How Failing To Get A Job In The Jewish World Gave Me Life

I’m on my way to a job interview. It’s probably the 20th at this point.

I’d been living off of unemployment, some freelance writing money, my wife’s part time teaching salary, and family help for the last few months.

I’ve never gone this long without a job.  Even when I first was searching.  Even when my resume had only one or two side gigs I had done along the way.  I’ve never gone this long without money.  And all while having children to care for, Jewish day school tuition to pay for, and living in Brooklyn.

It wasn’t supposed to be this way.  I had spent the last few years of my life pivoting my work so that I wasn’t only doing marketing.  I wanted to use those marketing skills, but combine them with my leadership skills, and run my Jewish nonprofit startup.  

More importantly, I deeply wanted to be part of a Jewish organization where I could finally commit myself to my values and my community during those 8 hours every day when we have the most to give to the world.  I didn’t want it on the side anymore, I didn’t want it to be a “passion” anymore.  I wanted the every day drudgery of actually taking those years of commitment into a world that I thought desperately needed voices like mine.

Even this, in truth, was my backup plan.  I had been working with my previous employer, Clal, which had been incubating Hevria, the nonprofit startup, as I worked with them to make it into my full time position.

Well, that didn’t work out.  And that is a story for another time.  The point that matters is that this job search was something that seemed, nominally, like the easier choice.  I had seen firsthand the work it takes to turn a nonprofit into a full-time job, and although I was making significant progress, the reality I was facing was that I’d be devoting 90% of my time to raising the funds for it, which was already leading to the organization being hurt by my increased absence.  In other words, working full time on my project meant spending less time on actually doing the work of it, and more time asking people to pay my salary.  The moment I realized this, I understood that the right thing to do, as hard as it was, to let go of the dream for now.

So I saw looking for a job as a sort of backup option.  My safety school.

After all, I had built up a name for myself in the Jewish world.  I mean, enough that people knew who I was when I’d send them my resume.  I had just been featured as a panelist alongside Michelle Obama’s former speechwriter, Sarah Hurwitz, had been on national television fighting against antisemitism, had joined all the “right” cohorts that Jewish startup entrepreneurs had been told to join (ROI! OOI! Hakhel! Retreatology! Kenissa!).  I had built an organization from the ground up that was now both a popular publication (this one) (with a sister publication) and a thriving in-person community. I was part of the leadership of the largest politically progressive orthodox activist group in America.  I was a popular writer in mainstream Jewish publications.

I’m not saying this to brag, or claim a grievance.  Rather, I’m sharing it to give you an idea of why I felt that I had successfully pivoted into the career I was dreaming of, even if it wasn’t within the organization I had founded: I could, finally, commit to Jewish work and communal life full time.

And so, at first, that’s where all my applications went.  JewishJobs.com became my new favorite website.  I networked with all my contacts.  I sent out emails to all those big time names I had connected with over the years.

I guess what I’m trying to say is that I tried to do things the right way.  I tried to make it work.

I came close.  I was repeatedly told I was a finalist for for some of my dream positions: ones where I could expand the work I was doing and apply the lessons from my experiences and help others grow and learn along the way.  

And yet, there always seemed to be something that prevented them from going from “finalist” to “final choice.”

What I assumed was the case became explicit in one of the many interviews, when the interviewer asked me if I would be willing to “suppress” my political views (her words).  The more interviews I went to, the more this came up: besides my organizational work, I had largely “made a name” for myself by being uncompromising in my views.  I was partisan politically while also being outspoken about issues I had faced as a person who chose orthodox Judaism later in his life.

And thus the need these organizations saw for me to suppress my views: it is hard to find a large, well-funded Jewish organization (that isn’t overtly partisan) that isn’t dependent on the good will of people on all sides of the political and religious spectrums.  This is largely what has made American Jewry as powerful and well-heard in the cultural American landscape.

It also happens to be what has largely contributed to their collapse in the post-institutional world we are rapidly entering.  

