Taylor Bickett

What a beautiful discovery. Taylor Bickett is a gem. What an incredible songwriter. What an impressive storyteller. Her latest single “i should’ve guessed” is definitely one of the best songs I’ve ever heard in my entire life. We rarely get to hear 4 minute songs these days so it makes me so happy to hear this length on “i should’ve guessed”. It’s the kind of songs you want to keep listening. The storytelling is so captivating, you don’t want to let go of it. It’s stunning.

“i should’ve guessed” is a song that should be remembered for a very long time - for the honesty, the emotion, the storytelling, the magical vocals and the timeless melodies. Taylor Bickett is an artist to watch.

Thank you so much Taylor for this conversation.

Go stream “i should’ve guessed” now, you won’t be disappointed !!

Photo credit: @pixelgash

Introduce yourself - what's your story?

I’m a 23-year-old singer/songwriter from Indianapolis, Indiana. I was an awkward, nerdy kid obsessed with books and Broadway who sang constantly (honestly, still am). I moved to Nashville 5 years ago for college, which is where I really got my start in songwriting, but it wasn’t until the pandemic hit that I realized I could have a future as an artist. I went home to Indiana in March of 2020, scared and devastated like everyone else, and found myself with nothing to do but sit inside and write music. I started posting some videos to TikTok, simply because I was bored, and never expected them to blow up the way that they did. I suddenly had hundreds of thousands of people wanting my music, which was a surreal (and kind of terrifying) experience. I released my first single, “Break My Own,” in January of 2021 and have continued to release music ever since. While it’s had its ups and downs, I am endlessly grateful for the way that little app changed my life. A few random facts about me: I’ve read the Harry Potter series 7+ times and I have an unhealthy obsession with string cheese and NYT crosswords.




What did you grow up listening to? 

I grew up listening to a mix of 2000s pop, young Taylor Swift, Broadway musicals, classic rock and country (usually in the car with my dad), and anything I could get my hands on. There are videos of me as a kid singing anything from “Killer Queen” to “You Belong With Me” to “The Phantom of the Opera” to “Lady Marmalade.” Seriously. I had NO idea what the last one was about - I just liked to imitate Christina Aguilera’s runs. 




When did you start writing songs? 

I always wrote little fragments of songs when I was a kid, but it actually wasn’t until college that I wrote a full song in its entirety. I had entered a singing competition, and when I made it to the finals, I was told (with less than a week to prepare) that I would have to perform an original song. I freaked out. I wasn’t a songwriter! I gave myself about an hour to panic, and then I sat down and wrote my first ever full song. It was about growing up, moving out, and learning to be okay with the confusion and is still very special to me (though I look back and cringe a little). I ended up winning the competition with it, and the songwriting bug never left :)




When did you know you could sing?

My mom always tells the story of how, when I was one or two, I was singing nonsense songs in my crib while her friend was at the house. Her friend said, “you know that she’s actually really on pitch, right?” and my mom said that she assumed that’s how all babies sang. Her friend assured her that her children did NOT sound like that, and that’s what made my parents curious if I had musical ability. They put me in music and theatre pretty young, and I can’t remember a time in my childhood when I wasn’t in love with singing.




What gave you the confidence to be an artist and release your original music?

I always knew that I wanted to be an artist, but before the pandemic, I didn’t know how to begin. Bored in quarantine, I just started posting little songs I wrote on TikTok and never in a million years did I expect them to blow up. The amazing and kind people encouraging me on the internet to release my music is what gave me the push to start!




What biggest lessons have you learned since the beginning of your career?

One of the biggest lessons I’ve learned in my short career thus far as an artist is that numbers, specifically on social media, don’t determine the quality of your art. It’s so easy to think, “this song blew up on TikTok, that must make it a good song” or “this song didn’t get very many likes, it must be a bad song.” The truth is that algorithms are unpredictable, and it’s important to trust your artistic judgment above all. The right songs will find the right people if and when they’re supposed to.




"i should've guessed" is your latest single - what's the story/inspiration behind this single?

