In my case, three out of my four grandparents were Jewish. My father’s parents came from Lita and Poland, and I remember my paternal grandmother lighting Shabbos candles in her home in West Palm Beach. My mother’s side has a colorful history: Her Jewish grandfather migrated from Eastern Europe to Israel in 1916, where he joined the Jewish Legion of the British army, serving in the 38th Battalion of the Royal Fusiliers. He fought under General Joseph Trumpeldor defending British territory against the Ottomans, later making his way to America, where he worked as a pharmacist in Yonkers.

His son, my grandfather, married a non-Jew, who came from a family that had immigrated to the US from Ireland in the 1630s. (Family lore says they’re related to the famous American lawman “Wild Bill” Hickok.) My mother is a spiritually inclined person, a gallery artist and world adventurer, and she encouraged my Torah pursuits. But she isn’t Jewish, and back then, I didn’t realize that that made all the difference.

My father had been a student activist at Boston University in the 1960s, but he went on to become a very successful and politically conservative lawyer whose career included serving as counsel for the Red Sox. I enjoyed a privileged childhood in Boston; my brother and I attended private school, learned classical and jazz piano, and mastered skiing at a very early age. (By age six I was a ranked skier.)

My father retired when I was still in elementary school, after which we moved to New Hampshire and I attended public school. When I turned 12, my father would drive me regularly from our home in Lincoln to Bethlehem, where there was a Reform synagogue that offered bar mitzvah classes, my first exposure to formal Jewish education of any sort. What a special zechus he had, spending hours driving just to ensure I would have a Jewish education. While we were in Bethlehem, we’d sometimes pass religious Jews walking home from shul — that was my first glimpse of religious Jews.

The summer after my freshman year in college, I went on a Birthright trip to Israel under Reform auspices. It wasn’t a particularly spiritual experience; my group thought Friday nights were meant to be spent clubbing.

After the trip, a friend and I decided to stay on and work at Kibbutz Ma’agan, on the southern tip of the Kinneret. It was an old-style kibbutz that raised bananas and dates, boasted a bar in a bomb shelter, and distributed ration cards in lieu of salaries. One Friday night, I was in the cafeteria, and I thought it would be nice to make Kiddush, so I poured grape juice and sang the words out loud. The next day, a member of the kibbutz administration pulled me aside.

“That was very inappropriate behavior!” he scolded.

I was incredulous. Wasn’t this country founded as a Jewish state?

In response, I decided to check out the other end of the religious spectrum. I’d heard of an outreach yeshivah in Jerusalem, and they told me I could come join for the summer zeman. But six weeks later, just as I’d accepted Torah as emes and committed to becoming frum, they dropped the bombshell on me, telling me I wasn’t even Jewish.

Being Jewish was still part of my identity, even if the yeshivah didn’t allow me to stay. Not sure how to handle the cognitive dissonance, I returned to college and threw myself into the experience. There I found a world where I was accepted as a Jew. I became the president of a Jewish fraternity; served as an intern at the Israeli consulate, working on issues like hasbarah — public relations about Israel — on campus; and wrote a memo for Senator John Kerry, then on the Foreign Relations Committee, stating that the only effective way to carry out a two-state solution would be to eliminate the Palestinian Liberation Organization. I went back to Israel in the winter of 2003, working with Daniella Weiss of the Yesha Council to build infrastructure in Kedumim. After that I headed to Australia, where I set out to do a comparative study of hasbarah on American versus Australian campuses.

While in Melbourne, I became very close to Rabbi Andrew Saffer of Aish Australia. He was actually my shaliach to pursue geirus. He made it clear, in a very kind, gentle way, that I was trying to dance at two weddings simultaneously and that I had to make a choice.

That was in the back of my mind when, a few months later, I transferred to New York University to pursue a degree in government and politics. I found I was gravitating socially toward frum chevrehs. That’s where I met Rav Chaskel Besser ztz”l, and I was enchanted. Reb Chaskel was a unique combination of statesman, gentleman, scholar, and rav from a previous generation. I went to his home on Manhattan’s West Side dozens of times. He could be on the phone with American businessman and philanthropist Ronald Lauder o­­ne minute, and former Polish president Lech Walesa the next. And his wife was a firecracker, a seventh-generation Yerushalmi…

After I met them, I couldn’t go back to the campus rabbis.

I had tasted something genuine and fulfilling, and was increasingly determined to pursue geirus, but now I faced a catch-22. Batei din want a conversion candidate to be learning in a yeshivah. But where could I find a yeshivah that accepted non-Jews?

One day I learned about a Russian yeshivah near Moscow called Ohalei Yaakov that had a tolerant attitude toward zera Yisrael. While there is no halachic requirement to teach Torah to this demographic, some yeshivos in Russia are lenient because of the assimilation that is unfortunately so prevalent in Russia’s Jewish community.

