Now I work in an environment where it would be accepted, even welcomed. I'm spending a lot more time in Temple, especially during the run-up to the Holy Days. I've spent several Friday nights at local assisted living facilities, leading services for the residents. But I find I'm more concerned about the message inherent in starting to wear a kippah than I am about actually wearing it.
Why am I concerned? As Leon points out, it's not an actual commandment. As such, the perceived obligation to keep our heads covered represents what is, to me, a stringent type of "Tradition As Law", in which the views of a particular rabbi (or group of rabbis) become as binding as the word of God. There is a specific mentality that takes tradition, turns it into law, applies it universally, and condemns - explicitly or implicitly - everyone that does not fall in line. Given the tendency for extreme religious observance to gradually become the norm, I feel almost obligated to resist just to maintain the middle ground.
There is also a statement made by adopting a new observance. What would you assume about a 30-something single guy [it should be noted my girlfriend objects to this description] that suddenly picks up a new, highly visible, religious habit? The "born again" or "baal teshuvah" implications are stronger than I'm comfortable with.
Is "being Jewish" now such a large part of my identity that I want to visibly distinguish myself at all times? Wearing a full-time kippah makes as much a statement at my temple as it does in at the grocery store, the bank, or the airport. I do not object to this marking, although I have equal reluctance to brand myself in general; I avoid wearing sword-shaped pendants despite my interest in fencing, I do not have cat pictures on my desk at work despite being a cat lover, and I do not put BSA logos on my car despite being a Boy Scout. No one of these defines my identity, and I don't want people to think of me as "the Jewish guy".
I also object to allowing ultraobservant "traditionalists" to define what qualifies as a symbol of Jewish identity. If I allow arcane rabbinic interpretations to define the expression of my Jewish identity, how can I object to their interpretations of dietary laws or conversion? I was thinking about this during Rosh Hashana, and was struck by how much the rabbi and cantor were falling over themselves to look Orthodox, even as the service was filmed and projected onto multiple screens, and a piano, violin, and cello accompanied the music.
There is an uncomfortable tension between these two ideas. Granted, Reform does not need to be a total rejection of Orthodoxy, but the "pick & choose" mentality, I think, really weakens Reform Judaism's theological arguments. Yes, a kippah has tradition behind it; it's what our ancestors wore, after all. But argument from tradition is a weak justification. There is a long history of distinctive Jewish clothing, most of them from traditions we'd rather not revisit.
I respect Leon for his courage and perseverance. I respect him even more for his thoughtfulness and consideration in making the decision. This ability to wrestle with God within your own life, to find the personal intersection between tradition and modernity, is to me the best attribute of modern Judaism. The process is more important than the result. It is how he and I remain friends not in spite of our different observances, but because of them.