interviewed by
ichur72
Like best: the convenience of living here. The city is large enough to have amenities (like grocery stores that stay open until midnight, and a cultural life), but small enough not to be stifling (e.g. 15-to-20-minute commute). It's large enough to have an interesting mix of people, but small enough to have affordable property values.
Like least: the politics. We are so strongly
a one-party town that it's nearly impossible for new
ideas to get a fair hearing. We have the same old people
making the same old mistakes year after year (the city
is flirting with bankruptcy now), but there really
doesn't seem to be a way to convince people to try
to change it. Suggesting that someone consider
voting for a non-Democrat goes over about as well as
suggesting that he kill and eat his own children
for the nutritional value.
2. What is your impression of Orthodox Judaism "from the outside", as it were?
Orthodox Judaism is not monolithic, just like no other movement is monolithic. Within the context of Orthodoxy I have had wonderful experiences and horrible experiences; I have been welcomed and shunned; I have participated and been only an on-looker; I have had good insightful conversations and been brushed off. It all depends on the specific people. So it's difficult to make any sweeping statements, but I will try to summarize my perceptions anyway.
Orthodox Judaism has a strong sense of community, probably stronger than the other movements. If I showed up in a strange city near Shabbat, I would expect that some Orthodox family would welcome me in, while if I called another congregation looking for hospitality I might get a puzzled reaction. (Might or might not; I know that my own Reform congregation can field this request, for instance.) In fact, the one time I did find myself alone in a foreign city for Shabbat, I sought out Chabad.
This sense of community is tempered by certain assumptions. Members of the community I've interacted with (who I otherwise do not know) assume that I am looking forward to producing a large family -- or, if their age-radar goes off, assume that I am very sad that I'm obviously unable to have kids. The family is central, and the idea that a woman (1) would not want to have kids and (2) would want a career seems strange to the people I've met. The Orthodox women I've interacted with (again, if I have no other shared context) have seemed to live in such a different world that we have trouble finding conversation topics -- and some of them definitely cast me as the mutant. It makes for awkward social dynamics. (Men, in general, have been unwilling to interact beyond "hello, the women's section is over there".)
I understand where at least some of this comes from, of course -- it's a cultural norm, and traditional halachic interpretations encourage this approach to family and community. I'm not dissing it; just observing. And obviously there are Orthodox women with careers, in fandom, in geek circles, and so on. They exist, but it's not the way to bet if I walk into a random shul in Passaic.
Theologically, I see an inconsistency that, ironically, is a charge some Orthodox speakers levy against the other movements -- picking and choosing to get the interpretation you want. Orthodox Judaism teaches that halacha, written and oral, came from God at Sinai, and that the codification we have now is true and mostly immutable. I would completely respect that if the principle were applied consistently; as it is, I have trouble understanding how rabbinic interpretations enacted long after Sinai -- such as adjustments for living in the Diaspora -- are ok, but the interpretations made by the Conservative movement within the halachic process as they understand it are problematic. There is obviously some key difference about how these two halachic movements have approached interpreation over the centuries (more centuries for the one than for the other :-) ). (Err, let's get the footnote out of the way for anyone else who's still reading: the Orthodox movement as an entity only dates to the 19th century, same as the others. They, however, assert that they are the inheritors to the centuries-old tradition before movements arose, so I'm using "orthodox" as shorthand for that even before there was "orthodoxy".)
I have run into some interpretations of halacha where the "obvious" intent seems clear to me, and yet someone finds a rules hack to get around that. There is the whole "Shabbos goy" situation in all its myriad forms, for example. Or making arrangements for a business transaction on Shabbat, but not actually handling the money or signing the contract, and therefore declaring it to be ok. It's not that the people doing these things are (necessarily) "bad Jews"; they see a rules hack as superseding the apparent intent. They see only trees; I see both trees and forest. Again, I stress that I am not criticizing it; rather, I am failing to understand it, and find myself put off by it with my current level of understanding.
