A Winding Road to Mitsvot

A Winding Road to Mitsvot

(This article consists of two sections with different purposes. The first is an account of how I came to take on the observance of mitsvot, and what was going on in my family while that was happening. Though it is my personal story, it touches on issues that will resonate with others in various stages of engagement with halakhah. In the following section, I address a broader set of concerns that could be useful for potential ba’alei teshuvah, converts, and those who may be connected to them.

I make no attempt here to speak for my brother, who was a friend and companion throughout. He is a very private person, which means that his story must be as absent from these pages as I can possibly manage without obscuring my own tale.)


I come from a family of Portuguese Jews of the Amsterdam rite who immigrated to upstate New York in the 1850s. They settled in the community of Poughkeepsie as merchants and tradesmen, and as the family grew into the fabric of American life their rigor in observing mitsvot diminished. Whether this change happened abruptly or gradually is beyond living memory, but we know that within two generations of our arrival in America, the expression of our Judaism did not extend much beyond simply having a Jewish identity.

When my father was a boy, his mother pushed the family to join a synagogue, and they eventually found a Reform Temple that his skeptical father could suffer through. While this gave him a basic Jewish education, he was unengaged in Jewish life as a young man, and our Sephardic surname gave him an easy pathway to blend in with a gentile crowd. He fell in love with an Episcopalian, and her eventual conversion to Judaism had more to do with her own spiritual journey than it did with her marriageability in his eyes. Feeling that proximity to Jewish resources should not constrain their living arrangements, the young couple moved to a small Midwestern college town where the work was good, and had two kids. Thus it happened that I was born in a Catholic hospital in downstate Illinois, taking the unlikely name of “Raif” from an Episcopalian priest, Reverend Ralph P. Brooks, Jr.

I credit the first glimmer of my parents’ interest in Jewish life to the fact that as a Jew-by-choice, my mother had a reason to think about her Jewishness in an adult way that my father rarely had before they met. Through helping to introduce her to the Jewish world, he was given a pathway back to it himself, slowly breaking down a sturdy reluctance. As they tell it, a pivotal moment occurred one Festival evening when they sat down to a meal of pork roast. Although they had eaten this dish before on holidays, this time they looked at each other and said, “this isn’t right, is it?” The seed was planted, and when my brother’s birth left them in need of a mohel and a Cohen, they were finally ready to make their first meaningful contact with the community in whose midst they had lived unobtrusively for five years.

By the time I was born, their journey had progressed enough that our household was not unlike many other American Jewish families on the liberal side of the spectrum. We were members of the local Temple, and we attended services at the Traditional minyan there as often as its intermittent schedule permitted. On Friday nights we made a point to recognize that it was Shabbat by lighting candles and having a special meal, and as the holidays came and went we marked their passing in at least some intentional way. My earliest years were colored by a definite knowledge that I was a Jew, and while I had a sense that this meant something significant, I could not have articulated what exactly that was.

Our Jewishness easily could have continued along those lines indefinitely, but the summer of 1986 marked a turning point that would change our family forever. My father had spent the spring semester in Uppsala for work, and my mother, brother, and I joined him that May for the last 10 weeks of his stay. We children were very young, and the process of acculturation marched along at the brisk pace with which that age is blessed. Although we had been away less than three months, I vividly recall a day when I could not determine whether ja and nej (“yes” and “no”) were English words or Swedish. This was not lost on my parents, and on the plane trip back to the United States, they grappled with the uncomfortable realization that our family knew more about being Swedish than we did about being Jewish! Eventually they agreed that if they expected us to take Judaism seriously, they had to give it a cardinal place in our lives.

Despite the clairvoyance of this vision, knowing how to bring it about was another matter altogether. My parents knew they wanted more, but what did “more” mean? What might they change, and how far or fast were they willing to take it? Whom could they turn to for advice in an unfamiliar world whose inhabitants might not share their values? How would they explain everything their children, who were nearly 4 and 8 years old and would be taken well outside their comfort zones? What would this be like with so few Jewish peers, and virtually none who were going through a similar experience? And that is to say nothing of the unforeseen questions, which arose frequently and could have demoralizing effects. All they could do was to try their best with the information they had – to jump in and deal with the awkward moments as they came up.

