My Jewish Story Part II: Birthright 2.0🚶🏼🛐

Andrew Murray Dunn
41 min readFeb 5, 2023


This is the second part in a three-part series on my recent pilgrimage to the holy land in the summer of 2022, set within a larger and ongoing story of my journey wresting with my relationship to Judaism. My intention is to better understand and enliven my own story, archive the rich experience I had, and share what I’ve learned outwards.

Preaching at sunrise after Lag B’Omer in Joseph Jacket

Table of Contents:

  • Part I: Wandering in Exile (My Judaism) —This part touches 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 chronicle the religious, political, and educational elements of the pilgrimage. My direct experience > analysis.
  • Part III: Meta-Teshuva (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 development 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 left unsaid; countless special moments and people who make up the story. I’m saving most of my commentary for Part III.

You do not need to have read Part I to appreciate Part II, though it sets the stage like Genesis does for Exodus. Part I 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.


Part II: Birthright 2.0

This part has three sub-sections: Religion & Spirituality, Israel & Palestine, and Personal Learning.

🕍 Religion & Spirituality

By the spring of 2022, I had it in mind that it I had done enough Jewish learning to prepare for a “Birthright 2.0” i.e. instead of short and touristy, surface level and nationalist propaganda-filled trip, I wanted something long and slow, open ended and self-directed, rich and soulful. A proper pilgrimage. To treat it as I would a ceremony, with requisite preparation and integration time. A context for learning and healing and growth. I especially wanted to tap into a vibe of “no agenda” so that I could dance with life in present, courageous, and creative ways that I had done in previous solo travel experiences. I knew that I often found holiness at the intersection of no agenda and open heart.

I actually deliberated going to Israel for months — there was an unexpected health challenge, financial uncertainties, wondering if going was just another escape, lacking a real welcome party upon arrival… I had to laugh when I found myself one morning praying to God for clarity on if I should go or not! Once I got the medical green light, I bought the one way ticket and started to feel into what this was really all about.

Instead of telling you, I can show you! This is the Pilgrimage Map I designed and printed before embarking (now marked up with notes, which are fairly private but hardly legible), which helped set intentions, keep me on track and reflective during the journey, and process the experience following:

Side A : Intentions. See Canva for closer look
Side B: Integration. See Canva for closer look.

This map consists of a vision board, collage of people relevant to the trip (in this case, people who had been influential on my Judaism journey to date, and those who I planned to see on the trip), key questions I wanted to ask, a guide for how to get into more of a flow state while traveling, a short list of Hebrew words to learn, a guide to local flora and fauna I wanted to look out for, a fire extinguisher page (what to do if feeling down or stuck), and then pages for notes on the project, learnings, special moments, changes I want to make in life upon returning home, and things I’d like to do differently on the next trip. A living document that is now a prized possession, amongst a stack of other maps I’ve made for various occasions.

Sure, there were plenty of question and topics I wanted to double click on, people to look up and ideas of what might happen. But to be honest, I had no real itinerary–let alone a place to stay on night one–just a strong sense that this was where I was supposed to be. I wanted to go deeper into tradition. To get closer to the essence of Judaism. Sara offered that it would be a great place to ask the types of questions I’m asking at this stage of my life. Simon explained that everything is the same as it ever was–the violence, the portals, the mystics in the woods. He recommended letting the land be louder than anything on top of it. And to eat lots of shawarma.

The main story here is of my intimate exposure to religious life, which was heaviest in my first few weeks out there, particularly around the holidays of Lag B’Omer and Shavuot.

Israel is a land of question, stories, paradox. Shortly after arriving I spent the weekend on my Chasidic friend Yaakov’s moshav (village) outside Jerusalem with family and friends. I knew things were off to a special start when my first night’s sleep was interrupted by what I thought was a pet climbing into my bed, but awkwardly realized was little Shira!

Yaakov had taken me for my first oceanic mikveh on the Big Island in 2017

This was my first fully “immersive” Shabbat — 25 hours of prayer, food, learning. Deep conversations relating the parshah and counting the Omer (verbal counting of each of the forty nine days between Pesach and Shavuot) to personal and collective events. My first few weeks would be full of these experiences as I hopped around Shabbat meals, Yeshivas, and introductions to kindred spirits. First impression was WOW Judaism goes way deeper than I realized. I had no idea there were libraries upon libraries of books, commentating on commentary on commentary on what is believed to be the word of God, the prophets who communicated with Him, and the sages who gave their lives to studying and teaching this wisdom. Physically impossible to ever know it all.

As somebody who values learning and wisdom, and had only just cracked open the Torah for the first time, I was moved by how central learning is to my tradition. I knew that Jewish learning was a thing one could do if they wanted to become a Rabbi or something, but I neither realized the extent to which learning remains a critical process throughout adulthood for more religious communities. I love learning, and have a knack for pattern matching within and across contexts. I didn’t know I could spend hours per days learning and pattern matching forever, and that would be considered a mitzvah to be celebrated. What would become available if I prioritized it?

I also didn’t know there’s a place on Earth where I could walk around all day asking the big questions I have about life, and have wise students and teachers give me their ear and heart left and right. Somebody referred to the city of Jerusalem as “torah cafe.” I called it a coaching festival. On my first Shabbat, it felt like I was on a learning crawl — a little bit here with these folks, a touch of solo there, a little more with that guy. It wasn’t long before I learned that I could just drop into any Yeshiva any time and learn, alongside all the young boys from Brooklyn who had never heard of Westchester. If I wanted to, I could even spend weeks, months, or years there. It became cliche to meet someone who had also just come for a visit and wound up staying.

One week into the pilgrimage, on the 33rd day of the Omer (a Kabbalistic holiday known as Lag B’Omer in which people light bonfires to commemorate the immense light that Rabbi Shimon bar Yochai introduced into the world via his mystical teachings), I had a powerful moment of religious homecoming that made me seriously consider if I was going to hit “Subscribe” on the whole shebang — move to Israel, check myself into Yeshiva, get matched with a partner and build our lives there…

The day began with an Old City digital detox + microdose adventure to turn up the volume a little bit on my Jerusalem wanderings. I prayed at the Kotel (Western Wall), got lost in the alleyways, talked to a shop keeper about the Quran, negotiated a scarf, sat and prayed in a church, agreed to wrap teffilin only if I could ask all the questions I had about it (omg, a daily ritual for binding mind and heart with action?!), and witnessed a thousand military and police personnel gathering to celebrate new recruits.