The Orthodox Jews I have met take their obligations seriously overall, and I respect that. (Some, sadly, take ritual obligations much more seriously than ethical obligations, and public ones more seriously than private ones, but every group has its negative examples.) I have perceived a sense of certainty among some that I would call excessive; when any person or any group claims to have the truth, as opposed to a truth, I worry -- whether it's Shas in Israel or the Christian fundamentalists here in the US. (Yes, I've drifted slightly into politics, but this certainty of what is and is not correct shows up in interpersonal interactions too -- just check any Jewish mailing list or newsgroup.) I have heard many more Orthodox than non-Orthodox Jews say "this is the way you must do things", and I don't think that's really what Orthodox Judaism teaches.
Err, I suspect I've wandered pretty far from the
intended question, but I'm not sure what to focus
on. I'd welcome followup discussion, and I hope
I haven't offended.
3. How did you choose the synagogue you go to?
A (different) rabbi had suggested I visit them, and when I stumbled on their web site on a day with an afternoon service (with convenient timing with respect to when I left work), I decided to pop in and check them out. I was warmly welcomed there (best reception I've received anywhere), and I liked what the rabbi had to say in his mini-sermon that day, so I went back for Shabbat, and then kept going back, and realized that the more I heard this rabbi the more I liked him. He was (and is) smart and insightful, personally traditional and open to other ideas, educated but not off-putting. Eventually we had some private conversations about theology and the Reform approach, and I lost the "flinch" reaction I was having to affiliating Reform.
So I guess I chose it because I liked the
people and the rabbi, and I now stay because that's
still true, and the theology fits, and it's a place
where I can feel free to participate, and I really,
really respect the rabbi. He's a mentor and a role
model.
4. How did you get into RPG and what's your favorite game?
I started playing D&D (the "blue set") with friends in high school because it sounded like fun. This was pure hack-and-slash dungeon-trashing; we didn't understand about role-playing. I continued playing in college, and eventually met up with people who were focused on story and character more than on combats. It took some getting used to, but it was much more fun that way, so I kept playing. I ran one AD&D campaign myself for several years (complete with plethora of house rules, like all D&am;D games...), but I wasn't good enough at story so the episodes didn't fit together. (And, frankly, I was making some of it up in real time, when players speculated out loud about things that sounded more cool than what I'd actually planned.) We had some neat characters, though. :-)
I've played in other milleuis -- Champions (superheroes),
malevolent future (Paranoia), horror (My Life with Master)
-- and other fantasy-based game systems (RuneQuest! chief
among them), and I find that I connect best with
sword-and-sorcery settings. (I'm not fussy about rules;
D&D, RuneQuest!, and (from what I understand of it)
GURPS are all fine.) I can imagine fantasy worlds
more easily than I can imagine a future world or
one set in a particular culture I don't know well (e.g.
Land of the Rising Sun). I've never played in a game
based on a specific fictional world, but I suspect I
would find it too constraining. Authors can't think of
and spell out everything; with something generic
like medievaloid fantasy with magic, there's a large
quantity of source material. (And one specific aversion:
I am so not into superheroes, for reasons I
can't really explain.)
5. If you could have any job in the world, what would it be?
Ethical billionaire. :-)
Ok, assuming we're talking about some approximately-full-time job that is financially necessary and for which I have or somehow could develop the relevant skills...
Several options have crossed my mind. I'll go ahead and toss out two from the considered-and-rejected list first:
Musical composer, for anything ranging from choral works to film scores: I've got some relevant skills here (not nearly enough, of course), and I get a charge out of seeing my work (any work) actually in use, but I don't know if I can be creative on demand and unless you're John Williams or the like the pay probably sucks. (Quirk: symphonies don't speak to me, though electronic music involving some of the same instruments does.)
Rabbi: ok, this has a lot of appeal, but you really, really don't own your time, and you're somewhat constrained geographically. (For example, if I were a Reform rabbi, there are exactly five places in Pittsburgh where I could theoretically be employed in that capacity, and for three or four of them I would still have to move house.) More significantly, though, it would cost me some amount of the relationship I have with my rabbi, and that matters. This is a field I might have gone into (had things developed differently), but is not one I am likely to go into now. On the other hand, I'm very happy to be able to be a lay assistant.
(Aside: not cantor. While I'm good at it and enjoy it, if I'm going to pursue a religious profession it's going to be as a rabbi, not a mere performer.)
