You Can’t Box Ashley Blaine Featherson-Jenkins In

The “Dear White People” star is showing the beauty of leaning into all of life’s seasons in her new OWN podcast, “Trials to Triumphs.”
Ashley Blaine Featherson
Ashley Blaine Featherson
Illustration: Chris McGonigal/HuffPost; Photo: Getty Images

I Run This is a weekly interview series that highlights Black women and femmes who do dope shit in entertainment and culture while creating visibility, access and empowerment for those who look like them. Read my Brandee Evans interview here.

Ashley Blaine Featherson-Jenkins has an inviting energy about her. It’s a warm aura that both soothes and activates you. Without uttering anything, it’s as if she’s saying, “I see you.”

She sits on the Zoom screen before me at the same desk she records her podcast, “Trials to Triumphs,” in her home office in Los Angeles. On the wall behind her is a sole portrait, showing her as Joelle Brooks, her character in “Dear White People.” It feels representative of not only what she’s built but also of where she’s going.

The Gaithersburg, Maryland, native has conquered a lot in her career so far. She’s created and starred in the Black&Sexy TV web series “Hello Cupid,” which provided a rare look on how colorism and desirability politics play out for Black women in the dating scene. She stole our hearts in “Dear White People,” playing an underdog college student who reflects so many young Black girls’ stories. And most recently she’s giving us laughs as Talia in NBC’s “Grand Crew.”

Featherson-Jenkins is still climbing. She’s not where she thought she’d be at this point in life, but she knows she’s exactly where she needs to be. She calls this a transitional season.

Earlier this year, the actor launched “Trials to Triumphs.” She came up with the idea in 2019 after her manager, Mike Smith, suggested she would thrive in the space. Having “Dear White People” creator Justin Simien as a guest on her pilot episode, Featherson-Jenkins tried to find a home for the podcast, but “no one really knew what to do with it.” Then COVID-19 hit.

She believed all was lost with the podcast until she linked up with Corinne Gillard, a senior producer at OWN whom she connected with after one of her regular Instagram Live conversations during quarantine. At the time, OWN was putting together a strategy to expand its slate of podcasts. With the original format Featherson-Jenkins intended, “Trials to Triumphs” went on to find a home at OWN as the network’s first official original podcast created from the ground up.

Now on a weekly basis you can find Featherson-Jenkins sitting alongside a guest who paints the beauty and pain of walking in the path destined for them. So far her guests have included Kelly Rowland, Danielle Brooks, Amber P. Riley and her husband, Darroll Jenkins Jr. Though people may mainly know her for acting, she refuses to get boxed in. The conversations feel very on par with the journey Featherson-Jenkins is on right now.

“Acting is really my first love, but it’s some things that even acting can’t do,” Featherson-Jenkins said. “There’s still the buffer of a character, which I love and that serves as a different type of inspiration, but there’s something so profound about just me and my guest being that and that’s it. There’s no script, there’s no lights, camera, action. It’s just authenticity. And I’m just, honestly, I’m just really, really proud of myself.”

Featherson-Jenkins “discusses getting vulnerable on her new podcast, creating the content that she wants to see and the season of growth she’s in right now.

So I first saw you on “The Number” and then “Hello Cupid,” which was one of my favorite web series to watch in college. I gravitated toward your style of acting. I remember thinking that you were special. If you could just teleport us back there, where were you mentally and where did you see your career going in those Black&Sexy TV days?

Oh, my goodness. That’s such a good question. Thank you for saying that about my style of acting. I’m such a fan of actors. I love TV. I watch so much television up until 2 o’clock every night. So it just feels good to know that somebody sees me as being very unique and having my own path, my own lane.

When Lena Waithe and I created “Hello Cupid,” we created it because I didn’t see myself on TV. At the time, I was like probably 24-ish and had been in L.A. for two, three years. This is like pre-“Scandal.” This is pre-“How to Get Away With Murder.” This is after, obviously, the golden wave of television for Black folks in the ’90s and the early 2000s.

