ChiTribe Jewish Influencer of the Month: Freddie Feldman @TheDorkyJewish Challah Art

@thedorkyjewish freddie feldman ChiTribe Business of the Month

Introducing Freddie Feldman, Challah Artist @thedorkyjewish

This month, ChiTribe shines a spotlight on a remarkable individual who combines tradition with creativity in a way that captures the essence of both Jewish culture and modern innovation. Introducing Freddie Feldman, a Skokie, IL-based challah artist whose unique approach to baking has turned the traditional Jewish bread into a canvas for artistic expression and his Instagram @thedorkyjewish is his platform to share his creations. Freddie Feldman hails from Rockland County, New York, and has made a name for himself in Chicago since his college days at Northwestern University. Growing up in a Jewish household rich in traditions and resilience, Freddie’s journey into baking was inspired by his family’s history and his mother’s legendary Hamentaschen. His evolution from a traditional baker to a social media influencer and challah artist showcases his passion for both his heritage and his craft. Learn all about Freddie!

@thedorkyjewish freddie feldman ChiTribe Business of the Month

Where are you from?

I’m Freddie Feldman, a challah artist living in Skokie, IL. I grew up just outside of NYC, in Rockland County (Monsey and New City). I moved to Chicago to attend Northwestern University and have been here ever since.

What Jewish traditions did you participate in growing up?

Growing up, I went to Solomon Schechter Day School for elementary school and attended the Prozdor high school program at the Jewish Theological Seminary. I’m the child of an immigrant and grandchild of Holocaust survivors, and that for sure shaped my Jewish upbringing. I got my love of baking and cooking from my mother. She was the “Hamentaschen Lady” with her own amazing recipe, which I still make yearly, and she makes all year around.

What do you do for fun?

Baking challah IS what I do for fun! I’m what some people call “neuro spicy” (ie. I have ADHD), so I do a LOT of random things for fun. I think it drives my wife and two teen kids a little crazy, but it keeps things interesting. For example, I’ve performed in the Jewish a cappella group Listen Up! for the last ten years, recently retiring to focus musical pursuits elsewhere. I have the most extensive collection of Tic Tacs, with 137 flavors and counting (see

When did you start sharing your challah creations on Instagram?

Like many others, I started baking a lot during the lockdown in 2020. Around April, I decided to try making challah, and it was so good. I had never made challah before because the braiding seemed tricky to do. It wasn’t nearly as hard as I thought, so I figured I’ll make one every Friday for Shabbat dinner with the family. We’re not shomer, but we like to have family dinners together on Friday nights and light candles, etc.

After making regular challot for five weeks, I randomly made a Jewish star one and posted it on Facebook. My friends were all, “Wow! That’s amazing, how did you do it??” I was like, “Uhhh I just made a star, how hard is that?” The following week I made a hamsa…and then baby yoda…and then Rick Sanchez…and then I just couldn’t stop. I’ve baked a challah every week for the past 200 weeks, only stopping for Passover each year, when I make artistic matzah.

Challah Images Courtesy of Freddie Feldman, @TheDorkyJewish

Where do you find inspiration for your weekly challah creations?

At first, I would plan them out all week beforehand. I would even do sketches. For a while now, I have waited until the day before or even that morning to decide what I will do. I like to follow what’s going on in the news, social media trends, or holidays and free-associate on topics. I work in AI at my job (Director of Voice & Conversational Interfaces for Wolters Kluwer Health), so when I get stumped for ideas, I even ask ChatGPT for suggestions, and it comes up with great stuff. It came up with The Count from Sesame Street when I was trying to think of a S’firat Ha’omer challah (get it??), which turned out to be a very popular challah.

How do you plan your Challah designs?

I think it’s all about breaking something down into “geometric primitives” to take a concept from programming (yeah, I’ve been programming for over 40 years). A primitive is a basic shape, like a line or a circle. I learned basic braids that I then use over and over, like a line (basic 3-strand braid), a rectangle (7 or 5-strand braid), or a circle (4-strand round braid), to name a few. Then, you put them together to make a larger object or shape. I’ve even developed new braids, like adapting the lanyard Cobra Stitch for dough when I made a Coba Kai challah. It’s fun and more analytical than you think.

I started out practicing with a tub of Play-Doh that I bought online. That way, you can take your time. You’re not racing against time like you are with live dough (it’s alive, constantly rising, and gluten proteins are fighting with you). 

What are your goals for your Instagram following?

I’m here baking a challah each week and trying to get the word out about it as best I can. I have 7400+ followers on Instagram right now, which is nothing to shake a stick at since I grew that organically, without “buying followers” like some people have been known to do. I want to keep growing that so that more and more people can see what you can make with basic challah dough. It helps keep a sometimes disconnected people like us feeling a little bit more together. All kinds of Jews and non-Jews love challah, and I try not to make designs that alienate anyone (although sometimes I can’t help it and get a little bit political).

How do your challah creations connect you and your followers to Jewish culture and traditions?

I think a lot of my followers aren’t Jewish, and I think that my challot show people there’s a lot you can do with dough, but also not to be so serious about things. Early on, when I made a Poop Emoji challah, I got a lot of backlash in one particular Jewish food FB group. Yes, people were actually upset with me for making a loaf of bread that kind of maybe sorta resembled poop (you know the Poop Emoji is actually supposed to be soft-serve ice cream though, right?). I don’t argue with people online; I simply say, “I’m sorry you feel that way,” they always drop it or even apologize. When they go low, we go high, right?

@thedorkyjewish freddie feldman ChiTribe Business of the Month

For those inspired by your work, how can they engage with you?

I always welcome suggestions, but I never promise anything. I have a particular set of criteria in my head that I stick to, so while your suggestion might be cool, or funny, or meaningful, it might not be something that I can do. I have done some commissions (like Nickelodeon), some collabs (like Microsoft & Tokin’ Jew), some fundraiser collabs (like one I did for World Central Kitchen/Ukraine with actor Joshua Malina), and I’m always open to more. 

I’ve been a public speaker for years (check out my talk at TEDxVienna a few years ago), and now I’m trying to book challah events at synagogues and other organizations. I also recently finished writing a manuscript for a children’s picture book, hoping to pitch it to some publishers & agents. 

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Rebecca Schwab

Rebecca Schwab

Rebecca creates best practices and executes marketing campaigns for Jewish organizations who are trying to reach the next generation of the Jewish community - specifically Millennials and Gen Z - through digital marketing, social media, online and in-person events.