So perhaps this shows some lack of creativity, but I'm going to say that I'd want to be a master and guru within my current field, technical writing for programmers. I know a lot about writing this kind of documentation, though ironically I never get very far when I contemplate imparting that knowledge in written form. Being able to work for companies like my current one, doing the kinds of things I do now, and being regarded as enough of an expert that it would make sense for me to actually write that book (or series of columns, or whatever), has a lot of appeal. And this type of job has a lot of benefits I find appealing, including lack of travel, interesting subject matter, daily interaction with other geeks, creativity (yes, really), and the ability to shape the software itself. A past manager once described me as (to use her words) "God's gift to technical writing"; I believe her callibration was off, but that would be a wonderful level of skill to aspire to. (You never actually get there, of course.)
Everyone knows how this meme works by now, right? If you want to be interviewed, leave a comment and I'll ask you five questions. You'll post the answers in your journal along with the same offer for other people.

no subject
With respect to "picking and choosing" -- well, for Orthodox Jews, Conservative opinions about halacha should be viewed and applied are problematic primarily because of the nature of the Conservative movement. It is my understanding that the C movement's "official" position is that the primary source of the Torah is G-d, but that the text of the Torah (particularly the Oral Torah) was filtered through people -- some degree of divine inspiration but human influences. In practice (and in my experience), many C rabbis use Wellhausen-style "higher criticism" -- which presumes from the beginning that the text of the Torah comes from human sources -- as a method for approaching the text. For an Orthodox Jew, this is problematic. Neither stance is consonant with the Orthodox belief that the Torah, both the Written and the Oral, come directly from Hashem. So decisions made about halacha by those who do not believe that halacha comes from a Divine source are suspect. I don't see this as picking and choosing. We view it as the rules of the game -- and if you're playing by a different set of rules, even if the differences are subtle and slight, you can't really call it the same game.
I also have a lot of difficulty with the idea that Orthodox Judaism didn't exist prior to the 19th century. The name didn't exist, but (IMHO) the idea did -- it's just that the divisions within the Jewish community as a whole were different. Either you were observant or trying to be so (according to the traditional view of interpretation) or you weren't. I see from what you wrote that you disagree with this. But this is how I see it.
>> Or making arrangements for a business transaction on Shabbat, but not actually handling the money or signing the contract, and therefore declaring it to be ok.
Individual people may do this, but I don't know of any rabbi who would give it a pass. The way I learned, it's certainly not OK. In any case, you may have heard of the concept of naval b'rishus hatorah -- it refers to someone who behaves badly yet believes he is OK b/c technically he has never violated the law.
On to another topic. There are O women out there who want (and have) careers. I've known plenty of them -- accountants, doctors, lawyers, businesswomen, computer techies, etc etc etc. (In some ways, you can say I'm one myself -- I may work from home and spend a lot of time keeping house, but I am an oil industry analyst -- been one for years, plan to keep doing it for however long I can keep making money off of it.) There are also women out there who, when they get together, talk about nothing but school/kids/carpool/etc. But I don't think it's a Manichaean split. Some of the limited-conversation types I've met are career women. Some have been stay-at-home moms. Some have held jobs viewed as more traditional for Orthodox women -- teacher, child-care provider, etc. I personally think this has more to do with personality than with career position or lack thereof. Some people just prefer to talk about a limited range of things. I wish it were otherwise -- even though I can chime in with stories from my baby-sitting years if I'm in that kind of environment, I prefer to talk about all kinds of things -- kids and Torah and politics and travel and emotions, whatever comes up. And I'm not the only person like this. Many of my friends feel the same way.
>> And obviously there are Orthodox women with careers, in fandom, in geek circles, and so on. They exist, but it's not the way to bet if I walk into a random shul in Passaic.
I hear you; I'm just trying to describe my experience and feelings.
Feedback welcomed!
part 1 of 2 (bumped into the limit on comment length)
No objection at all. :-)
I think I wasn't clear enough about "picking and choosing", for which I apologize. What I meant is that, from the outside, it appears that both Conservative and Orthodox adapt halacha to fit their needs, but the Conservatives say this is what they're doing and the Orthodox say it was all designed in from the beginning (within the rules of the halachic system). From the outside, though, they look the same. And that's without even touching the different groups that all fall under the umbrella of Orthodox Judaism but see halacha differently.
