My Jewish Story Part I: Wandering in Exile ✡️ 📖

Andrew Murray Dunn
37 min readDec 25, 2022


This is the first part in a three-part series centered on my recent pilgrimage to the holy land, set within a larger and ongoing story of my journey reconnecting with Judaism. My intention is to better understand and enliven my own story, archive the rich inflection point I’m in, and share what I’ve learned with kin and those yet to come.

My Bar Mitzvah 6/21/03. While I often think of it as a lame excuse for an initiation ritual, it’s actually kind of fitting that a young Jewish man would be given an intellectual challenge to be completed by public speaking and singing!

Table of Contents:

  • Part I: Wandering in Exile (My Journey) — This part will touch on the religious context of my upbringing, spiritual explorations in young adulthood, and journey of reconnecting with Judaism pre-pilgrimage.
  • Part II: Birthright 2.0 (My Pilgrimage) — Here I will chronicle the religious, political, and educational elements of the pilgrimage. My direct experience > analysis.
  • Part III: Metamodern Judaism (My Analysis) — This final part will explore the insights and questions I’m holding based on my diverse experiences, particularly as it relates to the state and future of Judaism, Israel and Palestine, and personal growth education.

Please feel free to skim (I’ve bolded key sentences) or skip around to sections of interest. There’s a lot here, and so much unsaid — it’s about more than just my relationship to religion, which is an exhaustive subject on its own. I’m saving most of my commentary for Part III. I’ve also made a number of parenthetical references for education and context.

This series is dedicated to my ancestors, especially my maternal grandmother Rose with whom I experienced the strongest thread of tradition, and great grandmother Libby (grandma Rose’s husband Murray’s mother), whose support and presence was felt on this trip. May their memories be for a blessing.

Finally, a little Shehecheyanu blessing, typically recited before the first time you do something, like writing publicly about Judaism:

בָּרוּךְ אַתָּה, יְיָ אֱלֹהֵינוּ, מֶלֶךְ הָעוֹלָם, שֶׁהֶחֱיָנוּ וְקִיְּמָנוּ וְהִגִּיעָנוּ לַזְּמַן הַזֶּה

Baruch atah, Adonai Eloheinu, Melech haolam, shehecheyanu, v’kiy’manu, v’higiyanu laz’man hazeh

In the presence of the Infinite, we pause to acknowledge and give thanks to the journeys that bought each of us to the here and now.


Part I: Wanderings in Exile

This part has three sub-sections: Inheritance, Seeking, Returning. tldr: Grew up reform, drifted away in teenage years, did lots of seeking in early/mid 20s, started returning to Judaism as I approached 30s. Skip to Part II if you only want to hear about my pilgrimage.

🐣 Inheritance

In the beginning, I was born at NYU Medical Center to Barbara Horowitz of Sheepshead Bay, Brooklyn and Charles Dunn of West New Brighton, Staten Island; children of first, second, and third generation immigrants from Ashkenazi shtetls (small Jewish villages) of the Pale of Settlement (Western region of Russian Empire that permitted Jews for a time) in modern day Lithuania (town of Lazdijai), Belarus (Olshan), Ukraine (Zhytomyr and Kam’yanets’-Podil’s’kyi), Hungary (outskirts of Budapest); by way of the Lower East Side, Williamsburg, Borough Park and other NYC neighborhoods densely populated by Jewish immigrants in the early 20th century. All came over pre-Holocaust. Classic stories of upwardly mobile, poverty → working class → small-business owning families in the tri-state area, proudly creating an ever better life for their posterity.

US Census records of great grandparents Hyman, Libby, and their children Murray and Phil

My siblings and I grew up in suburban New York in a reform Jewish (a more liberal and progressive denomination) household, attended a Jewish pre-school at a conservative synagogue (more observant of Jewish law), then regular New York state public school accompanied by twice a week Hebrew School classes at several temples in the reform to conservative range. You might say we were more “culturally Jewish” — proud of our heritage, but not really religious. Or as one comedian puts it, “I’m culturally Jewish, which means I have all the anxiety, stress, and gastrointestinal problems of regular Judaism, but without the comfort of god.”

Distinctions between major denominations of Judaism

Judaism was how we gathered as an extended family. I associate my late grandparents with the comfort food they cooked for joyous meals we shared on Passover, the high holidays (Rosh Hashanah and Yom Kippur), and Hanukkah. Some of my warmest memories from childhood are lighting Hanukkah candles and eating latkes with a table full of presents in the other room. I saw nothing wrong with the Judaism I grew up with. It was what it was, the only version of Judaism and religion I was exposed to. But it was clearly a secondary aspect of life. After school and special occasions only. We weren’t talking about it on the playground. I had no connection to or personal understanding of God — though I recall a faint image of how I visualized him: a tall, faceless man in a navy blue suit, standing at the bima, delivering baby me into the arms of my parents. We didn’t talk about God in the house. The only time it was voiced was when our Jamaican housekeeper Dell would mutter “Lord have mercy on these kids!” in response to whatever mishegoss we were up to.

In Hebrew School, I was frustrated by how much time we spent learning things we had no idea what to do with. Like how to write these funny letters and pronounce ancient words, but neither understand the meaning of most of these words nor the sentences they constructed. I’m not sure how much our teachers understood them either. There seemed to be no real purpose to it all. It baffled me that hundreds of people would travel for my Bar Mitzvah to see me read some words I had memorized but didn’t understand (Parashat Beha’alotcha — something about humility?), while I felt wholly unchanged in the process. And that was it for my Jewish education. Bupkis in the years following (there was continuing education available, but I don’t remember hearing much about it or considering it). How is this or could this be relevant to anything in this day and age? I would write one of my college essays on the tension, because it was one of the realest things I was grappling with in what was a relatively uneventful life up until that point.

We weren’t friends with too many non-Jewish families, nor were we friends with orthodox Jewish families. So my world was mostly people like me: upper middle to upper class, suburban, assimilated, reform, achievement-oriented, Ashkenazi Jews. Families of doctors, lawyers, business types with a similar story. We weren’t a very scientific bunch, but when it came down to it, we said that we believed in science and progress: the default religion of the modern world.