When I returned to my phone in the late afternoon, feeling full from another “best day ever,” I received an invitation from an Orthodox friend to join some buddies for a Lag B’Omer celebration. At first I politely declined, but rose to the occasion for what would be one of the more memorable nights of my life. A journey of fire, song, dance, prayer and storytelling on a ridge overlooking the Mediterranean on the horizon, where we discovered all different types of wisdom and support for each other. Somebody called me “Rabbi.” I felt moved to practice some Hitbodedut (meditation practice of talking Hashem in nature) and shed some tears at the realization that hurt people hurt people. I’ve been hurt and I keep hurting people. I have compassion for myself. And I don’t want to hurt anybody anymore (and, show up better for repair when I inevitably do).

Lag B’Omer in Jerusalem

🎙Here’s a 10min audio recording of the full story of the next few paragraphs

As the sun was coming up, I was invited to tell my story of reconnecting with Judaism. Speaking against a picturesque backdrop of the hills, with a low cloud cover beneath us, I glossed over much of what I have shared in Part I, honing in on the Rue saga, since it had often been a crowd pleaser when I told it. As I was getting to the Elohim part of the story (a particular chills-giver), all of the sudden we heard an ambient rumbling sound.

“Anybody hear that?”

“Huh. I don’t think it’s a plane...”

“Sounds like a space shuttle is launching…”

One of the guys then directed our attention to the horizon, where we saw a massive cloud of white smoke growing taller and wider. Mushrooming.

“Ummm, that’s a nuke boys.”

“We should get inside!”

“Shema Yisrael….”

“I think the world just started.”

This was the most awesome thing I had ever seen. Larger than life. Smoke thundering and billowing outwards in all directions. It felt like an assassination of Franz Ferdinand moment; like there would be a time before the nuclear weapon had gone off in the Middle East, and a time after. Did this have something to do with Ukraine? Syria? Iran? Was it a misfire? Fuck. Do we have gas masks? Why did I leave my big backpack in the city? Is this the end? Are we the only people watching this? Should we document and share with media outlets? We could sell it to fund that thing you were talking about last night? Blessings blessings blessings for everyone…

That was some of my process, at least. A couple of the guys were cool as a cucumber, accepting the moment as possibly their last. I turned on my phone and couldn’t find any chatter about it on Google or Twitter. At some point, the smoke started to dissipate and drift south, and we wondered if perhaps it had been a volcano in Greece or something. I later learned that Israel had plans to do some Iran testing, but that wasn’t scheduled to start for another week. The next night at Shabbat I happened to meet a big scary looking IDF (Israel Defense Forces) General and asked him about it. He kind of shrugged and said some words that were unsatisfying to my need to understand. I guess we’ll never know.

Whew. That was a big day to process. Friends had been saying “welcome home!” and it felt way more authentic than other spaces (queue montage to arriving at Burning Man, peyote ceremony, play party ). I felt belonging and pride. Like I was starting to get “it” after years of intellectualizing and dipping my toes into Judaism. Something big was clicking in. Am I about to become religious? Is this my path?

It made sense to me that in the arc of my lineage’s story, there would be a time of returning to tradition, and I would be one to naturally participate in that process based on my seeking nature. I would met countless Jews with the same classic story: they were meditating in India (or more recently, Peru), got the hit to come to Israel, and realized everything they were seeking outside Judaism was contained within; or they were hanging with indigenous elders who reminded them of having their own culture and land, so get to it. It seemed like now was a particularly exciting time to be back — it’s a miracle after 2,000 years in exile! Everybody’s returning! It’s all happening!! Tell your people to come now.

I wondered, what are the dynamics at play that had me wandering outside of Judaism for over a decade before I would even consider becoming more religious inside? How is it that out of thousands of those who grew up like me (reform and secular in the states), I don’t know a single person who has done the returning thing?

The religious adventures continued, as fellow adventurer Becca and I rented a car to travel the North for a week and a half, focused on the mystical city of Tzvat. We networked with Kabbalist artists, followed the trail of Rue wisdom keepers, met Rabbis with oral secrets, traded notes on our respective journeys. It was there I decided to start checking out Yeshivas. Yeshiva means “to sit.” It’s an adventure of the mind. At a Chabad Yeshiva I davened (recite the prescribed prayers in a Jewish liturgy) several times a day, practiced giving drashes (interpretations of text), read all 613 commandments and the Sefer Yetzirah, and came closer to believing in Revelation, prophecy and Moshiach–partially because of everybody’s constant excitement around these ideas (including claims of being able to trace their rabbinical lineage 80 generations back to Moses), but also because I concluded that something so profound like a collective experience of God must have happened in order to support the meticulous knowledge transfer and unfathomable resilience that the Jewish people have cultivated over the last three thousands years.

Shavuot sunrise at the Kotel with Elena and Danny. This song was on repeat at the time

There was a period of a couple of weeks where I was nervous to speak with friends or family back home because I wasn’t sure how they would react upon learning that I was becoming more religious and considering orienting my life towards Israel, where I had finally found community that put deep meaningfulness and quality of life at the center. That showed up for each other, lived on miracles, and enjoyed a strong sense of shared reality. Days of prayer, gathering, storytelling and personal growth vs. a bullshit computer job at WeWork in between Instagram, Netflix, Equinox. Where have you been my whole life?

I was identifying as Baal Teshuva-ish, Baal Teshuva meaning “master of repentance” but often translated to “master of returning” or “master of balance.” Somebody who strayed away from the path, and then came back (turns out “ to sin” means to stray away from intention). Baal Teshuvas have a special place in the Jewish community, because they bring childlike curiosity and wonder, in addition to gifts and expertise from the secular world. There was an allure to it–religious people would roll out red carpet to newcomers like me. I saw myself in Baal Teshuvas, but wasn’t fully convinced yet, weary of diving into things too soon. Slowing down has been my main life lesson in all domains.

