Taylor started her career as an unlikely country contender, defying industry wisdom about what would sell. By the time she arrived on the Nashville scene in the mid-’00s, the pop-country divas who’d been so dominant throughout the ’90s had largely receded from view, and those programming the radio format had it in their heads that their core demographic of grown women preferred to hear grown male singers. The country-music business didn’t yet see the point in courting younger listeners, major labels had a lock on radio airplay, and Nashville’s old-school division of creative labor, which defined “singer” and “songwriter” as two separate jobs, was still the rule.

CAREER BEGINNINGS

Taylor was only 14 when she was signed by the Sony/ATV Tree Publishing house. She’s the youngest songwriter to ever be hired by the music industry giant. She showed up to co-writing appointments with seasoned Music Row pros such as  Troy Verges, Brett Beavers, Brett James, Mac McAnally, and The Warren Brothers expecting to be underestimated, then persuaded them of her seriousness by presenting a dozen song ideas prepared in advance. She eventually formed a lasting working relationship with Liz Rose. They began meeting for two-hour writing sessions every Tuesday afternoon after school. Rose thought that the sessions were "some of the easiest I've ever done. Basically, I was just her editor. She'd write about what happened in school that day. She had such a clear vision of what she was trying to say. And she'd come in with the most incredible hooks".

Taylor also had a development deal with RCA, which she left voluntarily when they didn’t offer her a record deal after one year. The company wanted to keep her in development until she was 18. Swift later recalled: "I genuinely felt that I was running out of time. I wanted to capture these years of my life on an album while they still represented what I was going through". Taylor also stated that she didn’t feel like RCA wanted her to sing her own songs.

SIGNING WITH BIG MACHINE RECORDS

At an industry showcase at Nashville's Bluebird Café in 2005, Taylor caught the attention of Scott Borchetta, a DreamWorks Records executive who was preparing to form his own independent record label, Big Machine Records. She became one of the first signings, and her father, Scott Swift, purchased a three percent stake in the fledgling company at an estimated cost of $120,000. The singer began working on her eponymous debut album shortly after signing the record deal. She persuaded Big Machine to hire her demo producer Nathan Chapman, with whom she felt she had the right "chemistry". Taylor wrote three of the album's songs alone, and co-wrote the remaining eight with writers Rose, Robert Ellis Orrall, Brian Maher, and Angelo Petraglia.

TAYLOR SWIFT

Big Machine Records was still in its infancy on the release of the lead single, "Tim McGraw", in June 2006, and Taylor and her mother Andrea helped "stuff the CD singles into envelopes to send to radio". At this point, she transitioned from Hendersonville High School to homeschooling. She was a straight A student and got her high school diploma one year early.

"Taylor Swift" was released on October 24, 2006. As fans soon found out, it is best listened to on CD, because you’ll want to be able to flip through its scrapbook-style booklet. The printed lyrics contained easy-to-crack codes (strategically capitalized letters that spelled out the names of song subjects), and the acknowledgements ended with a postscript that captured the cheeky specificity of the autobiographical authority she claimed: “To all the boys who thought they would be cool and break my heart, guess what? Here are 14 songs written about you. HA.”