Behind the Scenes with Kelly Flynn

Each month, "Behind the Scenes" features an interview with a leader in our community designed to provide readers a glimpse into his/her interests and passions inside and outside of the workplace.

This month, "Behind the Scenes" sat down with Kelly Flynn, Co Executive Director of the Better Middlebury Partnership.

What is your hometown?

I grew up in Western Connecticut, in a city called Danbury, wherein it’s ‘claim to fame’ is being the national hat manufacturing center during the nineteenth century. In 2009, I moved to Vermont from New York City, to join my (now) husband who already living up here. I was motivated by the idea of living in a small rural state and am not surprised that I continue to love living here.

Where did you go to school?

After high school graduation in Connecticut, I obtained my undergraduate degree from Rutgers University in New Brunswick, New Jersey. After which I headed to law school at Pace Law School in New York where I earned my Juris Doctor.

First ever job?

My first ever job as a teenage was working in a toy store. I worked with a lot of my friends, and we just had a lot of fun!

Who was your greatest inspiration growing up?

My greatest inspiration growing up is certainly my mother. She was a working mother who handled it all with grace, even during trying times. She provided me and my siblings a stable foundation to have the confidence to take risks as adults.

Who do you most admire?

Those I admire most are people who value and act in the benefit of community. Vermont is a place where an individual can make a visible impact through day-to-day actions in our community, whether you have the capacity for large-scale community work or looking out for a neighbor. I have found an always present spirit of collaboration, sense of belonging and welcoming in my community; which continues if we all actively perpetuate it.

Favorite Vacation Spot?

Just recently my extended family took a well needed and once in a lifetime vacation to St. Croix. It was fantastic to have the ability to relax in a beautiful spot with the people I love!

Favorite movie, TV Show?

I love the experience of a movie in a theater, l always drag my kids to every age appropriate showing. One of the best birthday gifts I give myself is going to the movies, alone, in the middle of the day. Currently, I love going to the Middlebury Marquis free Saturday afternoon kids’ movie, where my family can have lunch and have a free classic kids’ movie. My point is, there are too many movies to choose from and a movie is best watched in a theater!

Favorite type of music?

My favorite type of music would be the music I grew up listening to, my parents’ favorite music. It feels ingrained in me as part of my childhood, they loved the Beatles, Sam Cooke, Bob Dylan and the Drifters to name a few!

Biggest Career Challenge?

Prior to living in Vermont and for my first ten years in Vermont I worked in corporate law. My biggest career challenge was realizing that my career does not have to a straight path. Learning that just because I have education, experience and enjoyment in one field, does not preclude me from professional enjoyment in a very separate field! It was a great lesson that life does not have to be static.

Typical work week?

In my current roles, I am finding that there is no ‘typical’ work week. A few months ago, I expanded my career to include the position of Executive Director of the Better Middlebury Partnership, with which I share with my CoDirector, Kathryn Torres. I am also still representing clients through my law practice. Both jobs are rewarding in different (and sometimes similar!) ways, but neither job has a regular 9-5 schedule.

What's the greatest career risk you have taken?

The biggest risk I took in my career was to leave my corporate job in 2019. It was a challenging position and I had truly wonderful colleagues, but I knew I wanted to do something local that had an impact on my community. It felt risky to leave a stable and secure job, but I am very glad I took the leap. These past few years I have meet so many wonderful people and feel so connected with my community.

What's the one thing you would like to see change in your business/industry?

One thing I would change about my industry, either as co-director of the Better Middlebury Partnership and as a lawyer, is the inclination not to reach out for assistance. Too many times I have seen others struggle to find answers that others in our community can assist with, I am guilty of this and often remind myself that collaboration and shared resources are available if you ask.