Change Is Good, Right?

Sure. It can also be profoundly nerve-racking and, ultimately, liberating—as Issa Rae, the star and creator of HBO's "Insecure," found out when she got a dramatic, life-altering haircut.

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The Inspiration Behind the Chop

There are layers to it. The most simplistic reason is that I saw poetess Natalie from the group Floetry in a music video when she was bald, and I was like, "Oh my God, she looks so beautiful and that must be so freeing. I want to cut all of my hair off, but I don't know if I can pull it off." I needed to do it because I had so many different hair textures going on, and I wanted a fresh start.

I think when you're young, you're so afraid to stand out, you're afraid to be unique and you want to blend in so that people don't talk about you or single you out.

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I toyed with the idea of doing it, and then I posted "I'm thinking about cutting off my hair" on Facebook. A bunch of my friends [commented] like, "oh my God, do it," or "no, you're about to be so ugly," or "what if you have a weirdly shaped head?" There was so much interest, and so many responses. I was like, "Oh, my friends are shitty, but this is interesting."

Real friends / How many of us / Will support a risky haircut? Photograph courtesy of Issa Rae
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Around that same time, I was coming up with the idea for my web show Awkward Black Girl, and I remember posting tweets that said, "Oh man, I wish I had an excuse to cut all of my hair off." I wish I had a traumatic experience. That's what I needed to be able to have an excuse to go bald.

Rae dancing with a long hair, don't care attitude. Photograph courtesy of Issa Rae

After seeing the interest that my posts got on social media, and then wanting to do a trailer for Awkward Black Girl, I had the idea to just do it for the trailers, and reveal what my bald head looked like there. I was able to use it as a plotline that shows that this character is going through something, and she cut off all her hair. It gave me the excuse, and it was the best thing—the most freeing thing I'd ever done.

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The Big Day at the Salon

I went to a salon/barbershop down the street from my place, and I asked one of my best friends to join me. He was very vocal and told me, "This is not what you need to do, but I'm going to come with you anyway so you can cry on my shoulder."

The people in the salon gathered around me and they were like, "What? You're about to cut off all your hair? That's what you want to do?" They were all witnessing it, and that, of course, made me more nervous. But I was pretty confident that it was what I wanted to do.

I remember the barber who did it, and he was kind of weird, but he complimented me the whole way through, saying, "Oh yeah, you've got the jaw structure for this…. Oh yeah, this is going to look right."

I thought about the absurdity of hair. It had been the source of so much insecurity growing up.

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With every strand of hair that fell on the floor, I felt nervous, but liberated at the same time. I think everything changed in those moments. I thought about the absurdity of hair. It had been the source of so much insecurity growing up. To not have to deal with that was a huge thing, and it was a definite confidence-booster. I felt like I was viewed differently after I cut my hair. People look at you like you're more confident when you have a bald head—like you have the audacity to be able to walk around like that.

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Career-wise, I only remember an ascension from that point. I don't remember looking back. I am currently growing out my hair just because I'm learning to take care of it better...and there comes a time when your head gets cold [laughs]. I feel like I want to look different and I want to try different things. That was something I wasn't really able to do before, so I'm enjoying experimenting with the various hairstyles I can do with short hair and seeing where it goes.

The Beauty Advice She'd Give Her Younger Self

In the process of dealing with her 29th birthday during the first season of Insecure, Issa (also the main character's name) works as a youth mentor.

Just work with what you have. What you have is you and that's beautiful, and it can be beautiful, and it's what makes you unique. When you're young, you're so afraid to stand out, you're afraid to be unique, and you want to blend in so that people don't talk about you or single you out.

The coolest people I remember were the people who didn't care what anybody else thought and were like, "I'm rocking this. I'm going to have blue hair. I'm going to wear my combat boots. I'm going to do this." I just didn't feel brave enough then. Now, I would just tell myself: "Rock who you are because that's special."

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The Products She Can't Live Without

Don't Shrink Flaxseed Elongating Curling Gel by Aunt Jackie's Curls & Coils, $10, naturallycurly.com.

Aunt Jackie's Don't Shrink Flaxseed Gel is my shit. It gives my hair the best shine and the best curls. I love it so much.

Raw Shea Butter Deep Treatment Masque, $13, sheamoisture.com.

I also love a lot of the Shea Moisture products, and Sienna Naturals, which is a newer high-end brand. I love their skin-care products and oils. Their scalp oils are the bomb, and you can use them on your skin, too.

Some Thoughts on Her New HBO Show, "Insecure"

Laughing at her own jokes, perhaps? It would be hard not to! Photograph courtesy of Anne Marie Fox/HBO

With Insecure, I wanted to tell a story that was more grounded than Awkward Black Girl. Here I am—31 now, 30 while producing Insecure—and it felt like my experiences and mindset were different. I wanted it to be something that reflected how I felt then, the adult relationships that I had, the friendships that I cherished so much at this point in time, and a lot of the insecurities that I felt in navigating a career, my own relationships, and even in my blackness, to a degree. I also wanted to reflect just what I deem regular black people, the people who I know who are just living life and going through things that everybody goes through. I felt like we haven't gotten a chance to do that since the '90s.

Without spoiling anything, this may or may not be a love interest for Issa. Photograph courtesy of Anne Marie Fox/HBO

I think the show Girlfriends paved the way for this show. Living Single is a show I took for granted when I was younger. Watching now, I'm like, "Dang, this is so relatable and so real." Then there was Martin, The Fresh Prince of Bel Air. I remember being a little girl and wanting to be a part of this in some way, and now, with this new cultural renaissance, I feel like I'm kind of living my little-girl dream.

Insecure premieres tonight on HBO at 10:30 p.m. ET!

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