She never said I have to go to work.
Not once. Not in 32 years.
"I always said I get to go to school. I get to go to practice. I get to do this."
That is Ann Manchester — known to everyone at Grandview High School in Colorado simply as Chester. Thirty-two years of teaching. Seven state soccer championships. Hundreds of students whose lives she changed before they even realized it was happening.
And now she is retiring.
But before she walked out of that building for the last time she sat down with Coach G on the Stay Teacher Podcast to share everything — the joy, the hard seasons, the students who broke her heart, and the philosophy that kept her showing up for over three decades.
Chester grew up in Omaha, Nebraska. Her parents were janitors in Omaha Public Schools — which she jokes gave her a backup plan if teaching did not work out.
She started college studying journalism. She loved writing. But something kept pulling her toward the classroom — and she eventually followed it.
Two teachers planted that seed early. Mrs. Mullen and Dr. Kerberg — a Spanish teacher and an art teacher — gave her rides to middle school every morning for two years. Both women went on to become administrators in Omaha Public Schools. But what Chester remembered most was not their titles.
It was the way they had fun.
"I always saw my teachers having fun. And I thought — I need to be there."
That feeling never left her. And 32 years later it was still the standard she held herself to every single day — if we are not laughing, something is wrong.
In 1994 Chester started teaching at North High School in Omaha. She made $7,000 for the entire year — as a graduate assistant through UNO's cadre program — while teaching full time and coaching girls basketball and boys soccer.
Seven thousand dollars.
And she loved every minute of it.
The community principal Mr. Harvey built at North High School stayed with her for the rest of her career. A group of young teachers in their twenties who supported each other, laughed together, and figured it out side by side.
"I'm still crazy tight with a couple of those teachers. That's a big deal — creating that community."
She moved to Colorado in 1996 and landed at Grandview High School in 2000. She never left.
Chester is living proof of what happens when a school creates an environment where students want to come back.
Four of her former students went on to earn master's degrees in special education — and returned to Grandview to serve the students who need it most. A former soccer player came back to teach math, coached alongside Chester, and won more state championships. Another former student Nicole married a Grandview grad and is still there today.
Not recruited from a job fair. Not hired from a college visit.
Grown right there in the building. Because they had a great experience. Because Chester showed them what this profession could look like at its very best.
"It's pretty awesome to see them come full circle."
Every conversation on the Stay Teacher Podcast follows the ROOTS Framework — five pillars that keep great teachers grounded through every storm of the profession.
Here is how Chester walked through her 32 years:
R — Reason
Two teachers who showed her what joy in the classroom looked like. A journalism degree that kept pulling her somewhere else. A father who had fun every single day as a school janitor — which taught her that how you show up matters more than what title you hold.
O — Obstacles
A constantly shifting educational landscape — from no computers to COVID remote teaching. Standardized testing that often confirmed failure rather than measured growth. Students who came to school homeless, traumatized, and struggling. A student whose shoes were falling apart — whose socks were poking through the bottom — and who needed more than a lesson plan.
O — Overcome
Community. Every time Chester faced something too heavy to carry alone she built a team around it. Soccer was her outlet. Bruce Brown's high standards were her compass. Travel, friends, family, and joy outside school kept her recharged and ready to come back.
T — Transformation
Chester's one-word answer was immediate — confidence. Not the kind that arrives overnight. The kind built year by year through parent calls, AP essays, yearbook deadlines, and coaching 22 colleagues the same way Bruce Brown once coached her. She did not feel truly confident until year six or seven. She wants every new teacher to hear that.
S — Stay
She found a great school. Great leadership. Great community. She never stopped finding things that brought her joy — soccer, announcing games, the academic bowl, a student-created club called TROHT — Teens Reaching Out to Homeless Teens. She built a family. And she never — not once in 32 years — dreaded walking through those doors.
One story from this episode will stay with you long after you finish reading.
Chester noticed a student whose shoes were so worn his socks were poking through the bottom. He wore the same clothes every day. He had no washing machine at home. Other students were pulling away from him because of it.
Chester and her co-teacher brought it to the counselors. The whole department pooled their money. They bought him new shoes and jeans. They arranged for him to wash his clothes at school.
"That was probably twelve years ago. And we see more and more of it."
That is what teaching actually looks like. Not just lesson plans and learning objectives. Showing up for the whole child so that learning can even begin.
To the brand new teacher:
It is okay not to know everything. Laugh at yourself when things go wrong — because they will. Ask for help. Nobody is judging you. Try new things and surprise yourself.
"It's okay. You're not gonna know it all. And that's fine."
To the ten-year teacher:
Find the things you love and do them. If they do not exist yet create them. Chester started a student-run homeless outreach club because a student asked her to. She announced soccer games for years after she stopped coaching. She built a department that felt like a family.
"If you're not having fun in the classroom, in the building, with your peers — find a new place. Or create the joy where you are."
Near the end of the episode Chester held up a photo. A team picture from 2008 — the year Grandview won its first girls soccer state championship. Coach G was in it. Chester was in it. Coach Brown was in it.
A moment frozen in time from a career that was anything but frozen.
Thirty-two years of showing up. Of building teams inside classrooms and on soccer fields. Of buying shoes for students who needed them. Of laughing every single day. Of turning colleagues into family. Of growing teachers from the students who once sat in her class.
"It flew by. It has absolutely flown by."
Ann Manchester never said I have to go to work.
She said I get to go to school.
For 32 years. Through every policy change, every struggling student, every championship, every early morning and late night.
She stayed because she found joy. She built community. She kept her roots deep and her standards high. And she left behind a school full of people who carry her influence everywhere they go.
That is not just a career.
That is a life's work.
Chester — thank you for your service. Thank you for your roots. And thank you for showing all of us what it truly means to —
Stay teacher.
Hear Ann Manchester's full story — including the student whose shoes were falling apart, the first girls state championship in 2008, and her powerful advice for teachers at every stage of their career — on the Stay Teacher Podcast.
If this story moved you share it with one teacher today. And if you have a story to tell reach out at stayteacher.com — we want to hear it.
Your roots run deep.
Stay teacher.
— Written by Ghirmay Alazar (Coach G)