As they lose donors (while working hard to retain the mega-donors who are making up the difference for now), members, engagement, and interest, micro-communities like the one I had started are on the rise.  

This is exactly why so many programs have been created to support our work by these larger institutions: large Jewish institutions are well aware that they have to find a way to be relevant to a world that is becoming fractured, partisan, and divided.  But even there, their power is in uniting these partisan micro-communities and organizations through the power of resources (nonprofit speak for money), and thus still retain their original approach.

In a way, their difficulty hiring me was a microcosm of this quandary: they can raise us up as separate entities, but we will never quite be insiders.  In a sense, especially as smaller organizations bend to their needs, we become serfs to these larger organizations, hoping to make them happy while clinging to our original missions.

So, as a leader of such an organization who also proudly represents what they stand for, I am not exactly an asset to a Jewish big tent organization: I am also a danger.  I belong on panels, as one of many opinions.  I belong in private discussions with these organizations, but never as their face.

If I get too close, I endanger their entire enterprise.  They have to balance the needs of a multiplicity of views, and so they can’t appear partisan, even if they support partisan endeavors.

Which brings me back to my drive.


It seemed perfect.  Finally, I had found a place that didn’t have the baggage of so many of the Jewish places I cared about.  It was a shul in upstate New York that was looking for someone to help attract a growing ex-Hasidic community that was growing in their area.  They weren’t part of any specific denomination, and they were completely funded by their own community, which meant they weren’t beholden to any interests but their own.  When I sent in my application, their rabbi called me the same day.  

He had seen me on the panel and he loved what I had to say. Which was, um, a good sign since I had proposed things like eliminating denominations and spending the tens of millions we spend on things like Birthright and kiruv to seed the growing mini-community movement in America (you can see why no one would want to hire me).  

Anyone on board with that had to be okay.

And besides that, the work I had done over the last few years in my nonprofit (hint: you’re on its website right now) had evolved into a home for many ex-Hasidic Jews.  I was suited for the job.  Over-qualified, really.  It was part time, in upstate New York, so I’d have to drive there regularly.  And I didn’t even have a car.  But I was both desperate to feed my family as well as excited by the prospect of having found a place that would be open to my style and approach.  

I was so excited, in fact, that I decided that I’d shut down my Twitter profile temporarily.  Twitter is where I’ve generally shared my most incendiary thoughts, and I was convinced that it was one of the main reasons I was having trouble.  I couldn’t hide all the writing I had put out, but I did what I could, also going through my recent Facebook posts and hiding all of the more controversial, political posts.

Again, I was trying to be good.  A bit.  I had been bending for so long, it felt appropriate to temporarily take a break from being myself so that I could be a father, a husband, a provider; all much more essential roles than my social media feeds.  And, ultimately, getting this job would mean finally starting towards the road of achieving my dream of working somewhere with resources (money) that could allow me to extend my work.

So I borrowed a friend’s car, and I drove up to the shul for my interview.


It was a two hour drive.  To pass the time, I decided to re-listen to the sermons of Martin Luther King Jr., which I had been obsessing over for months.

The first one I played was one of my favorites: “But If Not.”

In it, King described the story of Shadrach, Meshach, and Abednego as depicted in the Book of Daniel.  The story describes how the Babylonian King, Nebuchadnezzar, demanded they bow to a golden image of him.  They refused, knowing that it meant they’d be thrown in a furnace and burned to death (a similar story is told of Abraham).

He goes on to quote their words from the Torah:

“O Nebuchadnezzar, we are not careful to answer thee in this manner [sic].
If it be so, our God whom we serve is able to deliver us from the burning fiery furnace, and he will deliver us out of thine hand, O king.
But if not, be it known unto thee, O king, that we will not serve thy gods, nor worship the golden image which thou hast set up.” 

He goes on to explain a number of beautiful lessons, but his main point is a focus on the line where they say, “But if not…”  His point: true faith is knowing that even if we are thrown into the furnace, we’ll still believe.