One of the things drawing me in was the simplicity of it all. The modern world demands us to constantly make choices. It’s chaotic and overwhelming. Choose your own adventure! But really, here’s the main stream, and if you don’t like it, well, good luck because the alternatives are scary and there’s not much helpful guidance and support out there. I was fascinated and comforted by religion’s radical simplifying of life. Somewhere along the lines I had adopted the belief that a good life was one of full freedom with infinite choice, but my life had become increasingly scattered and disorienting. Different names and identities, distributed homes and projects, constant anxieties about what’s next. Paradoxically, in desperately trying to escape the modern matrix, I would find that designing a life of maximum time, freedom, and choice was its own form of slavery.

Another piece was the cultural coherence. The sages say this, say that. There’s a story for everything. Everyone is dancing to the same music. It’s like the prophets and sages are eternal influencers of great esteem. Sure, some dabble in worldly arenas of business and science and academia, but once they clock out they enter a world where everyone is on the same page, marching to the same beat. And it sounds good. There’s less uncertainty. And when there is uncertainty, it is met well. How do you make decisions? Pray! Ask a Rabbi! They’ll help you arrive at the answer for yourself. With the whole community bound to a shared ethics, conflict seems to get processed more easefully.

At the same time, there were plenty of things that gave me pause in Yeshiva, and orthodox Judaism as a whole. The early 20some boys, cracking off-color jokes about marginalized peoples, burning through junk food (now I know who is keeping Coca Cola in business) and single-use plastic because “Moshiach is coming, so whatever.” An odd juxtaposition of serious spiritual learning, and frat house shenanigans. Lots of knocking “confused American Jews” (referring to queer people) and “what’s happening on college campuses” (referring to social justice activism). And then the strict gender roles within families, anti-Palestinianism or ignorance of the occupation, and other bits of social conservatism that were newer for me to come into contact with. Lots of tensions between my values and alternative lifestyle, and the rules of orthodoxy. What would I have to give up? How would that impact my mental health? How would going deeper impact relationships with friends and family? Am I just running away from the grips of the main stream?

And then, as fast as this whole exploration came in, it faded away. I made a last minute decision to attend an ISTA Festival (many doors to the same room!) and afterwards move on to Tel Aviv where there was little religiosity in the air. From then on, I had a hard time re-connecting with that awe and emuna (faith, innate conviction, a perception of truth that transcends reason) that I experienced during the first chapter of the pilgrimage. Was it no match for the familiar pleasures of secular life? Did I succumb to fear of what others might think if I became too Jewish? A Baal-Teshuva friend Jacob explained that when Adam and Eve were kicked out of the garden, God placed two flaming swords at the entrance. The Torah is the garden, and the swords are all the weird customs that enable us to access its holiness (reminds me of how the dust of Burning Man or purge of ayahuasca prevents many from trying it). Was it young parts trying to protect me from the pain of feeling humiliated?

Oasis near Masada. Here’s a song that reminds me of this chapter in Israel
Fellow travelers in The Shuk
Summer Solstice at Ein Gedi — nature reserve near Dead Sea

Though it still felt important to spend more time in Yeshiva, to bolster my foundation while I was here and had the time. After nearly signing on to a month-long program at Conservative Yeshiva, I’d find a match with a small Yeshiva in Jerusalem called Simchat Schlomo, which described itself as “out of the box” orthodox in that they integrated lots of music and art, inspired by the late musician Schlomo Carleabach. Because I showed up in between cohorts, I essentially had private lessons with the Rabbi, which was super helpful for mapping out all the different threads of learning I had been exposed to. I got my hands dirty with some Gemara (talmud), examined the arc of a prayer service, debated the mitzvot…

I was never much of an academic type

Some of the questions I kept spiraling back to included:

  • What makes a good student? What makes a good teacher?
  • How to simultaneously live in the holy land, with pride in the miracle of a Jewish state, while standing up against injustice to Palestinians? How does the occupation jive with Jewish values?
  • What is truth in a land of such divisive and charged stories? How to connect with it?
  • How to hold the supernatural events described in the Torah, in a disenchanted secular world that claims it’s all just Harry Potter?
  • What’s the deal with mitzvot related to sexuality and gender?
  • How can I appropriately share and adapt Jewish ideas to my professional context? How can Judaism and the Abrahamic traditions of this land inform a more beautiful culture of entrepreneurship?
  • What are visions? How to be in right relationship with them? What does Torah/Talmud/Kabbalah teach about how to create in the image of God, i.e. to bring ideas into form in a beautiful, ethical and equitable way?
  • How to relate to inspiring Rabbis (and other leadership figures) with a controversial past?

I’ve spent time with many foreign cultures and spiritual communities, but never dipped my toes so far inside one, that is technically mine, but is vastly different than what I grew up with. It was such gift to have a foundation from which to access deeper layers. And to be on that journey with homies from the states. Feeding my thirst for meaning, community, history, understanding. And food! Deep bow to muhallebi, knafe, lachuch, kubbeh, and chraime.

I would leave Israel with more questions than answers. They say two rabbis, three opinions. Whatever is true, it was special to be in the land that gave rise to my people’s stories and culture. True to my namesake, Avraham spent his entire life searching for Ruach Elohim; an ongoing journey of searching for what’s real and true. The greatest destination is the continued search.

In Part III, I’ll share more thoughts on where I’m at today, what I see as the evolution of Judaism, the role of prophecy and Moshiach, anti-semitism and money and much more juiciness.

My first knafe!

🇮🇱🇵🇸 Israel & Palestine

I’m still forming my views on this topic. Here’s my story, which only scratches the surface of what I learned. I will attempt to share more analysis in Part III, acknowledging the tragic futility of the task.

I also want to signal my respect and compassion for those more intimately involved with Israel and Palestine than I am, no matter what side, especially friends and family who have or do serve in armed forces or have been impacted by violence.