So maybe we should leave Conservative Judaism out of it, to avoid problems some Orthodox have with some of their process. How did Modern Orthodox come about? They have many interpretations of halacha that differ from those of, say, the Chareidi, yet both groups say they are following correct process. I get the impression (please correct me if I'm wrong) that there is movement of people between these movements, so it's not just a matter of what you were born into. People can choose. Not willy-nilly or on an issue-by-issue basis, of course.
And even if we set aside intra-movement disagreements, haven't the rabbis been adapting halacha for at least a couple thousand years? Rabbis through the ages have added a number of fences (second day of Yom Tov, extra week of niddah, various stringencies around kashrut); the rabbis also, of necessity, changed how we worship and relate to God when the second temple was destroyed. It appears, from the outside, that innovation continued until around the time of the Shulchan Aruch. For some reason, though, we do not continue that innovation now, even in areas where it would do a great deal of good such as solving the agunah problem.
Um, I think I got off track again. Sorry.
It is my understanding that the C movement's "official" position is that the primary source of the Torah is G-d, but that the text of the Torah (particularly the Oral Torah) was filtered through people -- some degree of divine inspiration but human influences.
While I am not a Conservative Jew, that's my understanding too. I believe they are firm on Written Torah being divine, but Oral Torah passed through fallable humans.
I also have a lot of difficulty with the idea that Orthodox Judaism didn't exist prior to the 19th century. The name didn't exist, but (IMHO) the idea did -- it's just that the divisions within the Jewish community as a whole were different. Either you were observant or trying to be so (according to the traditional view of interpretation) or you weren't. I see from what you wrote that you disagree with this. But this is how I see it.
I meant that the movement as a movement didn't exist -- no need. But there were divisions within the community long before the reformers came along. Some divisions were geographic -- Ashkenazim and Sefardim saw (and see) halacha differently, for example, and I presume there were other geographical differences as well. Within a single community, there were major differences between the early chassidim and the mitnagdim, yet both claimed to be true inheritors of torah. Heck, these differences go back much farther -- the Phrisees and the Saducees were arguing about halacha even when the temple stood. I don't think there was a "one true orthodoxy" any time after the destruction of the second temple.
Re: part 1 of 2 (bumped into the limit on comment length)
From the inside, they look quite different. But I see your point.
>> I believe they [C] are firm on Written Torah being divine, but Oral Torah passed through fallable humans.
I don't quite see the point of taking this stance in light of the fact that in practical terms, the movement doesn't treat the Written Torah as divine. I believe that a number of professors at JTS teach the higher-criticism model, and I know that the C rabbi I talked to years ago was insistent about using this approach. The anecdotal evidence seems to indicate that he's hardly alone in this.
>> I get the impression (please correct me if I'm wrong) that there is movement of people between these movements, so it's not just a matter of what you were born into.
Yes, there is some movement. This is probably a good time to mention my dislike of labels within the Orthodox community. I don't think they're terribly descriptive or helpful, largely because I don't think they take into account individual eccentricities or preferences. I can give you an example from my own life. I've run into people who, when they hear I have a master's degree and work in a specialized professional field, assume I am in the Modern Orthodox camp (whatever that is). I'm not, at least as far as I see it; I'm more comfortable davening in shuls that are commonly described as right-wing and black-hat. I've also run into people who, when they hear where I like to go to shul, assume I have no secular interests and wouldn't want to discuss something like current affairs. Well, that's not true either. So what am I? Well, do I really have to define myself like that?
>> haven't the rabbis been adapting halacha for at least a couple thousand years?
I would define it less as adaptation than a process of finding new facets to the law. In any case, the fundamental understanding of what halacha is -- both oral and written coming directly from Sinai -- hasn't changed. As I mentioned before, the reason C views on halacha are viewed by O as problematic stems from the C conception of what halacha is and where it came from.
