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.)