Whew. I couldn’t spend months in the holy land without facing politics and justice. Well, actually, I could–I almost did–as many Israelis and American Jews are wont to do. How to broach such a complex topic in a safe and inviting way, amidst such a charged atmosphere and relatively personal knowledge and experience? I’ll try to speak from direct experience, ask questions instead of making absolute claims or placing blame, and explain my choice of certain words.

This poster is a remix of “Visit Palestine” by Franz Krausz

Starting with why I’m using the word Palestine — it’s neither an endorsement of a two state solution, nor a rejection of Israel’s right to self determination. It’s more like when I was physically in the place in which a majority of humans there refer to as Palestine (in addition to all but 10 nations on Earth), then that’s what I’d call it too. Further, the reality I experienced in Palestine was sharply distinct from my experience of Israel —from flag and language to architecture and culture (and, lots of similarities too).

A little more political framing basics (from Wikipedia): it’s important to know that the State of Palestine is governed by the Palestine Liberation Organization (PLO) and claims the West Bank (including East Jerusalem) and the Gaza Strip as its territory, though the entirety of that territory has been under Israeli occupation since the 1967 Six-Day War. Israeli settlements are civilian communities inhabited by Israeli citizens, exclusively of Jewish ethnicity, built on lands occupied by Israel. There are 144 Israeli settlements and over 100 Israeli outposts in the West Bank, which the international community considers illegal (though Israel disputes this), for a total of 770,000 Israeli settlers living in the West Bank.

My political curiosity wasn’t not there, it was just subordinate to my other interests in religion and spirituality, ethical entrepreneurship, seeing friends and having novel experiences. To give you an idea of how much of a blank slate I was, when a family member asked me not to go to the West Bank, I wasn’t really sure why not, or what the differences were between what had unfolded in West Bank and Gaza over the years. I had some general unease about Israel, and previously lived with friends leading Palestinian solidarity groups, but never bothered to understand what was actually going on. Very easy to ignore something uncomfortable happening on the other side of the world. And in my first couple of weeks bopping around Israel, it was easy to forget about, since it’s not regularly discussed in secular or religious society.

My first exposure came after taking a “dual narrative” tour of the old city (led by a Palestinian Arab man and an Israeli Jewish man, in which I learned that one could take a ~45 min bus from East Jerusalem to a city called Ramallah, a cultural and economic capital of Palestine. That night I mentioned to friends and travelers at the hostel that I was thinking of checking it out. Israeli Jews were generally concerned for my safety and cautioned against going deep into the West Bank, while foreign travelers and one Palestinian woman were like “Dude, just go, it’s fine. Well, it’s a fucked up situation, but you’ll be fine.” That sharp juxtaposition made me want to know more for myself. So I downloaded a few podcasts to get up to speed on the history of the [conflict/occupation/whatever word makes your nervous system relax] and caught the bus across the Green Line.

I mentioned that one intention for the broader pilgrimage was to tap into a certain flow that I had occasionally experienced while traveling solo in the past — a quality of curiosity, serendipity, learning, and connection that builds to a euphoria of best-day-ever omg-I-love-life vibes. The key is almost always putting my phone away, walking slowly without a destination, and talking to strangers. Who it turns out are mostly wonderful. To quote the late Jewish sage Ram Dass, “Everybody is God in drag!”

On the first leg of my missed-the-last-bus way home from my first visit to Ramallah, the kids in the van wanted to know “are you for Israel or Palestine?!” On the second leg, I met a man who told me he was praying to Allah one day when Jesus appeared and changed everything.

The first stranger I spoke to at the sweets store wouldn’t accept payment because it was my first time in Ramallah. The second stranger I spoke to insisted on serving me tea on his balcony. I was struck by how welcomed and safe I felt, and how distinct the culture was from Jerusalem just minutes away. I had it in mind to hunker down in a hookah bar for the afternoon to do some reading and reflection. I thought about what it means to travel ethically to places like Puerto Rico (where I’d lived earlier that year–thinking about educating myself on history, interacting with locals) and Palestine where the impacts of colonization are more recent and tangible. And what it would look like to participate in or lead trips that incorporated both the mystical and political. I was feeling proud of myself for making it here, with more context and sensitivity.

Or so I thought. Feeling elevated by the shisha and caffeine, I started bouncing around the lounge to strike up conversations with folks here and there. I was in a rich dialogue with two women in university trying to learn their perspective, feeling like I was doing a good job at building connections and trust across lines of difference.

All of the sudden the manager came over with a stern face to ask me for my passport. My heart started beating fast — I wasn’t sure if my safety was at risk, or what could unexpectedly erupt here. I wanted no trouble, but also felt some resistance to authority, and didn’t feel comfortable handing it over to him without understanding why. The manager didn’t speak English, but the girls exchanged some words with him and gave me a reassuring nod that permissioned me to hand over my passport. He took a quick glance, returned it, and walked away.

Big exhale. The girls then shared that a customer had complained, flagging me as a potential Israeli spy because of how I kept moving around to different tables and asking lots of questions. Things were especially tense that week on the heels of the killing of Palestinian journalist Shireen Abu Akleh by an Israeli solider. A low impact lesson in sensitivity, something I keep having to learn again and again.

About one month later, cosmic sib Jessie nudged me into joining a Breaking The Silence tour (an organization of veteran soldiers who have served in the Israeli military and have taken it upon themselves to expose the Israeli public to the reality of everyday life in the Occupied Territories) in the South Hebron Hills to learn more about the nuances of the occupation. While parked outside of a settlement, we watched a Palestinian man wandering a field get detained by two soldiers, tied to a chair in the baking sun to be “dried out” as our guide explained. Apparently a nearby settler had called the soldiers, who operate as a private security force for the settlement, to say they didn’t like this man walking around that land, which may have been completely legal. Moments later, a loud settler barged into our group, shoving his phone in our faces while to livestream “radical American college students from New York and Miami here to sabotage the State of Israel!!!!”

