Woman thanks boss who let her bring her son to work at dream job as men’s college basketball coach

Mothers often face unique challenges that can unfortunately frequently interfere with their dreams and career aspirations. Many employers unfortunately do not facilitate the delicate balance that a mother might need in order to thrive in both areas of her life. Luckily for Ashley Webster, this was not the case.

The 26-year-old mom was contacted last year with an offer she had always dreamed of: the opportunity to join the coaching team of Florida’s Saint Leo University men’s basketball team. But one thing “stood” in her way: she was already several months pregnant with her first child.

To make matters even more difficult, Webster’s trajectory was clear: with the child’s father no longer in the picture, she was set to be a single mom.

But the young pregnant woman refused to let go of her longtime dream career. She absolutely knew she wanted to make it work, but just couldn’t yet figure out how.

The Proposition

Her concerns soon disappeared when the head coach of the basketball team, Lance Randall, came up with an unusual proposition: he simply told her that she should bring her baby with her to work.

“He’s like, ‘Well, you can bring him with you,’ Webster recounted. “He was like, ‘We have plenty people in the gym that can watch over him and that way, he’s with you.”

PHOTO: Saint Leo University men's basketball coach Lance Randall poses with one of his assistant coaches, Ashley Webster.
Saint Leo University men’s basketball coach Lance Randall poses with assistant coach, Ashley Webster. Courtesy Pam Randall

Indeed, for the family-oriented coach, it was simple: it came down to knowing that Webster’s knowledge and skills would be an asset on his coaching team, so he just had to figure out a way to make things work.

“It wasn’t necessary for me to clear a path, but just to make sure she had the opportunity to do it,” the coach said. “OK, she’s eight months pregnant, she’s going to have a baby, she’s about to go into a male-dominated world, so we just have to make this work from our end. We just have to figure out how to do it.”

“I didn’t really do anything, we just said, bring him, we’ll figure it out,” he said. “It was a really special year to have him around.”

And as it turns out, things have worked out even better than anyone could have ever imagined.

Dream Team + 1

In February 2021, the 26-year-old mom welcomed her bundle of joy, Aiden, into her life. Just three short months later in May 2021, mother and son were heading in to work… together.

At first, Webster had many apprehensions on how the team would react to the presence of a tiny 3-month-old on their basketball court.

But, according to Webster, from day one, the entire basketball team unofficially adopted little Aiden, bringing him into their circle with open arms.

PHOTO: Aiden Webster attends practice for the Saint Leo University basketball team, for which his mom Ashley Webster is an assistant coach.
Aiden Webster attends practice for the Saint Leo University basketball team, for which mom Ashley Webster is an assistant coach. Courtesy Pam Randall

“Everybody looks out for Aiden,” said Webster. “I could walk out of the gym and I wouldn’t think anything of it because I knew Aiden was going to be OK.”

Aiden, now almost 2, and who is named after an uncle who is also a college basketball player, has essentially grown up on the court. He has gone, says Webster, from sleeping during early morning 6 a.m. practices, to zooming around court in his baby walker, to now running around the court on his own two feet.

Through it all, the team has always embraced him and he is a now an integral part of the larger family.

PHOTO: Aiden Webster attends practice for the Saint Leo University basketball team, for which his mom Ashley Webster is an assistant coach.
Aiden Webster attends practice for the Saint Leo University basketball team, for which mom Ashley Webster is an assistant coach. Courtesy Pam Randall

“Everyday that I was in the gym, he was there,” Webster said. “He brought, I would say, happiness – everybody was excited to see him. He’s a very happy baby, so he just gives off joy.”

For Randall, who has been the head coach of the Saint Leo men’s basketball team for 9 years, Aiden has in fact helped the team out as much as him being able to be at work with his mom has helped her.

“It became a really great thing for our guys,” he said. “We’d be on the floor in our film sessions and Aiden would come toddering over and fall in the lap of one of our guys and sit there and watch. It’s adorable.”

PHOTO: Aiden Webster, the son of Saint Leo University assistant basketball coach Ashley Webster, is pictured alongside the university's men's basketball team.
Aiden Webster, the son of Saint Leo University assistant basketball coach Ashley Webster, pictured alongside the university’s men’s basketball team. Courtesy Pam Randall

Randall adds that Aiden’s innocence and vulnerability has offered the team with an additional benefit: the presence of a young child can often help alleviate the high level of stress that typically comes with playing college level sports.