One of the first exploratory steps that they took was to increase their participation in the Traditional minyan at the local Reform Temple. In style, it was a “Conservadox” liturgy carried out under egalitarian principles, and the participants were united by a desire to actively shape their Jewish lives instead of relying on others to do it for them. We met many families and young people who would become lifelong friends and mentors, and the synagogue offered a handful of resources like an underdeveloped (but much appreciated) religious school, adult education groups, and lay leadership opportunities. Yet the Traditional minyan did not meet every week, and once we felt secure there we ventured into a small Orthodox minyan that operated out of the campus Hillel Foundation. At first this strange new expression of Jewish life was alienating, but it came with three friendly young families who reached out to us and made us feel less vulnerable. That such people existed and were so welcoming made us feel that we could have a place there, and they were a big part of why we kept coming back. Since the rest of the minyan consisted of college students, there was also a ready source of tutors to make up for lost time in my Jewish education.

All of this external exploration gradually worked its way into our home life, and that was a far more challenging, uneven process than what happened at synagogue. At some point, anyone who engages in Jewish observance must recognize that its origins lie in rabbinically articulated halakhah, and they will have to form an opinion about how that system relates to their personal practice regardless of whether they buy into it. At first it was easy for my parents to let halakhah remain in the background, but as our home life became increasingly defined by Jewish elements, it grew more difficult to ignore. Eventually they worked out a three-point policy of running the family, and this became one of the most conspicuous elements of my later childhood:

1. Engaging with mitsvot is a value, even if we have not defined that precisely. Our family practice will be influenced by halakhah, but it will not necessarily be dominated by the halakhic system.

2. It is easier to bring mitsvot into the home than it is to keep them up outside. Therefore, the best way of trying out mitsvot is to craft a home life in which there is a safe space for experimentation to occur. Creating this space is worth making compromises in the practical operation of our household, which may make us feel unsafe in other ways.

3. Once we leave the home on any given day, it is up to each family member to decide how far they personally want to take anything we have learned about Judaism and mitsvot. We may observe none of it or all of it; violating Shabbat and kashrut are just as much on the table as putting on tallit and tefillin.

Under these guidelines, we began bringing mitsvot into our lives in a process that developed over nearly ten years. We started off light, eliminating certain obvious items from the menu and finding more children’s books and play activities that were specifically Jewish. My parents read voraciously and redacted what they learned into a gloss that I could appreciate as a child, often focusing on holidays, parashat hashavua and other materials whose content refreshed regularly. As time went by, we took on more serious commitments like learning Hebrew prayers for synagogue and Modern Hebrew for ourselves. For several years before taking on the real thing, we kept a form of “practice kashrut” in which we had only one set of dishes but ate only meat or only dairy at any given meal. This was paralleled by “graduated Shabbat,” in which every few weeks we would take on a new required practice or forswear a forbidden one. The fact that the boundaries were in flux would sometimes put us into comically impractical situations, and we occasionally resorted to a “five-minute freebie” after Shabbat began in order to fix the things we had forgotten to set up in advance.

By the time of my bar mitsvah, our home space was fully shomer Shabbat and shomer kashrut, and I had enough Jewish literacy to read my entire 147-verse Torah portion in an Orthodox service with which I was very much at home. We also remained active in the Traditional minyan, which by then was the only destination to which we would drive on Shabbat. But as these sweeping changes unfolded at home and in synagogue, my personal practice in the outside world was in a completely different place. The three rules of the family contained an important compromise: although I had no choice but to learn enough about mitsvot that I could observe them if I wanted to, there was a fundamental recognition that nobody could force me to keep them against my will.

