[5] In a 2020 interview, she said that she loved Sailor Moon, Inuyasha, and Ranma ½, expressing her surprise that her dad would make them watch Tenchi Muyo!

[7] Several months after, Akana watched Margaret Cho perform on a Comedy Central special and laughed for the first time since her sister's death.

She first struck online recognition with a semi-popular internet video on Funny or Die in 2010 of her mother discovering she masturbates as a teenager after finding condoms in the trashcan revealed to have been used to keep her vibrator clean.

Akana became a public figure after meeting YouTube celebrity Ray William Johnson at a CBS Annual Diversity Showcase event in January 2012.

Prior, upon moving to Los Angeles, Akana gained a larger online audience and debuted as a YouTube personality by launching a web mini-series in March 2011 titled 10 Second Traumas, created with her then-friend Deirdre Devlin.

It gained mild traction after guest starring Katy Perry's brother David Hudson, but did not blow up until Ray William Johnson liked the videos in his public channel feed and in turn featured Akana and Devlin as "Video Hoes" in Ray's own web series Breaking NYC in July 2011, then starring in the 10 Second Traumas sketches himself.

With the encouragement of Ray William Johnson to start her own channel after accumulating enough recognition from the 10 Second Traumas series and her cameo roles in Katy Perry's "Last Friday Night (T.G.I.F.)"

music video and MTV's Awkward, Akana created her current YouTube channel in August 2011 and garnered an algorithm for her collaborations with Johnson.

Originally uploading sketches and vlogs from her phone, Akana began making comedic life advice videos featuring prop guns and use of cloning to convey cutaways related to her storytelling.

[20] One of her short films, Miss Earth, was partially financed by Brian Grazer and Ron Howard's production company, New Form Digital.

[24][25][26][27][28] Akana executive produced and starred as the lead role in the original comedy-drama web television series Youth & Consequences, created by Jason Ubaldi and released in March 2018 on YouTube Red.

[29] On October 10, 2019, she was featured in a 30-minute YouTube documentary created by SoulPancake in collaboration with Funny or Die wherein a variety of comedians discuss mental health called Laughing Matters.

In 2015, Akana released a clothing line, Ghost & Stars, which features several cat-themed designs as well as formal dresses, leggings, and a variety of T-shirts.

[41][42] In 2024, Akana rolled out her standup comedy tour It Gets Darker with an entire hour dedicated to telling stories about her late sister's suicide and the traumatic aftermath, her history with violent stalkers causing her to quit live appearances, and growing up as a Hawaiian-native Asian military brat.

"[44] In reviewing her video, "How to Deal with a Breakup", MTV wrote: "In this sketch, comedian Anna Akana envisions the flurry of activity inside the cranial command center of a newly single dumpee.