Palestinian Poet Mahmoud Darwish at Yasser Arafat Museum

That was about it for the first six weeks. I might have thrown on another podcast here, a late night conversation there with another Baal-Teshuvish traveler about how those hippie looking Jews we saw were probably settlers and why don’t we talk more about it. I had reached out to a Palestinian activist friend for more connections, and another wanted to connect me with somebody on the ground, but they didn’t pan out for whatever reasons.

Then just a few days before I was planned on leaving the country, I got connected with a Jewish American Israeli woman, who after going on Birthright and immigrating to Israel was radically changed by what she witnessed in the West Bank, and then moved to live and work in Palestine, supporting many social entrepreneurs for over a decade despite the fact that this is illegal according to Israeli law. I bussed over for what I thought would just be a network-y dinner, but wound up receiving a six hour download on the history and state of things from her and a Palestinian Canadian friend, a filmmaker working with Mondoweiss: a progressive Jewish publication that covers Israel/Palestine. Plus an invitation to come spend some more time in Palestine — they had a free apartment for me and motivation to show me around and immerse me (curious American Jew) in what they seldom get the chance to do, as Israeli Jews are prohibited from visiting, and Americans are generally scared, scornful, indifferent or unaware that traveling there is an option.

That Shabbat, I ditched my routine Jewish plans to go out with these new friends in East Jerusalem (didn’t know I was able to go there, either), where at the visionary Feel Beit culture house I made more friends including a mixed Jewish Israeli - Arab Palestinian couple and a woman involved with The Institute for Middle East Understanding, with a large Instagram account raising awareness of what’s happening there. The next day I bused over to the Educational Bookshop focusing on Middle Eastern culture and the Arab-Israeli conflict. Activated and inspired, I decided I would stick around the region longer. I would return to Ramallah for “Political Yeshiva.”

There I would meet a filmmaker who had been imprisoned (40% of all Palestinian men have been imprisoned, the majority of which are held in administrative detention, which means imprisoned without charges), befriend a man creating Al Jabal (The Mountain) startup accelerator with nature connection and personal development at the center, see a Christian Palestinian woman in Bethlehem who took me to church services in Arabic. I visited the Yasser Arafat Mausoleum and wandered the streets, read essays and watched documentaries, smoked more hookah and scrolled social media accounts representing entirely different shared realities. Then at night I’d meet up with my hosts and ask all the questions.


(Trigger warning: violence) The most personally impactful moment came while on a mini bus ride from Ramallah to Nablus, a major commercial center a couple of hours north. Sitting in the window seat on the right side of the vehicle, passing through a traffic circle I came face to face with an IDF soldier and his assault rifle aimed at the bus, tracking it’s moment to moment movement like a panorama photograph as we made our way around the curve of the circle. I hardly had time to process that before we drove through another circle to meet the same experience. And once more before we arrived at our destination. I don’t know if that was a common occurrence, but I couldn’t help but think about the impact on children, or any human, having that experience multiple times a day on their way to school or work. It was a clear example of what we had heard on the Breaking The Silence tour and what I’d been reading in political yeshiva, that the IDF’s mandate is to make life as hard as possible for Palestinians, so they eventually leave. I wondered if the way Palestinians are being treated today must feel similar to how my Jewish ancestors were treated in Russia just a few generations ago.

(Trigger warning: conspiracy) Another challenging moment arose unexpectedly on a second visit to the Educational Bookshop. A few months earlier at a party in San Juan, I was telling some dude I was thinking of going on a pilgrimage soon to Israel/Palestine, and he responded with a strange insistence that I “know my history” by looking into the Khazar hypothesis of Ashkenazi ancestry. I immediately felt mistrust around this controversial theory that Ashkenazi Jews are descendants of peoples from Central Asia instead of Israel, but also intrigue, as one of the biggest questions I’ve held during my reconnecting with Judaism era has been: “what was the path of my Ashkenazi ancestors from Israel to the Pale of Settlement between ~70 and 1800 AD?”

I didn’t give it much further thought until I heard echoes of the claim bubble up in conversations about Palestine. Then in the bookshop I came face to face with a “dangerous” book called The Invention of the Jewish People which explores this inquiry, arguing that most modern Jews descend from converts, whose native lands were scattered across the Middle East and Eastern Europe. I hesitated to pick it up, feeling the charge of such a heated topic leaping from the pages that I reluctantly thumbed through, put down and walked away, only to return to dive in like it was a former lover’s diary entry about me. (Note: I am not endorsing this theory, but sharing to illuminate my process of integrating historical complexities. I will expand on my thoughts in Part III).

I wrestled with what I read for several days, feeling like a rug had been ripped out under my feet. If some of these claims have merit, and my ancestors 20 or 50 generations back weren’t Jewish after all… if I don’t have direct ties to the people and God of the Torah… what does that mean for my Jewish identity and spirituality? What are my real roots? How much does that matter? Oy, could this be some cosmic joke, that most Palestinians are actually Jews who were converted Christianity and Islam, while Ashkenazi Jews are not actually from Israel at all? Ughhh so much unknown in such a fucked up situation alskdfjklsa;fjkladsf

Political Yeshiva was a hero dose of information from the “other side” that I had never been exposed to, even in the Oakland activist house — or maybe I was exposed, but I wasn’t really listening. I started slanging virtue signal-y memes on Instagram about decolonization and Israeli Apartheid, sensing that this was not where I truly was on the political spectrum, but felt strong resonance in the moment and that it was important to spread the awareness that I had unique access to there. And not only of the oppression, but of people living beautiful lives in the face of it.

It was so much heavy information. I felt angry that I had never learned about the Nakbah (arabic for “cataclysm”). The tight military industrial complex bond shared between the US and Israel (a world leader in surveillance tech because it has been “field tested” on Palestinians). The reality that the aquifers are in the West Bank. That Zionism was a classic colonial project of European intellectuals with almost no support from rabbis at the time. That nearly the entire international community condemns Israel’s actions, and yet most American Jews are trapped in a narrow filter bubble of misinformation and therefore blind support of the pariah state. It was disorienting to be learning all of this, while breezing through checkpoints because of my passport. I didn’t realize how many advantages and freedoms I had in life until I visited Palestine. I could see and feel Israel’s shadow and missteps.