The duality of lifestyle that this permitted helped to smooth over a lot of the challenges that a consistent practice of mitsvot would have presented in my younger childhood, especially given where we lived. It meant that I could eat in the school lunchroom or a restaurant just like anybody else, and that going over to a friend’s house was as simple as walking through the door. It meant that I could take part in weekend trips with my scout troop or go to the movies with my buddies on a Friday night. Most importantly, it meant that being Jewish didn’t make me “that weird kid” who had a daunting list of special needs and couldn’t do anything fun. But it also meant that I lived in two very different worlds which were largely disconnected from each other, a convenience that diminished personal guilt even as it left behind incipient questions about my identity and integrity.

During this plastic phase my religious development, two experiences in particular made Jewish life seem like something I might one day work into my practice on my own terms. The first was being part of the campus Hillel through the Orthodox minyan. This introduced me to a small chevre of Orthodox children my age, and even though they were in a very different place than me religiously, I had far more in common with them than I did with the kids at the Reform Temple (no judgment here, it was just a fact). It also brought me in contact with a self-replacing crop of Orthodox young adults who were excited by their relationship with mitsvot. Over the years, many would become tutors and older-sibling-like friends, while others surprised me by asking me to teach them things about Judaism that they did not yet know. I was particularly inspired by my bar mitsvah tutor, a brilliant young man who had learned the entire Talmud by his early 20s, and by the Executive Director, a Reform Rabbi who embraced halakhah as an adult during his time at the helm of Hillel. But in addition to these important individuals, Hillel put me in an environment where people with vastly divergent religious beliefs had to share a space together in mutual respect. If someone did something differently from my family – which was the rule and not the exception – I had to confront it and reflect on the validity of my own perspective rather than retreating to a space where I could not be challenged.

The other experience that shaped my personal relationship with mitsvot was attending Camp Ramah in Wisconsin. It was here that I first met people whom I could call my Jewish peers, for the home-vs.-outside model is widespread in the Conservative Movement, and for once in my life people actually understood where I was coming from. Since we were interested in being kids we didn’t really talk about serious issues like that in a formal way, but the daily fact of being around them was enough to start a whole new train of subconscious thought. The camp administration played a parallel role to that of our parents, creating a Jewish “home space” from the top down knowing that the campers were all over the map in terms of how they related to their Jewishness inside. We chafed against the artificiality of this environment and felt limited by its boundaries, yet we tromped enthusiastically back to camp each year, happy to be in an intentionally Jewish place.

Some Setbacks:

Admittedly, it is only in retrospect that I can articulate so many nuances of the family’s religious trajectory and of my quest to carve out a set of personal beliefs within that context. At the time it was happening, none of us fully understood the significance or consequences of the issues at hand, which left us exposed to unforeseen pitfalls. The above narrative might sound like a beautiful reengagement with mitsvot in which each family member was a united, willing participant, but it was also a jarring disruption of our family life in which personal anchoring could not always be achieved. On the many occasions where the outside world intruded into our home, I lamented the absence of a peer group with whom I could unpack my discomfort from a place of understanding. My parents simply could not be neutral sources of guidance since they had instigated the very changes that we all struggled with, and although there is a sense in which we went through this together as a family, there is another sense in which each of us went through it alone. Without a doubt, my family’s engagement with mitsvot was one of the most fulfilling and the most upsetting experiences of my life.

Probably the highest hurdle on this obstacle course arose just a few years into our journey, threatening the entire enterprise. My mother’s conversion from Episcopalianism in the 70s had been Reconstructionist, and it dawned on my parents that many Jews would have counted neither her nor her children among their number. They began to hear of stories in which “questionable” Jews had their identities challenged by busybodies and the well-meaning alike, and they knew that such an experience would be devastating to us after all we had invested in reclaiming our Jewishness. To resolve this, they reached out to a renowned Orthodox conversion authority in a nearby city, but that predictably dragged all of their unanswered questions about halakhah out into the spotlight. It took nearly two years of persistent follow-through to convince the beit din that they were serious, and in the meantime there was no choice but to allow them to intrusively dictate how we were to think about our Jewish lives. Insulting remarks and decisions had to be absorbed without recourse, the most hurtful of which was that the beit din positively refused to put my father’s Hebrew name on my conversion certificate even though he is a born Jew. It was a bitter pill for my parents, and they did not tell me that part of the story until I was 23 years old.

