Andra Day on New Album, Imposter Syndrome and How Less People-Pleasing Healed Her Voice

Early in her career, Andra Day was asked by a reporter which singer she wanted to model her career after. Her answer was Sade.

“The person was like, ‘OK, but Sade only releases albums like every nine years,’ and I was like, ‘Well, I’m not going to do that, of course, I’m going to release albums probably every two years, and here we are,” Day tells The Hollywood Reporter with a laugh. “Be careful what you speak.”

Like her music idol in the late ‘90s and early 2000s, Day is set to release her sophomore project, Cassandra (Cherith) on Friday, nine years after Cheers to the Fall debuted in 2015. There’s good reason for the near-decade gap, though. “Rise Up,” the second single from her debut, took on a life of its own, garnering a Grammy nomination for best R&B performance and a Daytime Emmy nom for her live performance of the track on an episode of The View. The song, a 4x-platinum success that still sits comfortably on the current iTunes R&B chart, then became the unofficial anthem of the Black Lives Matter movement and democracy, with Day performing the soaring ballad during the inauguration parade for President Joe Biden and Vice President Kamala Harris on Jan. 20, 2021.

One month later, Day made her acting debut, in perhaps the role of a lifetime, as Billie Holiday in Lee Daniels’ biopic The United States vs. Billie Holiday, for which she won a Golden Globe and received a best actress Oscar nomination. Her performance on the soundtrack earned her a Grammy.

There’s also the personal hurdle Day’s been working to overcome throughout the entirety of her career which has stalled new releases: imposter syndrome.  

“I’m very uncomfortable singing in front of people,” the artist who performed the Black National Anthem in front of 70,000 fans at this year’s Super Bowl surprisingly admits.

Couple that with the fact that she writes and produces her own music, which she likes to create as organically as possible, and the nine-year timeline becomes understandable.

“I might name the next album Slow Burn because that’s literally me,” says Day. “I feel like I’m a perfectionist, which I’m learning, are also the biggest procrastinators, but coming off the last cycle — and it was quite a long cycle because of ‘Rise Up’ — I really wanted to bring my band in the studio. I wanted to take a little more creative control and explore with them, like when we’re on tour and we’re just vibing and we jam together, and just see what we come up with. It’s the longer way around for sure,” she adds. “It just takes more time.”

Below, Day chats with THR about her “100 percent” autobiographical second album, faith and “being happier being me.”

What’s the significance of using your first name as the album title?

It took me a long time to like my name. Even just a few years ago, every scenario I would walk into where I would say my name, it always felt weird, but I’ve grown to really love my name. I love the meaning of it, which is “truth teller” and “encourager of men.” Also, it’s called Cassandra (Cherith) because it represents me accepting myself. I often will make space for other people but not really myself. So I’ve been working through imposter syndrome, through being disappointed with myself or being happy with myself and being OK with that. Like, it’s not super arrogant to celebrate yourself. So exploring me in all of those areas — arrogant, humble — just showing up fully and being laid bare.

How autobiographical is this project?

One hundred percent. There’s a song, “Narcos,” where I say, “Screaming at me on the tarmac before I fly/ Why you so insecure?” (It’s) 100 percent verbatim what happened. I didn’t want it to be autobiographical, though, just in terms of what I experienced, but how I actually felt. My struggles with people, my struggles with myself, my excitement about myself. I don’t know where it comes from, maybe the imposter syndrome, but I have this random guilt about showing up for myself. So, “Probably,” absolutely autobiographical. “Maybe Next Time,” autobiographical.

What was the writing process like?

Truthfully, the process was all over the place. I have a song called “Midnight” that I wrote 12 years ago. But, primarily, I would just get in the studio with my band and start jamming for hours. I record voice notes in my phone constantly. Anytime I have a little idea, I write it in my actual notes and also just living, really living. Every song and every source of inspiration came spiritually. A lot of times I have to pray to be like, “God make me open,” because sometimes we don’t realize we’re actually not paying attention as much as we should, so I need God to ground me to make me present so that it opens my understanding. Everything becomes inspiration if you’re open, I believe, even doing these movies. Billie is not a part of this record, but I’m transformed by that experience, so it’s going to be on the record.

Did you feel you needed to separate yourself from Billie Holiday with this album?

No. I probably should have. I do now in the aftermath (laughs). Honestly, it was impossible. I was so transformed and impacted by this character. It does not feel like a character I played. They actually feel like memories from life, which they are, because I was on set, and I was experiencing these things, but it feels like her life was actually my life. And there’s some truth to that, I think, as an actor, to a degree, at least for me. I kind of made a conscious decision to just let whatever I was experiencing as Billie spill over to the album. That’s probably why it’s a little spicier, a little pettier, but it’s still a blend between her and I. Maybe I’ll discover I should have had some separation but it all kind of blended together with me with this project because everything alters us.

You said that you ran from the role of Billie Holiday because you didn’t feel like you were an actress. Since that role, you’ve continued to take on more parts, are you feeling more settled into that identity now? 