Ohalei Yaakov wasn’t a simple option for me. I had to learn enough Russian to communicate, and the yeshivah was, by American standards at least, physically primitive, cobbled together from former stables. The plumbing was so bad the bochurim fixed it themselves. Breakfast was kasha with butter, lunch was fish and salad, and dinner was fish and borscht, every single day. There were a few Americans, but most of the guys were Russian, many from Uzbekistan, Georgia, Azerbaijan, and Ukraine.

Moscow looked a lot different back in 2006 than it does now. The Beslan school siege was only two years prior, and the Moscow theater hostage crisis four years prior. The street was xenophobic. I had a roommate who had served in the Second Chechen War. Another friend from Baku, with his darker features, always got harassed by the police.

But for all the challenges, it was exhilarating; for the very first time, I was surrounded by a chevreh of growth-minded mevakshim. Every fourth Shabbos, a kiruv rav from Georgia would come in, and the simchah that radiated from those Shabbos experiences left an imprint on me for life.

One day I went to the office of the rosh yeshivah, Rabbi Akiva Josovic, a son-in-law of Rav Aaron Lopiansky, the rosh yeshivah of Yeshiva of Greater Washington in Washington, D.C. I asked Rabbi Josovic for a Gemara. The rosh yeshivah, indicating their meager selection of seforim, said wryly, “It isn’t like Eichler’s here. But here — take this.”

It was a Gemara Berachos, and I worked my way through it using Rabbi Eli Mansour’s tapes. While I was going through the Gemara, I noticed a lot of Russian teitsh words above the text on the page. I turned to the back page and saw the notes — someone had made a siyum on this Gemara in the late ’70s, in Moscow. My breath caught when I saw that. This was a mesirus nefesh Gemara! It had been smuggled into the Soviet Union during a more perilous time.

During my stint in Russia, I earned money taking jobs teaching English. Somehow, I connected to a vice president of Transneft, the company that owns 95 percent of Russia’s pipelines, and he hired me. I’d shuttle between learning in my barebones yeshivah and tutoring in a swanky office in the city.

In 2006, I left Russia for Monsey, with a warm recommendation from Rabbi Josovic. There, I’d finish my conversion. Going to Russia had been a hugely circuitous, if exotic detour, but it offered me real growth, and it also primed me to connect years later with my wife, Rachel, a baalas teshuvah from a Russian family. In fact, Rachel’s brother is currently involved in the same yeshivah that gave me my start, and from the pictures I’ve seen of Ohalei Yaakov today, the facility is fully renovated with a much improved menu selection.

A few months of arriving in Monsey, I completed my conversion. In 2006, on Yud-Beis Elul, the Beis Din Ezer Mishpat declared me Jewish.

I hesitated over choosing a name. My parents had named me Joshua on my birth certificate, and Yeshaya at the bris they gave me, but I identified with the name Yisroel. I consulted the Skverer Rebbe, who told me to take the name Yehoshua Yisroel.

Now formally Jewish, I had to find my place in the frum community. At first I thought I’d settle in Monsey, but I tried several learning frameworks and couldn’t find a good fit. Eventually, I found a chavrusa, a Skverer chassid who was a cheder rebbi, and we’d meet regularly in one of the old-school batei medrash. I mostly hung out in the back, but it was amazing to spend time in such a place. I took in a lot by osmosis.

Then came what I see as the litmus test of my sincerity as a ger. I don’t want to share details — I believe that on my end, my job as a ger is to work on having an ayin tov — but I went through a terribly disillusioning experience after a business betrayal led me to navigate the protocols of a financial beis din on my own. I was right on paper but wrong on technicalities. It came down to yichus versus ger. Who could I talk to for advice? Who could I turn to for direction? I didn’t know! My contacts all told me the onus was on me to have done thorough research, but at that point it was too late.

I struggled bitterly with parnassah throughout the rest of my twenties. There were times I found myself down to my last five dollars, able to afford breakfast but perhaps not lunch or dinner. The Jewish community is helpful, and I’m grateful to organizations like EPI that help businesspeople succeed, yet it’s still possible to fall through the cracks and not find steady income to stay afloat. For about five years I struggled, alternating between feast and famine. Looking back at those years, they were, perhaps when I was most alive; bitter poverty forces a certain type of presence of mind.

In 2009, I moved to Flatbush. Always drawn to chassidus, I soon connected to the Bostoner Rebbe, Rav Pinchas Dovid Horowitz. I liked the Bostoner focus on avodah on mesorah, and the fact that outward appearance is secondary. My gray suit wasn’t an issue there.

I became something of a hoiz bochur to the Rebbe, helping serve meals on Fridays nights, helping build the succah, learning through shimush. The Rebbe really took me under his wing.

I learned a lot from the Rebbetzin, Rebbetzin Vella Horowitz, as well — the nuances of the chassidic court, her support for her husband, and practical halachic pointers.

The Rebbetzin has this amazingly funny sabra wit. I remember she once got nervous when I went to the dining room carrying an armful of plates.