After this was finally resolved, two other themes emerged as recurrent internal challenges for our family. The first was that as we took more of a mitsvah lifestyle at home, participation in the Traditional minyan at the Reform Temple became less of a fit for us. It was six miles from our house, which meant that we had to drive there even though we were phasing out the use of the car on Shabbat. Its membership did not keep strictly kosher, which progressively closed off the possibility of socializing at their houses. And although its liturgical form was remarkably close to Orthodox prayer, the handful of differences became increasingly salient. Complicating matters was the fact that each family member had a different take on what the right solution should be. Some of us believed that we could engage with mitsvot and go to the Traditional minyan with no inherent contradiction. Others felt that although we must do everything in our power to retain the wonderful friendships we had made, the minyan itself could no longer fulfill our religious needs. As these two viewpoints became irreconcilable, some of us crossed permanently over to the Orthodox minyan at Hillel and others continued going to both. While we have since found healthy ways to cope with this realignment, it tore a painful rift in the family at the time.

The other difficult theme was that the journey of a ba’al teshuvah looks very different for men than it does for women. When a man begins to take on mitsvot, the sky is the limit, and virtually no privilege or experience is barred from him. If he decides to observe halakhah in an Orthodox manner, he surrenders comparatively little of his public or private life as a Jew. But when a woman begins to observe halakhah, particularly if she is coming from an egalitarian community, she must have faith that the spiritual rewards of such a course will outweigh the sense of loss that she cannot but feel when accepting a diminution of her status. The first demonstration of this in our family happened a few years after my bar mitsvah, when my exposure to the Orthodox minyanat Hillel led me to adopt a more gender-conscious outlook to ritual without understanding how this would affect my relationship with my mother. After one Shabbat meal, she began to lead the zimun as she often had before, and I thoughtlessly blurted out that she “couldn’t do it” because she was a woman. Had they anticipated this situation, my parents could have come to an agreement about how to share halakhic spaces in our home, and might have challenged me to reflect on where this belief had come from. As it was, I surprised my father out of his composure, and he found himself justifying my rendering of the situation instead of supporting my mother in her hour of need. She was bitterly wounded, and we retreated into a surly defensiveness as her justifiable anger blew up in his face. Curiously, the version of the story that I remembered years later cast my father as the initial objector who provoked her outburst. I take this as an indication of how far my position on women and halakhah has changed in the meantime.

By now we have been navigating these minefields in our family life for many years, agreeing on a set of compromises and truces that have taken the teeth out of the problem, if not the sting. Our unconditional love for one another has meant that we try to meet each family member were they are, knowing that no single choice will satisfy everyone. If I said that we have worked out all the issues and are going along just fine, it would plainly be a lie, but we have made a lot of progress. Sometimes it is better to serve an unusual mix of ingredients in a salad bowl than to burn them in a melting pot.

Taking the Tiller:

Until my early teens, the development of my Jewish self took place in an environment in which my parents were the principal actors. While I could define my own boundaries within their story, it was they who set the ship in motion and oversaw its general course. The first time that I made an independent decision about my relationship with Judaism happened the summer after seventh grade, through a situation that was created unintentionally by the staff at Camp Ramah. Since the administration valued having services three times a day, campers would frequently get into trouble for leaving their kippot in their bunks, and I took to wearing one all the time as a purely practical measure to prevent this from happening. The morning after I returned to the real world, I thoughtlessly plopped a kippah on my head just as I had done every day for the past two months. Looking in the mirror, I was quite surprised that I didn’t want to take it off. It just “felt right,” whatever that means, and I have worn a kippah every day of my life since then despite the many eyebrows that it raised among my peers in the beginning.

