Questions, Questions, Questions

The rav of my childhood, Rabbi Joseph Deitcher, z"l, taught that, in Judaism, it was always permissible to question, as long as questioning didn't stop you from doing. I've had reason to reference this concept many times over the years, usually in the context of the weekly vort I give at my shul during seudah shlishit. I live in a community with a very large, very newly BT population, many of whom are still trying to figure out this whole frumkeit thing. Many of whom are "shabbos frum" and not yet at a point where they are careful about (or aware of) other mitzvot that impact the other six days of the week.

Why do I bring this up? Because, for the past month or so, I've found myself really questioning why I do what I do. Why I live my life this way. Don't worry, I'm not falling off the derech. Just taking a close look at who I am right now. For example, do I only wear skirts because I truly believe that wearing pants is beged ish, and not tznius? Or do I only wear skirts because I'm used to it and would feel awkward going outside in pants? Or do I only wear skirts because it's what people expect of me? The act remains consistent- I only wear skirts. But the motivation is so very different. I'm trying to figure out what motivates me right now, in this current phase of my life. If I'm doing what, according to some, is the right act but for the wrong reasons, is that enough?

Wearing skirts is an easy example. This questioning, however, is bleeding over into every single aspect of my life. Well, with the exception on my kitchen. Never once have I questioned why I keep a kosher kitchen.

I suppose this is all part of one larger question: How frum do I want to be? I was at a meal this past shabbos with a couple of very nice, very BT families that are on the fast-track to fanaticism (IMHO). When a women who was once working towards her PhD starts talking about not sending her daughters to college, I get the willies. Experiences like that draw a nice, bright line in the sand for me, and I have no intention of crossing it.

In essence, I guess I'm having a Modern Orthodox moment. How modern can I be without leaving the world of Orthodoxy, and how frum can I be while still staying modern?