She is best known for her YouTube channel, ContraPoints, where she creates video essays exploring a wide range of topics such as politics, gender, ethics, race, and philosophy.

[9][12][14][15] She left Northwestern with a master's degree (subsequently stating, "The idea of being an academic for the rest of my life became boring to the point of existential despair"), and moved to Baltimore, Maryland for a relationship, which ended up failing.

[9][16] After quitting her PhD program, Wynn taught piano, and worked as a paralegal, Uber driver, and copywriter, eventually deciding to begin making video responses to the alt-right and Gamergate on YouTube.

In 2016, she began the ContraPoints channel in reaction to the Gamergate controversy and the increasing prevalence of right-wing YouTubers, shifting her content to countering their arguments.

[9] In her videos, Wynn utilizes philosophy and personal anecdotes to not only explain left-wing ideas, but to also criticize common conservative, classical liberal, alt-right, and fascist talking points.

[26][27][28] In February 2020, Wynn set all her videos from before August 2017, the time when she began her gender transition, to private, stating that they "no longer represent the person I've become".

Regardless of the viewer's interest or lack thereof in internet culture wars, YouTube Nazis, or any of the other wide-ranging subjects covered in its videos, they're funny, bizarre, erudite, and compelling.

[22] Journalist Liza Featherstone, in The Nation, recommends the channel, saying that Wynn does a "fabulous job" acknowledging her opponents' valid points while debunking weak arguments and revealing the influence of a sometimes unacknowledged far-right political agenda.

[33] In November 2018, after a ContraPoints video about incels reached over one million views, The New Yorker carried a report on the channel, describing Wynn as "one of the few Internet demi-celebrities who is as clever as she thinks she is, and one of the few leftists anywhere who can be nuanced without being boring.

"[34] The Verge has called Wynn's "confident and indulgent" persona in ContraPoints as "decadent" in "the mold of Oscar Wilde by way of Weird Twitter," commenting on her postmodern rococo set design and the "bewildering" variety of characters she deploys.

[38] Linguistics professor Lal Zimman said about pronoun introductions, "Wynn is absolutely right that people engage with that practice in ways that can be somewhat problematic".