Meet Anna

Hi, thanks for visiting my site! I’m Anna Callahan, I’m a software engineer and mom, and I love living in Medford.

I moved to the area in 2003 and fell in love with it.  Our family moved to Medford in late 2020 and now we live near Tufts park. In the summer you can often find us at the pool — sometimes we’re there more than once a day! We love to be involved in projects where a small (or large!) group of volunteers makes amazing things happen. For example, we enjoy playing in School of Honk, this year we did the North Cambridge Family Opera, and we loved the Medford Cardboard Canoe Race. :D

I went to high school near Chicago and I remember my mom saying that she spent 70% of the family income on rent so that my sister and I could go to good public schools. I got a BS in Math from the University of Michigan, and then pursued my passion of playing jazz trumpet.

I did not make a lot of money as a jazz musician, so I understand how difficult it is to live on very little. I was wrongfully arrested and jailed in 2000 while attending a peaceful protest, and it really opened my eyes to racial disparities in our criminal justice system. I’ve always been a renter. My husband and I like to joke that we went for 20 years without a car, and then bought a 20-year-old car.

After moving to Ball Square in 2003 I worked as a software engineer at a variety of startups, creating mobile apps in Objective C and web apps in Django. I got married and had my son in 2014. In 2016 (while living briefly on the west coast) I got involved in presidential politics and then local politics — I have such a passion for it that I left engineering to devote to it full-time. I helped a number of progressive candidates get elected to the city council and mayor of Berkeley, CA.  I helped get Berkeley’s public financing of elections law passed and then served on the Fair Campaign Practices and Open Government Commissions. 

Since 2017 I’ve worked with The Incorruptibles, which trains grassroots groups and candidates in a new model of political organizing that elects better representatives of working people to city government. I trained dozens of groups (in states including CA, OK, KS, PA, MA, RI among others) to build local power by creating coalitions and expanding the electorate.

While running for state office in 2020, I interviewed people in Medford and Somerville to understand how COVID was affecting us. After my campaign, some of the folks on my team and I created a map of local minority-owned businesses and interviewed some of the owners.

I also run the Incorruptible Mass podcast, where my co-hosts and I aim to help people understand and transform state politics. 

I am fascinated by how we re-invigorate democracy, especially on the ground at the local level, so if you ever want to talk about it, don’t hesitate to reach out!

I hope to meet you at your door, at an event, or on the phone. Or at the pool!