In MLK’s much more eloquent words:

“But if not” — do you get that? That these men were saying that “Our faith is so deep and that we’ve found something so dear and so precious that nothing can turn us away from it. Our God is able to deliver us, but if not…”
This simply means, my friends, that the ultimate test of one’s faith is his ability to say “But if not.” 
You see there is what you may call an ‘if’ faith, and there is a ‘though’ faith. And the permanent faith, the lasting, the powerful faith is the ‘though’ faith. 
Now the ‘if’ faith says, “If all goes well; if life is hopeful, prosperous and happy; if I don’t have to go to jail; if I don’t have to face the agonies and burdens of life; if I’m not ever called bad names because of taking a stand that I feel that I must take; if none of these things happen, then I’ll have faith in God, then I’ll be alright.”
That’s the ‘if’ faith. You know, a lot of people have the ‘if’ faith.

As with all of his sermons, he started off by making these points thoughtfully and slowly.  But as the sermon progressed, his voice rose, the urgency rose, to the point where, even from these years and miles apart, he gripped me with what was a call of spiritual life or death:

And I say to you this morning, that if you have never found something so dear and so precious to you that you will die for it, then you aren’t fit to live. 
You may be 38 years old as I happen to be, and one day some great opportunity stands before you and calls upon you to stand up for some great principle, some great issue, some great cause—and you refuse to do it because you are afraid; you refuse to do it because you want to live longer; you’re afraid that you will lose your job, or you’re afraid that you will be criticized or that you will lose your popularity or you’re afraid that somebody will stab you or shoot at you or bomb your house, and so you refuse to take the stand. Well you may go on and live until you are 90, but you’re just as dead at 38 as you would be at 90!

The words hit me like a thunderclap.  A man speaking to a congregation of people who were literally putting their lives on the line for the causes he spoke of.  A man demanding they understand that if they aren’t willing to risk their lives for the cause, they are already dead.  A man who himself would be killed less than a year after he gave this sermon.

And he also happened to mention people afraid of losing their jobs.  Suddenly, that issue, in the face of the struggles he described, seemed so minor, although I knew it wasn’t. 

Why had I been willing to put myself in this position in the first place?  Why had I written in the way that I had, why was I willing to lose support for the work I was doing, risk ostracizing myself from others, and subject myself to things like community backlash?

It was because some part of me that this great cause, this great opportunity, was standing before me.  As it is before so many today.  We live in a world currently dancing on a razor’s edge, ready to fall and die or jump and live its true meaning at any moment.  Where children are put in camps, but where minorities are willing to fight for them.  Where authoritarians from around the world are rising, as well as the those demanding uncompromising visions of human rights.  Where the very reason all the evil we’re seeing has happened is that, for 8 years, America imagined what it would be like to embrace a world where a Black person could be president and where Black lives could matter, and for many it was too much.

At the time Martin Luther King gave this speech, he was the most hated man in all of America.  He was facing his own backlash, one that had become a predictable part of American history, as America faced what it would really cost to integrate schools and create the world that King uncompromisingly demanded of them.  One where economic inequality was as central as racial inequality (since the two coexist), one where unending militarism was slowed down, and one where humanity finally dedicated itself to truly providing justice, equality, and humanity to all.

It was in this environment, not the fairly tale dream we have of his life, that he gave this sermon.  

And while it seems minor, I suppose that hiding my Twitter account felt more symbolic than anything: it was an act of silencing myself.  And hearing King’s words, I knew what he meant about being dead at 38.  I was 34, about to turn 35, and this all seemed like a big symbolic moment for me: would I choose life?

And it wasn’t only symbolic, as much as many people may like to imagine that social media is inconsequential.  Twitter is maybe one of my largest platforms.  Only months earlier, I had been able to use that very platform to bring attention to antisemitism in Britain, by pure luck getting Alexandria Ocasio Cortez to respond to me (this is the magic of Twitter, honestly).

