Olivia was discovered by the director of Rising Productions (Vision Factory) while attending the Okinawa Actors' School, subsequently signing to Avex Trax as part of the Japanese idol group D&D.

Producer Tetsuya Komuro thought Olivia would be perfect for a project he was planning along with Jean Michel Jarre.

After a hiatus of more than a year, Olivia began to take control of her career, releasing her seventh single "Sea Me" on December 12, 2001.

This marks her switch to one of Avex Trax's sub-labels, Cutting Edge, from which she continues to release singles and albums.

[7] Her releases became increasingly rare and sporadic thereafter, with a video clips collection appearing four months later.

2003 saw a complete style change and an onslaught of mini-albums as she began a series of collaborations with her brother, Jeffrey Lufkin.

[9] Alongside this, Olivia decided to launch a rare-items fashion label called Black Daisy Ville with her friend Friedia Niimura (Rin Kozue).

It featured the best material from her four mini-albums, and introduced two new tracks, "Alone in Our Castle" and "Fake Flowers", as well as two re-arrangements.

After releasing The Lost Lolli, Olivia went on an unofficial hiatus except for a performance at the "Halloween of the Living Dead" concert hosted by Hyde on October 30, 2005.

In 2006 she provided vocals for the lead vocalist character Reira Serizawa in the fictional band Trapnest as a part of the anime adaptation of Nana.

[10] She produced songs under the alias Olivia Inspi' Reira (Trapnest) alongside fellow Avex artist, Anna Tsuchiya, who plays the role of Nana Osaki, the vocalist for Trapnest's rival band Black Stones.

"A Little Pain" was Olivia's first release for this role in which she first made the general theme to the lyrics, then wrote the song in English.

The single is about "Reira's loneliness, pain, and strength," as Olivia found that she could relate well to the character.

Following the success of these releases, Olivia's first US appearance was scheduled for the Asian entertainment convention Pacific Media Expo held in Los Angeles, California in October 2006.

In addition to the singles previously released, the mini-album also featured the songs "Dream Catcher", which was used as the ending theme for the live action television drama series of Jigoku Shōjo; "If You Only Knew", which was used as the main theme for the Korean drama The Snow Queen; and an English version of "Wish".

Later in February, the compilation album Olivia Inspi' Reira (Trapnest) was released featuring the singles from the Nana and some new songs.

A new song, "Bleeding Heart", released on March 19, 2008, was a collaborative effort with her brother, Jeffrey Lufkin.

Following the release of this mini album, Olivia held a live show on October 24, 2008, at Shibuya Womb.

On December 30, 2008, Olivia participated in a duo showcase with Inoran in which she covered a few of his songs such as "Owl's Tear" and "Monsoon Baby".