We went through the motions of celebrating select holidays, gradually attending synagogue for fewer of those holidays and major life events once all the kids were post-Bar/Bat/Beit-Mitzvah age. When we did go to schul for holidays, the MO for my siblings and I was to sneak out of services and hang with friends, or dig into the rainbow sprinkle cookies before we were supposed to. To sanctify a friend’s coming of age ceremony, we played “the penis game” from the pews. Friday night chicken soup, challah, candles and blessings faded away as we prioritized going out to get faded. Kosher-wise, we regressed from no pork or shellfish in the home, to lobster and shrimp and bacon on rare occasions, to “whatever, who really cares.”

It’s not entirely clear when and why my ancestors’ relationship with Judaism started trending in this direction, from following Halakha (Jewish law–the 613 mitzvot or commandments from Torah) to not knowing what that word means. Something about the economic and social advantages of assimilating into American society. Something about forgetting the painful experience of poverty and pogroms in the old country. Perhaps they lost the story much earlier during the Jewish Enlightenment that swept Central and Eastern Europe in the 18th century, striving for optimal integration into surrounding societies. I don’t think any of grandparents or parents thought that Judaism was particularly awesome, just that it was something worth passing on, though with further dilution in each generation.

High Holiday ironic Snapchat post c. 2014

🔭 Seeking

I showed early signs of truth seeking and existential inquiry — passionate about foreign cultures, tickled by esoteric topics like aliens and UFOs, often wondering what the meaning of everything was. My favorite movies growing up had to do with history (Indiana Jones), space (Armageddon), the meaning of life (Click). I remember moments of existential dread when I’d take the tiniest of dilemmas–such as having misplaced my pen to do homework with–and extrapolate the consequences out to the limits of the universe, feeling utterly alone and confused by the mystery of existence. Like WTF is all of this, actually? Hello!? Why are we here? Is nobody else thinking about this?

As I’ve written about extensively, I felt intense pressure of expectation, perfection, achievement — common wounds of assimilated American Ashkenazi Jews. A dense modern malaise, which I believe inspired this seeking posture. It also generated unhealthy coping mechanisms: binge drinking, social media addiction, womanizing. At some point in college I decided I would be atheist because my roommate in the nominally Jewish fraternity we joined and a girl that I liked identified as atheists. Seemed like the cool thing to do to reject religion, but I didn’t have much of an analysis for why. It didn’t feel like I was giving up anything in order to claim atheism. So the first and only time I experienced overt anti-semitism–some drunk WASPY kids throwing coins at our chapter house, yelling and laughing “here’s some pennies you f*cking Jews!” I was confused about how to react, because I didn’t feel personally impacted.

There were some strange, ineffable moments in those university years — killer hangovers in which I felt like I had access to a wellspring of wisdom, a meditation with a girlfriend’s father that showed me a flash of Oneness, stargazing that prompted writing a theory on life in the universe, a week where I spontaneously felt on fire like in NFL Blitz, moments of inspiration and awe and flow in entrepreneurial projects and travel adventures. To the dismay, confusion, or pity of many around me, I resisted recruiting for the conventional internships and job opportunities that a Wharton grad was expected to pursue because I felt this desire for something “More” and would grab on to every spec I could find — job interview to teach English in Japan, talk from professor about his personal journey to the East, mushroom trip with fraternity brothers in Fairmount Park (I didn’t feel anything). My friend Pratham extended an unbelievable offer to live and work with him in India, which was tempting but somehow felt unrealistic at the time. I moved to NYC for a startup job after college and continued the party.


And then I tried LSD three times in one summer. Which opened me up to a sense of unity with all things, a renewed childlike-wonder, insights into the laws of nature and how they reflect in the human being. Best days ever. Acid seemed to eased some existential angst and perhaps low grade depression, revealing a vast inner world and affirming a sense that there was more going on than what we think is going on. My fellow trippers and I would start to talk about “The Universe” (but definitely NOT God, no no) and show up to life with a little more curiosity and playfulness.

Shortly after, I met Pratham again for tea and he invited me to India once again. This time I jumped at the opportunity to escape my matrix and see the world. I’ve often said that this move had no spiritual motivations–I don’t think I knew or cared what an ashram was–but in hindsight it’s clear that I was spiritually parched and this invitation was a big cold glass of something that I knew would be supportive.

And thus, like Avraham Avinu, I left my father’s home and boarded a one way flight to Amritsar, India in October of 2013. I wrote about my experiences there in my first memoir To Live Is To Know For Yourself What Is True. After a month of working and getting settled, I set out for a week of solo travel. On that Friday night in Udaipur– the same week that Parashat Veyetzi with Jacob’s ladder is read–alone and without internet for the first time since elementary school… my life came to a cinematic P A U S E.

“That night I could not sleep. It wasn’t the stained sheets or howling packs of dogs outside the low window that wouldn’t lock. Geographically further than ever from a single person I knew, in the absence of WiFi, in a city I had not heard of that morning.. I felt free. I wrote, I read. I looked up at the ceiling for hours pondering my choices over the last few years. Who I had become and why. What I was doing now and the meaning I was constructing from it. It was Friday night and I was alone to enjoy my company, traveling further inward. I cried. This was my first encounter with solitude–it was euphoric.”

My first peak experience–a moment of awe, ecstasy, or sudden insight into life as a powerful unity transcending space, time, and the self–was a single moment of solitude, after 23 years of go go go, do do do, more more more, win win win, take take take. The first time I had time and space to express the pain in my heart, listen to the yearnings in my soul, and wrestle with what had filled the gap in between them. Coming down from that mountain top, I would dive into books from Hinduism, Buddhism, and the modern self-help world to see what I’d been missing. It brought me so much joy to learn new ideas, cross reference them with my lifestyle, ask and discuss the big questions. I spent some time with the Hare Krishnas, where I got a real look under the hood of a whole different religious system, amongst a series of ineffible synchronicities. I started thinking about God, though not through a Jewish lens. I wondered if I could engage these questions for an extended period of time, maybe even as a career. But the conventional success voices in my head told me I had to get back on the normal career track, so I did.