And here I was, shutting down my voice so that I might get a job… a job that would only care about my tweets if they planned to ask me to “suppress” them once I was hired.  Was that what I wanted?  Was that what I was put on this earth to do?

I decided, then and there, as King finished his fiery sermon, that I would make my Twitter account public again as soon as the interview was done, no matter the result.  Whatever was coming, I would deal with the fallout, but quieting myself was not an option.

(And I am now publishing this only days after a video I captured of police arresting a Black teenager on the subway went viral and helped bring attention to New York governor Andrew Cuomo’s plan to increase police presence on the subway to prevent people from not paying for their tickets.  As I write this second draft, I can’t help but think that about how it was King himself who convinced me to keep the channel open that would allow the video to enter mainstream discussions.)


On the drive back, only an hour or so after the interview (and thus, after I had made my Twitter account public again), I received a call.  It was the rabbi.  I didn’t get the job.

I thanked him, hung up, and smiled.  The message, I felt, was clear: I wouldn’t get a job I deserved in this field unless it came directly from God.  They didn’t want me, and maybe I shouldn’t want them.


After months of being broke, desperately wondering when I’d finally pivot my career to Jewish leadership, and dreaming of a place that would value my voice, I gave up.  

I put all my energy into finding a job in an area I thought I was done with: marketing at startups.  This was how it had all started for me, and for a long time, I felt that going back to it would be an admission of failure: doing so would mean I couldn’t work in the Jewish world as a leader.

But after the King sermon, after not getting this last job, this job that I was overqualified for, that would have required a huge sacrifice of time and a huge pay deduction, it no longer felt like failure; it felt like following a path God had been patiently waiting for me to take for a while.

It was when I had worked in startups that I had done some of my best work: I didn’t need to worry about the consequences of my words or to wonder if this or that stakeholder would lose faith in me.  I was able to fully fight, fully commit, in a way that I just couldn’t when I was trying to work in the Jewish world.

Being myself had gotten me this far, and I was no longer willing to try to be good anymore.

The Romantics believed that most people got God and Satan confused.  I think they were on to something: very often, doing the right thing means going against what we think of as the better path.  It means letting go of what we once thought was right so that we can fully commit to a deeper truth.


A day after my rejection, I applied to every interesting startup I could find.  Two weeks later, I was invited to interview with a startup.  It just so happened to be on my birthday.

As I arrived in the office (a co-working spot in Manhattan), I heard Hebrew coming from all around me.  It wasn’t so surprising, since if you work in an area with a lot of startups around, you’re bound to hear some Hebrew.

The company itself was originally based in Switzerland, so I figured it was just that: normal startup world stuff.

The interview went okay.  I flubbed a question, and figured I didn’t get the job.  But at the end, the CEO told me something I didn’t see coming: the entire workspace was filled with Israelis because this was the center of an incubator made to help Israeli companies succeed in America.  He was an investor, and his COO was also Israeli, who he’d want me to interview with next.

I walked out of the interview laughing to myself: of course I couldn’t avoid Jews, even when I tried.  I looked up, and happened to notice that a Chabad house was literally across the street from the office, and laughed again.

Two days later, on my Hebrew birthday, I interviewed with the Israeli.  He saw that I was an activist, and when I explained that the job I had with the word “Trumps” in it (Torah Trumps Hate) was anti-Trump, he said, “Well, you know that we like Trump in Israel, right?” I nodded that I did, and laughed to myself again.

The interview was about as Israel as it gets (I really wish I could share the details), and I walked out on a kind of high.  Something about this job felt like destiny.

Two days later, it was the Friday before Rosh Hashanah.  I got a call from the CEO.  I got the job.

I took a deep breath.  Grateful for the job.  Grateful to have found the next stage of the journey.

But more than all that: grateful that I could live now.  Not just the physical life that a salary allowed me to live, but the spiritual one that meant I could be truly me, with my voice, without looking over my shoulder anymore.  I could write what I cared about, say what I stood for, fight for what I was meant to fight for.

I had just turned 35, and I was alive.