Hailey Whitters has long been a celebrated singer-songwriter in Nashville, writing songs for artists like Little Big Town (“Happy People”) while pursuing her own career as a solo artist. She documents her artistic journey in opening track “Ten Year Town,” an honest and moving account of the struggles faced by musicians moving to Nashville hoping to hit it big. Across the rest of her second album, Whitters shows off her wry humor, charming sass, and plainspoken vulnerability, situating herself as a left-of-center, song-driven artist in the vein of Kacey Musgraves or Miranda Lambert. And on the standout track “Janice at the Hotel Bar,” Whitters draws inspiration from a real conversation in a hotel bar with a spirited older woman, offering up nuggets of wisdom like “Pay all your bills but give some away” and “Get on the pill if you ain’t ready to start a family.” To celebrate the one-year anniversary of The Dream, Whitters tapped a handful of her closest friends and collaborators (not to mention one of her idols, Trisha Yearwood) to join her on five new tracks for the appropriately titled deluxe edition, Living the Dream. “It’s all people who had a hand or played a part in me being able to say, ‘I'm living the dream,’ as a result of putting that record out,” Whitters tells Apple Music. “It just was life-changing for me, career-changing.” Below, Whitters walks Apple Music through Living the Dream’s bonus tracks. Fillin’ My Cup (feat. Little Big Town) “Little Big Town, they were the first artist that ever recorded one of my songs and took it to country radio. So, I'm waiting tables, I'm trying to save my money, get my money together for the making of The Dream, and those royalty checks started coming in from them. So they, quite literally, made it possible for me to be able to put out music and put out that record. I mean, hearing them all mic'd up and someone hit ‘play’ and getting to hear all their voices on it, it was just really cool.” Glad to Be Here (feat. Brent Cobb) “I've known Brent for a long time. And he's inspired my own writing so much. I found myself often saying, ‘I'm just glad to be here.’ So, when we were thinking of songs for the deluxe, I was wanting to write a song about that. And Jake [Gear], my producer, he was like, ‘Well, Brent, he already has one called “Glad to Be Here.”’ And that song is so perfectly describing how I felt. It feels like me sitting in my backyard in the lawn chair, barefoot, picking cherry tomatoes off the vine.” How to Break a Heart (feat. Lori McKenna & Hillary Lindsey) “We had a few days on the calendar just to write, and then it would like leak over into ‘Let's crack a bottle of wine and just sit on the phone for three, four hours and gab and gossip and just have fun together.’ I love personifying the heart. Like, ask it out, take it, pick it up in your pickup truck. It's kind of a fun girl-power anthem.” How Far Can It Go? (feat. Trisha Yearwood) “I wrote that song with Nicolle Galyon and Hillary Lindsey, and literally, the MO was, how do we make a modern-day ‘She's in Love With the Boy’? And then we started doing this deluxe idea and we were like, ‘Oh my god, if we could get Trisha Yearwood on this, that would just be absolute heaven.’ ‘She's in Love With the Boy’ was literally my hairbrush microphone song, making family members sit and watch me perform that song. So to get to actually have her agree to it and then get to hear it is just kind of this weird full-circle moment.” The Ride (feat. Jordan Davis) “Jordan and I have known each other for several years, and I thought it was so badass that he took me out on tour. I mean, not only being a female and stuff, but also just the fact that I was an unsigned artist at the time. So he was a big part in this journey for me. I feel like that song really complemented both of us well. It’s about the road to getting there, and enjoying the view as you're going and not just getting so caught up in the destination.”