Hailey Whitters

by Carl Wiser

By 2019, Alan Jackson ("The Older I Get"), Martina McBride ("The Real Thing") and Little Big Town ("Happy People") had all recorded Hailey Whitters' songs, but she was back waiting tables in Nashville, looking for her break as an artist. Writing with Brandy Clark, she came up with "Ten Year Town," where she sings about being "twelve years into a ten-year town," wondering if she should pack up her guitar and head back to Iowa. Good thing she didn't: After posting the song on social media, Whitters earned pages of positive press and landed a spot opening for Maren Morris. Her album The Dream, loaded with songs about sussing out what's really important in life, followed in February 2020, a time we'll all now remember as "the good old days."

Released ahead of the album, "Janice At The Hotel Bar" has earned an audience and a hashtag. Written with Lori McKenna, the song tells the true story of an 80-something woman who chooses vodka over dessert and knows the value of time well spent. There is now an Instagram page devoted to stories about the women like Janice in our own lives.

Like McKenna, who wrote Tim McGraw's musical credo "Humble And Kind," Whitters shines a kind of ambient light with her songs that comes out in her performances. We spoke with her about how her dreams have evolved since coming to Music City, and how collaborative songwriting works under quarantine.
Carl Wiser (Songfacts): How has the world of Nashville songwriting adapted to the pandemic?

Hailey Whitters: We've been using Zoom a lot. The first week everyone was just trying to figure out what to do, and then everyone adapted to Zoom pretty quickly. So now, I feel like I'm co-writing even more than I was before just because it's so easy to log on and grab a few hours to finish something up or start something new. So, I think we've adapted really well. People are writing a lot of songs right now, and that's been a really creative outlet for this weird time.

Songfacts: What kind of songs are you writing about?

Whitters: The same stuff I was beforehand, although I did write one song that was kind of an uplifting, hopeful song when I was feeling really down on one of those days. I'd seen what looked like a mother and probably a teenage daughter sleeping in their car, and that really hit me. We've all been locked up in our houses, seeing things on the internet, but it's a different thing to go out and really see how this is impacting people.

So, that day, I wrote something I felt was my first song about what's happening in the world. I've been trying to keep positive, uplifting topics going. I'm not writing a whole lot of sad songs right now.

Songfacts: What happens to a song after you write it in one of these sessions?

Whitters: That was one that I felt really close to, so maybe I would have played it out at a show or something, but since that's not possible right now, I got on my social media and performed it for my fans on a live stream. I felt like that was something very real, that I had seen, that was relevant. The hook on it is, "Even when it's bad I've still got it pretty good," and it's a reflection of where I'm at right now during this quarantine. So that was the quickest, easiest way for me to deliver it to fans. I just felt like the message was really important and really relevant to what's going on right now.

Songfacts: What's the name of the song and who did you write it with?

Whitters: It's called "Pretty Good" and I wrote it with Caroline Watkins and Lee Miller.

Songfacts: Pre-pandemic, after you write a song with a group of people, what then typically happens to it?

Whitters: I turn it in to my producer, who has an ear on everything that I'm writing, and then either it's something that gets placed on hold or gets recorded by another artist, or if it's something I feel is very important for my next record, we will hold it for my upcoming projects.

Songfacts: And once you perform a song, I guess that makes it yours in a lot of ways.

Whitters: It's kind of strange. For example, I wrote "Happy People" that Little Big Town recorded, and I've seen fans on social media like, "Well, is it Hailey's song or is it Little Big Town's song," and I don't think it has to be that black and white.

You know, I get to tap into being a songwriter and also an artist, so if I write a song that doesn't land on one of my records or my projects, it's still an extension of me and my creative process, and there are some that I still enjoy to play.

I don't hoard my songs. If anyone wants to sing something that I've written, I consider that a win, just spreading the words and the music and the song. So if something's on a record of mine, it may be perceived that it's not for anybody else, but I don't see it that way.

Songfacts: Tell me about writing "Happy People" and how you came up with that whole concept.