As it turned out, this particular habit would have a far greater significance for me than I anticipated when I first adopted it. For reasons that are only tangential to this narrative I began hanging out with “the bad kids” at school around this time, forming meaningful friendships that would affect the next few years of my life for both good and ill. Unlike many of them I did well in school, but I readily adopted their freewheeling lifestyle and became a source of worry for my parents. On a fateful Friday evening a few months after my bar mitsvah, I met up with one such friend to hang out, and we decided to see if we could get our hands on some beer. While this would not have been hard for under-aged college kids at a party campus like my hometown, we middle schoolers were too young looking to pull that off, and petty theft was more our line. Strolling into a convenience store not half a mile from where I would pray the next morning, I engaged the clerk in conversation while my friend snuck back to the cooler and stuffed a six-pack into his oversized jacket. After a brief round of small talk, the clerk noticed my kippah (yes, I was wearing it even then!) and began asking me an intelligent series of questions about Jewish practice. It turned out that he was an observant Ethiopian Christian, and he was fascinated by the concept of a divine law governing all human behavior. I found myself describing halakhah and mitsvot in terms of “we do X” or “we don’t do Y,” and the whole time a little voice in the back of my head was saying “...uh, aren’t you stealing beer from this guy to go under-aged drinking on Shabbat?!‘We’ my aunt Fanny!”

When I got home that night, I decided that I had crossed a line with myself that I could never repeat. To recover my integrity, I had to either try and keep mitsvot in a real way or stop representing myself as someone who does. Aware that both choices would involve giving something up, I decided to try the mitsvot option for a period of one month and see how it felt. My parents were supportive of this even though I couldn’t bring myself to tell them the real impetus behind it, and I was pleasantly surprised to discover that my motley crew of friends deeply respected the direction I was headed in. While on the surface they were a shady bunch that exerted a “bad influence” on me, I don’t think that I could have gotten through the transitional period without them. They were nearly all gentiles, yet they arranged our social gatherings so that I wouldn’t need to drive or use the telephone on Shabbat, and they went out of their way to buy kosher products if they planned on sharing food. At school, they aggressively put down the slightest whiff of disrespect for Jewish practice on the part of others, whether accurate or perceived. Even the curious risked their ire, and I sometimes had to call off their dogs as they defended me in their endearingly foul-mouthed way when some well-meaning student asked me to explain “them goofy strings hangin’ offayo’ belt.”

I sensed that I had made the right decision when I didn’t even notice how the first month flew by. The structural duality of my religious life was finally beginning to disappear, and with friends and family rooting for me I wanted to do what I could to close the gap at a pace that worked for me. For the first year I simply brought the mitsvot into my personal life without attempting to change its secular and hedonistic nature, treating halakhah as a set of logistical limitations within which it was still possible to keep the company that I kept before and do most of the things that I did before. Though imperfect, this stage was well suited to a high schooler with limited personal space who lived outside of a major Jewish center – only an exceptionally strong kid could have withstood the isolation that would have accompanied the abrupt adoption of a Torah life. The next major development came somewhat serendipitously, when a story that is unrelated to this text drove me to abandon all of my friends in a single night. Although I still looked for a band of misfits when carving out a new social niche, the tenor of my new existence was more loving of general mankind than in the group I had left, and willy-nilly this fit better with a halakhic worldview. In practice, the seriousness of my observance of mitsvot increased only by degrees, but the attitudinal change was paramount, and it made my personal life feel more Jewish for the rest of my high school experience.

