A tuxedo-clad host stood stoically at the door to Boston's Oak Bar—an elegant, old money-ish lounge in the city's Fairmont Copley Hotel. A sign by the door read "proper attire required," and I glanced skeptically at my worn Chuck Taylors. The cool sound of jazz poured into the lobby from the bar's dark, classy confines, and the man behind me said of the tune, "I think it's a quasi-merengue."

That analytical comment happened to come from the person my boyfriend and I were in Boston to visit, clarinetist (and my mate's longtime friend and Sandy High School bandmate) Dave Heikkinen. It occurred to me at that moment that perhaps too much knowledge is a bad thing, that maybe an artist can know so much about his or her craft that they're unable to enjoy it in a basic, natural way. Heikkinen had graduated earlier that day with a master's degree from the Boston Conservatory, and while I swayed to the Oak Bar band's melodies—thinking about what fancy cocktail I might order inside—he studied its rhythms. Meanwhile, Dave's roommate, a doctoral student at M.I.T. and classically trained vocalist, mumbled something about bossa nova.

Heikkinen—who performs mostly chamber, classical and opera pieces—has an entire category on his iTunes titled "me." From it, the 28-year-old proudly played us a very difficult, progressive and esoteric piece (I mean, what the hell is a 1/4 flat note?) called "Tricolor Capers," which he executed in a seemingly effortless manner. But, throughout "Capers," Dave self-consciously pointed out anything he perceived as a fault in his playing. Later, when Dave broke out his clarinet and muscled through part of "Flight of the Bumblebee" from memory, as well an improvised version of Dixieland classic "Basin Street Blues," he seemed far more at ease. Of course, goofing for friends and performing for scholars are vastly different. But why does all that expertise have to suck the fun out of things?

Similarly, Dave's opera-singing roommate, Gustavo, proved an overly cautious karaoke singer later that week. While Dave belted out a fantastic rendition of "Sweet Transvestite" from Rocky Horror and my boyfriend butt-rocked the hell out of Bon Jovi's "Livin' on a Prayer," Gustavo was more restrained with his delivery, noticeably concerned with each note. The whole experience made me wonder if faulty-voiced folk singers or young punks who learn just enough chords to communicate their message are better off. I wondered if musicians like Heikkinen—who have every tool in the language of music at their disposal—have a hard time finding their voices amid all that information. I'm not saying training begets negative results; I'm just saying it might be best, once we've absorbed assloads of knowledge, to let it go every once in a while and just enjoy music on more of a gut level—the way we fell for it in the first place.

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