Blogger-Like: Meet Kindsey, Your Insecure Set ‘Connect!’

By Kindsey Young


Hey, Insecure Fam! I’m Kindsey Young, a 28 year-old writer from Prince George’s County, Maryland. We just wrapped Season 3 of Insecure, where I was fortunate enough to be in the writers’ room as writers’ assistant I know you’re probably wondering how I got here... I like to say it’s a mixture of hard work, luck and timing. It’s kind of surreal when I type it all out, but here’s the recap: Like a lot of Issa Rae fans, I was already hooked on her back in the Awkward Black Girl web series days. Fast forward to 2016, I was in grad school studying producing for TV, and hear Issa is getting her own show on HBO. Having watched her journey, I was inspired to see someone who looks like me and relates to me. One random day, (it was Thursday, August 8, 2016. I know ‘cause, receipts), I got on Instagram, went to Issa’s page and literally slid in her DM’s. I wrote her a message about how I was proud of her, and how I planned on moving to California to pursue writing and do what she does once I graduated. It was one of those moments where I knew she wouldn’t respond, but I wrote it anyway, ‘cause, manifest.

A few months later, during Insecure season 2, Issa announces the #InsecureOnSetContest. She was looking for two best friends to be on-set Production Assistants. My best friend Candice and I felt like this was the perfect opportunity to take a chance. Long story short... out of thousands of entries, we won! And just like that, we left our lives on the east coast behind and up and moved to L.A. This was the beginning. It still blows my mind. For one, I had never won a contest in my twenty-seven years of life, so winning this was like a dream. And two, what I said in my message to Issa a year ago has now manifested! I’ve always been taught to say the things that you want to happen out loud. Thanks, Mom. If I never believed it before, I do now. You be knowing.

The experience as a production assistant on set was amazing. So much was learned, so many great bonds were made, and it was just an overall inspiring thing to be a part of. The crew was very diverse and full of women, which was a beautiful sight to see. In the midst of grabbing coffee, moving traffic cones and tending to my PA duties, I made my aspirations clear: “I’m a writer.”

Season 2 wrapped and a few months had gone by when I got a message from Issa: They were looking for a writers’ assistant for the Season 3 writers’ room. My. Heart. Dropped. The next thing I know, it’s October, and I’m sitting at a table with Issa Rae, showrunner Prentice Penny, and all the talented writers of my favorite show! The making of season three was officially beginning — and I was going to be a part of it. I would have never thought this is where I’d be after only six months in L.A.

Having the opportunity to be part of the writing process for Season 3 was an experience I can barely put into words. I learned so much from Issa and all of the writers, and gained some much-needed writing confidence along the way. The room’s conversations, debates, laughs, stories and experiences we shared — are all of the ingredients that went into making a season that we hope everyone is going to enjoy. I remember when folks used to say, “It’s not work if you’re doing what you love.” Well, they were right, y’all.

Once we finished writing the scripts, I got to spend a good amount of my time on set. And so to put the cherry on top of this big ol’ Insecure cake, I've been given the opportunity to be the Season 3 on-set blogger for HBO! So, I'll be feeding you all some fun extras from our cast, crew, and writers of Insecure throughout the season. I can’t wait for everyone to watch and see what we’ve been up to! Make sure you follow @insecureHBO and #BloggerLike to check out my future posts from

- Kindsey

Check out new episodes of Insecure every Sunday at 10:30 pm, and head to the Blogger-Like page for updates all season long.