The Graffiti of the West Bank Barrier in Bethlehem

Of course, that’s not the whole story, and it would be ludicrous to think I know anything at all as a fresh outsider exposed to a handful of stories, but it was at least scratching the surface of the side that had been most hidden from me, and therefore the most valuable and revealing. Returning to Jerusalem, I caught up with a couple of American friends who had studied or lived here much longer than I had, revealing layers upon layers of context I hadn’t been exposed to. From all sides of the political spectrum, including off it and above it. Gosh, it never ends. It’s humbling in a way. Who and what to believe? The religious woman on a settlement near Hebron has a wildly different perspective than the intellectual in Jerusalem than the activist in Ramallah. How to hold all those views? If I am to try to help out in any meaningful way, how and for whom to to direct my energy?

A final piece I’ll share is about my visit to an Israeli settlement. A new friend from the aforementioned Lag B’Omer night had invited me, and his friends had encouraged me to take him up on the unique offer to visit this “visionary outpost”–something about the look in peoples’ eyes there. “They’re living it.” What was “it”? Having hung around a number of “visionary” land projects in the United States, I was curious what this meant. I rented a car and drove up for a quick Shabbos turnaround. The first thing that struck me was the natural beauty of the place. Perhaps the most beautiful landscape I had encountered thus far on my pilgrimage. Expansive, undeveloped, biblical. Somehow, biblical. Joseph’s well was apparently nearby, but not advised to visit.

View looking south from Mevo Datan

I was also struck by how similar the vibe is to some of the intentional land-based communities I’ve spent time in around the Americas, with two major differences. One being time elapsed since displacement of the people previously there (50 years in Israel vs 150 in California vs 300 in New York). In Occupied Palestinian Territories (OPT — the name designated by international law) the military presence is still there protecting its pioneers, whereas in Northern California for example it has long since faded into the background to the point that most residents today don’t even know that there was a state-sponsored California Genocide. Another difference: whereas many land-based communities in the states are organized around an amalgamation of spiritual traditions (a little bit of Osho, some Lakota, a touch of Marianne Williamson), those Israeli religious settlements in Palestine are committed to one thing: to Torah till the end, through a millennia-old prophecy of returning to the land that was promised to them in a covenant with the creator of the universe. In it for the long haul, living on the edge, willing to die for something greater than international law.

That said, it was a holy experience. Mikvah in a cistern. Transporting chickens between coups. An eight hour shabbat dinner full of joy and wisdom. Family dynamics that made me desire having a family. Life is really good out here! I didn’t catch an ounce of anti-Palestinian sentiment. When I respectfully broached the subject, the response was something like “instead of getting caught up in the theory and politics, we’re just trying our best to live a beautiful, loving, wholesome life, connected to the sacred and the Earth, and teach that to our kids.” I get it. That is indeed a beautiful and courageous act in our times. It’s just really hard to reconcile with the material, political reality. There was a lot of talk about sharing these wonderful things with others, but I don’t think that included land and neighbors of different traditions.

I tasted why this settlement life is desirable (apparently a third of the cost of living). Jews have been praying for thousands of years to have this experience. After generations of vulnerable wandering and unfathomable discrimination and trauma, they have the opportunity to live the dream, under heavy protection. Crossing the border back to Israel, to the confusion of the multiple guards who came over to pepper the rare American visitor with questions, I had heaps of questions on my mind. I wanted to engage this topic more and its intense intersection of colonialism, theology, psychology, justice. I regretted not visiting a refugee camp. I regretted not talking to more soldiers. I regretted not spending more time in Palestine. I regretted not engaging with Israel and Palestine sooner in my travels, sooner in my life.

  • What the role is of American Jews in Israel and Palestine? What is my role?
  • How can more Jews around the world get exposed to what’s happening here?
  • What would a metamodern or integral politics approach to peace building look like?
  • What is the role of plant medicine and other forms of trauma healing here? What will it take to soften the hearts of those with power?
  • How can I talk about this subject without injuring relationships with those I care about?
  • How can it be another way?

📚 Personal Learning

If there was a third dimension to my pilgrimage, I’d call this broad net “personal learning.” This section will encompass family, therapy, and career. It will also touch on life post-pilgrimage.

Weaving The Diaspora

The icing on the cake came in the final days of the pilgrimage: reconnecting with long lost(ish) Israeli family. As the story goes, my mother had visited Israel as a teenager and recalled meeting a second cousin named Eti Soladucha near Haifa, but they lost touch and had no way to contact each other fifty years later (if she was on social media, she was going by a different surname). Before I left for Israel, I told my mom I would make it my mission to find Eti.

Distant American archivist relatives Ed and Bernard were able to dig up names and addresses of two Israeli family members, from the 90’s, with one likely deceased. What was I going to do–drive out to random suburbs and ring the doorbell? What if they don’t live there anymore, or are even alive? I de-prioritized the search, until a new Israeli friend Mor generously asked if there was anything I needed help with. She knew of a service that could find the landline phone # associated with a given address, but when she called she only got the answering machines. Then my phone was stolen twice in Tel Aviv, Mor and I fell out of touch, and I dropped the family business once again.

Until my final week, when sitting bored on a park bench I decided to give the numbers a call myself, even if it led to an embarrassing conversation with a complete stranger or a relative who only speaks Hebrew. This time, a woman named Ahuva picked up, and in broken English we were able to establish that we shared some DNA. The next day I visited her in the Tel Aviv suburbs, streaming my mom in by video chat to see Ahuva and I having lunch over photo albums… with her sister Eti!