I went to Israel twice during this young adult phase: once with my family at 18, a sort of graduation trip that I remember as one of our best family vacations; and then Birthright Israel at 24 (the free trip for Jewish youth, funded by barons of liquor, casinos, and hedge funds), immediately upon returning from my year in Asia. Birthright was cool, but overshadowed by the reverse culture shock and isolation of traveling with a group of young adults asking a very different set of questions than I was.


Fast forward a few years — after getting fired from a startup I’d poured myself into, I decided FUCK THIS, I will never again work on something that is not nourishing my soul or serving the whole. As much as I possibly can, I’m going to prioritize exploring my curiosities because this is California dammit and I know there’s something more here than pretty hills and vintage stores. That year was my first Esalen visit, Burning Man, meditation retreat and so on–a steady drip of synchronicity, expansion, and open doors into what seemed like the secrets of life and the universe. I also started working on a passion project about shifting my relationship with technology, which led to joining forces with a team whose mission would define my next three years: Siempo and reimagining the smartphone experience.

Working in the emerging wellness / humane tech space gave me permission to “work on myself” with no shortage of personal development and spiritual-but-not-religious modalities to experiment with. “Leadership training” in Northern California often felt like a Brazilian steakhouse where the waiters buzz around with a variety of cuts of meat. “Would you like some of this? Some of that?” “Sure why not! Might as well try em all! I can’t believe I get to engage these juicy spiritual topics as part of my career after all!” Besides, all the investors and thought leaders are telling me: “heal yourself, so you can heal the world!” amongst a bottomless feed of flashy mysterious opportunities that promise the next big breakthrough–without consistent practice. These peak experiences made me come alive. So I made them my way of life. Whether sitting phone-less by a creek or in prayer with medicinal plants, connecting with expanded states of consciousness, creativity, and clarity was where I found holiness after decades of searching for it. And boy did I have a lot of chutzpah in those years.

Churascuria, or eating contest? source: Healing from Healing. For what it’s worth, I haven’t done all these things! But I do know a lot about the world of transformation, and feel like I’ve learned some important lessons that I’d be happy to share if you are feeling curious about anything on the menu.

In hindsight there are plenty of things I would do differently. One of the key challenges to my seeking was that I lacked proper guidance (that one might get, say, from a rabbi), and would get caught in the spiritual cul-de-sac, hopping from one peak experience to another, going very wide but barely deep. e.g. I joined a spiritual community with a holistic awakening program (Luminous Awareness Institute) that combined elements of qi gong, Buddhism, subtle energy healing, western relational practices and so on. But I slept through many of the lectures and didn’t do the homework. People said “Welcome home!” but it didn’t really feel like home.

Throughout this period of spiritual expansion I don’t recall many sparks around Judaism — I wasn’t even attending high holiday services, representing an extreme low in my relationship to tradition. I do remember always finding joy in connecting with another Jew in these spaces — like oh hey you found your way here too! As if our departure from Judaism to California’s new age soup was the promised land, and everybody else (religious or secular) was crazy. My belief system became a now cringey hodgepodge of indigenous shamanism, pop Buddhism, the human potential movement and mindfulness technology. I subconsciously bucketed Judaism in the doesn’t-provide-me-with-meaning category, while keeping my antennae up for almost anything else shiny and new to thirst my quench for meaning.

Note: I can sometimes get self deprecat-y and critical about my seeking years, often for storytelling effect. I also want to acknowledge the good and the beautiful experiences, the valuable learning and growth, the impact of the relationships of all stripes. I metabolized a lot of life. Maybe it was a necessary process. I sincerely believe the paths of tomorrow’s leaders must involve a serious commitment to personal development in order to bring innovations into the world or steward organizations in a good way, and we’re still figuring out what that culture is like. And if I’ve learned anything, it’s that the full outcome of any choice is unknowable, in a process of forever revealing itself. I imagine there will always be a seeker part of me. “To seek meaning is to find it. To fail to seek meaning is to be without it.” Forrest Landry.

To its credit, seeking would prime me to later relate to aspects of Judaism that I don’t know if I would have been able to grock otherwise. For example, praying to “Great Spirit” in sweat lodges with Native American elders made sense in a way that reciting lines from a book to God did not before, but would later. Without transcendent visions via meditation, breathwork and other modalities, I don’t think I’d be able to understand a fraction of what I can reading mystical texts. Same with appreciating myths, archetypes, symbols, even astrology (I’ve never been big on it, but I get it!).

February 2020 🌵👽 Occasionally I’d hear passive aggressive comments about my “seeking.” Um, yes I’m seeking… are you really okay with the state of your inner and outer world? And, there is a healthy balance to navigate 😅

🌀 Returning


Yeah, my tuches did a lot of seeking…

In perhaps the moment of straying furthest OTD (Off the derech, or path of observant Judaism) in Dunn family history, I sat in an ayahuasca ceremony (plant medicine used ritually for healing by some indigenous peoples of the Amazon), without noting or caring that it was the same time as Yom Kippur. There was a small water alter in the center of the room that we were encouraged to pray at. I didn’t have much of a relationship with prayer, but when I approached the alter I suddenly realized the holiness of this day in the Jewish calendar, and bore my heart open to 27 years of shallow or missed ritual. I was able to access an endless well of things to ask forgiveness for, and to forgive others for. I then experienced my first purge (typically vomiting — believed to release stuck emotions and trauma). It was the most meaningful Jewish experience I had ever had.

Meanwhile, in the Luminious program I noticed myself gravitating towards the handful of Jewish folks amongst 80 hippies from a variety of religious and spiritual backgrounds. I was fascinated by conversations on comparative religion and moved by the little Shabbat dinner crew we assembled. Something about the way they held their Judaism was fresh, inspiring, relevant. It resonated. Elegantly integrating the meaningless drilling from my childhood with the spiritual insights I had encountered as an adult.