By the time I graduated I was committed to the general direction that I had been going religiously, but the next step could have taken many different forms. I had lived an Orthodox-looking lifestyle for four years and was used to it, but I understood that its prime motivation was a striving for personal integrity before God, not an endorsement of the halakhic system per se. The only thing that I knew for sure was that I was not ready for college, having been worn out by the unremitting cycle of school and summer camp that left me ahead of my years in some respects and deeply immature in others. Because I still had religious questions, I thought it would be useful to spend the next year in Israel, which my parents encouraged. However, I had a profound suspicion of the yeshivah world because of its reputation for predatory indoctrination, and I began searching for Hebrew-language-focused programs as a more ideologically neutral alternative. The ensuing school shopping only underscored that there weren’t too many people like me in the Jewish world: if I found a program that had a high enough level of Hebrew for me, it could not accommodate those interested in keeping mitsvot, while all of the programs that accommodated mitsvot were invariably yeshivot.

After a not inconsiderable struggle I took a second look at the yeshivah courses, eventually finding a non-judgmental, left-leaning Orthodox program with Hebrew-only classes called Yeshivat Hakibbutz Hadati at Ein Tzurim. It was a huge gamble: with little preparation I traveled 6000 miles from home to spend a year in an out-of-the way agricultural community where I had no prior acquaintances and only a dim idea of what the courses would be like. The daily schedule began at 6:30 am and ended at 10:30 pm, so there would be precious little escape if I didn’t enjoy the environment. But the Lord works in mysterious ways, and as it turned out I hit the jackpot. Not only did the staff succeed in making Jewish texts and halakhah come alive for me, turning a detached interest into a budding passion, but they did so in a loving way that met me where I was. Never did they demand that I cease thinking critically or surrender my sense of self-worth, and I finally had a model of a truly modern Orthodox thinking that aligned with my own innate values.

Only when I returned to the US for college did I fully appreciate the change that was manifest in my Jewish outlook. During my year abroad I successfully maintained a long-distance relationship with a gentile girlfriend at home, but once we were back in the same city, things fell apart. It rapidly became clear that I was uncomfortable with the halakhic challenges posed by our relationship, even though they hadn’t seemed to bother me the previous year. I wanted to make it work because we loved each other and had invested a lot in staying together, but the only long-term solution would have been for her to become a Jew, and neither of us had any illusions that this would be a good fit for her. Although our interpersonal issues were still the ultimate reason behind our (multiple) breakup(s), I am certain that the religious development that I had undergone was a significant contributing factor. When I finally got over the pain of separation, I was surprised by the sense of spiritual closure that came with resolving one of the last great contradictions in my religious life. I am still not entirely sure when I started to think of myself as a “real” Orthodox Jew, but I could not date that point until sometime after her absence from my life felt right to me.


Since my return to a life of mitsvot is the subject of this article, I will leave the many evolutions that reshaped my Orthodoxy in the ensuing ten years for another time. Suffice it to say that I have evolved a great deal in the interim, and owe a deep debt of gratitude to the people and institutions that have helped and encouraged me along the way. Chief among them is my wife, who has kept me on my toes in a beautiful quest of reflective growth over the seven years we have been a couple, and who supported me in my recent decision to join the rabbinical seminary at Yeshivat Chovevei Torah. Her loving and well-articulated challenges of my ideological positions are an important part of the Jew that I am today, and have affected the way in which I interpret the meaning of my story before we met. I have great hopes for what we will accomplish together as a Jewish household, and wherever we end up we will have come a long way from my parents’ Festival dinner of pork roast 35 years ago.

Reflections and Analysis

Just because a personal story is meaningful and transformative does not necessarily make it a universal model that everyone should emulate. That being said, the pathway I took to adopting Orthodoxy covered a fertile ground that could speak to a variety of people involved in a ba’al teshuvah or conversion story, whether as central actors or as elements of their emotional, religious, and social context. Because of this, I have shared my outlook on some of the central issues concerning the adoption of mitsvot, with the acknowledgement that my interpretation comes from a subjective experience. I published it because I believe that it will contribute to an important discussion, but I also make no claims of infallibility.