Re-uniting with Ahuva and Eti

Turns out there were dozens Solodohas in the area! Children, teenagers, parents, grandparents and even one great grandparent who regularly gather for Shabbat and especially high holiday meals with Miriam, the 95-year old matriarch. That Friday, I’d brunch with 7 more family members, and on Saturday celebrate a birthday with 15! Nobody on the American side of the family had visited in nearly 30 years. Upon hearing that I had been in Israel for 10 weeks, everybody wanted to know why I didn’t contact them sooner! “If you come again, know that you have big family!” (and I won’t need to stay in hostels 😹)

🎙Here’s a 16min audio recording of the reconnecting with family story

Merging family trees
WhatsApp group created for family across Europe, Middle East, and America

These Israeli’s are descendants of my maternal great grandma Libby’s brother Yonkel, who decided on a razor’s edge to leave Belarus in the 1950’s for Israel instead of the United States. I’ll never forget piecing together the family tree, realizing specific pieces of shared life experience with various relatives, feeling cared for as if I were family. They really reminded me of my extended family in the states, just more Israeli and more of them! One of the things I’m most proud of doing on pilgrimage is re-stitching these diasporic family relationships, which have resulted in cousins reconnecting and seeds planted for future contact.

But that’s not all. There was one more special family member to see. The American archivists knew of one more relative, Sarah, from a similar branch of the family. But the Solodohas didn’t know her well, because she grew up in America, and now lives on an Orthodox settlement outside of Hebron. She’s religious, while they (like my family) are secular, and so the highly segregated nature of the nation prevents contact. I was determined to meet this religious relative. So on Sunday, I met Sarah in Jerusalem to take a bus to a very different world.

A world of dozens of grandchildren. Of marriage to a rabbi who traces his ancestry 22 generations to the great medieval commentator Rashi. Of a politics so foreign that it stretched the limits of my multi-perspectival capacities. It was challenging to experience a family member in their outspoken beliefs, and powerful for me to stay in my heart even though some of the things that were said were personally painful and tempting to dispute. I was choosing to be in relationship with this new grandmotherly figure in my life (that I really enjoyed spending time with!), rather than be right. And it demonstrated to me the depth of intensity and emotion that has been involved with the conflict.

As it turns out, Sara had been teaching yoga in the 70's in Woodbourne, New York when somebody told her that she should go to Israel. Which she did, making teshuva and aliya (immigration to Israel). Get this: Woodbourne was the exact same town I was in when somebody told me to go to Israel. Though most of the American and Israeli family thinks she’s crazy, my dip into religious communities gave me the ability to connect with her socially conservative vibe, even if it wasn’t for me. I’m grateful that a little respect and curiosity allowed me to share a special connection with the one family member that I know of, living or dead, who has a deep connection to the tradition of the last three thousand years of my ancestry.

🎙Here’s another 16min audio recording (part II) of the family story

Sarah and Avraham

Receiving to Give

Remember that therapist I said I was going to start seeing after the minyan? Well, it took a few months to actually do it, and another few months to find somebody I really clicked with. Just before departing, Nickee and I had our first call, and have been doing weekly calls ever since. I actually applied my late Grandma Rose’s inheritance towards the pilgrimage and a few months of therapy, as I couldn’t think of a better use of ancestral resources. Thank you SO MUCH Grandma! I am spending it wisely like you always insisted.

There’s a way in which travel–especially long-term travel–can bubble up stuff from all aspects of life, serving as a clear mirror to look at how one is showing up with relationships, money, family, career, God, politics, etc. Turns out it’s all connected! This pilgrimage would turn out to be quite the summer school for me, with the blessing of regular check-ins with Nickee to navigate emotions and process what was happening in relatively real-time, plus monthly check-ins with Sara for guidance on the pilgrimage itself.

This is where the Pilgrimage Map came in handy, as I always had my pocket journal on me to record big insights and lessons as they arose. I don’t know about you, but I find it really challenging to actually learn my lessons. Something happens, I have a sense of what I might do differently next time, next time inevitably comes and I totally forget what I was going to do! The Greek poet Archilochus reminds us “We don’t rise to the level of our expectations, we fall to the level of our training.” The poem Autobiography in Five Short Chapters by Portia Nelson sums it up well:

Here’s a video version.

I feel like I’m on Chapter 2 or 3 in many of the streets I walk down. Whether feeling anxious about a new romantic connection, or inadequate in social settings, life continues to give me opportunities to do something different, and therapy has served as a dojo to practice going inward to triggering moments (of which there is always plenty of fodder each week) and building a connection with little Andrew. The progress is slow and nonlinear, but oh so sweet when I get a little win in there.

Some of the themes we looked at during the pilgrimage included anxiety around public speaking at Shabbat tables, feeling scarce about money, anxious attachment with new connections, having difficult relational conversations, unrealistic expectations across the board, perfectionism. Turns out much of my wounding (a lot of it cultural, as I’ll expand on in Part III) has to do with intense feelings of inadequacy, or fear of being exposed as a failure.

One theme I kept coming back to was around Giving and Receiving. If you’ve been on a Birthright Israel trip, you might recall visiting Avraham Loewenthal at Tzfat Gallery of Mystical Art. He has translated and compiled several books (free PDF download) on the work of the Kaballah master Rebbe Yehudah Leib HaLevi Ashlag, aka the Baal HaSulam.

Describing four general stages of spiritual development (in Spiritual Principles):

I’ve been chewing on this one for months. I received hard on this pilgrimage. So many people opened their homes, cooked meals, made connections for me. What did I give? And when I gave, why did I do it? Acknowledging my tendency to be hard on myself, I really feel like I’ve been a skimmer throughout my life, typically focusing on what I can get out of people. Not wanting to give up my freedom and autonomy, even when a friend is in need. Idolizing myself. These are common traits of a young man living in a hyper-individualistic culture devoid of spiritual meaning.

I feel like the majority of my life has and is hanging out in Stage One, with intellectual understanding of Stages Two and Three, but limited experience there. I literally created Giving holidays to force myself to embody this higher orientation! Hoping that it might make the behavior more natural, or at least give me the power to turn it anytime like an Uber driver. But I’m very far from that.