>> the rabbis also, of necessity, changed how we worship and relate to God when the second temple was destroyed
This isn't how I understand it. The three daily prayer services are meant as substitutes for the three daily services in the Temple, and the way I learned it, the basic form of the siddur was drawn up during the Babylonian exile after the destruction of the first Temple. I don't see this as changing the way we worship and relate to G-d as much as providing a new outward form for what is essentially the same process. Yes, there are differences -- obviously, reciting the mishnayos detailing the composition of the incense is not exactly the same as actually burning the incense on the altar. But they are meant to correspond to each other -- since you can't do this, then do this.
>> we do not continue that innovation now, even in areas where it would do a great deal of good such as solving the agunah problem
Well, actually, there are innovations -- I would cite Rav Moshe Feinstein's ruling on the status of the Ethiopian Jews as one, or his ruling on the kashrus of milk in this country. And with respect to the agunah issue, it may interest you to know that it has become SOP for a beis din to require only one witness in cases where the court is trying to confirm the husband's death. This doesn't solve the problem of a woman whose husband is just being a jerk, but it's a pretty big deal, IMHO, given the otherwise near-universal requirement for 2 kosher witnesses.
Re: part 1 of 2 (bumped into the limit on comment length)
I'm not in a position to judge. I hang out with (some) Conservative Jews (the handy C rabbi is actually away on sabbatical), but I don't know all the details of what's officially canon, commonly-held belief, uncommonly-held belief, or apostacy.
Yes, there is some movement. This is probably a good time to mention my dislike of labels within the Orthodox community.
Ok, thanks for the explanation. I've mostly heard within-O labels from Orthodox Jews (seeking to differentiate themselves from the others), not from non-Orthodox, so I didn't realize this was potentially problematic. And let me re-emphasize that my sample set is relatively small.
Incorrect generalization based on affiliation isn't limited to the Orthodox movement, of course. I get a fair bit of "you do $mitzvah? Why? You're reform!", and not always from Reform Jews. People in general need to learn to deal with individuals and not stereotypes.
This isn't how I understand it. The three daily prayer services are meant as substitutes for the three daily services in the Temple, and the way I learned it, the basic form of the siddur was drawn up during the Babylonian exile after the destruction of the first Temple.
I agree so far. But: the obligation for Temple service is different from the obligation for daily prayer. Levites and kohanim performed the Temple service; all men (or if you're egalitarian, all adults) are obligated to daven. A Jew in Temple times was required to show up three times a year; we're required to daven three times a day. So the obligations aren't parallel, though the one certainly finds its roots in the other. I suspect, but do not know, that the rabbis worried that because davening is a mere shadow of the "real" service, we had to do it more in order to maintain the connection.
Was there even a systematic approach to tachanun in Temple times? Yes, the Tanakh certainly records cases of people making individual pleas to God, but those cases weren't part of more formal service. Was tachanun required, or just permitted?
Well, actually, there are innovations -- I would cite Rav Moshe Feinstein's ruling on the status of the Ethiopian Jews as one, or his ruling on the kashrus of milk in this country. And with respect to the agunah issue, it may interest you to know that it has become SOP for a beis din to require only one witness in cases where the court is trying to confirm the husband's death.
Thank you. I don't know the ruling about the Ethiopian Jews or about the one-witness handling for death. Was cholov yisrael (pre-R.Feinstein and in the US) halacha rather than chumra, then?
Re: part 1 of 2 (bumped into the limit on comment length)
>> Was cholov yisrael (pre-R.Feinstein and in the US) halacha rather than chumra, then?
Yes. It is still halacha, but Rav Moshe's ruling created a kulah (leniency) by making it possible to say that US gov't standards were strict enough that cholov stam was equivalent to cholov yisrael. As I understand it, his psak was worded in such a way as to indicate that cholov stam should only be used in situations where cholov yisrael was not available or prohibitively expensive, and even then it should be given to children and not drunk by adults. Obviously, his ruling has been expanded on since then -- otherwise we couldn't eat Oreo cookies. :)
part 2
Are pledge cards on the seats at high holy days, and selling aliyot on Shabbat, apocriphal stories?
In any case, you may have heard of the concept of naval b'rishus hatorah -- it refers to someone who behaves badly yet believes he is OK b/c technically he has never violated the law.
