Because It's A Duty

One of the things I don't like about kiruv is how it tries to emphasize the "fun" and "rewarding" parts of Judaism as reasons to become religious.  Look at the programs Aish and Ohr put on, the assurances they make about the benefits of a religious lifestyle.  Look at the parties Chabad loves to put on with alcohol flowing like water and endless singing and eating.  The assurance is all there: become a religious Jew and life gets better.  You connect with your heritage!  You get more spiritual!  And that's why you want to become religious!
Except that it's not true.  Life doesn't get better.  You don't necessarily connect with your heritage and spiritualism is hit and miss depending on what kind of a person you are.
Now the opposite isn't true either.  Life doesn't get worse, for example, when you're religious.  Maybe once upon a time it did but considering how well Jews have become integrated into modern society and the abundance of kosher food and other necessities for religious life it's really not that much of a burden to be frum nowadays, at least until the tuition bill for your child's cheder arrives.
So then why do it?  Why do I do it?
Because it's a duty and a sense of duty is what makes a person's life more meaningful.
I don't like modern kiruv tactics because they play into exactly what's wrong with Western civilization and why it's on the decline.  When it comes to rights and responsibilities the West has indulged itself in the former since the Enlightenment and tried to rub away any traces of the latter at the same time.  The United States has a Bill of Rights but no Bill of Responsibilities.  Canada has a Charter of Rights and Freedoms but no corresponding document detailing Responsibilities and Obligations.
Why does this matter?  I would suggest that the emphasis on rights over responsibilities is one factor is why so much of Orthodoxy seems to be going in either no direction or the wrong one.
On the surface of it, that sounds absurd.  After all, isn't an Orthodox lifestyle one duty after another from dawn to night?  Don't we spend the entire day doing one routine or ritual after another?  From Modeh Ani to krias Shema at night, it's one thing after another.  How could I suggest we don't take duty seriously?
I think the answer is because we don't really see it as a duty.  We give lip service to the idea, of course, with every Baruch Hashem! we shout but how much of what we do is because we like the idea of what we're doing?  We show up in shul because we like the social aspect.  We wear big, fancy talleisim and $1500 sets of tefillin because we like how it looks.  We grab every last chumra we can find not because we're so worried about what God will think.  We're worried about the neighbours.  Will they think us deficient?  Do we want to outfrum the Jonesbergs? 
In a strange way, our affluence has negatively affected our Judaism.  It's one thing to live a happy, kosher life in a community where there's plenty of restaurants and well-stocked supermarkets, surrounded by people who don't particularly care about one's religious affiliation and in a society where one's religious rights are protected by law.  We start to take things for granted.  We start to assume we're entitled to certain things that previous generations saw as luxuries or unattainable.  And it spoils us.
There is a different reason to keep the mitzvos but it doesn't sound sexy like the Aish approach.  It's word which is dirty in our society: duty.  It's not fun and games that makes me walk to shul in the pouring rain on a cold November morning.  It's not the calorie content that makes me walk past the Pizza Pizza display in the mall without stopping.  And it's not a fear of gallstones that keeps me from having some ice cream a couple of hours after a steak dinner.
It sounds joyless and really, duty is joyless because it's not about personal satisfaction.  It's about maturity.  It's about saying that one's personal needs and desires need to be put aside because of more important responsibilities.  It's about saying "I want it but I can't have it right now and I accept that", not something society around us gives much value to.
Look around at our frum society and you'll see too much of it.  On the right, we have every increasing stringencies in all areas of life made possible only by our affluence.  Honestly, would the kollel culture be 1% of what it is without the generosity of the Israeli treasury or the welfare system here in North America?  How many people would insist on only cholov Yisroel and super-triple-mehadrin meat if it cost ten times the price it currently does?  And how many people would say you need a fluorescent light bug checker from Artscroll as a minimum for checking your vegetables if such a device was prohibitively expensive?  We have taken the really good times life has afforded us and used them to make a Torah lifestyle more and more difficult.  And why?  So we can pat ourselves on the back and say "Look how frum we are".
This is wrong.  This is not being frum.
Frum is wondering if one has given enough to charity each month.  It's showing up early at shul on the night of the blizzard because you want to be sure they got a minyan not because you need it but because the old guy who sits down the bench from you is saying kaddish and you know he'll make the effort.  Frum is looking around shul for someone who looks lonely and inviting him for Shabbos dinner.  It's taking the $30 000 you were going to spend on your kid's simcha and spending 2/3 of it on something your community needs so that the kid learns that giving to others is the best present to ask for.  Frum is being polite and modest and modest isn't about sleeve length.  It's about knowing one's true significance in the grand scheme of things and not trying to act like one is higher up than that.
None of that is sexy or spectacular and much of them it's not that personally satisfying.  But it is what Judaism demands of us.  The Prophets didn't rebuke our ancestors over their lack of black hats or not-quite-elbow length sleeves.  They reminded us of our responsibility to our fellows.  Being machmir in anticipating and meeting the needs of others without a concern of "what's in it for me" is the only really chumra we should be worrying about.
We need to step back and see the forest beyond the leaves and twigs we're all so conscientiously focused on.  We need to see the grander purpose and do a real chesbon hanefesh on how close to that purpose our daily activities bring us?  Are we living a live of faux-kedushah by rote or a real life of holiness through determined actions?
When we begin to do this, all the other stuff we learn and do will come to have meaning.  Until then, we are no different than the nations around us no matter how much we pretend to be.