Prior to stardom, Swift received a publishing contract with Sony/ATV Music. Over the course of that period, Swift composed over 250 songs solely or collaborating with other songwriters, mostly with Liz Rose or Robert Ellis Orrall, and refused to hand them away to already established acts with intentions of someday singing them herself.
When later signed to Big Machine Records, Swift compiled her eponymous debut album of material written during her publishing contract, and expected to do the same for her second album. She said, "I've been very selfish about my songs. I had this dream of this project [Taylor Swift] coming out for so many years now that I just stockpiled. I'm so happy that I did because now we have a second album full of songs and a third album full of songs, and I don't have to lift a finger."
However, when embarking on her first and second tour as opening act for Rascal Flatts andGeorge Strait, respectively, Swift continued to compose numerous songs. "I’ve written a lot of songs by myself lately, especially since I’ve been alone so much on the road," she said. "I do love writing on the road — I usually write at the concert venue. I’ll find a quiet place in some room at the venue, like the locker room."
As a result of writing subsequent to touring, Swift self-penned most of the material. "I've written like eight songs for the second album by myself. If you're in Arkansas, who's there to write with?" During vacation days from touring, Swift collaborated with Rose, musician John Rich, and singer-songwriter Colbie Caillat.
In the writing process, she was heavily influenced by Sheryl Crow's candidness and truthful, yet vulnerable storytelling, and Brad Paisley's touching, yet humorous nature; she opened for Paisley. She sought to prolong with centering romantic love the theme of the album.
Primarily, she did not want to alienate her fans with songs about life on the road, for she could never relate to songs of the sort when younger. She continued, "I really try to write more about what I feel and guys and love because that’s what fascinates me more than anything else — love and what it does to us and how we treat people and how they treat us. So pretty much every song on the album has a face that I associate with it." Despite her revelation of not having kissed a male in two years, Swift said the album was not wrung dry of such inspiration because she still underwent breakups and felt its core emotions.
Adding it did not "take much [for her] to get that sort of emotion out in a song", she explained physical intimacy did not have to resort to kissing to feel disappointment, frustration, or heartbreak. Despite having written numerous new songs, Swift decided to also include previously written tracks, believing there were stories she did not have the opportunity to put out with Taylor Swift, and still desired to.
Having grouped over 75 songs, recording with Nathan Chapman, who produced all but one song on Taylor Swift, commenced soon after having completed touring with Strait; in the process, Swift made her record producing debut. Thereon, her and Chapman recorded and cut an abundance of songs to keep the best material on the album. Thirteen tracks were intended out of Swift's fondness for the number; she attributes it to be her lucky number.
To aid in choosing the songs, Swift performed various new tracks – "Permanent Marker", "Missing You", "I'd Lie", "Sparks Fly", and "Fearless" – at the Gold Country Casino in Las Vegas, Nevada on May 29 and May 30, 2007; only the latter song was chosen for the album. By January 2008, Swift had recorded approximately half of the songs that would remain on the final cut of Fearless.
The remainder of the songs came in the last two recording sessions: one held in March 2008, the other held sometime in the summer of 2008. When asked to describe the album, Swift commented, "It’s the same kind of album I made (in 2006) — just two years older. Sound-wise, it’s the kind of songs I like to write, which are country songs, but I guess because of the subject matter and because of some of the melodies I love to use, I guess they have crossover appeal."