There was this lull period, and I didn’t see young Black women in their 20s living their best, or just going through all of the things that I knew I was going through. And Lena didn’t see that either, being a writer and wanting to write and create content. Black&Sexy was a place that was holding space for artists like us at that time, and really, we created the show out of necessity. I wanted to work, she wanted to work, and we came up with something. I was hungry, and I was determined for people to know we exist and we are worthy of having our stories celebrated, and we’re interesting and we’re dope. We’re not a monolith. And I feel like that’s what you got from Robin and Whitney on “Hello Cupid.”

I just remember the story being unique as far as taking on this very real issue of colorism and desirability, and flipping it into something that felt graspable for its audience. I just don’t think that it got its due justice. I wish that even more people would’ve been able to watch and enjoy and relish all of it in real time because I think in a way it was ahead of its time.

I think so, too. We were all coming up together. Issa was doing “Awkward Black Girl,” and then there was “Roomieloverfriends.” We were all really coming up together and really wanting to make content that was true to our experience. And you’re right. In a lot of ways, “Hello Cupid” was ahead of its time. We were exploring a subject matter that nobody really wanted to touch, and we were exploring with Black folks, you know what I mean? We weren’t, at that time, really getting our due like we should have. So we carved our own lane.

What did creating that show and working on it teach you? What did you bring from that experience onto your other projects, especially going into “Dear White People”?

One, to relish in my uniqueness. I’m realizing this now that I’m 10 years removed from “Hello Cupid,” but I think after “Hello Cupid,” I started putting myself into this box that I convinced myself that the industry was putting me in. I wanted to conform a little bit. It felt like maybe if I conformed and was more middle-of-the-road, then there would be more opportunities. But the truth is if “Hello Cupid” taught me anything, it’s being unique and different and having your own ideas and starting your own projects and championing yourself. That ultimately has afforded me the opportunities that really mean something to me in my life and that are contributing to the legacy that I want to build.

“Hello Cupid” taught me if I could do it then, I could do it again, and I could do it again and I can do it again. All it takes is me believing in myself and remembering where I came from. I always love when people bring up “Hello Cupid” because, for me, in a lot of ways, it’s in the recesses of my mind, but it wasn’t that long ago, and it was very much so my people’s introduction to me. And I have to honor it for how wonderful that is. That’s an amazing thing, and I love whenever people bring it up because it shows that I was seen then and I’m seen now, and especially for the growth.

You were speaking about how, essentially, you didn’t necessarily see your uniqueness and that the world was trying to box you in. When were you able to begin to break that box and really lean into your authenticity in a way that felt more natural to you?

There’s never been a season in my life where I didn’t see myself necessarily, but there’s times in which I’ll say I’ve seen myself more clearly than others. I’ve honored myself better than at other times. That’s just life.

I think that getting married last year changed something in me in a really beautiful way. I think it shifted my world view, and my perspective, and my goals and my ambitions in the best way possible. Marriage, in a lot of ways, requires me to see myself the way my husband sees me. And nobody sees me as being greater, more talented, beautiful, kind, smart and all of the things.

Although I created the podcast before I got married, it all wasn’t really solidified until after we got married. And I think that type of support and being seen and encouraged to see myself at the highest vibration possible has really propelled me into what now I consider, although it’s a tough season of my life, I think one of the most important seasons of my life. Everything that I’m doing on this podcast, I have this knowing that it’s propelling me into something great or something bigger, continuing to get even closer to where I’ve always been destined to be.

What makes this a tough season in your life?

It’s tough because it’s very transitional. A lot of things are changing, and there’s a lot of unknown. But also it’s just because this season of my life isn’t how I thought it would be. It’s not going according to plan. I’m not saying that it’s going wrong.

If I’m asking God to order my steps and I’m trusting the universe and everything is going according to plan, then I realize it’s not going according to my plan at all, it’s His plan. And so I think that it’s an important season. The reason it’s tough is because it is challenging me to not need everything to go according to my own plan, and to be extremely open to things that are outside of my plan that could be even more so for my benefit.