I didn't know the name, but I've encountered the behavior. To me, arguments that rely on very fine hair-splitting, and that seem to permit a questionable activity, are suspect. Setting aside business (maybe they make an argument that it's different if it's not private mundane business?), consider some of the creative ways to get around carrying when you're not in an eiruv. Is it really both wrong to carry a house key in a pocket and permitted to tie it on a string, hang it around my neck, and call it a necklace and thus an adornment or clothing? I think I have more respect for the person who says "look, I'm carrying my house key, and I'm not ashamed of that" than for the one who says "it's not really a key, nudge nudge, it's just a necklace that happens to open my house, wink wink". And, I guess, I'm kind of sad that some of that creative energy isn't going toward solving some of the bigger halachic problems of our time.
Aside: a respected O rabbi once asked me to turn on a coffee pot on Yom Tov. I never did understand that one. (I was a gentile at the time. I guess to him I still am.) I may joke around about caffeine, but I don't believe deep down that one can launch an argument for this based on pikuach nefesh. :-)
On to another topic. There are O women out there who want (and have) careers. I've known plenty of them
Thanks. I know a few (mostly on LJ or in fandom or the SCA), but don't know how common they are. It could be, after all, that there are lots of them who never come to Shabbat services, which is the primary place I've interacted with O women en masse.
I hear you; I'm just trying to describe my experience and feelings.
Thank you! I appreciate it.
Re: part 2
Not at all. I didn't realize this is what you meant. I'll have to ask why this is considered OK. My guess is that it doesn't take the precise form of a sale; it's rather a bidding process with no binding promises to pay made. But I'll have to ask, because I don't know.
>> I guess, I'm kind of sad that some of that creative energy isn't going toward solving some of the bigger halachic problems of our time.
I'm curious: What would you say are the bigger halachic problems?
>> I know a few (mostly on LJ or in fandom or the SCA), but don't know how common they [career women] are.
It depends on the community. If you're talking about a very black-hat (Litvish or Chassidish) community where most or all of the members have been observant all their lives, the number is likely to be smaller. In Modern Orthodox communities, or places where there are many baalei tshuvah, the number is likely to be somewhat larger.
In any case, I should mention now that I have certain reservations about the term "career woman" -- it seems to be a somewhat narrowly defined idea. Reminds me of something I once read about how it's more common for boys to refer to their summer lawn-mowing stints as a "business" than for girls to call steady baby-sitting gigs a "business". I personally don't see why a woman who teaches for 20 years straight in an Orthodox day school in order to plump up the family's finances doesn't have a career whereas someone with an MBA who works as a stockbroker does. It strikes me as a white-collar vs. blue-collar thing, with only white-collar jobs meriting the label of "career". OK, rant over with. :)
business and careers
I've heard individuals conduct business on Shabbat, but I assume rabbis don't condone that. Rabbis would have to condone the pledge cards etc, though, so that's why I asked about that one. Thanks for the clarification below.
In any case, I should mention now that I have certain reservations about the term "career woman" -- it seems to be a somewhat narrowly defined idea. [...] I personally don't see why a woman who teaches for 20 years straight in an Orthodox day school in order to plump up the family's finances doesn't have a career whereas someone with an MBA who works as a stockbroker does.
Err, I think they both have careers. My impression -- possibly flawed, but this is what I've seen through my small window -- is that most Orthodox women do not have careers at all, and most of those who do have ones that are commonly considered to be "women's work", like teaching children. I think a teacher has just as much of a career as the MBA does, but that the teacher is the more common occurence -- and that the stay-at-home mom is more common still.
bigger halachic problems
These are big ones that come to mind at the moment; I haven't thought enough about this to be confident in any "-er" or "-est" labels.
Agunah (where the husband is being a jerk). I wonder if there aren't creative ways to annul the wedding in some cases, for example.
Limitations on women: since it is important to a significant number of people (see, for example, Women of the Wall), it would be good to spend some effort on figuring out what the minimum restrictions on women's participation in the community really are. I suspect that a lot of politics and stubbornness have set in over the years; can we find some way to break through that and work together with both sensitivity for people and respect for halacha?