“I used to be a waiter in Manhattan, I can do this!” I said.

“But that wasn’t with my fine china, was it?” she responded.

Slowly, under my rebbe’s care, pieces of life starting coming back. I found chavrusas for night seder. Coincidentally or not, all of them were first-grade rebbis; it was great — they had lots of patience for me. During the day, I worked at odd jobs, including stints teaching in boys’ yeshivos. This went on for six years, from 2009 until 2014. Eventually, one of my fellow mispallelim connected me to a real estate company, and I was finally able to launch myself professionally in the marketing field.

Association with a rebbe came with unexpected perks. People took chances on me. I took chances on them. And I learned so much from the community. They gave me understanding of a derech hachayim, a way to live one’s life.

In a certain way, PR and marketing is a transactional business — if my marketing helps you achieve your goal, you learn to trust me, and we develop a successful relationship. I’m now the creative director of OHR, a New York City–based full service marketing and branding agency.

I succeeded professionally as I started succeeding personally, baruch Hashem — and the two are related. Many of these initial business transactions blossomed into lifelong friendships. I’m not saying that it all was peachy keen, but it was a positive way to start integrating into the community. Hashem sends guides, I learned, if you are open to guidance.

My first years as a Jew left me feeling that geirim don’t have a place in Klal Yisrael. The Rebbe had done much to mitigate those feelings, and I wanted to prove to myself that indeed we do have a place — a very special, unique, admirable place — among Hashem’s people. I decided to record some of the Torah I learned along the way in a manuscript. I started putting together Sefer HaMiddot, a primer on Judaism’s main topics that features primary Torah sources in bite-sized chunks. It took me two years, and by 2019, I was looking for letters of haskamah. When I got a haskamah from Rav Reuven Feinstein, something shifted for me. If I can make it to a Rav Feinstein-level rav, I reasoned, the system does work for — and with — geirim.

I went to Monsey, to a talmid muvhak of Rav Feinstein who had facilitated the haskamah process. As is the custom in heimishe batei medrash, I brought along some bourbon. After I read him the haskamah, I poured him a shot. He demurred, saying he had to drive.

“I thought you might say that,” I said, and I reached in my bag for some grape juice. We made a l’chayim and bentshed each other.

That was a beautiful moment for me, because that was when I truly internalized the Torah’s stance on geirim. In fact, the Zohar writes that the entire purpose of galus is bring back the netzotzos hakedushah — sparks of kedushah all over the world — and those sparks become geirim. But when we are ashamed of who we are, and we try to just blend in, we limit the chance for others to know what a resource we are, and we forget our own chashivus, our unique potential to impact the world, our raw enthusiasm for the entirety of Torah. Yisro. Rus. Onkelos HaGer. Avraham ben Avraham. They all brought fresh modes of thought into Klal Yisrael.

To be honest, it’s hard. It’s hard, and it can be lonely, and there can be a stigma — and for that reason, some feel the best way forward is to hide their identity. But obscuring your identity can lead to depression and helplessness, G-d forbid. I know — I was there.

In 2010, I got a ride home from a bar mitzvah with the Rokeach family. We hit it off, and I became a ben bayis in their home. When I needed surgery and was hospitalized, Mrs. Chaya Rochel Rokeach sent me meals, and later when we were discussing it, I mentioned how much I appreciated — no, how much I actually needed — that support. She told me she’d been thinking, What if we weren’t there to do that for him? And she’s right! Without the background or familial support Jews are born into, geirim need a special type of chizuk and care. We need guides, we need sponsorship families, we need individuals with an open eye to take responsibility.

I’ll never forget when Mrs. Rokeach told me she’s not doing me the favors — I’m doing them for her.

“What do you mean?” I asked, confused.

“Our children are always excited when you come over,” Mrs. Rokeach replied. “Our children appreciate how lucky they are to grow up frum when they see that you chose this despite the hardships.”

There are as many as 800,000 zera Yisrael in this country now, children of mixed marriages who often identify as Jewish and are approached by campus outreach staff (with Jewish fathers, they typically have Jewish last names).

I’ve been working on a book to introduce these people to the concept of zera Yisrael, hoping to help others avoid the awful letdown I had the first time I went to an outreach yeshivah. I want to gently show them they cannot sit on the fence: They must choose between converting properly or embracing their status as a non-Jew.

As for me, the incredible trek since that first haskamah gave me the courage and the push to co-create the Bracha Institute, a COVID-era online initiative based in Jerusalem that teaches about harnessing the power of brachos with kavanah. I think this was a zechus to help me meet my bashert — the first seminar session launched at the end of April 2020, and I was introduced to Rachel eight days later.

Rachel encourages me to be open about these issues. And so I turn to you: Help geirim post-geirus. It can start with a simple Shabbos invite, but whatever it is you choose to do, help those who have fought so hard to be called Yidden.

(Originally featured in Mishpacha, Issue 860)