I get that having children changes the giving/receiving equation dramatically. But until then, how can one grow? On the next couple of maps I made, I’d include sections for “Ways to Give” to try to bring more of it into my daily life. Slow going. It’s almost as if I need to focus my attention daily on this intention (prayer), have somebody holding me accountable (community), go through experiences that dissolve the ego and orient me towards a path of service to the tribe (rites of passage). Things are going to keep getting hard out there–I want to be thinking a little less of myself when the times come. I know this is one of my main growth edges.

On a special summer solstice road trip to the dead sea area, I felt the urge to understand what’s the deal with the dead sea? Not the scientific explanation, but one that might be found in biblical commentary. A cursory Google search yielded an explanation that resonated in my heart:

In Israel there are two major bodies of water. One is the Sea of Galilee, filled with fish and surrounded by lush foliage. The other is the Dead Sea, 10 times saltier than the oceans of the world. No seaweed, plants, fish or any living thing of any kind live in or around or near the water. Both the Sea of Galilee and the Dead Sea are fed by the Jordan River.

There is really only one difference between these two bodies of water, really only one thing that causes the Sea of Galilee to be beautiful and alive while the Dead Sea is barren and lifeless. The difference is that the Sea of Galilee takes water from the Jordan River, and then it gives water back to the river. The water simply passes through the Sea of Galilee. As a result, the Sea of Galilee is full of life and beauty. The Dead Sea, on the other hand, only takes water, but it gives nothing back, and as a result it sustains no life. Those two bodies of water bear witness to a truth of human life. It is in receiving and then giving back that life and hope are sustained.

The same is true in our spiritual life. If you and I have spiritual input but no spiritual output, we will become stagnant, lifeless, bitter, and caustic. However, if we like the Sea of Galilee are receiving and giving back, we become vibrant, healthy and life-giving.


The end of my pilgrimage would yield beautiful beginnings. It was my second to last night in Israel that I caught up with an old professional contact Randima at Center for Humane Technology. They had been searching for an Innovation Lead to support solution-side work. I had not considered full-time collaborative engagements for several years, part of me dreading a return to a professional world in which I felt so challenged.

Fortunately, Nickee supported me in feeling and listening to the emotions that were trying to protect me from pain I had previously experienced with authority figures. Sara helped me see how this role was exquisitely aligned with my purpose and would give me a platform to express more of my potential. Rabbis helped me understand the importance of commitment and being two feet in. I felt pride that in following my intuition and curiosities in a meandering sabbatical-y period of slowing down, personal healing, participating in all-win politics, writing, starting my own coaching/consulting practice, prototyping tools, and orienting towards education… I rendered myself qualified for a new-to-the-world role with high alignment and impact potential. I have been happily employed for 6 months now.

Upon leaving Israel, I re-joined Jessie in Turkey for a few days of her Sephardi ancestry exploration + R&R, then a week and a half of ferry hopping around Greece with my bluetooth keyboard in tow (I hadn’t brought my computer abroad, and had a fantasy of spending my days in paradise writing about the journey you have been reading). Scoot, eat, write, swim, nap, repeat. + learn about philosophy, mythology, and education. + an awkward experiment of purchasing a small bottle of Ouzu on the beach in a Hemingway-esque inquiry of what happens when Andrew writes drunk? He stares at the stars and falls asleep!

Upon arriving back stateside, I thought I would sit down, write this piece, and feel like it would sufficiently cover a major period of transformation in my relationship with Judaism. But the story continues to live itself out. The day after I returned, I met with the man in the woods (see Part I on “Syrian Rue”) and another friend interested in creating a women’s retreat. Since the minyan last summer there hadn’t been another Jewish x Rue gathering, though not for lack of interest or ideas. We wanted to discuss what’s next. First we thought about it for awhile. Then realized we should ask the plants.

Expanding on that initial dialogue in which the plant spirit identified as Elohim, a channel opened (communication with a source believed to be outside the person’s body or conscious mind) that allowed us to ask questions and receive answers under the starry sky. What questions would you ask God? We had lots of questions. About Rue, healing, prophecy, Moshiach, Israel, Jewish women. It was another beyond-imagination experience that only yielded more questions, including how to be a good scribe.

Returning to my social media in August, I saw a number of friends preparing for Burning Man (transformational arts festival) and was swiftly FOMO-captured into making arrangements to get out to the high Nevada desert for the fourth year, this time with the Jewish camp called Milk & Honey, famous for our 1,000 person Shabbat (see video I took). Aside from that powerful service and dinner, moving much of the crowd to tears, there wasn’t too much Jewish about camp–we even cooked bacon one morning. But there’s something very Jewish about the whole Burning Man experience for me: being in the desert, in community, receiving wisdom. Some campmates and I felt curious about how we could bring more Jewish wisdom to the playa in the future: song circles, talks on mysticism, an Ezekiel’s chariot or Merkaba art car…

Shabbat at Milk & Honey. Burning Man also gave me a chance to adapt the Life Map concept into what I’d call PlayOS, which would be my first real personal artistic gift offering for the Burning Man community.

The high holidays in New York and California were another high voltage shul hopping experience between Temple of the Stranger, Temenos, Lab/Schul, Wilderness Torah village life Sukkot festival. Slumber party shabbat dinners spawning WhatsApp/Signal groups of new constellations of friends weaving more invitations and ideas at the edges of Jewish culture. Fiddler on the Roof in Yiddish. Collaborating on a Sukkot Map template. Questions. Loads of questions…

Which catches us up to this moment (Tu BiShvat!) of writing and sharing about my adventures, following all the threads of new relationships and collaborations.

Whew. What a trip it has been. Thanks for tagging along.

The pilgrimage is over. The pilgrimage of life continues.

My prayer is that if you feel a connection to Israel and Palestine, or another ancestral homeland, that you find a way to explore what’s there for you.

May the story of my pilgrimage inspire you to craft your own journey based on the questions in your heart, political learning, and family ties.

Aaaaaamen 🙏🏼

Burning Man 2021: Waking Dreams

I’d love to hear your reactions to Part II! Resonance, questions, feedback. Part III will be more commentary than storytelling, so I’d love to know what questions you are thinking about, so I may address them. Contact info on my website: Subscribe to my Substack to get notified of Part III + future writing.