For Parents:

One of the most meaningful experiences for a Jewish parent is to witness a continuity of Jewish life unfold through their children and grandchildren. Yet this is not always something that happens organically, even in a household with a specifically Jewish atmosphere. While I recognize that the Jewish developmental environment in which I grew up was not ideal, it instilled two important values in me that I believe are transferrable to an a priori situation:

The first is that positive modeling sets a followable lead. If you expect your kids to connect with mitsvot when they grow up, then it is important to demonstrate that Orthodox Judaism is an “intellectually sound, spiritually compelling, and emotionally satisfying” way of life that enriches your experience together as a family. By consciously bringing out the greatness of Jewish life and welcoming your kids to access why you appreciate it, you increase the possibility that they will attach a similar significance to it. If you allow it to become an arbitrary, authoritarian system that continually emphasizes what can’t be done, then a negative take-home for your children will hardly be surprising. To put it in other words, you may not be in control of the Torah itself, but you have tremendous power to frame it in a way that shows why it is worthwhile for one to follow its precepts.

Parallel to this is the importance of recognizing that your children will one day grow up and enter a world in which their association with Judaism and the Jewish community is entirely voluntary. The more you can make observance of mitsvot an informative, empowering experience that gives them the tools to continue on their own, the more likely they will be to want to claim mitsvot for themselves. If they passively receive a version of mitsvot where the difficult choices are either handed to them ready-made or forced down their throats, then Jewishness may come off as something to be devalued or cast aside. No technique is guaranteed, but my experience suggests that these two values can smooth an admittedly difficult way.

For Ba’alei Teshuvah and Converts:

There are many reasons why someone might adopt a life of mitsvot, which means that each person’s path will take a different course than then next – will travel at different speeds and produce different results. Because of this, it is vital to maintain an intentional and ongoing conversation with yourself in which you articulate what you are doing and what you hope to achieve by it. This is particularly true since your journey will not take place in a vacuum, and may have extensive consequences for the people you know and love:

• What about your previous life do you feel was not working for you?
• What aspects of assuming a life of mitsvot do you believe will address that?
• What changes and sacrifices might you need to make along the way?
• Is what you hope to get worth what you are giving up?
• Who else besides you will be affected by what you are going through?
• What conversations might you need to have with them about what is happening?
• What style and rate of change will accommodate your needs and theirs?
• According to what parameters will you evaluate your progress?
• Whom will you look to for mentorship and guidance?
• What social and educational resources will you use to stay informed?
• What qualifies these mentors and resources as authoritative for you?

You may not be able to answer all of these questions at any given time, but knowing that you cannot answer an important question is better than not knowing that the question even exists. If you keep up good communication with yourself and those around you, then you will be better equipped to meet the inevitable obstacles as they come, and you will maximize your potential to grow and learn from the experience. It will be useful to ask yourself questions like these every few months, to compare your experience with your goals and assess whether you need to make any adjustments.

On the Rate and Definition of Progress:

My experience has been that taking on mitsvot gradually is less overwhelming. Once you buy into a halakhic worldview, it can be tempting to hold yourself to a binary standard that uses unequivocal language like permitted/prohibited, authentic/inauthentic, and right/wrong. I will suggest that this thinking can impede a successful assumption of mitsvot for two reasons. First, halakhah is by its very nature the outgrowth of dispute among rabbinic authorities, and unanimous agreement about a given halakhic problem is the exception, not the rule. The most renowned sages in each generation have disagreed about issues of every kind, making the halakhah more of an oscillating band than an undeviating line. Going from zero to sixty and holding yourself to such a demanding standard overnight creates the possibility that you will find the burden of mitsvot too heavy to bear, and might give up the enterprise entirely. Second, halakhah is so rich and all-encompassing that you will not be able to understand it fully at first. When attempting to adhere to a system with which you are not completely acquainted, you must resort to the stringent position in cases of doubt, which means that the form of Jewish life that you observe will be much more rigid than for people who are aware of accepted leniencies. This too can lead to an experience of an unforgiving system that asks more than you can give, and may be fatally discouraging.