Would you say you’re in a state of surrender right now?

I say surrender every five seconds on my podcast. It’s my life’s challenge. It’s my life’s work, to master the art of surrender and to lean into being more obedient.

It’s hard. It’s so hard.

Yeah. I’m a planner. I think I have everything together. I think I know everything that’s supposed to happen. I have my life planned out for the next 15 years, but life be like, “Girl, you think you know what you’re doing? You don’t know what you’re doing.”

Life be lifing.

I said that today to my best friend. I was like, “Life is lifing.” You know what it is? The best way I can describe it is growing pains. Growth doesn’t always feel good. But for the most part, growth is always for your betterment. Nobody wants to stay stagnant, and I feel like my life is calling me to do what I’ve always wanted to do, which is to continue to grow, continue to become better, continue to be the best version of myself. But in the midst of that, in getting there, it’s not always easy.

Even though things may not always seem the most clear, you speak with such clarity that it feels very much like you have a handle on what’s going on right now. Even listening to the podcast and hearing how, even in this conversation, it feels like you learn more about the next step ahead in real time.

It’s true. But that’s why it’s difficult. If I were unaware, then this season, I wouldn’t call it tough. I would just be out and about, but I know what’s happening. I know I’m in a pruning season. I know that I’m in a season where I’m having to really excavate, really, really go deeper than I’ve ever had to go before in order to get as high as I can possibly get. I’m incredibly aware of what it is, and I think also the awareness is what helps me with my podcast, my head isn’t in the clouds. I’m very much so down to earth, and I’m down in the trenches with what’s going on, and also just being really vulnerable about what I’m going through in order to really be able to connect with my guests and listeners as honestly and as authentically as possible.

That has to be hard, though. Have you always been able to be that vulnerable, or was that a process?

The podcast has brought out a lot in me. I feel like if you were to poll my friends, they would probably say I’m the most vulnerable. I’ve always been like that.

But when I started the podcast, I was like, what are people going to think? I’m an actor; are people going to be like, “Why is she doing a podcast?” If I’m honest, I had a fear of being judged for not doing what people expected me to be doing. I’m not playing a character. It’s just me. So now people are free to judge my thoughts, opinions, ideas, whatever it is. Whatever they want to say, it’s about me now. It’s not about a character that I’m playing.

But what I realized is why do I always have to be an actor? I’ve always been a multi-hyphenate. I’ve always done so many things. I’ve always had so many gifts that lend themselves to other careers and opportunities. It was me who decided that I needed to fit in some box, and I am choosing to break out of the box. And what I’m finding is that there has been such love shown to me in this season of my life, and it’s because I think it’s clear to other people, too, I’m exactly where I’m supposed to be, and I can be in more than one place at a time, and I will be.

So it’s almost like, get used to it, everybody. I have gifts. I’m leaning into them, and if you want to come along for the ride, I am so happy to have you. You might see me on TV. You might see me on the big screen. You might see me behind the mic. You might see me doing something live. Expect the unexpected, but know that I’m in a season where I’m refusing to not lean into all my God-given gifts.

Ashley Blaine Featherson-Jenkins as Joelle Brooks in "Dear White People."
Ashley Blaine Featherson-Jenkins as Joelle Brooks in "Dear White People."

Why “Trials to Triumphs”?

I created the podcast that I wanted. I think that’s always the rule of thumb when creating content: Create what you want. And so I have always been inspired by the trials in people’s lives and how they overcame them. To me, that’s where the lessons are.

I think oftentimes, especially with celebrities or people who are widely known, we just celebrate their triumphs. We can’t appreciate the triumphs unless we know what happened before they got there. And that’s what I wanted to get into in hopes of providing inspiration, hope, joy, motivation to others, just like I have. There’ve been so many people, just along my journey, that just shared the real with me, just shared the truth. Not the glitz and the glam, but the truth, what was behind the curtain. And I’ve held on to that in times that I felt like I was experiencing a similar situation or a similar season in my life.

