I'll take an earnest person over a hip person every time, because hip is short-term. Earnest is long-term.
Earnestness is highly underestimated. It comes from the core, while hip is trying to impress you with the surface.
"Hip" people love parodies. But there's no such thing as a timeless parody, is there? I have more respect for the earnest guy who does something that can last for generations, and that hip people feel the need to parody.
When I think of someone who is earnest, I think of a Boy Scout who works hard and becomes an Eagle Scout. When I was interviewing people to work for me, and I came upon a candidate who had been an Eagle Scout, I'd almost always try to hire him. I knew there had to be an earnestness about him that outweighed any superficial urges toward hipness.
Think about it. Becoming an Eagle Scout is just about the only thing you can put on your resume at age fifty that you did at age fourteen - and it still impresses.
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