and whether it is something worth re-thinking.
[Whether this potential deterrent is bad is a separate question; I'm just curious about whether it even is a deterrent. I can see arguments for trying to deter people (or certain types of people) intentionally, but I suppose that's irrelevant if the image doesn't affect the probability that first-time readers will return.]
An anecdote:
When I've had people shoulder surf while I was visiting the site, everyone asked, "LessWrong? What's that supposed to mean?" (5+ people). When I explained that it was a rational community where people tried to improve their thinking, they immediately began status attacks against me. One used the phrase "uber-intellectual blog" in a derogatory context and another even asked, "Are you going to come into work with a machine gun?" They often laughed at the concept.
Nobody commented on the graphic.