We decided on Friday, February 13th to pull papers to run for a seat on Milton’s Board of Assessors. Seventy-five days later we had a result. Our campaign received 2,742 votes compared to 2,095 votes for our competitor. CallahanCan turned into CallahanDid!

We pledged to have some fun with the campaign and we definitely did. What follows are notes from the campaign trail.

Stories from the doors. We hit the doors and met our neighbors all across town. Door knocking can be a grind, lots of people not home and many others not coming to the door. But the people who did answer were universally nice and we definitely received votes from neighbors who appreciated us taking the time to introduce our campaign to them. We spent plenty of time in the precincts near our home but also made a point to door knock in precincts 6, 7, 8, and 9 where we were less known. It paid off, we lost all four of those precincts but narrowly in three of the four.

Our kids. Brenna and Devan were home for the final weekend and door knocked and held signs at standouts for their dad. It was fun for me (and hopefully them) and brought me back to my first campaign for town meeting 26 years ago when they helped me win by being a cute image on a campaign flyer. This time around, they convinced neighbors to vote for me, suggested social media strategies and provided a boost in the home stretch. How great is that?

Campaign soundtrack. Brenna and Devan also suggested at least one song to our quirky campaign soundtrack – You’ll Always Find Your Way Back Home by Hannah Montana, which evidently is having a moment 17 years after its release. We also featured the offbeat – songs like “I’m a Good Dog”, staying focused on “Happy Wednesday”, “Mail Carrier March” (when our mailer hit) but used classics from Sheryl Crow, Bruce Springsteen, Queen, Sabrina Carpenter, Bachman-Turner Overdrive and others. Stay tuned for the campaign soundtrack release.

Surrounded by women. Women power political campaigns, at least the winning campaigns! And from our campaign manager, Carolyn Cahill, and campaign treasurer, Niki Boyson, to our volunteers like Katie Conlon, Sheila Dunphy and Deborah Felton, to Eileen and our daughters, women helped me win this campaign. We had our share of men too (looking at you Mike Zullas, Chris Hart, Winston Daley, and Matt Morong) but women always power our campaigns thanks to the indefatigable efforts of Judy White-Orlando, Luisa Pena-Lyons, Meghan Haggerty, Janet Ferone and so many others.

Forums. It was great to have an opportunity to reach voters in a variety of forums that took place during the campaign. A highlight was the MiltonSpeaks forum produced by Milton Access TV and featuring the Milton High School Debate Team and Milton Times. There was a forum at Fuller Village and one sponsored by the West Milton Neighborhood Association as well as the annual meet and greet at the Council on Aging. We are enormously grateful for these organizations and appreciate each of the events where we made our case directly to voters.

Endorsements. Do endorsements matter in local elections? I’m not completely sure but when you pull in support from Maritta Manning Cronin (65 years and running as town meeting member from P4); Carolyn Cahill (P1 TMM, local realtor and friend); Joe Reardon (P7 TMM and friend); and Jim Henderson (former assessor) it sure doesn’t hurt your chances. We built a campaign from the beginning that was determined to compete in every corner of Milton and the results show that we did that. Each of these endorsers put their name next to mine when they didn’t have to and I am grateful and humbled by their support.

Eileen. You can’t run a campaign alone and when you have a life partner (and secret weapon) like my wife, Eileen O’Connor Callahan, you have a invaluable campaign asset. She wouldn’t let me lose. When we were both tired, she pushed me to do a few more doors. She did all of our campaign signs and ads. She advised me on strategy and she kept me steady when a few cranks on social media took their shots (we got called a “mortgage grifter” and a “real f*cking tool”). I told people on the doors that she should be on the ballot instead of me! Thank you, Eileen.

Campaigns for these townwide positions are hard. We raised $6,600 in the most expensive race for Board of Assessors in town history, breaking the record from the 2012 race. Thank you, donors. We knocked on 750 doors personally and the campaign reached double that. Thank you, volunteers. Our mailer went to every Milton household. We lost five pounds with hundreds of thousands of steps. Thank you, doorknocking. All for the privilege of being a member of the Board of Assessors and a $125 per month stipend! Thank you, Milton.

“A republic, if you can keep it.” This Benjamin Franklin response to Elizabeth Willing Powel’s question: “Well, Doctor, what have we got, a republic or a monarchy?” resonates today. We run these local campaigns to control what we can control. At a time when our national politics are unhinged, driven by an authoritarian wannabe, we want to serve our town and our Commonwealth and move our democracy forward. Talking to neighbors, building community and encouraging everyone to vote – young and old, townie and newcomer, immigrant or native-born – is one small way we can do that.