Good Will Hunting: Herrera Has A Great Target

Three years ago, Will Herrera was cleaning the Staples High School guidance suite. The hard-working custodian was on his usual 3 to 11 p.m. shift.

A poster caught his eye. It advertised Norwalk Community College‘s Summer Bridge program.

Will had tried college once before. But he was young; the pressure of studying, while juggling work to pay tuition, was too much.

No one in his family had gone to college. His parents had not even finished 5th grade, in their native Colombia. But a relative’s wedding gift of 2 plane tickets to New York gave them a foothold here.

They arrived with green cards in 1985. They worked hard — in New York, Detroit, Florida and Connecticut — while constantly emphasizing to Will the importance of education.

Will Herrera, in the Staples High School library.

Will attended a magnet school in Bridgeport. He dreamed of becoming a teacher, like those who were influencing him. But he too had to work — he began cleaning YMCAs when he was 15 — and in 2013 was hired as a custodian at Bedford Middle School. He moved to Staples 3 years later.

That guidance poster for NCC marked a turning point in his life. He decided to give college another shot.

Caring admissions officers helped him through the admission and scholarship process.

Will took courses in English, math, environment, pyschology, creative writing, philosophy, computer science and public speaking. He got involved in extracurricular activities, like planting trees at Veterans Park.

All the while, he worked the 2nd custodial shift at Staples.

He considered dropping out just short of graduation, when his mother — who had battled breast cancer twice before — was diagnosed with ovarian cancer. But she urged him to persevere.

This past May, Will graduated from NCC — with a 3.51 GPA, and cum laude honors.

His goal of becoming a teacher grew stronger than ever.

Will applied to Sacred Heart and Southern Connecticut State University. He was accepted to both.

Though SHU is much closer — just 2 miles from the home he bought in 2015 — he chose Southern. Its education program and resources are better suited to his needs, he says.

This semester, Will takes 4 courses, in the morning and early afternoon: Teachers, Society and Communities; Introduction to Special Education; Math for Elementary Education, and Health.

Meanwhile, he continues to work the 3 to 11 p.m. custodial shift at Staples.

Oh, yeah: He’s also a board member for the custodians’ union.

Will Herrera works at Staples — as a student observing teachers, and as a custodian on the second shift.

Part of his coursework involves classroom observation. He’s doing that at Staples — the same school where, a few hours later, he cleans classrooms.

Observing science and world language classes, he’s intrigued by how teachers handle their work: creating lesson plans, leading discussions, handling a wide variety of learning styles, and doing the thousands of other things educators do every day.

“Education is stressful,” he says. But he notes that everyone in a school — teachers, counselors, custodians — deals with stresses. There are issues of time management, collaboration, priorities — you name it.

Staples world language teacher Julia Svec has loved having Wilson observe her Spanish and Italian classes.

“I knew him from working here,” she says. “I saw how bright and enthusiastic he is, with a great personality.

“He is very aware of different learning styles. He established great rapport with the students. They really appreciate him.”

She is impressed with the way he handles his demanding job, his studies and his observations. “It takes courage and perseverance,” she notes. “He is so inspiring.”

Will’s dream is to be a secondary school Spanish teacher. An administrative or leadership position might follow, at some point.

He’ll earn his bachelor’s degree from Southern in 2021, and will have completed his student teaching.

He’ll apply then for jobs.

If there’s a position open in Westport, I know many people at Staples — in the  classroom, and on the custodial staff — will be honored to recommend him.

25 responses to “Good Will Hunting: Herrera Has A Great Target

  1. Arlene Gottlieb


    Sent from my iPhone


  2. This story made me so happy! What a great role model for our kids. Hard work, following your dreams…may Will find all the success he deserves! We are rooting for you!

  3. Julia Lynne Gross

    Such an inspiration! What a role model for Staples students! Thanks for sharing.

  4. Nancie Rinaldi

    What a fantastic and inspiring story! If I were a student I’d love to have Will as a teacher.

  5. Debbie O'Malley

    Thank you for profiling Will – this story made my day.

  6. Michael Alpert

    In all my years of reading Dan’s blog, this just might be my favorite story!! Incredibly inspirational and motivational. I cannot wait to share with the kids and make sure they appreciate that stories like this will become less and less likely in the new world order — unless we change things now!

  7. Admirable work ethic & aspirations- Westport is fortunate to have Will Herrera @ Staples.

  8. Dan- Is Will eligible for Staples Tuition Grants? It would be great if he could get assistance with the cost of his degree. He is part of the Staples family.

  9. Armando Pineda R

    Hola primo que historia me encantó y de verdad me,siento muy orgulloso de ti.
    Y Dios Bendiga tu caminar tus proyectos y tu y tu familia. Y logres consolidar todos tus sueños muchas Bendiciones y Exitos.

  10. A story that is the epitome of individual motivation. And so, a beautifully motivating story!

    Congratulations, Will!!!

  11. Michael Alpert

    Maybe there is a way for the Westport/SHS community to help him obtain his degree? A GoFundMe campaign or some other sort of fundraiser at the school?

  12. Great story to begin my day. Good luck to Will. Mary Condon

  13. A true role model and a wonderful story!

  14. What an inspiring and hopeful story! We need stories like this in our current world…

  15. Congrats to Mr. Herrera!

  16. Kathryn Coster

    Such an inspiration…great luck to Mr. Herrera!!

  17. Ray O'Sullivan

    “He’ll apply then for jobs.” Maybe he can teach Dan grammar. Should be “He will then apply for jobs.”


  19. Wilson Herrera

    Thank you everyone for your wonderful comments, it’s very much appreciated to know that my story is inspiring to so many. My gut says that I’m on the right path. I am very grateful for all who took the time to read the article, and dan for allowing me the platform to share my story.

    Have a great rest of the week, inspire someone today and have a safe Halloween !

    -Wilson Herrera

  20. Hey there! If you’re interested in donating towards Will’s tuition, click on the link below:

  21. I would like to alert Will – and anyone who is pursuing an accredited degree program of ANY kind (College, graduate, post grad, vocational) – that Mensa Foundation has a scholarship program that requires only 1 thing: an essay up to 500 words. You don’t have to be a Mensa, you don’t submit grades, recommendations, financial information of any kind. Just an essay – it’s that easy to apply. There are general awards, and special awards for certain areas of study, LGBTQ, veterans, students coming back after several years away, and more. Even something for veterinarians doing continuing ed. Last year 2 students from Fairfield County won awards, including one from Westport. I encourage all students to visit