She is known for her Trilogy Truth, Lies and Deception, her acting work in Pelleas starring alongside Alice Eve, and is represented by 3 Arts Entertainment.

[2] After turning down a job in banking, she worked in Southern France selling yachts and high performance cars to fund acting school.

In 2013, Pickering was cast as the principal role as John Lennon's first wife, in an adaptation of the novel Mersey Boys centered around The Beatles, and in its Off-Broadway play.

[11] Pickering then had a supporting role in Leave Yourself Alone selected for the 2016 Anthology Film Archives Theater in New York City[12] and released on VOD and Amazon Prime in 2017.

[16] In 2018, Pickering was cast in a principal role in Pelleas co-starring alongside Alice Eve and Benn Northover and directed by film maker Josephine Meckseper.

[18] In 2019, she completed shooting in a principal role co-starring alongside Blanche Baker and William Sadler in a 1950s thriller Alice Fades Away with a United States theatrical release for 2020.

[25] Pickering first performed her own creative writing airing on live radio for The Fall of Babylon show on Resonance FM in London.

[34] As a radio play podcast it was selected as a top ten finalist for HBO's ITV festival broadcasting live in October 2018 with Pickering performing.

[35] The full play Beach Break was awarded a scholarship from Rocaberti Writers to mentor with HBO's Kelly Edwards, in an adaptation for screen in 2021.

[38] The plays as a trilogy first showcased at The League of Professional Theatre Women, and included Beach Break, Cat and Mouse, and Sylvie and Sly.

[21][39] Pickering played a lead role alongside Robert Bradford, Koel Purie and Eugenia Kuzmina, directed by Christopher Mack and Pulcherie Gadmer.

[42] In October, 2022, Pickering's full play Bad Victims opened at The Courtyard Theatre, in London, directed by Erica Gould.

Pickering's writing style was described as "Sarah Kane meets Noel Coward with the deviousness of Phoebe Waller-Bridge to flip a scenario on its head.

[48] In 2018, she was a participant speaker and selected film maker at United Nations for Create2030, engaging artists in Sustainable Development Goals,[49][50] attending at UNNIGO 2018, and UNGA2018.

[50] Pickering performed as the lead actress for experimental feature film Kubricks directed by Dean Cavanagh and produced by Alan McGee.