n October 2010, Singh started a YouTube channel under the pseudonym "IISuperwomanII". She has explained that the name Superwoman was prompted by a childhood idea, making her believe she could do anything.
n March 2015, Singh began a world tour called "A Trip to Unicorn Island", adapting her YouTube content and including singing, dancing, music performances, comedy, and her parent characters. Her tour covered India, Australia, Hong Kong, Singapore, Dubai, Canada, Trinidad and Tobago, the United Kingdom, and the United States. She documented the tour in her first feature movie, A Trip to Unicorn Island, which also describes how YouTube fame is affecting her life.
Her first book, How to Be a Bawse: A Guide to Conquering Life, was released on March 28, 2017. The book reached No. 1 on the New York Times bestseller list. She won the award for Best Non- Fiction at the 2017 Goodreads Choice Awards. Her 2017 world tour was centred around the book release and key concepts she discussed.
In March 2019, NBC announced that Singh would host a new late night talk show, A Little Late with Lilly Singh, which succeeded Last Call with Carson Daly following its series finale later in the year. The show premiered on September 16, 2019 to positive reviews by critics.