Whitters: It was my first time writing with Lori McKenna. I went up to Boston, where she lives, and got out of Nashville. I like to go up a day early and just get settled, so I did that. I had never been to Boston, so I went walking around the city and realized very quickly it's a very expensive city. I was just a broke songwriter at this time, so I went to the park - I can't remember what park it was, but it was a beautiful, lush park in the center of what seems such a bustling city. And it felt like walking into that park, everything just kind of slowed down. There were couples sitting on blankets, dogs running and children laughing, and it was just this really serene slow-down in the middle of this big, bustling city. I just sat there and people-watched and felt the energy, and that title popped into my head. I logged it down in my catalog of ideas and the next day when I was writing with Lori I threw that title out to her and we just started writing that.

Songfacts: How did it change your life after Little Big Town recorded it?

Whitters: Well, I was sitting in the Boston airport a few days later getting ready to leave and my publisher texted me and was like, "Hey, Karen Fairchild asked if the band could hold this." I was shocked.

That was a big song for me. It was my first single at country radio. I went to the ACMs and got to see them perform it on the awards show. It was a very validating feeling after so many years of wondering if I was on the right path and if I was ever going to see the light at the end of the tunnel.

Songfacts: But then, two years later, you come out with "Ten Year Town," where you have these feelings of doubt and you're wondering if you ever will make it, even though you've got a cut for Little Big Town.

Whitters: Yeah. It's a different thing being a songwriter trying to build a writing career, and trying to build an artist's career. I was feeling very frustrated with my artist's career and wondering if I should just hang that up and just be a songwriter. And I realized I still had things I wanted to say as an artist that weren't being picked up by other artists as a writer, so I felt like there was a voice that still was there that wasn't being heard, and I realized I still wanted to pursue that. I still wanted to make records and I still wanted to perform my own songs. I still really wanted to do the artist thing.

Songfacts: As a songwriter, you have to not just get the cut to Little Big Town but you also have to get in a room with somebody like Lori McKenna, who is an established hit-making songwriter. How do you go about doing that?

Whitters: Years of my publisher emailing her publisher. I don't know how that exact ask went down. I am such a Lori McKenna fan - she is someone I just idolize. I think we wrote that song in 2017, so I had a pub deal for five years at that point. I'd been in town and I'd had a few cuts on Martina McBride. One of the songs that Martina recorded of mine was one that I just wrote completely by myself. I can't speak on behalf of Lori, but if I'm a fan of somebody's song, I want to write with them. But it was years before I was able to get in that room.

Songfacts: When you sign a publishing deal, are you walking into an office every day and working 9 to 5?

Whitters: Yeah, it is kind of like that. In the non-quarantine world it's pretty much Monday through Friday walking into a publishing house, which can be anything from a cozy bungalow house on Music Row to some of the more corporate ones which are a little more sterile - you feel like you're walking into a cubicle room.

But you walk in and some days it's with people you've been writing with for years, and you have an established level of comfort with, and some people you're meeting brand-new. I always say that songwriting is like free therapy: You sit and talk and try to find some common ground. Songwriters can have some of the most intimate relationships with each other. We're talking about feelings, we're talking about life, we're talking about experiences, and I think that is really cool and something you can only get being a songwriter.

You find some sort of common ground and start writing. The sessions usually last a few hours. Sometimes we call it quits after a few hours, get back and hammer it out that night. It's just a matter of how the creative process and the inspiration is rolling, and some days it's like rolling up the sleeves and really hammering it out.

Songfacts: How does the payment work? I'm wondering if you get a steady paycheck or if you only get paid if you place a song.

Whitters: Once you sign a publishing deal you're getting an advance, so it's like I get a monthly paycheck, but once you start getting songs recorded, it becomes a process of royalties and you have to pay off your advance before you start making your own money.

Songfacts: So you're kind of on the clock there - you have to produce something.

Whitters: Right. You have a certain quota of songs that you're expected to turn out, like contractually commit to per year, as well.

Songfacts: But it doesn't matter how many songs you come out with if nobody records them.

Whitters: Yeah, it is tricky. I remember Jeffrey Steele telling me he wrote a song that went on to Rascal Flatts that sat around for 15 years - Rascal Flatts wasn't even a band when he wrote it. So songs that I'm writing now, I may not even know who the artist is yet, and those songs could end up getting recorded years from now by some artist that walks into town. And Carnival, my publishing company, they still own those.

Songfacts: As an artist, does it help that you write your own songs?

