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The Trust Project

Original Reporting This article contains firsthand information gathered by reporters. This includes directly interviewing sources and analyzing primary source documents.
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Computer literacy teacher Jack Bookout demonstrates a student project of engineering a traffic light Nov. 22, 2023, at Mitchell High School in Colorado Springs. Bookout, in his first year of teaching computer science, robotics, and other hardware literacy to high schoolers, worked in information technology for more than 20 years in the U.S. Army. (Olivia Sun, The Colorado Sun via Report for America)

Twenty years in the military taught Jack Bookout the delicate balance of patience and diligence he needed to command his next platoon: classes of 14-, 15- and 16-year-olds who show up to his room each day and confide in him about struggles they have far outside Mitchell High School.

Spending the first half of his career in the military shaped Bookout, 50, with a level of discipline he lacked through most of his childhood. But he’s thoughtful about the ways he talks to his students experiencing moments of teen angst.

“If you show that you’re getting frustrated with them, they lose trust in you,” said Bookout, who began teaching computer science classes at the Colorado Springs high school this fall. “In the Army, you can’t afford to lose trust. Transferring that over into the education world, if you show that you have no patience for somebody or for a group of people, they’re going to lose trust in you because you’ve lost trust in them or because you’ve lost patience in them.”

Bookout is one of a growing number of military veterans helping Colorado combat chronic teacher shortages after the pandemic made the high-stress job of teaching only more demanding. Colorado schools were short by more than 9,700 teachers and support staff, including school counselors and nurses, during the 2022-23 school year, the most recent year of available data from the Colorado Department of Education. Of the 8,294 teaching positions that needed to be filled, 722 remained vacant for the school year, state data shows.

Many veterans spend years in the military refining skills highly sought after by schools and bring firsthand experience from the field that prepares them to take over a classroom, school administrators say. That includes expertise in energy, outdoor recreation leadership, engineering, health sciences and audio, video and film technology. And that’s on top of softer skills like communication, time management and empathy.

Computer literacy teacher Jack Bookout demonstrates a robotic hand Nov. 22, 2023, at Mitchell High School in Colorado Springs. Bookout, in his first year of teaching computer science, robotics, and other hardware literacy to high schoolers, worked in information technology for more than 20 years in the U.S. Army. (Olivia Sun, The Colorado Sun via Report for America)

“They have so much to give,” said Colleen O’Neil, associate commissioner of educator talent at the state education department. “They are community- and service-minded or they never would have been in the military. And they’re in every single corner of our state and our nation. The least we could do is help support them into another profession that they could just thrive at.”

“Raising up the skills that our military veterans have”

Colorado used to build a teacher pipeline of military veterans through a federally funded grant program, Troops to Teachers. But funding for that program, which helped pay for veterans to pursue a teaching credential, expired in October 2020. 

In response, Colorado lawmakers in 2021 passed legislation that, in part, created an educator recruitment and retention program to support military veterans and others shift into teaching careers. Military members interested in becoming teachers can also pursue an alternative teacher license through the University of Colorado Denver’s ASPIRE to Teach program.

Colorado in recent years has also sharpened its focus on helping veterans understand how they can translate what they’ve learned in the military to career and technical education, or CTE, classes desperately needing quality teachers, O’Neil said.

“We all just got better about raising up the skills that our military veterans have,” she said, and “understanding what the skills our military members are bringing that we don’t necessarily recognize by paper.” 

Computer literacy teacher Jack Bookout teaches subjects like computer science, robotics, and other hardware literacy at Mitchell High School in Colorado Springs. Bookout, in his first year of teaching high schoolers, worked in information technology for more than 20 years in the U.S. Army. (Olivia Sun, The Colorado Sun via Report for America)

That’s largely happened through a certificate process that awards a provisional CTE authorization to professionals who demonstrate background experience and knowledge.

That authorization takes the place of a teacher’s license, allowing someone to teach a specific CTE course for three years. They can then renew that credential and receive a professional CTE authorization, which is renewable every five years, according to O’Neil.

But the number of military veterans who have decided to take up teaching in Colorado isn’t clear, O’Neil said, as it is optional for people to identify their military service when completing state paperwork.

Embracing a new sense of community

The state education department issues credentials on behalf of the Colorado Community College System, which designs the guidelines and requirements for the CTE authorization and has been the main driver of steering more military veterans toward careers in education.

Jordan Whittington, who served in the Army as a combat medic for about four years, has largely taken the lead in helping veterans see the possibility of pivoting to a teaching career. His department has steered at least 15 veterans through the credential approval process since September.  

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“So many of them get lost, and without that purpose of community and service anymore when they get out they lose that we used to call being part of a tribe,” said Whittington, CTE program director of health science and public safety at the community college system. “You lose that tribal feeling of, I have a purpose to do this and people rely on me to do these things.”

