December Alumni Perspectives: Shay Totten '91

What a year, right? 

As I reflect on 2025 and my work here at Bennington, I am thankful for the many alumni who have stepped up to help organize and host get-togethers, including our successful All-Class Reunion in October, have connected with and supported current students, and, most importantly, pledged to help write Bennington’s next chapter.

In short, I am so excited to be doing this important work with fellow alumni and while much was accomplished in 2025, we still have a lot of work ahead of us this coming year.

We will: 

• Relaunch the Alumni Association (which was disbanded in 1997) and begin to host regular alumni events throughout the country.
• Welcome new alumni into the fold at Commencement.
• Welcome a new president to campus in the Fall.
• Launch a more effective alumni-student mentoring program
• Bring more alumni into the classroom to share their post-Bennington experiences with current students

Do you have other ideas? Or, are you interested and able to host a small gathering in your community, please email me.

When I returned to campus in September 2024, I knew there was a lot of work to do–especially rebuilding the connections between alumni, as well as alumni’s connections to students, and the College. 

Like many of you, my love for this place never waned–no matter how angry I was at times for the actions of its leaders. I feel lucky to have been back here and lend an alumni’s perspective to my colleagues on staff. There are some very deeply committed and caring staff who continue to make this place special for today’s students (a.k.a. alumni-to-be).

The reasons to rebuild and strengthen those connections are all too obvious: Liberal arts education in our country is under attack and small colleges like Bennington with a small alumni base are vulnerable. As we approach Bennington’s centennial, it’s all that more important to reflect on how this remarkable experiment continues through all of us–current students and alumni.

First, there’s a course titled Life After Bennington: A Curated Exposition of Bennington Alumni and How They Transitioned from College to Career, which will feature roughly a dozen alumni over the course of the Spring term. This course is proving popular as we filled all 40 seats with requests to add more! This course will feature presentations and conversations with Bennington alumni to provide guidance to current students about how to leverage their own experience in designing their education to the next step in their growth: designing a career. If you’d like more information and to be considered as one of alumni visiting speakers, email me, as I may have a slot or two still available. We are prioritizing in-person presenters but are also open to virtual presentations.

In recent months, we announced pilot projects that will put alumni in the classroom in the Spring. The first—Bennington Networks—was set to launch in Spring 2026 and pair alumni mentors with Bennington seniors for a full term to help them prepare for a post-Bennington life. While it’s not proceeding in the way we imagined, I am working to ensure that nearly 100 alumni who stepped up to become a mentor are connected with a current student. Stay tuned.

If you haven’t checked out Bennington Connects—a closed community for alumni and students to connect about mentoring, Field Work Term, and job opportunities—please do. You can find alumni by region, profession, and class year, too. 

As the Bennington Alumni Association begins to take shape in 2026, this online resource will become a hub for people to continue networking outside of events as well as post job opportunities or seek new opportunities and offer support for each other. 

Thanks to all my alumni volunteers and dear friends who’ve made this year as successful as I could have hoped. I look forward to seeing many of you in person as we bring alumni together in communities throughout the country.

First up, New York City on Thursday, January 22. Keep watch on your inbox for details—coming soon!

Onward,

Shay Totten ’91
Director of Alumni and Constituent Engagement