This is one of my most honest songs yet - pretty much everything I wrote about happened in real life. I had feelings for someone who was just a friend, and I became infatuated with them. I over-romanticized every interaction and convinced myself that we were soulmates. I even thought they might feel the same way, but then one day they started telling me all about the girl that they were seeing. I wanted to puke but pretended everything was fine (as you do), and got off the phone and immediately went downstairs to cry to my roommates in the kitchen. There’s a line that says “I should’ve guessed I’d be crying in my kitchen,” and it was inspired by that real life event.




Could you describe the songwriting/production process for this single? Who helped you create it?

The songwriting process for this one was unlike anything I’ve ever written. I wrote the first verse, which is all about over-romanticizing someone, before I knew that they were seeing someone else. It was just a bittersweet, hopelessly romantic verse about a person that I had feelings for. I set it aside for a week or so; I couldn’t really figure out where to go in the chorus. Then, I found out about the other girl. I don’t know exactly what possessed me to go back to that song from before, but I added a chorus that flipped the narrative from sweet, wistful longing to “damn, I really needed a reality check.” It worked better than I could’ve imagined, and here we are! I wrote it all by myself, but it was produced by Tone Def, who has produced most of the other music I’ve released so far! He’s one of the most talented people I’ve worked with and has yet to miss the mark - I’m so grateful for him.




What did you feel when writing this song?

Oh, you know, just absolute emotional turmoil and agony :) Really, though, it’s a complicated song for me. Part of me loves that I get caught up in the moment and romanticize everything - it’s what makes me special. Part of me wishes I’d stop, because it leads to disappointment when reality isn’t quite like what I dreamed up in my mind. 




What's your favorite thing about this single?

I think I just love how raw and honest this one is. It’s like a little slice of my brain put into a song forever.

As an artist, what is the hardest part? And what is the best part?

The hardest part of being an artist, for me, is the comparison. No matter how much you achieve, someone will always be doing more. It’s something I work on every day, and still have a long way to go, but I’m trying to focus on being grateful for the amazing things that I do have and proud of myself for the things that I’ve worked hard to accomplish.

The best part of being an artist is a total cliché but so true. Knowing that my music has positively impacted people’s lives is something that I’ll never fully wrap my head around and makes me so grateful and honored to be a musician! Getting messages and comments about the ways that my songs have impacted people never fails to make me emotional. I’ve also had some fans come to my shows or recognize me in public and tell me in person how much my music means to them - that’s kind of the coolest thing in the world.




How's it like to be a woman in the music industry? What message would you give to women out there?

I think this is a tough topic because while I have certainly seen some difficulties as a woman in the industry, I also recognize that it can be infinitely harder for women of color, trans women, and other marginalized groups. I have been fortunate to have a relatively easy time in the industry by that standard. However, there are some things that have stuck with me - a teacher telling me that I smile too much to be taken seriously as a woman in the industry was one that I don’t think I’ll ever forget. I’ve also had my looks debated and analyzed in ways that a man would never have to deal with, and that’s something that all women in the music industry go through. The best advice I can give to women in the same shoes is to not put up with the bullshit. Call people out when it’s safe to do so and stand up for yourself and other women in the industry. There were definitely times that I bit my tongue that I wish I wouldn’t have, and I want to be bolder and braver when it comes to those things. 




What are your thoughts on today's music industry? If you could change one thing, what would it be?

Today’s music industry has opened up an incredible opportunity for people who don’t have infinite funds, connections, or label deals - regular people are seeing success in music due to TikTok, and I think that’s really important. That doesn’t mean that I think that social media is being used in a healthy way in the industry. If I could change one thing, I would let artists be artists again, not content creators. I would have labels stop demanding TikTok virality or bust in lieu of the hard work that they were brought on to do for the artists. I would have long-form content become important again, as opposed to 15 second clips in an endless scroll.




What advice would you give to artists out there?

My advice to other artists (which I’m not sure I’m qualified to give - most days I have no clue what I’m doing) is to trust yourself. ESPECIALLY WOMEN. Don’t let people belittle your opinions or thoughts; YOU are the artist. Trust your gut and create what you want to create!




In your opinion, what would make the world a better place?

I think everyone should spend less time online. I get that that’s ironic coming from me, but I deeply believe that our mental health, our interpersonal interactions, our ability to think for ourselves, and more would all see incredible improvement if we just put the phone or computer down a bit more. (I’m awful at it, but trying). 





Connect with Taylor:

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Spotify