Far better, I will suggest, to try things out slowly in an ongoing process of experimentation. Take on one mitsvah for a while and see how it feels, then add more in a rolling process that moves at a pace that is manageable for you. Don’t be afraid to say that it doesn’t feel right or that you aren’t ready yet, or to stop doing something that you started if that is what you need. When you begin to introduce yourself to observant communities whom you might look to for mentoring, be open about the fact that you are not exactly sure where you are going, and have not yet adopted mitsvot completely. If they reject you because of this, then it is not a safe place for you in any case. Ideally, you should be able to find a social support network that understands your vulnerability – that helps you along the way at your own speed without taking advantage of your weaknesses to perpetuate their own agendas. Sometimes the journey can be as meaningful as the final destination, and it is helpful to do your traveling in a company that is open to this even if they have never been in that kind of place themselves.

On Pseudo-Authenticity and Oversimplification:

Many of us have had at least some exposure to forms of Orthodox Judaism that are led by charismatic figures who appear enviably self-assured in the world of mitsvot, and who wear the label of “authentic” Judaism proudly on their sleeves. They seem to have an answer for every challenge and a gem of sagacious advice for every seeker. No problem in the world appears to ruffle their sense that the black-and-white system that they present to all comers is unassailable from every possible angle. They project confidence in a reality that is filled with uncertainty, and their magnetic personalities have a broad appeal to many who suffer from the gnawing sense of doubt that eats at us all.

I would advise newcomers to the world of mitsvot to be extremely cautious around such people. Their brand of one-size-fits all Judaism is not necessarily suitable to everyone, and until you are in a position to critically assess the things you hear from them yourself, they will wield all the apparent power and credibility that comes from superior knowledge. This is not to say that you should avoid the kinds of experiences that they have to offer, but rather that if you do decide to explore in that direction, you should keep some important things in the back of your mind:

The understanding of Orthodoxy that these leaders represent is a product of historical revisionism. As they would have it, Orthodoxy is the one authentic branch of Judaism that existed from the revelation at Sinai until today, emerging from the massive upheavals of the Haskalah (Jewish Enlightenment) entirely unscathed. In reality, Orthodoxy is a direct response to the Haskalah, and it represents a novel departure from the looser heterogeneousness that preceded it. While today’s Orthodoxy shares a commitment to halakhah with pre-Modern Judaism, its leaders were only able to defend the halakhic lifestyle by instituting unprecedented social and religious innovations that would have been viewed as dangerous and seditious in a prior age. The reforming denominations may have created the initial rupture by stepping outside of halakhic norms, but the mere fact that they are innovative does not make them any less “authentic” than their Orthodox brethren.

Something else to remember is that life, like halakhah, is filled with gray areas and contradictions. People are inconsistent, morality can be equivocal, and we know very few things with complete certainty. When you encounter someone who tells you otherwise, regardless of whether it is in a Jewish context, you should take a step back and get another perspective on the situation. Critical thinking is an instrument that will serve you well here as in many other places, and abandoning it need not be a pre-condition for membership in the halakhic community.

In Summation:

While the preceding paragraphs highlight that adopting a life of mitsvot is not a simple undertaking, it can nevertheless be a source of meaningful growth and spiritual fulfillment if carried out lovingly, seriously, and introspectively. I would never recommend that someone start down this path merely because they are a Jew or want to become one. However, I believe that if a questioning soul goes into it with and open mind that understands and validates the risks, there is a potential for profound enrichment that could be worth the toll that it takes.

A final note that I will add is that during the writing of this article, I unearthed many dusty memories of an adolescent’s unfolding spiritual development, and was forced to synthesize and interpret them through the eyes of an adult who has moved on to another place. By engaging in this important introspective exercise, I recognized that the knowledge I acquired from those now distant experiences is an ongoing part of who I am today, and if only for that it was worth putting pen to paper. If I may be indulged in a parting recommendation, I will suggest that anyone, regardless of where they are in relation to mitsvot, stands only to gain by taking the time to think about what being a Jew means to them and how they came to the ideological space that they currently inhabit.