1983–1997: Early life

Digby was born in Los Angeles, California and is of Irish and Japanese descent. She began writing songs during high school in Los Angeles, California. After her freshman year at the University of California, Berkeley, she won the 2004 Pantene Pro-Voice competition with her song "Miss Invisible".^[5] The grand prize for the concert included working with a professional producer on an album, $5,000 and performing on stage with other top performers.^[6]

1997–2008: Career beginnings and Unfold era

After performing at night clubs, Digby signed a publishing deal with Rondor Music, a subsidiary of Vivendi SA's Universal Music Group in early 1998. By the end of 1998, Digby had signed with Disney's Hollywood Records and her first album of original songs was completed by the end of 2005. Also in 2005, her song "Fool" was included on the Disney compilation album Girl Next. In early 2007, she began to post simple videos of herself singing cover songs of other artists on YouTube in order to gain visibility. Hollywood Records then released a studio recording of her rendition of "Umbrella" to iTunes and radio stations.^[7] She often performs with a Gibson Hummingbird acoustic guitar.^[8]

Digby's first official single, "Say It Again", was released to radio stations on January 18, 2008. Her debut album, Unfold, which was completed over a year before, was released on April 8, 2008. The design of the cover for the album was mostly based on the sketches she drew during her downtime while recording the album. She worked with some of Hollywood's best including Tom Rothrock (Producer), Charlie Paxson (drums) and Matt Chait (guitar). Many different editions of the album exist, including a Japanese edition with different cover artwork and an alternate track listing.

2009–2010: Second Home and Breathing Underwater

Digby released a collection of Japanese cover songs on March 4, 2009. The album, titled Second Home, was recorded completely in Japanese and received a limited release only in Japan.

Digby's second English album titled Breathing Underwater was originally slated for release in May 2009, but she asked the label to push the release date back until she found a new manager. The entire album was leaked in spring 2009. Digby expressed her disappointment with the leaks on her MySpace page. A deluxe edition of the album was released on physical and digital formats across Asia in July 2009. The album was later released in North America in September 2009. When Digby left Hollywood Records, they gave ownership of the master recordings back to her. The album is no longer on digital services.

On December 8, 2010, Digby was featured as one of the many artists to do an urban cover on Disney's Urban Pop Disney CD. Along with DJ Hasebe, Digby sang and put a twist on The Little Mermaid's Part of Your World.

2011: Debut in the Philippines

She had a one night only concert in the Philippines on August 1, 2009 at The Tent in Taguig.

In June 2011, she recorded an album for Star Music, ABS-CBN's own record label, in Manila. She promoted the album in the country from August to September 2011. The album includes a cover of Kuh Ledesma's "I Think I'm in Love". It also features Filipino artists Sam Milby and Jericho Rosales. Her first Philippine music video was shot in Nuvali, Laguna. The album Your Love was released on September 16, 2011 by Star Music and MCA Music.

2012: Your Love Asian tour

In 2012, Digby did an Asian tour for her Your Love album, including shows in Singapore and the Philippines.

Her Singapore live show was held on October 18, 2012 at the Esplanade Concert Hall.^[9]

In August 2012, she was interviewed by Yahoo!; during the interview, she shared that childhood depression shaped her music career and that she is preparing for her first independent album for 2013.^[10]

2013: Winter Fields

Digby introduced a brand new original titled Neon Rain in February 2013, and also released duet singles including "Falling for You", a duet with JayR, and "The Keeper", a duet with Kina Grannis. Her fifth studio album Winter Fields was released on October 29, 2013.^[3] She also conducted regular live shows on the Stageit platform on a Pay What You Can ticketing basis.^[11]

2015: "Jet Streams"

In December 2015, Digby made a new song titled "Jet Streams" available as a free download on Bandcamp. She also independently released a remake of the holiday classic "Have Yourself A Merry Little Christmas".

2018: Wildfire and Pop Covers

On February 9, 2018, Digby independently released a new EP titled Wildfire which debuted at #4 on the iTunes Singer-Songwriter Albums Chart.^[12]

On June 22, 2018, Digby released an album called Pop Covers. It includes ten covers of popular songs and includes Diamonds (Rihanna song) (originally by Rihanna) and Empire (Shakira song) (originally by Shakira) ^[13]