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"Comment: The lessons about life I want to teach my students," Dorchester Reporter (April 26, 2018)
"The World is Threatened By Our Students' Voices, and We Have to Teach Them to Be Brave," Education Post (April 12, 2018)
"Arm Teachers with Resources, Not Guns," with Sean McComb and Josh Parker, U.S. News and World Report (March 7, 2018)
"Working with Young People Means I Get to Witness Small Acts of Humanity All the Time," Education Week Teacher (February 20, 2018)
"I Know White Teachers Can Be Biased Against Kids of Color Because I Was," Education Post (February 13, 2018)
"Sydney Chaffee: Teaching the Next Generation," Trend Magazine (Winter 2018)
"Balancing the Brain and the Heart," Transforming Education Blog (November 27, 2017)
"Is It Possible to Have Strong Public Schools and Choice?" The Line (October 2017)
"Helping Teachers Become More Effective is Worth Funding," The Huffington Post (October 30, 2017)
"National Teacher of the Year Sydney Chaffee on How 'All Teachers Can Be Leaders,'" Gates Foundation Blog
"Teacher Reflection: Why I Put My Students on Stage," Teachers' Top Three, Massachusetts Department of Elementary and Secondary Education (September 16, 2016)
"The 2017 National Teacher of the Year on the Mom who Changed How She Talks to Her Toughest Students,"Chalkbeat (June 20, 2017)
"Teacher Voice: 'I realized that my education had occurred within a racist system that privileged Eurocentric achievements,'" The Hechinger Report (June 19, 2017)
"Rejecting The Myth Of The 'Super Teacher,'" WBUR Cognoscenti (May 2, 2017)
"Teachers Must Be Ready to Engage," The Standard: The Official Blog of the National Board (April 19, 2017)
"Risk Failure," Heinemann Digital Campus (April 3, 2017) - Requires subscription
"How Mentoring a Student Teacher Got Me Through the Five-Year Itch," Education Week Teacher (October 2013)