“College basketball coaches can be a little bit cranky at times and maybe you’re going to have to be a little tougher and enforce some things,” said Randall. “So I think it’s easier to just focus on the message when your head coach is holding a toddler under his arm and he’s laughing while you’re maybe barking instructions to your team.”

PHOTO: Aiden Webster, the son of Saint Leo University assistant basketball coach Ashley Webster, is pictured alongside the university's men's basketball team.
Aiden Webster, the son of Saint Leo University assistant basketball coach Ashley Webster, hanging out with the university’s men’s basketball team. Courtesy Pam Randall

Webster echoes her boss’s thoughts:

“There would be times during practice I remember it would very tense,” she said. “And there would be Aiden giggling and laughing on the court, and it would just shift the mood, so it was awesome to have him there for sure.”

Randall added jokingly that he is much looking forward to having Aiden on the Saint Leo team in 17 years.

“This is the longest recruiting process I’ve ever been a part of,” he said.

From Hurdle to Dream Come True

For Webster, the only woman on the coaching team, the ability to bring her young son with her to work has made all the difference.

“When I was first pregnant, I started looking at day care and I distinctly remember putting the prices into the calculator and was like, ‘I obviously got it wrong because there’s no way day care is this expensive,'” she said. “So for me not to have to go find day care, that was huge because as a single mom it’s very hard. You’re working on one income.”

PHOTO: Ashley Webster, an assistant basketball coach at Saint Leo University, holds her son, Aiden.
Ashley Webster, an assistant basketball coach at Saint Leo University, holds her son, Aiden.
Courtesy Ashley Webster

For the single mom who is a college basketball player herself, making ends meet was a struggle in itself – even without the added hurdle of paying for day care. In addition to her job as assistant coach, she has needed to taking on odd jobs and overnight shifts in order to cover her and Aiden’s expenses, during which time her parents would watch over Aiden.

Webster’s very busy schedule means that her time spent coaching the team with Aiden around is also the most time she gets to spend with her young son.

“It was the hardest year of my life,” said Webster. “But my happy place was coming to the gym.”

PHOTO: Aiden Webster, the son of Saint Leo University assistant basketball coach Ashley Webster, is pictured alongside the university's men's basketball team.
Aiden Webster, the son of Saint Leo University assistant basketball coach Ashley Webster, is pictured alongside the university’s men’s basketball team. Courtesy Pam Randall

The cherry on top? The positive male influence Aiden now has almost daily in his life.

“It’s just ironic because his dad is not present, and I work with the men’s team, [so] he’s surrounded by a bunch of good men, good role models,” Webster said, adding, “I’m blessed that it worked out that way.”

“It was like he had a bunch of older brothers that looked out for him and loved him,” she added. “So it was great to see the soft side of the players because they weren’t all so manly and macho.”

A Family-Style Approach

Randall said he didn’t think twice about giving Webster the opportunity to bring Aiden with her to work.

“We have four kids ourselves so my kids have grown up in the gym,” he said, referring to himself and his wife, Pam. “We’re very much a family and faith-based program and school, so for us, just having each other, that’s the greatest value and asset.”

PHOTO: Aiden Webster, the son of Saint Leo University assistant basketball coach Ashley Webster, is pictured alongside the university's men's basketball team.
Aiden Webster, the son of Saint Leo University assistant basketball coach Ashley Webster. Courtesy Pam Randall

Online, Randall’s “family-style” approach to coaching is going viral after Webster posted a TikTok video describing how he and the team have welcomed Aiden after offering her what she called a “once in a lifetime job.”

Webster, meanwhile is eternally grateful to what she refers to as the Saint Leo “village”; her very precious new “family” that has helped make her dream of being a college coach come true.

“Outside of my family and friends, it’s just me and Aiden, so to have all those brothers and male role models for Aiden was amazing,” she said. “I’m blessed that it worked out that way and I’m forever grateful.”

@ashhhmazing

Forever grateful for the opportunity I was given ! Crazy Aiden really grew up in the gym 🥹🤣 #ballislife #ncaabasketball #saintleouniversity

♬ Follow me if you like skiing – Isaac

What a wonderful story! It’s so endearing to see how the entire team and coaching staff have embraced Aiden and given Webster this important career opportunity, despite her being a mom.

Share this story if it warmed your heart, and if you want to say a big thanks to Coach Randall, too!