I wound up seeking coaching support from Simon, one of those cool East Bay spiritual x justice-oriented Jews in Luminous, and will never forget the call in which I decided to ask him some questions about Judaism. He blew my mind explaining how prayer is a mindfulness practice, that Judaism at its core is a mystical and earth-based shamanic tradition, how Jews assimilated into whiteness, and that the word “Israel” comes from the Jacob’s Ladder story and refers to a people who struggle with the paradox of worldliness and holiness. He then mic-dropped an interpretation of the Shema, V’ahavta, and V’haya im shamoa (considered among the most important prayers of Judaism), something like the following (I’ve since added my own flavor):

שְׁמַע יִשְׂרָאֵל יְהוָה אֱלֹהֵינוּ יְהוָה אֶחָֽד׃

Yoo listen up! Everybody who wrestles with the mysteries of life.
Remember that it’s allll connected #oneness

וְאָהַבְתָּ אֵת יְיָ אֱלֹהֶיךָ, בְּכָל-לְבָֽבְךָ, וּבְכָל-נַפְשְׁךָ, וּבְכָל-מְאֹדֶֽךָ. וְהָיוּ הַדְּבָרִים הָאֵלֶּה, אֲשֶׁר אָֽנֹכִי מְצַוְּךָ הַיּוֹם, עַל-לְבָבֶֽךָ: וְשִׁנַּנְתָּם לְבָנֶיךָ, וְדִבַּרְתָּ בָּם בְּשִׁבְתְּךָ בְּבֵיתֶךָ, וּבְלֶכְתְּךָ בַדֶּרֶךְ וּֽבְשָׁכְבְּךָ, וּבְקוּמֶֽךָ. וּקְשַׁרְתָּם לְאוֹת עַל-יָדֶךָ, וְהָיוּ לְטֹטָפֹת בֵּין עֵינֶֽיךָ, וּכְתַבְתָּם עַל מְזֻזֹת בֵּיתֶךָ וּבִשְׁעָרֶֽיךָ:

Take these words to heart:
Love life with all you got.
Your life, others’ lives, and all life on Earth.
Show your people how it’s done.
Speak about it wherever you go.
Morning to night.
Put reminders in physical and digital spaces.
So you don’t forget to love life.

יג. וְהָיָה אִם שָׁמֹעַ תִּשְׁמְעוּ אֶל מִצְוֹתַי אֲשֶׁר אָנֹכִי מְצַוֶּה אֶתְכֶם הַיּוֹם לְאַהֲבָה אֶת יְ־הֹוָ־ה אֱלֹהֵיכֶם וּלְעָבְדוֹ בְּכָל לְבַבְכֶם וּבְכָל נַפְשְׁכֶם. יד. וְנָתַתִּי מְטַר אַרְצְכֶם בְּעִתּוֹ יוֹרֶה וּמַלְקוֹשׁ וְאָסַפְתָּ דְגָנֶךָ וְתִירֹשְׁךָ וְיִצְהָרֶךָ:15.טו. וְנָתַתִּי עֵשֶׂב בְּשָׂדְךָ לִבְהֶמְתֶּךָ וְאָכַלְתָּ וְשָׂבָעְתָּ. טז. הִשָּׁמְרוּ לָכֶם פֶּן יִפְתֶּה לְבַבְכֶם וְסַרְתֶּם וַעֲבַדְתֶּם אֱ־לֹהִים אֲחֵרִים וְהִשְׁתַּחֲוִיתֶם לָהֶם. יז. וְחָרָה אַף יְ־הֹוָ־ה בָּכֶם וְעָצַר אֶת הַשָּׁמַיִם וְלֹא יִהְיֶה מָטָר וְהָאֲדָמָה לֹא תִתֵּן אֶת יְבוּלָהּ וַאֲבַדְתֶּם מְהֵרָה מֵעַל הָאָרֶץ הַטֹּבָה אֲשֶׁר יְ־הֹוָ־ה נֹתֵן לָכֶם

If you remember and act accordingly,
Your internal and external climate will stabilize.
Your body will be nourished and work will flourish.
But watch out for cheap substitutes! False idols of market and self.
That path is lame and ruins the game for everybody.
So seriously, do as much as you can to remember that it’s all connected.
So you and the next generations may thrive
As stewards of this beautiful planetary home.

Wow. Duh. What could be more important than daily reminders about how everything is connected, and that if we forget this and bow down to false Gods or treat life without sacredness, then… well, the official translation goes:

יז. וְחָרָה אַף יְ־הֹוָ־ה בָּכֶם וְעָצַר אֶת הַשָּׁמַיִם וְלֹא יִהְיֶה מָטָר וְהָאֲדָמָה לֹא תִתֵּן אֶת יְבוּלָהּ וַאֲבַדְתֶּם מְהֵרָה מֵעַל הָאָרֶץ הַטֹּבָה אֲשֶׁר יְ־הֹוָ־ה נֹתֵן לָכֶם:

He will close off the heavens, and there will be no rain, and the ground will not give its produce, and you will perish quickly from upon the good land that the Lord gives you.

Whew. That’s some strong medicine for us right now. Maybe it would take drawing our attention to this idea a few times a day so we don’t forget as we go about making choices that have implications on the health of our ecosystems. Because we. keep. forgetting. How do we remember? Some scholars believe that when the Torah was written (or received, depending on your beliefs) around 3,000 years ago, in the collective memory of people of that region was the collapse of Mesopotamian empires some centuries before, due to the familiar over-farming, managerial incompetence, failure to adapt to drought (i.e. human-accelerated climate change). Our ancestors are trying to help us remember through Torah, trying to teach us how to navigate a dynamic and mysterious world through prayer. Apparently Jews are particularly good at sending messages through time. Freakin’ brilliant.

Eitan Kedmy Mandala Art

Learning alternative interpretations of those prayers inspired me to take a closer look at the prayer book during Rosh Hashanah services that year. What were we actually reciting year after year, in community, dressed in our best? I was surprised to find that many of the prayers were a variation on “God is dope!” lol. Even the Mourner’s Kaddish. Is God that dope? What is God, actually? What is the wisdom here that countless ancestors felt was important to give their lives to, choosing death over conversion to a different faith?

