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I Spent Years Being Jealous, But Then I Realized I Had What I Wanted All Along

I Spent Years Being Jealous, But Then I Realized I Had What I Wanted All Along


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During the first 4 years after starting Jew in the City, I worked for free. I didn’t know how to fundraise, and so I basically volunteered for a cause I deeply believed in. After these early years of actually losing money by working (to pay for a babysitter while I was never compensated for my time), speaking requests started coming in, and suddenly I was on the speaker’s circuit and eking out a modest living.

My wonderful husband wanted to celebrate this milestone and bought me a fancy travel bag. It was a bit of a splurge, but he knew that I had felt kind of junky for years, not bringing in a paycheck, despite working constantly. The bag was well-made, with all sorts of pockets and storage slots. I loved it, that is until the first time I got to the airport and realized it was missing something major: that space in the back where a suitcase handle can get fed through, so you can stack your carry-on on top of your suitcase.

And every single time I traveled, which was about once a month (I couldn’t leave my family more often than that), I would be rushing through the airport, with my fancy carry-on bag perched on my rolling suitcase – the whole contraption regularly tipping over. Simply looping the carry-on straps over the suitcase handle never worked. I’d loop the straps around double, triple, to no avail. It always fell.

I’d look around at all the organized travelers, who had that slot in their bags, just breezing along through the airport. I was discombobulated and a mess. They were stress-free and smoothly sailing along. I thought about getting a new bag – the kind everyone else seemed to have – but it seemed irresponsible and indulgent to stop using an expensive bag – just because I wanted to be like one of the cool kids in the airport and have that slot for stacking. So I just stuck with what I had and regularly tipped over, sometimes knocking into people, and regularly feeling foolish.

Well – many years later, not only did I find a way to make a living from my passion, I was able to secure seed money, hire a staff, and build a real organization. I have learned how to fundraise, and I am not afraid to ask for money, because the work we are doing here is literally saving lives. To celebrate this new era of professional success, my husband bought me a new bag. This time a briefcase. #bosslady

As we were discussing styles and sizes and features, I told him “It must, must, must have this slot in the back, so I can finally successfully stack and roll in the airport (like all the other smooth execs!).” So we found the perfect bag, and when it arrived last week and I unpacked it, I couldn’t believe what I found.

At first I didn’t find the slot in the back for stacking. But then as my hand reached into the back pocket, I discovered a zipper which can be opened, to allow the rolling suitcase handle to feed through. And when I discovered how this bag was designed, I laughed, but also wanted to cry. Because the bag that I had had for years, that I had been clumsily schlepping along, had a zipper in its pocket too that was meant for the same exact thing, and I just didn’t know why it was there or what it was used for.

And as this all played out in my head, I thought about the members of Project Makom. And how my little stupidity plays out in their lives in serious ways. These are people raised in a life with Torah and mitzvos, but the way these things were presented to them, never worked. Some may have looked out and seen other Jewish people happily enjoying their “bag” (i.e. Jewish experience), but they never knew how to do it themselves. To them the bag was useless, worthless, an outright mistake.

But when we reintroduce Jewish teachings and practices to them – this time the right way, in a healthy way, in a positive way – they  can’t believe it. They discover that they actually had the foundation for their happiness all along. They just needed to know how to use it correctly.

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  1. LOL I had a six-month obsession with finding the perfect bag with that slot! I used to spend my free time surfing the internet looking for it. (And guess what, it doesn’t have an actual name and half the descriptions don’t even mention it even when it’s there, so just try googling for it!) I even drove 1/2 hour to a huge discount luggage outlet I had gone to in the past only to find that it had closed. I eventually did get one but I actually don’t like it as much as my old bag, so I just throw the old bag over my shoulder and somehow life goes on just fine even when it does not meet your dream of perfection. But your story is much funnier and more philosophically profound. 🙂

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Allison Josephs

Allison is the Founder and Director of Jew in the City. Please find her full bio here.

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