Author: Gretchen Massey

What years did you attend WAA?

I started Woodlawn in 2011 at the age of 8 years old. I instantly fell in love with theatre and performance, but more in love with the version of myself that I became: confident, loving and understanding of people.

What program(s) did you participate in at WAA?

I spent 10 years in dance lessons, voice lessons and full productions.

How did WAA make a lasting impression and impact on you?

I love the arts and I love the people in them. Woodlawn gave me the confidence as a performer, the opportunities as an inspiring educator, and the ability to choose my own career path with the intensive education and training I received. 

What areas of study did you pursue after your time at WAA?

After I graduated from the elementary and middle programs, I got the opportunity to intern and later instruct intro classes of theater at Woodlawn. Woodlawn graciously saw my potential and gave me the opportunities to confirm that my passion was in teaching. I later went on to be a co-founder of Penguin Project of the Sauk Valley, a Woodlawn partnership for children with special needs to get involved in the arts, before moving out of the state. 

What is your current job/career?

After my time at Woodlawn I graduated from University of Wisconsin Milwaukee with a degree in English and Education with a focus on Urban Education and Restorative Practices. I went on to work in regional theatres, libraries, schools and other non-profit programs. I taught in six different schools during my time there, including teaching music and literacy classes to infants-preschoolers. My love for arts and education turned into a passion, and I am now a certified high school English teacher in downtown Milwaukee. 

I am proud to say that I am in my first year of teaching with my certification, and have debuted the first performing arts program in a Title I school. I teach ninth and 10th grade English, along with the brand new classes of drama and speech, with inner-city students. Along with that, I am making curricula for creative writing and journalism. My students are consistently learning personal growth skills in the performing arts program, which ties directly into why I fell in love with education and English: to give power to words, voices, and empower students to share their own stories. 

On top of that, I am a writer. I have my own writing blog and have been published in a literary magazine. 

Do you feel that your time at WAA had an impact on your current position/career path?

Woodlawn allowed me to explore both experiences as a performer and educator, and helped me find my passion of urban education. My long-term goal is to teach in restoration education, helping children and adults who are going back to school after a hiatus to get their education. 

What years did you attend WAA?

I attended Woodlawn officially beginning in 2011 through 2016, but I never really left. I volunteered for Woodlawn’s kids’ and junior productions as an alumni assistant from 2014 until 2021, then was hired in 2022 and have been working there ever since. I’ve taken a few more classes off and on. I also participated as a performer in the Theatre in the Park show at Woodlawn in 2024 and 2025.

What program(s) did you participate in at WAA?

I primarily participated in Woodlawn’s kids and junior productions, beginning with AristoCats Kids in 2011 and ending with Alladin Jr. in 2016. I also attended a few writing, sewing, cooking and drama classes in those years. I volunteered during rehearsals and shows for theatre productions beginning with Jungle Book Kids in 2014 and ending with, ironically enough, Jungle Book Kids in 2021. Since then, I have worked at Woodlawn as a stage director, assistant director and director for many kids and junior productions. I also teach theatre and educational classes when I can. 

How did WAA make a lasting impression and impact on you?

Woodlawn, not to be dramatic or anything, changed my life. I was a very shy, quiet kid who was terrified of crowds, loud noises and talking to anyone, including my teachers. Why my parents signed me up for a theatre production, I’ll never know, but it was the best thing they could have done for me. It took me a few years, but I eventually came out of my shell and transformed into the confident person I am today, primarily thanks to my experiences in theatre. If not for Woodlawn, I would not be on the career path I am now, and I can’t even begin to imagine what kind of person I would be. 

What areas of study did you pursue after your time at WAA?

I went on to study psychology, social work, and theatre in my undergraduate studies, and am now pursuing my master’s degree in social work. 

What is your current job/career?

I currently have a lot of jobs! I am interning at Hope Cancer Wellness Center as a social work intern; substitute teaching for Dixon Public Schools in elementary special education; on the directing team for the fall play and group interpretation team at Dixon High School; and working for Woodlawn as the director of the winter musical, assistant director for the summer musical, and teaching theatre and educational classes.

Do you feel that your time at WAA had an impact on your current position/career path?

Woodlawn absolutely had a huge impact on my current career path, especially because I currently work there! My time volunteering with WAA fostered my love of working with children, which led to both my social work and substitute teaching jobs. And, of course, Woodlawn played a critical role in my love of theatre. I have participated in more than 70 theatre productions over the years, and almost half of them have been with Woodlawn. Special shout out to Faith Morrison, Ashley Aurand and Mardi Huffstutler, all of whom were once my directors for Woodlawn shows when I was a kid, and now are my co-workers here and my friends! Shout out also to Anne Whalen, my aunt, who was previously an employee with Woodlawn and one of the major reasons I started attending!

What years did you attend WAA?

I attended WAA during my 8th grade year, around 2011. That was the first time I had access to a formal art program outside of school, and it became an impactful experience for me.

What program(s) did you participate in at WAA?

I participated in an 8th grade level scholarship visual arts class, which I was only able to join because I received financial assistance at the time. That support truly made it possible for me to take part in the program, and I’m still grateful for it.

How did WAA make a lasting impression and impact on you?

WAA had a profound impact on me. It was the first place where I felt genuinely encouraged to further my skills in art. Having my artwork displayed for the very first time at WAA was an incredibly meaningful milestone. It gave me confidence that I hadn’t experienced before as a young artist. The instructors and the creative environment all played a huge role in shaping my artistic identity during such a formative period of my life. The lessons and encouragement I received there stayed with me throughout middle school, high school and well beyond.

What areas of study did you pursue after your time at WAA?

After WAA, I went on to earn my BFA in Illustration from Ringling College of Art and Design in Sarasota, Florida. Going to an arts-focused college was an experience that expanded my artistic and professional skills. It helped me understand the many career paths available in the field and that the arts is still an achievable career path.

What is your current job/career?

I currently work as an admissions counselor for the Milwaukee Institute of Art and Design (MIAD). In this role, I guide high school artists as they prepare for their creative educational journeys. I offer portfolio feedback, answer questions, and get to travel to various cities to present to high schools. If you’re a senior high schooler or know an artistic student who would be interested in learning about MIAD, please reach out!

Do you feel that your time at WAA had an impact on your current position/career path?

Absolutely. My time at WAA played a major role in the path I’m on today. A significant part of my job involves speaking with students about their artwork, encouraging them, and helping them understand fundamental concepts in art and design, many of which I was first introduced to at WAA. The confidence, exposure and foundational knowledge I gained there not only shaped me as an artist but also prepared me for a career where I can now support and inspire emerging artists in the same way WAA supported me.