This was a tough time for relationship with family. Out of concern for all the changes I was going through in California, my parents encouraged me speak with our hometown Rabbi about my alternative lifestyle. Rabbi Greenberg reflected: “It seems like there’s something stirring in you beyond a natural desire for growth. You’re running around the world in search of something, when you should be building a home, a family, a profession. That’s what life is about, not grand esoteric pursuits of healing the world.” I couldn’t really hear him at the time. Thought he was out of touch. And yet something did feel nice about building a connection with a religious leader of my tradition of origin.

After a period of nomadism, including participating in a beautiful 1,000 person Shabbat ceremony at Burning Man, I was invited by Hadar–another one of those hip Jews from Luminous–to live in the queer-justice-Judaism-community-living home she had just started in the “North Oakland Shtetl” called Olives & Roses with Binya, Elena, A-Ro and Muki, where I’d lightly engage in creative conversations, events, and books about Judaism (e.g. The Sabbath by Abraham Joshua Heschel, Seasons of Our Joy by Arthur Waskow, Magic of the Ordinary by Gershon Winkler). There was a meaningful identity shift here; I took pride in telling people that I lived in a Jewish home and participating in the wider shtetl community. But my priorities were still my new age glob of interests and heads down hustle on the startup.


I’ll never forget the words I heard at a 10 day Vipassana meditation retreat:

“Ultimately you have to take one decision. You want water, you dig ten feet, don’t get water, a different ten feet, you keep on digging in different places. Some day you must be sure I will get water here, then dig, come to that stage. I don’t say only remain with me. You try, and whichever path seems more compatible to your ideology, your thinking, go ahead. I don’t condemn.” — Founder S.N. Goenka

I realized I had been digging endless shallow wells, and not really finding water. But was I willing to admit it and make a change?

That Passover, on the heels of giving my first eulogy at my grandmother Rose’s funeral, I felt inspired to step into greater religious leadership within the family–mainly because nobody else was. The length of Seders with our cousins had slowly declined over the years from ~30 minutes to 20 to the previous one tapering off after 5 minutes into jokes and drinking games. I approached my uncle Ken, who typically led the Seder, to ask if he would be open to sharing or passing the torch, to which he agreed, giving me max 20min. I scrambled to wrap my head around the holiday, and proudly taught what I needed to learn; albeit to a tough crowd. It was joyful and empowering to draw inspiration from the raw story, interpretations through the ages, and rituals from friends in crafting an experience that I sensed would best communicate the essence of the story and engage my jaded audience.

Maternal grandparents Murray and Rose Horowitz
Paternal grandparents Abe and Dorothy Dunn


As fate would have it, I spent much of 2020 quarantined with a revolutionary political movement, where as the only Jew in the room I’d occasionally make jokes about how my inherited Ashkenazi anxiety was feeling off about, for example, planning radical direct actions to take down the two party system.

During Pandemic Pesach, there were lots of memes flying around the internet about how we were living through actual plagues. I found myself curious about the relationship between the holiday and current events around the world and in my life. What are all these holidays really about? So cool that they serve as annual reminders to reflect on a unique aspect of life, personally and collectively, through rituals with loved ones. Wait, rather genius — infusing time with lessons and teachings that are anchors to guide, heal and teach us? Usually centered around stories and some embodied activity (more right-brain ways of transferring wisdom)? So we don’t forget! They can be real holy days, if we relate to them as such. Months (lunar) too — see Living Jewishly’s Sacred Time podcast.

MiSaviv: Hebrew Circle Calendar offers a new old path for the Jewish year — new because the design comes from our time; old because the Hebrew calendar is rich in cycles and only recently came to be represented in conventional tables or lines.

That fall, my cosmic sibling Jessie of School of Living Jewishly turned me on to a book called This Is Real And You Are Completely Unprepared by Zen Buddhist Rabbi Allan Lew. Listening to the audiobook quarantined from my parents’ basement, I was blown away by the genius of the “Days of Awe” holiday season: reenacting the journey of the soul through the world from birth to death. And especially Yom Kippur: a dress rehearsal for our death bed. A collective ego death. Annual collective transformation. It was starting to make total sense how the calendar has helped Jews be so resilient through uncertain and catastrophic times.

Meanwhile, I was beginning to feel oversaturated with new age culture, waves of conspirituality and tribal warfare on my newsfeed, and general sense of exhaustion from a multi-year roller coaster of transformation in a destabilizing society. I felt confused and unmoored, less connected to other traditions I had dabbled in, unable to reconcile all the bits of muddy ontologies I’d picked up in this healing session or that retreat, and an authentic desire to be more connected to my own tradition. I thought Rabbi Greenberg may have been on to something. I wanted to find ground and write about my experiences as a way of processing them, so that winter I parked myself for four months in a Mongolian Yurt in Mt. Shasta with no wifi and minimal human connection.


It was a much needed time to slow down, reflect on the chaos of the previous years, and come back to myself. In parallel I participated in my friend and teacher Sara’s eco-theology / decolonization course called Remembering For Life that invited me to read the first chapters of Genesis, get curious about the phenomenon of taking practices from cultures other than my own, and explore my family story. I didn’t know the names of any of my great grandparents until then, only vague notions of where they came from and indications that life was harder. Was it like Fiddler on the Roof? How did they relate to socialism? Zionism? Chasidism? What was it like living in extreme poverty under constant violence, or at least the threat of it?

Their names are Hyman Horowitz and Libby Soladucha, Abe Schwartzman and Ida Plotkin on my mom’s side; Sam Meyer Dun and Esther Dun (the second ’n’ potentially added at Ellis Island), Edward Feurstein and Pauline Konigsberg on my dad’s. I learned about the life and destruction of the shtetl that Hyman and Libby came from, that Ed installed the plumbing of the first synagogue in Staten Island, that Sam was one of eight children raised single handedly by his mother Bubby after his father mysteriously disappeared. That several members of Libby’s family were active in the Partisan Resistance against the Nazis in the forests of Poland, and that I actually do have family who lost their lives in The Holocaust. Also stories of child abuse, abandonment, theft and cheating, depression.

