Will Haskell’s 100,000 Bosses

Like many people during the pandemic, Will Haskell found himself with unaccustomed time on his hands.

Unlike many people, his job involved constant meetings, every day and night, so he had even more free time than most. Haskell is a State Senator.

Like many people, he decided to try his hand at writing.

Unlike many people, he actually completed what he set out to do. And unlike nearly everyone else, he turned his project into an actual, real book.

100,000 First Bosses: My Unlikely Path as a 22-Year-Old Lawmaker will be published officially yesterday. And not by any vanity press, either. This is a legit, Simon & Schuster book.

It’s one more chapter (ho ho) in the remarkable story of the Staples High School graduate/still-youngest-member-of-the-Connecticut General Assembly’s life.

Haskell was a Georgetown University senior when he decided to run for the 36-member Senate. He enlisted his roommate as campaign manager. He gathered a hard-working group of committed volunteers, from even younger than himself (14 years old!) to those older than his grandparents (they remember FDR!).

Four years ago, new college graduate Will Haskell became State Senator Will Haskell. He unseated an incumbent who had been in office longer than he’d been alive.

Now he wants to inspire his peers — and the next generation — to do the same.

100,000 First Bosses is not a “how-to” book. “I’m not qualified to write that,” Haskell says. “Every campaign is different.”

What he does is pull the curtain back on his own experiences. He talks about the surprises and drudgery of knocking on doors; the lessons learned as he learned the ropes in Hartford; the successes he’s had, and the mistakes he’s made.

State Senator Will Haskell,

His book, he says, is “my thoughts on the weirdest first job someone could have right out of college.”

Most people have 1 or 2 bosses. Haskell is beholden to the 100,000 residents of State Senate District 26. It stretches from Westport to Bethel.

Throughout the book he emphasizes the perspective of a 20-something, still finding his way in a complex, troubled America, with tons of problems my generation has dumped on his.

Climate change, gun violence, college affordability — all those are very real issues to Haskell and his cohort. And they’re issues, he argues, that his generation can address and solve.

But to do that, he emphasizes, they must be in positions of power.

Haskell’s unique perspective — and his equally unique literary debut — was helped by someone his own age: his editor, Carolyn Kelly.

Like Haskell, she’s in her first job. In fact, this was her very first book.

It is a very 2020s tale. “She knows everything about my life. But we’ve never met,” Haskell marvels. We did everything online.”

Kelly taught him how to craft his story to appeal to “people who might be uninterested in politics. Lots of people don’t know who their state representative is, and have never been to their state capital.”

The State Capitol in Hartford is Will Haskell’s workplace. Have you been there?

He hopes his book will be read by them though, and spur them to think about running for office. Maybe they’ll encourage a colleague to do so.

Or a grandchild.

He had not thought of running for office either, back in the day. But when Barack Obama left office, he told the nation’s young (and “young at heart”) to push for progress from the grassroots up.

Haskell had no idea who his state senator was. He found out — and realized he did not agree with some of her positions.

The rest is history.

And history-making.

Gun violence is one of the issues State Senator Will Haskell has worked on.

Though much of the state — and nation — are polarized politically and socially, Haskell says that his 2 terms in the Senate have made him very optimistic. He realizes, he says, that one person can make an impact.

Through his book, he hopes to share that optimism.

Yet Haskell is leaving politics. He announced last month that he will not run for a 3rd term. Instead, he is heading to law school. (He’s also getting married, whenever the pandemic allows a large group to celebrate.)

In 100,000 Bosses‘ final chapter, Haskell writes about struggling with that decision. He frames it as a way to show that as important as political action is, one’s entire life does not have to be defined by it.

He also notes that just as he went to Hartford as a new, young voice, there’s now an opportunity for another new voice to follow his.

Haskell’s book is not like many politicians’, It does not read like a stump speech, nor does it paint an overly rosy picture of his profession.

He writes candidly of the difficulty of affording rent in his own district, and of watching a focus group pick him apart, one flaw after another.

Still, he says, “it was a blast to write. People took a chance on sending me to the Senate. Now I hope they’ll take a chance on buying and reading it.”

Spoken like a true author.

Not bad for a politician, either.

(Click here to order 100,000 First Bosses: My Unlikely Path as a 22-Year-Old Lawmaker.)

10 responses to “Will Haskell’s 100,000 Bosses

  1. Mika Brzezinski interviewed Will on Morning Joe (MSNBC) yesterday! I have a feeling we will see Will again, hopefully in the not too distant future.

  2. Well done, Will. I have ordered a copy for me and another for my grandgirls. Best of luck in the future. We have been lucky to have you.

  3. Linda Montecalvo

    We are so fortunate to have had Will represent us and his story is an inspiring one that I hope encourages young people to run for office. I’m so delighted to hear he will be returning to school this time to study the law. I’m sure we will see him again on the National level. I wish him every bit of success. An amazing young man for sure. His example is now out there for young leadership to step up – who’s next?

  4. If you have ever met Will you know what an engaging, enthusiast young man he is, well beyond his years. I love the title and message if his book; all elected officials should feel the same way – they are beholden to their constituents and should constantly strive to understand where they (the majority of “they”) stand on the issues, and be guided accordingly.

    I am quite sure Will will be successful at wherever his journey takes him.

  5. Can you be an up-and-comer if you’ve already up and come? 🙂 Congratulations to Will on all his accomplishments. And yes to all Jack Whittle says, above.

  6. Thank you for your leadership, Will and for being an advocate for land conservation. Good luck!

  7. Elaine Marino

    This kid is so cool! I normally would say, “He has a bright future ahead of him” but since his “past” is already beyond bright, he has an “off the charts” future ahead of him.

  8. Clark Thiemann

    Congrats to Will and hope to see him do great things in the future. Wouldn’t it be neat to have another person who is up and coming have a shot to run for the seat going forward? While I very much respect Mr Bernard and everything he has done for the town and community I hope we keep our eyes open to the next Will Haskell in the campaign!

  9. Carl Addison Swanson, Esq.

    I have dealt with the young Senator many times over, especially during the last year. While not only being a fellow Georgetown Hoya, Will actually has a sense of humor and likes to get things done. A refreshing change from the elderly do-nothing legislative branch which apparently can not get anything done in DC these days? Safe travels young Will. I hope your choice of law school is the right one . . . I quit the law after being lied to for 20 years. Safe.

  10. Will is a true public servant. He always shows up, whether it’s to a March or rally to support the most marginalized in our community to checking in children as the go to get their covid vaccine or assisting with parking at a PTA fundraiser at the drive in. He has responded to each email I have sent with a thoughtful response. He had one agenda – make our state a better and safer place to live and visit. Our county would be better off if all our elected officials shared his empathy and integrity.