No, but I’m still saying yes because, apparently, I like self-harm and torture. The last one that we did, The Deliverance (release date TBD), in some ways, I felt was harder than Billie. In some ways, Billie was definitely harder, and in some ways it was harder than Billie. Lee told me… I freaking love him, he’s just a legend and so great at what he does, and the way he also loves on me and encourages me, and all of his actors, honestly, and utilizes their talent and their gifts. He said, “I can’t believe I’m saying it, but I actually think you’re better in this than you were in Billie.” So I don’t know that I’ll ever really be settled. 

I did an interview one time, a roundtable with a few people, and Michelle Pfeiffer was in it, and I was asking, “When do you get confident in it?” and she said, “Never. I go into every role scared that I’m just going to totally mess it up and blow it, and if you start to feel like you’ve got it, you should probably hang it up.” So, I’m starting to accept the fact that this will produce an incredible amount of anxiety in me, but I might thrive on it. I’ve got ADHD so I might be one of those people. But If I’m agreeing to do a project, it’s because I believe in it, and I really want to be great, and I want to make sure they get a great result and that’s always going to come with some pressure.

Your vocal cords experienced some damage from smoking cigarettes for the role. Where are you now in the healing process?

The process of healing my voice is still going on. I’ve gotten with a new vocal coach who’s amazing. His name is Rob Stevenson, and he’s very clear about the science and the biology of the voice so he has all of these really amazing techniques. I think it’s also a hump in my head. I need to get consistent with these things, and I need to be confident that I can hit certain notes. Or if I can’t anymore because of things that have occurred, that’s OK. It’s just a different type of voice. You’re supposed to be quiet as a singer, which I think is the craziest conundrum that God ever created because singers are loud by nature. But for the last few months, I’ve tried to be a little quieter, a little calmer, do less people-pleasing. That’s actually helped my voice. That sounds really crazy but less entertaining. I can love you, but I don’t have to cater to everything so stepping into myself has actually helped.

There’s only one feature on the album. Why Wale for “Heavy on My Mind”?

I have a lot of social anxiety, so it takes me a while to get comfortable around people, and he got right in there. I think he’s so freaking talented. I’m a huge fan. I think he’s phenomenal, and we just liked working together, and we both had this idea of maybe doing a joint EP. So we’re actually talking about it and have a few other songs. I’ve started to work with more people, artists I love, but it did take me a long time to get there because of imposter syndrome. I’m very uncomfortable singing in front of people in the studio. I’m very uncomfortable singing in front of people. So I don’t know why I do this job. Because of that imposter syndrome, I feel like it really, in some ways, caused me to not do more collaborations. So now I’m just trying to step into that and say “yes.”

You performed at the American Black Film Festival Honors in March, and you seemed so comfortable onstage, especially when you started improvising and giving the audience a bit of Sunday worship service.

Well, listen, that ain’t me, that’s God. We’re not going to block that (laughs). I think I’m going to incorporate that, too, more and more. It’s this balance, especially as a woman, as a Black woman in America, and as a believer, of show up with not too much of your Blackness. Show up with not too much of your womanhood. Show up with not too much of your faith, and I’m finally getting into a space of it’s for who it’s for because moving any other way, for me, has become like faithlessness. So trust. Trust you’re here for a reason. Trust that God is working. Trust in His Holy Spirit. Some people will be like, “We hate this, eww,” but that’s fine. You can’t control that. And that doesn’t necessarily dictate my impact.

The last two songs on the album, “Still” and “Thank You God,” touch on your faith journey.

I love “Still” because the song in itself is a journey. It’s one of my favorite songs. In the beginning, I’m acknowledging the fact that life is cyclical. Why am I still so heartbroken? Why am I still in love? I’m still in this place, God, I’m praying, and I’m seeking you, why am I still? I’m meditating, I’m practicing peace. And then, in the midst of that, the discovery goes from asking why am I still stuck to realizing, “Oh, I’m still.” I actually have peace. It’s the idea that the work will bear the fruit. It was a reflection of me looking back on the album, on my life, and all those things, to be like, “Wow, I might be in this difficult place now, but look at all the progress and that practicing those things, believing for those things will take you from being stuck still to actually being still and having that peace.” I wanted to leave that as a gift for the listeners for sticking it out with me and listening to the end.

Talk about putting your mom on the final track.

I love my mom’s voice. My mom is a praying woman. She’s the reason I have the faith that I have today, so it was important for me to have her voice. My mom’s so funny. I was like, “Do you want to say something?” And she said, “No, I don’t need to say nothing. I’m just gonna read the word. I’m just gonna say what God says.” So as we were going through the credits of the record, my mom said, “I’m sorry, what are we doing? That’s not me. I didn’t write that.” I said, “I know, mom. It’s a composition,” and she said, “No. I don’t want people to think that we’re taking God’s credit.” Then when it came to the money, which I said is for your services, she was like, “That doesn’t go to me, it doesn’t belong to me.” She was having no parts of it. So I said, “OK, mother, we’ll tithe.”