Hyman and Libby (great grandparents) with children Phil, Harold, Murray

I found myself eagerly seeking a connection with the past–devouring the history of pogroms (violent attacks on Jews in Russian Empire), intrigued by stories of the Baal Shem Tov (18th century Jewish mystic and founder of Hasidism), and hooked on Judaism Unbound podcasts (proclaiming that we are entering a golden age of Judaism where everything is up for re-imagination) and lay-of-the-land books like Here All Along. It was in this season that I started to peel back the layers of depth that Judaism has to offer, and better understand why many facets haven’t been accessible to contemporary Jews. I wanted to look at all the things I had learned before the age of 13, and re-learn them at 31 with more informed, widened eyes. Getting lost made rediscovering things anew that much more meaningful.

Disconnected from my typical spiritual social life of the Bay Area, I desired to connect with more Jewish friends more often; schlepping five hours to Portland for Pesach, where I got another stab at facilitating a Seder for friends that turned into a marathon love fest of laughter and magic. The only two friends within a 200 mile radius–Julia and Isaac–lived on a hill outside Ashland, so I made the trek up there several times for Shabbat. During my final visit, I expressed to Isaac (a real mensch, might I add) my fear that some of the practices I cultivated during this time in Shasta may not persist out in the “real world” that I was to return to. His suggestion was to create a solid Shabbat practice — get still, do things that bring me joy, try to limit productive/modern activities.

And so, for nine out of ten Shabbats in 2021, I turned off my phone at sundown and gathered with Jewish friends or family for dinner and a relaxing evening. Upon waking up, I’d keep my phone off, go out into nature, take a few drags of a spliff, and just enjoy this life for a few hours. Breathe, stretch, shake, reflect, integrate, laugh, marvel, notice, think, feel, journal, play. A personal ceremony. Time outside of time, to access the eternal. Sometimes I’d practice talking to strangers, or making somebody’s day. This practice became a tuning fork of sorts, helping me metabolize life from the last week-long cycle and get clear on the upcoming one. I’d typically turn my phone back on in the early afternoon, but sometimes would let it roll until Sunday morning for a total of 42 unplugged hours (or 25% of the week!). So good. A nervous system reset. Recharge. Gratitude. Love. It’s such a gift that there is a regular context to reconnect with the things that make one come alive, and tools and practices to create the conditions for however one uniquely experiences holiness.

Through observing the holidays and Shabbat more closely, I was really getting that Judaism offers a solid operating system for navigating existence. Somehow the rhythms of my life were even starting to match the holidays in mysterious ways. I’ll never forget when I caught Delta variant in summer 2021, there was one awful day when I could hardly move, let alone eat. My body destroyed. The next day I learned that it had been Tisha B’Av, a major fast day to commemorate the destruction of the second temple.

In the interest of ramping up my Jewish learning, I enrolled in Wilderness Torah’s Intro to Earth Based Judaism course, and began sitting for weekly virtual Or Halev meditations. And then there was the Jewish Psychedelic Summit (see videos). Over 1,500 Jews joined a virtual conference to learn, connect, and inquire. It wouldn’t be hyperbole (and is probably obvious by now) to state that psychedelics guided me back to Judaism — a trend that has been observed by a growing list of rabbis and is foundational to organizations like Shefa and Jewish Entheogenic Society which are aware that the mystical experience reliably induced by, for example, psilocybin has shown to bring people back to faith and prayer (in addition to caring about the climate change, breaking addictions, reducing anxiety and depression, cultivating more kindness and compassion, etc etc — they have a habit of revealing what we need to take care of in our lives), of which Judaism has the lowest rates of major world religions today. How about that 🤔

The kicker, if you ask me, is that Judaism offers a phenomenal support structure for coming down from the mountain top of a peak experience, a process known as “integration.” How do take the insights from the experience and process them into your life? In fact, that’s one way of interpreting the Torah — a whole nation just experienced God at Sinai… now what the hell do we do? The more I learned about Judaism, the more I understood how it was a culturally appropriate, time tested, integration structure to process life experiences from the sacred to the mundane, in a way that I had been struggling with through other traditions that I only had so much relationship/accountability to or attention span to really dive deep enough. Not to say they wouldn’t be effective; there’s just something unique about having the foundation of thousands of hours invested through childhood.

I had been (and still am) taking a serious break from big psychedelic experiences and the culture surrounding them, going so far as writing call-out essays on transformation (see first third of the piece), but wanted to stay on the pulse of this uniquely personal corner of what has been called the Psychedelic Renaissance (growing decriminalization, FDA approvals as breakthrough therapy, cultural revival). On a panel about the ancient influence of plant medicine on Judaism, I learned about the Biblical Entheogen Hypothesis that highlights striking connections between Jewish scripture and two plants that grow in the region: Syrian Rue and Acacia, that when consumed by themselves are not particularly psychoactive, but when in combination create an entheogenic (meaning “generating God within”) experience similar to ayahuasca. Was Moses or the other prophets working with these holy plants?

It seems plausible. Syrian Rue has been used medicinally and ritually in cultures across the Mediterranean and Middle East —burned as incense to ward off the evil eye, inspiring tales of magic carpet rides, treasured amongst Sephardic Jews in midwifery. Acacia wood, central to Egyptian and pre-Islamic Arabian mythology, is mentioned throughout the Torah, namely in the construction of the Ark of the Covenant (housing the 10 commandments) and the Tabernacle (the first temple), and a likely candidate for the Burning Bush. Several species of Acacia that grow in the Negev and Sinai contain DMT — a naturally occurring psychedelic compound.

Moses with the Burning Bush, by Marc Chagall

One month later, I paid a visit to a man in the woods who had provided some emergency relationship support the previous year, and was surprised to open his refrigerator containing a mason jar with Rue written on it. He shared that he had been experimenting with this hypothesized plant combination of Syrian Rue and Acacia (a combination he called “Rue”), which was similar to ayahuasca (commonly associated with a “feminine” plant spirit essence) but had a distinctly “masculine” or father-like quality to it. Rue seemed more clear, more direct, more powerful.

As the story goes, upon asking the plant spirit in ceremony “what is your name?”

The spirit responded “I have many names. Names are things that are given to us.”

“What name resonates with you the most?”

