Early career

As a Wall Street executive, Siskind was a pioneer and expert in the distressed debt trading market. She became the first female Managing Director at Wasserstein Perella & Co. in 1996, at the age of 31, and later ran trading departments at Morgan Stanley and Imperial Capital, where she was also a partner.^[7][8] Siskind worked 20 years on Wall Street before retiring in 2006.^[9]

The New Agenda and political activism

Siskind was an early supporter of Hillary Clinton during the 2008 United States presidential election cycle, having previously supported Clinton's re-election bid to the United States Senate, and having taken her daughter to meet Clinton at an event in 2006.^[10] Siskind has drawn criticism from liberals for voting for John McCain over Barack Obama.^[11]

In August 2008, Siskind co-founded The New Agenda in her living room with 30 Hillary Clinton supporters who alleged sexism and misogyny were at play during the 2008 election.^[12][13] The New Agenda is a non-profit organization "dedicated to improving the lives of women and girls by bringing about systemic change in the media, at the workplace, at school and at home".^[13] As of August 2019 she is president of the organization.^[14][15] It focuses on issues that affect the success of women, including pay discrimination, sexual assault and sexual harassment.^[9]

Siskind was reported to be one of the earliest supporters of the Me Too movement, sparked by a tweet from Alyssa Milano on October 15, 2017, for which Siskind tweeted her own support within the first hundred minutes.^[16] In October 2018, in the days following the Pittsburgh synagogue shooting, Siskind posted on Facebook that she was organizing an anti-hate vigil in her Westchester County community. After a local newspaper ran a story about it, Proud Boys founder Gavin McInnes and his family, who lived in the nearby community of Larchmont, New York, appeared at Siskind's door without invitation or forewarning; she called the police.^[17]

The List

Siskind speaking at the We The People march

In November 2016, Siskind started keeping a weekly list of not-normal events of the Trump administration, and posting the lists on social media.^[9][18] Siskind indicated that she did not intend to merely recite normal political disputes, but to catalogue "things that are uncharacteristic of our democracy".^[18] In September 2017, she was named in Politico's 2017 "Politico 50".^[18] In March 2018 she compiled the first year of weekly lists and published them as The List: A Week-by-Week Reckoning of Trump's First Year. In June 2018, Siskind started The Weekly List podcast to accompany the lists;^[19] writing in Forbes in July 2018, Jo Piazza listed this as one of the "Podcasts Created by Women You Need to Be Listening To Right Now".^[20] In July 2017, the United States Library of Congress began archiving her weekly reports.^[18] Siskind acknowledged in an interview the following year that a downside of taking such a highly public stance is that "I can tweet things that are inarticulate and be attacked for months and get death threats".^[21]

In 2018, The List: A Week-by-Week Reckoning of Trump's First Year was called one of the best books of 2018 by Carlos Lozada of The Washington Post.^[22] Her podcast was also recognized by Marie Claire in 2019.^[23] Siskind also organized the 2019 We the People March, a national march advertised as an event to remind elected officials that they work for the American people.^[24] The march took place on September 21, 2019, in Washington D.C., with others in various cities across the United States.^[24]

In 2021, Siskind donated The List collection to the Annenberg School library. The List was archived along with Siskind's podcast and other content she had created.^[25]