Picture this: a plastic baby doll with a golden disco ball for a head, sprawled out like it’s casually power-napping on an album cover. That, my friends, is the artwork for If It All Works Out, the first half of Sir Woman’s ambitious two-parter album series. And yes, in an age where tracklists are shrinking faster than attention spans, we’re downright giddy that some daredevils still go beyond the sacred ten-song limit.
But wait—there’s more. For If It Doesn’t, the baby pulls off its sequin-splattered head in a dramatic party trick, and suddenly, we’re knee-deep in nightmare fuel. A real “choose your own adventure” moment, if you will. While we could use these albums as a musical Magic 8-Ball to determine our own fate, we’d much rather get the inside scoop straight from Sir Woman’s front-runner, Kelsey Wilson. We sat down with her to talk all things album-making and, more importantly, the high-stakes challenge of picking a tour setlist when you’ve got a plethora of musical riches.
Double Album
Our first taste of this project was ‘Who You Gonna Love,’ a track that captures the album’s ethos—rooted in a relationship unraveling. What made this song feel like the perfect starting point?
‘Who you gonna love’ felt like the perfect first single to drop because I literally wrote it as a love song for myself and others I know in the industry who can get caught up in the thick of things and forget how magical they are outside of the music “business.” It’s easy to put a lot of pressure on yourself to keep making a bigger and bigger splash… everything has to be more successful than the last thing, and you are constantly comparing yourself to others and how their careers look from the outside in.
I was beginning to let the pressure get to me and change my sound a little bit so I “fit in” more…Then I realized that I don’t care if people think I’m not pop enough for pop or not R&B enough for R&B… if they can’t put me in a box that’s because I shouldn’t be in a box and if I can’t stand by my sound and what feels good to me it’s not worth it. I gotta love myself and what I’m doing first and foremost because this industry is fickle and will make you lose your damn mind.
You’ve pulled a bit of a Taylor Swift move with If It Doesn’t as a companion piece to the original album—cleverly mirroring that fork in the road. What made you decide the story needed two albums? Were there moments where you had the temptation to switch tracks between them to fit each narrative better?
Honestly, by the time I finished the first record, I had become a completely different person and was having trouble connecting with the narrative at the time. While recording the record, I lost my sister and my dad a year apart from one another, and by the time I finished mixing/mastering all those happy new love songs, I felt there was a whole different story I needed to tell.
I had planned on just releasing one record, but all of a sudden, I had so much to say and so much to process…and music has always been how I process things. I started writing and just couldn’t stop. A quote that has helped me through a lot these past few years is, “If it works out great, if it doesn’t, even better.” While both albums stay true to my overall Sir Woman message of self-love/joy/empowerment… the second album definitely comes from a darker place. I had a deeper hole to climb out of mentally for that one.
The album covers complement each other in some ways but are strikingly different. If It All Works Out plays with yellows and features a society-standard, photoshopped body superimposed on yours. Meanwhile, If It Doesn’t leans into blues, with a baby’s disco head ripped off and you barely visible. What were you aiming to convey with each visual?
I had the idea to combine the records by separating them by mood chart and making 69 mood rings that the listener could put on, and the changing colors would tell them which album they needed. Basically, songs for a good day and songs for a bad day…Both albums will make you feel better, but one (the second ) can do a little more heavy lifting. It felt like the second album brought out more blues/greens/purples…emotional colors..and the first album felt more gold/red/orange… bright sunshine dance party of self-love.
Tour
Blending the songs sonically is one thing, but translating that visually—especially with a tour coming up in March—is a whole different challenge. With two albums shaping the narrative, have you faced any unique hurdles that wouldn’t come with touring just one album (even though touring various eras seems to be the norm now)?
Most definitely. Honestly, it’s just a lot of material… and crowds always want to hear the “old stuff.” Even your biggest fan doesn’t want to just hear the new album, so you have to arrange setlists in a way that everyone gets what they came for.
Naming the first track of If It All Works Out ‘Circles’ feels like hitting that irresistible loop button — where you listen to an entire album only to start all over again. What endlessly replayable album inspired you most while creating If It All Works Out?
I don’t know how normal this is, but whenever I’m writing, I can’t listen to a lot of music. It’s like the only room I have in my head for music is whatever music my head is making, hah. And until that body of work comes out… there’s no room for anything else. I’ll listen to podcasts and brown noise playlists to try and give my head a break sometimes. Funny thing, though. I just now made the connection, but Mac Miller’s album Circles was definitely the last album to hit me like that. It’s funny how hard you can be influenced and not even know it’s happening, haha!
Personal Touches
This record is packed with big musical moments—from the soulful trumpet intro of ‘I Know Better’ to those jittery keyboard riffs midway through. Which sonic highlight are you most excited to jam out with the crowd on tour?
Actually, the last song on the album is called ‘Making My Way’…and I wrote it as a sing-along so that every night, we all sang something with the audience for our lost loved ones. I started the song when my sister passed away. The first verse and the chorus came to me immediately…then it was too heavy for me to finish. My dad died a year later, and the second verse just appeared as a message to him. I thought the best way I could honor them and all of the people we’ve lost is to sing it with as many people as possible, as loud, and with as much love as we can.
You mentioned on 93.3 KGSR that your other band, Wild Child, leans toward commercial success, crafting songs for movies, while Sir Woman feels more authentic. Which of the 11 tracks on this album hits closest to home for you?
‘Making My Way.’
‘Don’t Do Forever’ is one of the few tracks where the soulful instruments take a backseat, leaving only the raw vulnerability of your voice—constantly reminding yourself of the reasons to avoid commitment. What made this song deserving of such a stripped-down moment?
At first, I was thinking of all these crazy string arrangements, grand piano, maybe some flute.. but when we tracked it live, just guitar and vocals, it hit me so hard and sounded so precious I didn’t want to touch it. It felt just as fragile as I felt when I wrote the song…just balancing on the edge of this high dive at the beginning of a new relationship that felt so important. I’m not sure if I want to dive in and risk losing everything and hitting the bottom.
Musical Legacies
This album stands strong without any features, especially with the mixture of tones from your band, but if you could bring in any musician—past or present—to appear on a track, who would it be, and what do you think they’d add to the mix?
We just lost her, so I’m gonna say Roberta Flack… singing lead on Who You Gonna Love. She could replace me just so I could hear it, hah.
The lyric “but I’m making my way” is the album’s final line. What do you hope this album will help carve out for you as you continue your journey?
I hope this album brings a lot of strangers together and makes everyone feel less alone. I hope I can continue making people feel good about themselves as I figure out how to navigate this human experience with as much unconditional love as I possibly can for myself and others.
Don’t be that person who waits for both albums to drop before diving into a full-blown binge-listen. We need you in the obsession trenches with us now. Stream If It All Works Out here, and then start emotionally preparing for If It Doesn’t on May 16. How will you survive the wait? By talking to us about your favorite tracks, obviously. Hit us up on Twitter, Instagram, or Facebook—we’re ready to spiral with you.
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