“Elohim.” (one of the Hebrew names of God)

The man in the woods later received a vision to bring together a minyan (the quorum of ten Jewish adults required for certain religious obligations) with the intention to connect with God via this particular brew of sacred plants, that might be relevant to the origins of our ancient tradition. The experience would be offered as a gift. My soul perked up and creative juices started flowing. One thing led to another and on the full moon in Elul in the shmita (sabbatical) year, we gathered for a Shabbaton (educational and celebratory Shabbat retreat) that was either the first of its kind, a long lost tradition resurrected, or the tragic climax of Raiders of The Lost Ark.

I’m happy to share more of the strange and incredible story upon request, and maybe someday will collaborate on a deeper cut of a saga that is very much still emerging. In short, for me The Minyan was the best Hebrew school class ever, meets mens circle, meets initiatory experience (the Bar Mitzvah I never had?). A giant leap forward in my Jewish learning, identity, faith and devotion. And one of the most challenging experiences of my life.

It felt like I was lying on the ground, surrounded by a circle of ancestors, and then the doctor–or what I experienced as a male being of light–rushed into the room, took a knee, and stayed by my side for hours, doing nothing but holding love and space for my process: wrestling with my infinitely wandering mind all night long. I was forced to look at that which I didn’t want to look at. Namely how living in my head (as a coping mechanism to protect me from the pain of being of being exposed as inadequate) wreaks havoc on my body and takes me out of connection with the present, even when that present is of divine nature. After years of countless peak experiences and sporadic practices in service of “working on myself,” I decided it was time to see a therapist.

Some additional, personal headlines from the experience:

Judaism is home. I love being Jewish. I love fellow wandering, wondering Jews.

This was Judgement Day: stepping into a room wth God. How am I really doing?

The base level soundtrack of my life is: “The world is scary. People are scary. Love is scary.”

Anxiety is killing me. I will not pass this on.

History is speaking to us. Every thing existing today has an important message.

Let my people grow!

There’s holiness in the taboo.

Importantly, Rue was like one course of a celebratory feast–nourishing, and far from the only medicine of the weekend, which could be found in brotherhood, ritual, prayer and nature. Singing, storytelling, learning, questioning. I don’t think any of us will forget chanting the Shema together, or laughing in unison at one friend’s observation of Jewishness throughout time as a never ending vibration of “oy yoiy yoiy yoiy yoiy..”

We accomplished our mission, agreeing to wait and listen for the next set of instructions. I thought a lot about how these plants might have an important role to play in a troubled world. How we had to run pretty much as far into the wilderness as possible (rainforest shamanism from halfway around the world) to receive these gifts. What’s the deal with there being trauma-healing medicine in the ground of the place on Earth that has born witness to millennia of violence and hatred, and nobody is talking about it? If Rue wants to share its medicine with the world, what can be learned from the fraught globalization of ayahuasca? How to synthesize biblical prophecy and contemporary revelation? What is my role in all of it? Rue is now a character in my Jewish story and will thread through to Parts II and III.

In the rich Jewish holiday season post-minyan, I’d go shul hopping over to LabShul for Rosh Hashanah, up to the Catskills borscht belt for a Sukkot rainbow gathering where the man in the woods and I shared the Rue story with the neo-Hasidic community, and down to 770 in Crown Heights (home of Chabad HQ) for Simchat Torah. It felt like a festival circuit; I didn’t realize how much variety and depth there was in how others observed these holidays year after year. So much satisfaction in moving my vocal chords to songs from childhood, grateful for the drilling that etched the words inside my heart.

Jamming in the sukkah at The Teyva community in Woodbourne, NY

Most notably: I started reading Torah. Wait a minute — you mean there’s an ancient book, still read ritually and communally, with timeless teaching stories on how to live well? That influences the lives and cultures of nearly half the world’s population, and as someone who considers themselves a voracious reader, writer, student of history, and lifelong learner–I’ve never bothered to open it? Every week there’s a different energy to tap into? That some believe it’s the word of God, others write it off as Jewish mythology written by extremely wise ones, still others are afraid to touch it? That it can be read on four different levels (Pardes —literally, hinted, interpreted, mystical)?

I gotta check this out! I found pleasure in peeling back the layers of foundational Western civilization source code. Understanding the stories and details behind pop culture references. Seeing parts of myself in Avraham (iconoclasm and hospitality), Joseph (black sheep, sensitivity and fluidity), Moses (denouncement and leadership). Noticing how the themes of the parsha (weekly Torah portion) showed up in my life. I wondered, why isn’t the Torah consistently ranked in Time’s inventions of the year? Can the startup or business world use a a kind of Torah?

Between my Chavruta (study group) from the minyan, watching biblical cinema (+ Noah, Exodus, Ben Hur), buying a Joseph-like coat and having technicolor dreams... my life was starting to look pretty Jewish. Attending Jewish yoga classes. Sampling a different NYC synagogue most Fridays. Incorporating more prayers into my day to day, such as modeh ani — the first words one utters upon waking, essentially expressing thanks for living another day with and committing to serve life. Further embracing the aspects of my identity that seemed relevant to a Jewish person: writer, ethicist, wanderer, thinker, mystic. Gleefully sharing all that I had learned with fellow Jewish friends. Turns out I was far from the only one getting curious about their roots. Something was certainly in the air…

While at a Sukkot gathering in Woodbourne NY (Catskills), a new mystery wrestling friend Elchanan and I were chatting about Judaism and festivals when he said pointedly “dude, you should go to Mid-Burn! (the regional Burning Man that takes place in October in the Negev Desert) and it felt as if somebody had punched me in the stomach. I was overcome with this nauseous feeling of ughhh, nooo, I can’t have my life take another radical left turn again right now… But it planted a seed, prompting me to think about what might be in store if I were to visit this hyper-relevant place at this stage of my adult life, on my own terms.

I was relatively nomadic, and wondered where in the world would be best for me to go next, sensing that I wouldn’t have so much flexibility forever. Israel was a place I had high energetic and legal connection to, and a moderate amount of social connection to, yet I had hardly spent any time in, save for those two week-long trips at 18 and 24. Trusting that if I was feeling the pull to Israel now (only just opening up to tourists post-Covid), then I’m bound to meet others I’m meant to meet who are getting the same call.