Whitters: For me, yeah, because I know where the story came from. I felt it when I came up with the idea. I think that does help me tap into a personal element when I am delivering the song to fans and to an audience - I get to tell my story.

Songfacts: My favorite song on The Dream is "Living The Dream," and in that song, you talk about how "the dream" is different for different people. Can you talk about how your dream started and how it has evolved?

Whitters: I was young when I was first in town, and I would've told you the dream was a tour bus, thousands of fans, plaques and awards, making a lot of money and radio success. As I've grown and as I've evolved, it sounds really simple and fundamental, but I've realized that the dream is getting to create for a living and to have a job that allows me to feel and just be here.

It sounds very simple, but that has become the dream to me, and I'm lucky I get to do this for a living. I feel more at peace with that than setting these expectations in my head for what I was supposed to achieve.

Songfacts: So, it's not about being famous and getting on a tour bus. Why is it that you want to be an artist?

Whitters: Because I love doing it. I just really love creating - being able to tell stories through song, being able to document what I'm feeling, what I'm seeing. And then I like to be able to see those perspectives resonate with other people, especially when it's something like "Janice At The Hotel Bar." That song was special to me, but to get to see it take on a whole new life with #WomenLikeJanice, where people post photos of "the Janice" in their lives, it feels so much bigger than songwriting and being an artist. It feels like you're tapping into an element of what it means to be human, and you're this outlet to share stories. I think that's a really cool thing to get to be that vessel for people.

Songfacts: Has the real Janice been identified yet?

Whitters: She has! She lives in Jersey and has heard the song. When we released the song, everyone started hashtagging #FindJanice, and her granddaughter reached out. She commented on my social media and said, "I'm Janice's granddaughter, I'm with her right now and she loves the song."

So, she has definitely been identified and we pre-quarantine had big plans to try and meet her. I am really looking forward to the day we get to crack open a bottle of wine together and hopefully just play her song. I would love to play it for her in person.

Songfacts: One of those Martina McBride songs you wrote is pretty interesting in these times. It's called "The Real Thing," where you're writing about living in the digital world and how it's not quite up to snuff compared to the real world. Can you talk about that song and how you feel about it now?

Whitters: It still feels relevant. I love that song, I love the second verse:

We got cyber clouds and digital streams
Sometimes I gotta shut it down


I'm a big advocate of that. Maybe it's just my nature - I'm bad at technology, I'd rather be outside, and my personal preference is things that are real versus things that are fake or temporary.

I like songs that feel authentic. I like food that's coming from local sources versus manufactured. In today's day and age, I think our culture is driving us towards things that are fake and manufactured, and it might be a little old school, but I like scratching the surface a little bit and just finding things that are real and that I know are going to last.

Songfacts: Another song you wrote about identifying what is important in life is the Alan Jackson song "The Older I Get." Can you talk about that one?

Whitters: You know, I have a sister that's 11 years younger than me and it's fun to watch her grow up because in a way I feel like I am seeing myself grow up. I just started thinking about time and age, and how we evolve as we get older. My mom probably looks at me and thinks the same thought.

So I just started thinking about things that happen the older we get, and I know for my sister right now it's friends and things like that, and for me, it was starting to change a little bit as I was turning 30.

I was talking to Adam Wright and Sarah Allison Turner, my co-writers, about that, and we just started writing all these verses. Adam's wall in his room is a chalkboard, so we just wrote I think 15, 20 verses to that song. It was really anything from "the hangovers are worse" to deeper things like "the more I pray," and we just started cherry-picking the ones that we felt put the song together.

Adam sent it to Alan, and Alan hit us back and said, "I really love this, can you change the first verses to something a little deeper." Because we started kind of light and then eased into the more profound things, but he wanted to go all the way from the get-go. So we went back and pulled out some of those other verses that were a little bit deeper and he recorded it.

It's a huge compliment. Alan Jackson is my favorite songwriter of all time, and he's written so many of those songs of his that I love, so I knew that he was coming at it from a writer's perspective as well, so it was pretty cool to have him care enough to really want it to be perfect and to come back with that critique. My only sad thing about that song is there is no physical evidence of it anywhere. I would like to see my name in print next to his, but it's all good.

Songfacts: You can hear the song though. It's on YouTube and streaming.

Whitters: You can hear it, totally. I'm just a nerd and want like a CD package so I can show my kids one day and be like, look at this!