Who is a Jew: this is divisive, and it gets worse with every generation. While Beit Hillel and Beit Shammai disagreed with each other quite strongly on matters of halacha, they still saw themselves as part of one community and they still intermarried. Even if reconciling with the Reform movement is a lost cause (I'm not saying one way or the other), isn't it worth trying to find common ground with the Conservative movement to prevent big-time schism?
Who is a Jew II: can we do anything about the regretable (IMO) disruptions caused by patrilineal descent, perhaps building on the idea that you can convert a child without his consent? Orthodox Jews don't care about internal Reform matters, but when one of those patrilineal children wants to marry a more observant Jew you have all sorts of problems. Is there anything that can be done to mitgate these resulting problems, given that the Reform movement is not going to go away? That is, the Reform movement isn't going to agree that these children aren't Jews; what if anything could the Orthodox community do to "make" them Jewish by O standards to prevent problems later? (Yes, I realize that there are all sorts of possibilities for offense here, and that's going to be part of the problem to be solved. I don't have answers here, only questions.)
Easing fences: if I understand it correctly, Orthodox Judaism in general would like to see all Jews become more observant. I suspect there are non-trivial numbers of Jews who would like to do just that but are overwhelmed by limitations they have not lived with all their lives. For example, most American workers don't have enough vacation days to fully observe the yomim tovim with yom tov sheni, but in the 21st century, when we know precisely when the new moon occurs, isn't yom tov sheni unnecessary? I'm just using this as an example, and perhaps my premise is flawed, but I have a suspicion that more people would try to do things in accordance with (O) halacha if they thought there weren't bunches of additional hurdles that don't seem to be from Sinai. So, broadly, are there things that can be done to reach out to the non-observant? (Note: this last is my understanding of a problem facing Orthodoxy in particular; the previous items are problems facing everyone.)
Re: bigger halachic problems
I think one way of addressing the agunah issue is to address the issue of divorce. Yes, there are times when divorce is unavoidable and necessary, but it seems to me that the best way to head off the problem is to reduce the likelihood of divorce -- not by repealing the civil laws that provide for no-fault divorce, say, but by trying to get people to do more pre-marital counseling and consulting with friends, family, rabbis, etc so that the possibility of marrying someone who has a mean streak is reduced. The problem with this, obviously, is that it doesn't do much for the people who are in trouble now. And for that -- well, I like the approach The Jewish Press takes. Every week, it prints the names of men who have been put in cherem for refusing to grant their wives divorce decrees. It tries to get the word out so that these men will be subject to social sanctions -- not allowed to get aliyos at shul, not allowed to say kaddish on yahrzeits, not allowed to get community honors, etc.
As for outreach -- well, there is a lot of this. Chabad does a lot of it, and they have their own formula for it that (IMHO) has worked well. Their general attitude is that every mitzvah a Jew does is good, no matter what else they're neglecting or ignoring. I have also seen a good bit of this in the Litvish community. The kollel in Dallas does a tremendous amount of outreach in the wider Jewish community -- classes, speeches, events, all sorts of stuff. The rabbis are very warm and friendly, and they do their best to meet people where they are -- encouraging them to be more observant without criticizing them for what they don't do. The shul I went to in Dallas also did a lot of this. There are other kollelim and shuls around the country that take this approach as well. Efforts are being made.
Re: bigger halachic problems
I agree that a good way to reduce divorce is for couples to spend more pre-marital time talking through issues. It won't always happen, and you'd really have to rewrite halacha to force it, but we could do better in this area. (Changing civil law on this, as you say, would be a bad idea.)
How well do the social sanctions work? Obviously they don't work well on non-religious schmucks (who never attend shul anyway), and business boycotts can be hard to organize and harder to keep going.
Re: part 2
So I asked why this is OK, and here's the answer I got. When you say you will pay money for an aliyah, for a Yom Tov pledge campaign, for a hakafah on Simchas Torah, this isn't a business deal. Rather, it's tzedakah, which is a mitzvah, and you are allowed to plan ahead to do mitzvos on Shabbos & holidays. It would be quite different if you agreed to sell a few shares of stock while talking to a friend on Shabbos -- that's an obvious no-no.
Re: part 2