CT senator details ‘unlikely path’ to lawmaking in new book

Photo of Alyssa Seidman
State Sen. Will Haskell (D-Westport) has written a book. “100,000 First Bosses” will be available for purchase on Jan. 18.

State Sen. Will Haskell (D-Westport) has written a book. “100,000 First Bosses” will be available for purchase on Jan. 18.

Cathy Zuraw / Hearst Connecticut Media file photo

The introduction of “100,000 First Bosses” — a new book by state Sen. Will Haskell (D-Westport) — brings readers directly into the room where he performs his job.

Here, Haskell recalls drafting legislation for the program that would eventually fund free tuition at Connecticut’s community colleges, but he does so without the filter of rose-colored glasses.

Then a freshman senator, Haskell described feeling hesitant when answering questions from the nonpartisan attorneys who were helping to craft the bill.

“My toes crunched and my shoes felt too small, like they did when I didn’t know the answer on a chemistry test,” he writes.

This conversational tone is prevalent throughout the book, which Haskell decided to write after the 2020 election.

Following his upset victory in 2018 — which unseated a longtime incumbent — Haskell began getting calls from dozens of young people who also had aspirations for public office. The funny stories, mistakes and advice he gained along the way can be found in “100,000 First Bosses: My Unlikely Path as a 22-Year-Old Lawmaker.”

Haskell, who is not running this November for re-election, spoke with Hearst Connecticut Media ahead of the book’s release.

Hearst: The introduction stresses the need to vote young people into all houses of government. How do you feel your time in office has strengthened representative democracy within your district, or even the state?

Haskell: People buy into the promise of representative democracy, but it’s not representative. There’s really not enough young people at the table where decisions are made.

As a state senator I saw firsthand how much of a difference it can make for a constituent to call their state representative. If I get 10 calls about a bill it’s gonna shape how I spend my time in the legislature.

Free community college and paid family medical leave were stripped out of the (federal) Build Back Better Plan, but those were actually accomplished in Connecticut. I really believe if we direct even a portion of the activism we have for Washington towards our local and state governments then we’ll start to see transformative changes in our community.

Hearst: Some of the chapter names (“You Can Never Wear Shorts Again,” “Drinking From A Water Hose”) imply that being a politician is not all glitz and glamour. How do you believe your book will re-frame how society perceives young people running for public office?

Haskell: It’s a peek behind the scenes of what it actually looks like on a granular level to get your name on the ballot, and show people it’s not as hard as you think. The takeaway is that more people should run for office, but (there are) many un-sexy tasks that come with trying to get ... your community to support you.

During the campaign I had trouble connecting with middle-aged men who were deeply skeptical about electing someone younger than their kids or grandkids, but I also had older constituents who were excited about finally passing the torch to our generation — something President (John F.) Kennedy had promised decades ago.

Hearst: The book’s title is derived from the number of constituents you represent. Can you recall an experience you had with a constituent(s) that drove you to write the book?

Haskell: The day we went to Ridgefield High School for (its annual) mock election in 2018. The first question I got was on cannabis legalization, and I was honest that I supported it so long as we enacted strong regulations to keep people safe. We ended up winning that mock election, and (it reflected) the fact that young people are really eager to see candidates their own age on the ballot.

Young voters are a core part of (the Democratic party’s) coalition, but we don’t do a good job of meeting voters where they are. … I spend as much time going to high schools as I do going to senior centers … to understand in a meaningful way the needs of the next generation.

Hearst: Do you have a favorite chapter or part of the book that was easier to write than the others?

Haskell: Chapter 28, “When Optimism Arrives in the Voting Booth.”

Hearst: What’s one piece of advice you hope someone who was in your shoes will gain from reading the book?

Haskell: (If) you’re interested in politics, being young is not a liability — it’s an asset. People will be excited to lick envelopes, call constituents and knock doors for your campaign.

We may not know what it’s like to have a mortgage or start a small business, but we have a host of other experiences and perspectives our older colleagues might not yet know or understand. What this job has taught me is that underdog candidates can still pull off a win, and when we do we have a chance to change public policy.

Hearst: You recently announced you would not seek re-election this fall. In addition to law school, do you see yourself mentoring young politicians who hope to make a splash as you have?

Haskell: As I was writing this book I was asked to think about a fundamental question: Who is the intended audience? It’s somebody who is feeling pessimistic … or frustrated (with) the direction of government and wants to see more done, but doesn’t know how to go about making the changes. It’s their voice that we so desperately need.

I hope other unlikely candidates pick up this book and ... it makes everyone feel a little optimistic about the state of our politics. When I launched my campaign I felt pessimistic about where we were heading, but now, as I prepare to leave, I feel more optimistic than ever before.

“100,000 First Bosses” hits store shelves Jan. 18.

alyssa.seidman@hearstmediact.com