On the episode with your husband, you called this podcast your greatest career accomplishment. Can you expand on that?

Man. It’s, like I said, it’s all me. It’s all me from the idea to every aspect of this podcast. Everything. And I’m just really proud of that. And I’m proud of doing long-lasting work that is actively changing people’s lives. To be a part of something that is providing weekly inspiration to people is part of my purpose work. Acting is really my first love, but it’s some things that even acting can’t do. There’s still the buffer of a character, which I love and that serves as a different type of inspiration, but there’s something so profound about just me and my guest being that and that’s it. There’s no script, there’s no lights, camera, action. It’s just authenticity. And I’m just, honestly, I’m just really, really proud of myself. I’m just really, really, really, really proud.

What’s crazy, I’m getting emotional. I don’t know that I’ve said that to myself until this moment.

Oh, wow.

But I’m just really proud of myself. Other people have said it to me, but I don’t know that I’ve said it to myself.

What was the most defining trial for you that you turned into a triumph?

There are so many. Now I know how my guests feel on my podcast. Honestly, my husband and I, our relationship, in so many ways, was tough for a long time. There was a lot of unknown. There was a lot of confusion, a lot of immaturity, a lot of stagnation. And, for me, he’ll say differently, but there was a time where there just wasn’t a lot of hope. I’m just like, “I don’t know that this is going to be what I felt it could be.” I remember being like, maybe I was wrong.

And I wasn’t. We weren’t wrong. We had a lot of growing up to do. A lot of healing to do. But our relationship is the most triumphant thing in my life. It’s the thing that I’m most proud of in my life. He is the person that I’m most proud of in my life. His growth is one of the most beautiful things I’ve had the honor to witness.

When I think about all the things that I’ve done in my career, I knew that “Trials to Triumphs” had the potential to be what it is now and what it will go on to be. I always knew. I never really doubted that. Same thing with my character in “Dear White People.” I knew who Joelle would and could represent for Black women. I knew from the moment I read it. I knew I had to answer the challenge and the call, but I knew what I had the potential to do with that character.

So many things I knew. Our marriage is one of those things that’s a “Trials to Triumph” story, and it’s a beautiful one. It’s a really, really beautiful one because we are most definitely triumphant.

What do you think your calling is?

My calling is to inspire in each and every way that I can. I want my life to be an inspiration. I think my calling is to always make sure that Black women are seen, and I know that I can’t do that for the world, but I can make sure that Black women always feel seen by me.

Every interaction I have with Black women, anytime I’m on a show, a podcast, a movie, whatever it is, I want to make sure that Black women are like, “Yeah, that’s sis. She’s us,” and I don’t want there to be any confusion about that. That’s really important to me. I would say I want my career to feel like a love letter to Black women, always, first and foremost. And I will say that until the day I die because that’s how important we are to me.

I think my calling is to be a light amongst darkness. I think I’m just meant to be a light.

What is the big dream or goal that you have for yourself, whether it be in Hollywood, through podcasting or otherwise?

The reason I’m struggling with this question is because, of course, I have a million things. I want to lead a series. I want to have a blockbuster movie. I want this podcast to run for years and years and years and to become a talk show. But going back to talking about that box, something about right now naming all of these things that I want next feels in a way limited. It’s almost like I know whatever I say is aiming too low. And it’s not because my goals are low. It’s just because I know God has something much bigger for me. So I’m in a season where I want to keep it open. I want to surrender to finally being really excited for just whatever’s for me, not whatever I have planned for myself.

What do you want your legacy to be?

I want my legacy to be full. I want it to be honest. I want everything I leave behind to be authentic and, in a way, timeless. “Trials to Triumphs,” for example, is timeless. Joelle, to me, is a timeless character. She’ll always fit. She’ll always matter. She’ll always mean something to someone. Just as two examples, that’s what I want. That’s what I want.

This conversation has been edited for length and clarity.


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