Originally published on It’s Not Where You Start.

What did you want to be when you grew up?

When I was in the first grade, I had a really spectacular teacher named Mary Caiza. She exemplified everything you could ever want in a teacher. She was kind and caring and made every student feel like a superstar. She encouraged creativity and imagination, and modeled these traits by telling us stories of her playful dogs (named Jack and Jill) and bringing in photographs of her neighbor’s duck-shaped mailbox that changed outfits as often as Barbie.

One day, she gave us an assignment to write and illustrate a poem. I still remember my first-grade thought process. “Everyone else is going to write a rhyming poem, but I know that poems don’t have to rhyme. I’ll write a poem that doesn’t rhyme so that mine will stand out. I don’t know what to write a poem about, but I really like Where the Sidewalk Ends, so maybe I can rip that off.” Please note, I was envisioning pastiche, not plagiarism.

So I wrote a poem called “Where the Sea Ends” (oh, the cleverness of me!), and I drew a beach with some seagulls, and handed it in. I (thankfully) can’t remember the actual content of the poem (although I do still have it, in a box that will get unpacked as soon as I remember to borrow my parents’ scanner so I can preserve its contents). But I do remember Mrs. Caiza’s reaction. She enthused about my effort and encouraged me to keep writing. It was that moment that I decided I wanted to grow up to be a writer.

Of course, being me, I wouldn’t be happy unless I grew up to eclipse Shakespeare. In fact, my Harvard application essay was about this very notion. If you’re going to do something, why not aim to be the best at it?

When I was in high school, I got very involved in Judaism via USY, the youth group of the Conservative Movement which, contrary to its name, is one of the liberal streams of Judaism. My time as a USY leader shaped the man I grew up to be, probably more than any other experience in my youth. And one thing became clear to me as a teenager: when I grew up, I wanted to be an involved Jewish layperson. But I definitely did not want to be a Jewish communal professional.

Oops.

I’m now in my ninth year of full-time Jewish professional work. By and large, I have no regrets. I am lucky to do meaningful work, for nonprofit organizations that I can wholeheartedly support — and I do so not only with my efforts, but also with my philanthropic dollars.

But there are three factors in my teenage pledge that linger. Jewish communal professionals tend to work themselves to the bone, largely because we care passionately about the work we do. As a teenager, I looked at some of my role models and mentors who devoted themselves to the community at the expense of having successful family lives, and I feared that might happen to me. I’m 32 and single and still worry about that, although this year proved to me that I can make room for a relationship if I concentrate on making it a priority. Given my personality and my neuroses, I don’t know that either my tendency to workaholism (that is, my addiction to workahol) or my relationship-avoidance (which I hope I’ve conquered) would have played out any differently in another line of work.

My second fear is that I wouldn’t make room for the writing I want to be doing. That’s been true. I’ve got a hard drive full of abandoned drafts, enough blog posts floating out in the ether to fill several books (if only my particular brand of solipsism could sell!), but no discipline to sit down and write every day. And definitely no discipline to sit down and write with purpose every day. This blog is my latest attempt to at least get in the habit of making time to write, even if it’s not the kind of writing I most want to do. You can see how successful that’s been.

My third fear is that the ideas of what it means to be a Jewish leader instilled in me back in USY have stifled my creativity. USY was (and is) very big on the idea of being a דוגמה (dugmah), an example. To lead one’s peers, to be a leader in the Jewish community meant being more observant of Judaism and being better behaved than everyone else. It took me about a decade to untangle myself from the idea that being “more observant” meant the observance of the particular mitzvot (religious rules) that USY expected of its youth leaders. I admit, I still don’t understand rabbis who love social justice more than Shabbat, but I understand that there’s room for that kind of leader as well. But I think I’m still stuck within a paradigm that says (at least in my neuroses) that visible Jewish leaders need to be well-behaved.

This isn’t just a USY thing. I’m sure many Jews who grew up in largely non-Jewish communities learned at some point that they represented “The Jews” to everyone at school, work, or elsewhere. To be a Jewish leader, this gets extended to representing “The Jews” to Jews as well. Many non-Orthodox Jews (and, who knows, probably Orthodox Jews as well) expect their leaders to follow Judaism in ways they never would want to follow for themselves. This is particularly true of clergy — many Conservative congregations don’t have a single congregant who keeps kosher or observes Shabbat, but those congregations would freak out if they saw their rabbi at the McDonald’s drive thru on a Saturday afternoon. But (in my head, and possibly only in my head), I apply this to myself as well.

It’s gotten better since I stopped working with kids. I feel a great responsibility to be a good role model to kids, in part because I benefited from some fantastic role models myself. And I also feel great that I’ve been able to be an unexpected role model to kids in various ways, like the years I had bright green hair under my yarmulke (which I wore daily for the last two years of high school and the first two years of college). It’s very important to me that I’ve been able to model being an openly gay man involved in Jewish community. But…

Well, I’ve always been something of a rebel. The green hair only scratched the surface. Had I not been involved in Jewish community, had I not had this “what would everyone else think” voice in my head, what kind of radical might I have been? I toyed with publishing zines in high school, with performance art in college. I’ve performed in drag and like to shock people into thinking about familiar subjects in new ways.

But how shocking can I be as a public leader in my community? I started Fuck Yeah Stephen Sondheim and connected it to my Facebook and Twitter pages. Does that cross the line of what I should be presenting to professional contacts, to former students? I don’t think the word “fuck” is so shocking any more… but we all like to pretend it is.

Earlier this week, Y-Love posted a link on Facebook to a Moment Magazine blog post called Now THAT’S Offensive! Politically Incorrect Suggestions for Religious Blogs. Naturally, I was inspired to immediately create one of the suggestions, Fuck Yeah Torah Portion. There’s not much there yet. But it’s a great idea, in the model of Punk Torah, to break down some of the barriers that keep people from Torah, which is, after all, pretty fucking awesome.

The reaction to this on my Facebook page ranged from a Conservative rabbi admiring the idea but admitting to not being able to type the word fuck to an Orthodox friend asking me to take it down because it’s נבל פב (nivel peh, or bad language). Of course, Y-Love, who is also Orthodox, called the instant creation of the site an “awesome attack,” so, hooray for diversity.

Now, I don’t believe there’s a problem with using the word Fuck to promote Torah, and I responded to my friend’s objections by quoting the book of Proverbs at him. In Hebrew. From memory. (Go go gadget master’s degree!) See, our people have a tradition of favoring connection to text over language. Proverbs says we must educate each person על פי דרכו, in his own way. Maimonides wrote about the permissibility of reciting שמע (Shema, a credo recited three times daily by observant Jews) in the vernacular. And so on. And I believe that one man’s profanity is another man’s (or generation’s) vernacular. (And let me here acknowledge Punk Torah for already doing this, although not necessarily with the profanity.

But clearly the one negative comment got under my skin, because a couple days later I’m still thinking about this. How much of an obligation to good behavior do I have? If I want to have a shadow career as an edgy performance artist, a foul-mouthed teacher of Torah, a radical leftist political organizer, or a writer of controversial material… when does that start to rub up against the role I play in the community, the role that pays my bills?

If I had it to over again, would I try my hand at being the performance artist / writer / organizer by day and Jewish communitarian at night instead? Maybe. But can I ever imagine being the kind of person who can really and truly push boundaries and run roughshod over taboos without looking over his shoulder to wonder what his mother / teacher / community thinks? I don’t know.