Songfacts: What is the most important thing that you've learned about songwriting and the industry since coming to Nashville?

Whitters: That you've just got to be yourself. I know that sounds very fundamental, but I came here really knowing nothing about how this world works, so I guess ignorantly so, I was myself. And then I got really sucked into looking around and seeing what everyone else was doing, and especially in those times when you feel like you've been here forever and you still haven't gotten where you want to be, it's really easy to start looking at what everyone else is doing and trying to just do that. It really took me kind of giving up on it, giving up on myself a little bit, to realize who I was, what I was doing here, what I came here for, what I wanted to accomplish. So now that I've been through that cycle and feel like I came out on the other side a little bit, it's easier for me to say that and to know what it means.

But I think Nashville has a way of molding you into something once you've been here long enough, and it's important to remember why you came here in the first place.

Songfacts: You didn't say anything about song structure - you talked about how it's more about personal development in that you have to essentially find yourself, which is kind of interesting.

Whitters: Uh-huh. I think what's most important as a songwriter is the personal development. It's less about the formula. You know, Are we doing A-B? At the end of the day, I'm going to say something the way I want to say it, so I think personal development is the most important part because you have to know a lot about yourself and a lot about people to be able to write songs about that exact thing.

Songfacts: You worked at a restaurant for a long time. What's it like being in the service industry in Nashville?

Whitters: I loved it. I thought it was very humbling to go back to waiting tables after having a little bit of success as a writer and then as a touring artist. It was interesting to go clock into a job where nobody knew who you were, nobody knew that you had written a song that Alan Jackson recorded. You're just dumping out coffee, wiping down tables.

I remember one time Dean Dillon came in and I waited on him. It was really strange because Jon Pardi came in once and not only two years before, I had been opening shows for him, so that was a really interesting experience.

But I'm grateful for it. It kept me grounded and it kept me level. I worked outside of town a little bit, so it's not like I was seeing peers and industry folks every day. But it helped me get a little bit outside of the industry and helped me get outside of the process and outside of my head. That really helped with the making of this record.

Songfacts: Is everybody in Nashville that's in the service industry a songwriter or singer?

Whitters: It's pretty common.

Songfacts: Is there a particular person that you model your career on?

Whitters: When I first moved here I just loved the Dixie Chicks so much. I don't know if I was necessarily aspiring to be like them as much as just wanting to make the kind of music they made. But I love how Dolly Parton has had such longevity and is so identifiably her. I look more at the music that people are making. Maybe somewhere in between a Kacey Musgraves and a Lori McKenna. Both can be in front of these large audiences but also have an intimate relationship with their fans. I think that's really important.

Songfacts: Is there a song by another artist that had a huge impact on you?

Whitters: One song just blows my mind is "Humble and Kind" by Lori. She wrote that by herself. It was Grammy Award-winning, but it feels so simple. It's a song that people will remember forever - that level of greatness that she can pull off so effortlessly always has me in awe.

I remember the first time I heard "Remember When" by Alan Jackson. I was young, probably 12, 13, and cleaning the house. I remember stopping and I had to hear every single word that he was saying.

Songfacts: What is the most important thing you learned from one of your other co-writers?

Whitters: Well, I have something that I learned from a publisher that I thought was important. My publisher friend, Frank Liddell, said to tell the truth, because it's more interesting, and I feel like that's great advice.

Barry Dean told me one time - this is more of like a person trying to navigate the business - to find your people or your place that keeps you grounded, that keeps you centered, and hold on to that. Hold on to them as you navigate your career. I thought that was great.

And from a craft standpoint, I was writing with Tom Douglas last month and it was really interesting because he's another one that is such a prestigious writer. We just kept kicking around this idea, and he was like, "But why does this matter? Who's going to care?" That sounds really harsh, but he carries ideas with such gravity. So "How is this important?" is really inspiring to me because that's how you become somebody great, and that's how you become a hall-of-fame songwriter like Tom Douglas. So I really try to think from that angle. I try to think, "Who does this song need to be heard by, and how is it going to matter to them?" That helps really dig into the heart of the idea.

May 18, 2020
Here's our interview with Tom Douglas. The best way to stay up to date with Hailey is on Facebook or Twitter.

Photos: Harper Smith

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