Jesse Singal is a journalist and author, and has written for The New York Times and New York Magazine. During our conversation, Jesse talks about freedom of speech in America, the effect of woke culture on journalism, cancel culture in our society, and the reaction to his Atlantic article, When Children Say They're Trans, published in 2018. Jesse writes on Substack and co-hosts the podcast Blocked and Reported with Katie Herzog.

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(00:00) Intro

(01:01) Get to know Jesse Singal

(02:45) How did Jesse get interested in podcasting, writing, and journalism?

(05:12) Jesse talks about Jonathan Haidt’s work and how it helped to shape his outlook on America, and on life

(06:45) What about Haidt’s work changed Jesse’s sensibilities about people who disagreed with him?

(09:15) Where are we right now with regards to freedom of speech and woke culture

(11:16) What is meant by woke culture?

(12:42) What trajectory led us to this point?

(15:08) Jesse’s take on the percentages of the American population that's fomenting woke culture

(17:39) How does Jesse explain the insistence on not using a phrase (like “pregnant women”) for fear of offending?

(19:12) Jesse’s article for The Atlantic, When Children Say They're Trans

(21:38) Jesse’s reasons for writing the article When Children Say They're Trans and the response it received

(24:52) Why is it that a percentage of children regret their transition?

(27:52) Jesse cites an example of a child who considered it a mistake to undergo transition therapy

(29:53) Why is there a pushback to a more conservative approach to transition therapies for children?

(32:08) Do we have the statistics to know what percentage of children under the age of 14 who transition later believe it was a mistake?

(35:26) Does Jesse believe that journalism in America is in a state of peril?

(40:21) Jesse’s advice to aspiring journalists who want to have the freedom to explore ideas and write openly

(42:11) Jesse talks about his plans for the future

(46:15) Getting the independence to openly share his thoughts

(50:17) Journalists and news outlets that Jesse recommends