When my family moved out of our childhood home last fall, I started writing a Goodbye letter to the town of Armonk. I wanted to highlight the connections between achievement culture, materialism, mental health and resilience; while offering a vision of a more beautiful community of education, healing, and service (including a plug for religion as a resilience practice). Not only was it the most read essay I had published that year, but I wound up meeting with three local rabbis in 36 hours who wanted to discuss it! Feedback I received from them and other readers included: “I think the questions and topics you are struggling with are some of the most important of our lives.” “Thank you for articulating what many of us can’t!” I not only read once but THREE times [including aloud with my boys].”

Then last winter solstice, I participated in my second Circular Time reflection exercise. I was just getting hip to the cycles and how religions like Judaism make clever use of the calendar to schedule rituals in time, at all time scales (from breath to death — day, week, month, year, 7-year shmita, jubilee, lifetime). A friend and collaborator Naomi and I were wondering what it would look like to get clear on our intentions for the upcoming year and schedule them into our cycles. Better yet — what if, like how prayer books are designed to focus our attention on what matters most–we made mini booklets of personalized content that would be most useful for us to reference at different times on these cycles? (We were definitely not talking about what a new religion would look like 🙈)


I’d wind up prototyping a number of Life Maps: a physical and digital expression of what is most important to me. A pocket sized, foldable, ritual artifact to guide my attention back to what matters most. A context to regularly slow down, unplug, reflect and recalibrate. Something more valuable to spend time with than my phone! A precious memento that captures what is authentic to me in this phase of your life. A very Jewish invention if you ask me. I’ve since made Life Maps for new moon cycles, a new project, a party, my pilgrimage, a job interview, as a gift for Burning Man, an offering for Sukkot, a workshop for college students.

Thinking about how much more meaningful the holidays had become in the past couple of years, I decide I wanted to prioritize participating in more of the Jewish holidays (including lesser known ones like Tu Bishvat, Shavuot, Tisha B’Av, Tu B’Av), as well as some personal holidays I had created (Giving to Strangers, to Nature, to Body; + the anniversary of my wake up call in India). Plotting them all on a circular calendar gave me a sense of the different themes I might be engaging with each month as I approach the holiday centered around a specific life theme:

The Life Map (aka Soul Map, or Devotional Booklet) unexpectedly became a primary creative project for me this past winter (see recap), serving as a vessel for fresh ideas moving through me. With this new project, I had a strong intention to attune to the process in a new way (I’ve started dozens of things — what have I learned from those experiences?): to go slow and see what wants to emerge (inspired by Sister’s Business Birthing Handbook: A Theory of Trimesters), vs. try to rush and control the outcome. What does this want to be? At some point it became clear that this was a sort of religious or spiritual tool, if not a personal development tool, which are all kind of the same thing. I wondered what I could learn if I went to a place where people have been crafting such tools for thousands of years. This became a primary justification for why it made sense for me to go to Israel in the spring of 2022. A research trip!

Finally, just before Pesach, I was crashing at my friend Greg’s in Miami and picked up a dose of politics in Capitalism and The Jews. I was shocked realizing the connections between a highly educated diasporic merchant minority enjoying disproportionate success in capitalist societies, anti-Semitism and ethnic nationalism. How the Jewish people are a relatively elite dense global mycelial network, and the unique opportunity that affords us to take meaningful action in service of a more beautiful world.

Vibing on Moses and my perennial kvetching about achievement culture, I’d write the following musings on the 1. Passover Story as it relates to 2. Personal and 3. Collective Transformation, from the perspective of somebody who grew up close to the heart of empire:

In hopes of a better life for their posterity, our forefathers sent us down the main stream (1. Nile | 2. Achievement treadmill | 3. Neo-liberalism)

Cozied up in Pharaoh’s court, disconnected from Earth/justice/spirituality-based culture, and the pain of life on Earth (Growing up in palace | Assimilation, dissociation | Late stage capitalism)

Until something pulls on our heart strings, and we can no longer stand idly and ignore the dissonance within and suffering without (Killing the Egyptian | Awakening | Systems collapse)

Retreating into the cultural wilderness, to learn who we are and what we’re here to do (Burning Bush | Initiation | Collective Sensemaking)

Returning to the palace, leveraging our unique position in the web of life to speak truth to power and act (Confronting Pharaoh | Labor/resource/lifestyle transition | Systems Change)

Freeing ourselves and our people from the hypnosis of individualism, separation, fear, distraction, materialism (Crossing Red Sea | Servant leadership | Collective liberation)

Into the mystery, towards the promised land (Sinai | Faith | Emergence)

That’s my spiel! The stage is now set. A clear returning direction has been charted. It is from this moment in my Judaism journey that I will make my way to Israel and Palestine in mid-May 2022. That story is the focus of Part II. I was at a ripe point in my Jewish learning to take some time in the holy land for an open-ended, self-directed pilgrimage (or, what I like to consider a personal Birthright 2.0).

I set out to simply write about my time in Israel and Palestine. Then I felt inspired to include more on the arc of my relationship to Judaism, in an age of physical and spiritual exile. Later I could see the connections between the holy land, Judaism, and the various streams of work and life I’ve been focused on: technology, ethics, systems change, education, culture, plants, healing, resilience and more. I will do my best to reconcile these themes in the coming parts.

Aaaaaamen 🙏🏼

I’d love to hear your reactions to Part I! Resonance, questions, feedback. It’s really nice to know when somebody made it to the end, is curious about this, challenged by that. I’m here to chat about it!

Part III will be more commentary than storytelling, so I’d also love to know what questions you are thinking about. Contact info on my website:

If you haven’t already, subscribe to my Substack to make sure you are notified when future writing is published.

Special thanks to those not named in this piece who were influential in my Returning journey pre-pilgrimage: Bentzi, Yaakov, Osher, Danny, Ganga, Jem, David, Pam, Becca, Jeff, Alexa, Ben, Mathew, Zev, Aaron, Daniella, Melissa, Scott, Adam and many more.

Chag sameach! (I published this on the final night of Chanukah, 5783)

Sukkot in Joseph Jacket