We’re excited to introduce you to the always interesting and insightful Jess Bouchard. We hope you’ll enjoy our conversation with Jess below.

Alright, Jess thanks for taking the time to share your stories and insights with us today. Was there a moment in your career that meaningfully altered your trajectory? If so, we’d love to hear the backstory.

Growing up, I wanted to be an orthodontist for several reasons. The original inspiration came from my childhood babysitter, who had braces that initially terrified me. But when my mother explained they were like jewelry for her teeth, I became fascinated. I spent years studying every smile I saw, diving into the science of teeth.

My path shifted during my first year of college when several professors encouraged me to consider writing and, more importantly, teaching. Up until then, I had been a closeted wordsmith and poet, keeping that side of myself hidden. Having professors truly see me beneath the surface was transformative—it gave me confidence and helped me redefine how I saw myself. I changed my major to become an English teacher, beginning a journey of helping youth find their voices and explore their humanity.

This shift not only led me into teaching but also into advocacy, where supporting others in their growth and self-discovery became my passion. Teaching and advocacy are deeply intertwined, and empowering others to realize their potential has been the core of my career. It eventually brought me into a leadership role with Queer Connect, where I continue to work toward fostering inclusive spaces and uplifting the voices of marginalized youth.

Jess, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

Growing up in rural upstate New York, I felt the isolation and grief that comes with being a queer young person without representation and inclusion in my community. I spent a lot of time being on the outside and not being invited to the table. To be honest, I thought that would be most of my life, so I anticipated that for my adulthood. I didn’t know what I didn’t know, and what I did know was that I didn’t fit in nor did I know how to.

I eventually became a teacher, because I wanted to be the adult I needed when I was a student. I wanted to be the positive adult that walked along side our most vulnerable youth. Being a teacher grew into me being a school administrator, which also opened the door for me to join the local LGBTQIA+ organization in my town and flex my leadership muscles. I started as a Board Member, and today I am the Executive Director for Queer Connect in southern Vermont. Our full team is made up by volunteers, including myself, because we all deeply believe in our mission to provide resources and visibility to LGBTQIA+ individuals and families, especially youth in our sleepy corner of Vermont. Many of us were not included at the table growing up, so everything we do, we aim to bring support, love, and affirmation.

I am incredibly proud of the community we are growing, because I know the work we do is life-saving. It’s our sincere dream to grow Queer Connect to have a physical Pride Center and move from being volunteer run & grass-roots-y to cast our net wider, full-time.

How about pivoting – can you share the story of a time you’ve had to pivot?

Pivoting is equal parts hard and transformative, pushing you to grow in ways that are often uncomfortable but also perspective building. For every single “no” I’ve encountered, a “yes” has arrived in disguise. I began my earliest days of teaching in higher education, teaching College English at a community college in Texas right after I graduated from my Master’s program. I wanted to be a college professor, because I enjoyed working with adults and loved my time being a college student myself. I left higher education not because of the students, because I loved my students and the spaces we grew together, but because I needed to do some of my own personal healing from harm I endured as a young student. Being back in the classroom with middle and high school aged students, gave me the gift to turn inward and reflect, but then also reflect out, serving as a mirror for others.

This last year, I spent a year as a principal, and though leading a school aligned with my professional goals, I missed working directly with students. The time commitment I had to give to my school, also meant I couldn’t be as deeply involved in my volunteer work with Queer Connect. I have since left and now am doing direct equity and justice work for a school district, which allows me to be more balanced. Closing one door opened another, which continues to open more, because I am able to be open in a new way. I remember thinking, “this wasn’t my plan, but plans change, and that’s okay.”

Leaving a school community that I served for a long time gave me more time to refocus on Queer Connect and build the structure with my Board in a more meaningful way. We are a passionate team of volunteers that recognizes a deficient in our community, so we are here to grow it. Changing my trajectory gave me that opportunity, and that feels really empowering to me.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

One of the biggest challenges of being a leader in any capacity, and truthfully, just a human of the earth, is not allowing the outside voices to alter your own values and the way you see yourself. I’ve found myself at different times putting on “different hats” almost like different versions of myself, because at those moments, I believed the critiques of others were valuable. It took me some time to realize that constantly adapting to others’ perceptions was distancing me from my authentic self.

One lesson I had to unlearn was the belief that I needed to mold myself to fit others’ expectations in order to be successful or accepted. Instead, I’ve come to understand that true leadership—and true fulfillment—comes from staying grounded in my own values, even when external voices challenge them. Learning to trust my inner compass has been a vital part of my journey, allowing me to lead with authenticity and confidence.

Contact Info:

• Website: https://queerconnectbennington.com
• Instagram: queeconnect.bennington

Image Credits

Greg Nesbit Photography