Whittington, who was deployed to Iraq, oversaw soldiers running aid stations, managed field operations and trained soldiers and officers in medical care. He was ready to move on from both the military and medicine and switched to pursuing a teaching license, partly influenced by his family of teachers — and later on by a passion for “helping shape young minds.” 

He completed a bachelor’s degree in biology and a teaching license from Metro State University and from there began coaching high school football at Standley Lake High School in Westminster before beginning teaching at Arvada West High School. Whittington also earned a CTE credential in health science in 2016 and started working for the Colorado Community College System almost three years ago.

He knows the emptiness that surfaces after leaving the military and what it’s like to lose the feeling of ease that comes from being surrounded by comrades who understand one another.

A school, Whittington said, can often be a stable landing place for a veteran, one where they can adapt to a new sense of community.

“That teacher community feels pretty tight because you’re all dealing with the same population of kids,” he said, “and you’re all trying to do the best you can for that population of kids.”

“These are your people. Take care of them.”

Bookout, the Mitchell High School teacher, was a telecommunications and information technology specialist during his military career, focusing on cybersecurity and IT maintenance. While a platoon sergeant at Fort Eisenhower — originally Camp Gordon, then Fort Gordon — in Georgia, he trained countless soldiers, teaching them how a satellite terminal on the ground communicates with a satellite in the air.

The military sent Bookout all over the world — he lived in 11 places in 16 years and was deployed to active combat zones three times. He credits the military for helping him mature into a capable and regimented adult, but after the military ordered him to move again once he hit 19 years of service, he decided to request retirement for the next year in 2016. Bookout said he was emotionally and physically drained, especially after constantly uprooting his family.

Computer literacy teacher Jack Bookout teaches subjects like computer science, robotics, and other hardware literacy at Mitchell High School in Colorado Springs. Bookout, in his first year of teaching high schoolers, worked in information technology for more than 20 years in the U.S. Army. (Olivia Sun, The Colorado Sun via Report for America)

He worked three different jobs related to IT with one also focused on computer forensics before finding his way into teaching with help from an old military friend, CarrieAnn Mathis, who has helped Whittington at the community college system pique more veterans’ interest in working with young students.

Mathis, CTE program director of engineering, technology and media arts at the community college system, also specialized in communications in the Army for seven years but could no longer serve in the military because of medical disabilities she developed while deployed in Iraq. 

The U.S. Department of Veterans Affairs paid for her to complete a teaching license, and she became a middle school technology teacher in Texas before moving to Colorado, where she eventually became a high school teacher in Grand County.

Mathis instructs Bookout and other veterans-turned-teachers to manage their students the way they managed their soldiers.

“I give them the guidance of, ‘this is your platoon,’” she said. “‘These are your people. Take care of them. Build a relationship with them, and then everything else will follow. You have a relationship — that kid is more likely going to do work.’”

In some ways, that means simply being there for students when they have a bad day and leading with compassion.

“Your soldiers aren’t going to be able to go to combat if they’re worried about getting food on the table,” Mathis said. “Same thing with the kids. If they don’t have food on the table, they’re not going to do well in school that day.”

Mathis has mentored Bookout this school year as he has adjusted to teaching computer science courses. CTE educators authorized by the state typically rely on a mentor to help them master skills like lesson planning, and they also enroll in community college classes that coach them on some of the finer points of teaching, such as strategies to best help students learn, O’Neil said.

Bookout has only been at the helm of his classroom since mid-August, but he already can’t imagine parting ways with any of his students once they graduate. He has landed in a career that he said he was probably meant for all along, and the military propelled him there.

“I haven’t had this much fun in a job in a long time,” said Bookout, who also serves as the high school’s head baseball coach. “I tell the students every day that I’m grateful and happy that I see them and that I get to hear their voice. And I ask them every day how they’re doing.”

Computer literacy teacher Jack Bookout teaches subjects like computer science, robotics, and other hardware literacy at Mitchell High School in Colorado Springs. Bookout, in his first year of teaching high schoolers, worked in information technology for more than 20 years in the U.S. Army. (Olivia Sun, The Colorado Sun via Report for America)

And his students — some of whom pull him aside to open up about their personal lives — have renewed his sense of purpose.

“It just made me feel like I was a member of the community again,” Bookout said, “like I was actually doing something good instead of just wandering.”

He doesn’t yell at his students like a drill sergeant the way others might expect or command them to raise their hands to speak up in class. Rather, Bookout knows the surefire way to motivate his students is to build them up by constantly pointing out their strengths.

“It helps people realize that they are capable,” he said. “And they believe in themselves a lot more.” 

Erica Breunlin is an education writer for The Colorado Sun, where she has reported since 2019. Much of her work has traced the wide-ranging impacts of the pandemic on student learning and highlighted teachers' struggles with overwhelming workloads...