Through Mom's Eyes: Simple Wisdom From Mothers Who Raised Extraordinary Humans by Sheinelle Jones - 12

The Seeds Planted Young Really Do Manifest Themselves as You Mature, One Hundred Percent

Tina Ann Drew, Jessica and Ashlee Simpson’s mom

In 2014, Forbes business magazine’s chairman and editor-in-chief, Steve Forbes, interviewed Jessica Simpson in front of a packed audience of women entrepreneurs, leaders, and philanthropists, describing her career as “astonishing” in both its breadth and longevity.

A decade before she was sitting on that stage talking business strategy with some of the top business executives in the world, Jessica was a pop star and queen of one of the hottest reality shows of the time. Her little sister, Ashlee, was also becoming a household name, as a singer and budding actress in her own right.

When it comes to the entertainment industry, the odds of becoming a household name are not good. Your chances of achieving longevity as an entertainer are even slimmer. And the likelihood of going on to a successful career in business, especially after your star has lost some of its shine? Let’s just put it this way, many have tried, most have failed. Yet, sisters Jessica and Ashlee Simpson managed not only both to succeed as entertainers, but to then launch a now twenty-year-old fashion empire that has reportedly grossed more than $1 billion to date. Just as noteworthy (at least, from a mom’s perspective) the sisters also rebounded from divorces to remarry and raise children. Through it all—including her own divorce from their father—their mother, Tina Ann Drew, has been in her daughters’ corner and by their side.

“Honestly, I dreamt of being a mother from the time I was young,” says Tina, who is now also a doting grandmother. “I was a mother by the time I was twenty. I got married at eighteen, had Jessica at twenty, and Ashlee at twenty-four. So, I was definitely a young mother, but it was, like, the only thing I ever wanted to do.”

Although it was her dream come true, “It was hard,” Tina admits, recalling the family’s early years in Texas. “Their dad was a youth pastor, and we were very poor. We rarely had a car when Jessica was born. It’s those times that made us really strong today. We moved around a lot because we’d go from church to church and help kids. Our passion was always teenage kids and helping them out. I was an aerobics instructor and personal trainer, and we both had all kinds of jobs just to keep the family going.

“I would take [our] kids with me and have aerobics classes in the church—Jessica always called it ‘Jump for Jesus,’ ” Tina adds, laughing.

While the young family moved frequently, some churches would provide a parsonage for them to live in, but these places usually left a lot to be desired. Calling some of them downright “scary,” Tina says she would “decorate ’em up,” doing her best to make them feel homey. Eventually, they’d move on, which meant the girls had to change schools. “They were pretty much used to it,” Tina says, adding that the silver lining was the sisters developed a close relationship.

Tina’s stories of those years made me think of my dear friend Jolen, whose father was in the military and, like the Simpson kids and so many others, they moved around a lot. Jolen always talks about how, with each new school, she would decide who she wanted to be. We laugh about it now, but she says that even as an elementary student she was always aware that she could use a move to reinvent herself. It can be a challenge and a test of resilience as a child but, today, you can put Jolen in any room and she can carry a conversation, network, and be comfortable and confident doing it. I admire that.

It’s easy, as parents, to think that our children’s stability depends on our staying put in one community, but modern life often requires us to move between cities, or even countries, to satisfy career goals, family obligations, or lifestyle needs. It’s nice to know that our kids’ sense of security is more dependent on our consistency in showing them how to be adaptable than any one address or school or even friend. With strong, loving parental support, our kids will be okay no matter where life takes us—or them. Tina clearly believes in the power of the sibling bond too.

“Jessica was four when Ashlee was born and, literally, she was like her second mother,” Tina recalls. “I’d find her under [Ashlee’s] crib, like, with a blanket, laying there just to watch over her.

“They were both their own girls,” she adds. “They had different qualities, but huge hearts. Ashlee was a little more rebellious. [If I said,] ‘Don’t walk across that line,’ you know, she would put her foot over it kinda thing. Jessica was a little more submissive, a bit more pleasing, whereas Ashlee would be like, ‘Hmmm let me show you what I can do.’

“I have two sisters myself, so I’m the youngest of three,” she explains. “We’re still very close and all in our sixties, all grown with grandkids and everything. It’s just a really beautiful thing to have a sister. I think there’s nothing that replaces that. It’s a very unique relationship. They understand you better than anybody, even better than your own mother.”

As she talks, I can’t help but wonder if the family that bonds together and works together does chores together. I’m always curious about whether giving a child chores at an early age is part of the secret sauce for helping them learn independence. But every time I think I get closer to cracking that code, another mom puts me right back at my imaginary starting line, Tina included.

“I was terrible, I spoiled my kids,” she says. “I would make their beds, and I would organize their closets. I was really bad about that.”

I also want to know, was she a harsh disciplinarian? “Not harsh or anything like that, but they knew they could push me so far and then they couldn’t push me any further,” Tina says. “But we laughed a lot, we just found a lot of joy in life.” One thing Tina took very seriously though, was Jessica’s blooming talent, beginning at just three years old.

“She’d be singing in the back of the car, and I would be, like, ‘Wow, she has a voice.’ She would be singing in harmony with Gloria Estefan, you know, like in 1983 [when] Miami Sound Machine was huge. She started singing in church and musicals and she loved it. It’s, like, when she put a mic in her hand, she came alive. It was just passion; I could see it in her. She was never afraid. She wanted to do it. I would say to any parent, never push your kids to do things they don’t want to do. I feel like their passions rise to the top.”

Apparently, it was the same for Ashlee. “Ashlee was a performer,” Tina says. “She didn’t sing as much at the beginning, but she was a dancer. I mean, that kid came out of my womb dancing, and that was her favorite thing to do. I wasn’t going to be, like, you need to go run track or something. Just watch your kids, because you’re going to start to see what they really love to do and you pick up on those things and you just help them, encourage them.”

For Jessica, that meant singing, followed by dance competitions, which she eventually started to win. When she was twelve, an announcement in the Dallas Morning News for open-call auditions for the Mickey Mouse Club changed their lives.

“About twelve kids were chosen from the United States and Canada, and they flew us to Orlando for two weeks to Disney World to go to Disney Camp,” Tina recalls. “That was, like, Ryan Gosling, Justin Timberlake, and Christina Aguilera—these are the people who were in camp with Jessica.” Talk about an impressive class.

“A lot of the kids had done things like Star Search and they had portfolios,” Tina says. “Jessica had sung in the church, you know what I’m saying? That’s all we had. We went with a Polaroid and, like, her school picture. We were very innocent and very naïve.”

Jessica wasn’t chosen, but the experience was pivotal. “We learned a lot,” Tina says, adding, “because of that, I was not lettin’ those kids out of my clutches. I was gonna be the helicopter mom. I was gonna be the mother that stayed with my kids in the industry [to] watch over them and make sure they were never alone on the road or anything. I was gonna be their companion, ’cause it was scary.” But when seventeen-year-old Jessica got a record deal in 1997, Ashlee was in ballet school in New York and Tina couldn’t be in two places at once. At the time, Tina’s husband, Joe, was still active as a traveling youth minister. After experimenting with taking Ashlee out of school to join her big sister so they could all be together, Tina made the decision to have Ashlee join Jessica’s act as a backup dancer and their dad stepped in as their manager.

So, what do you do when you have more than one child with the same dream? How do you make sure it’s not so competitive that it damages their relationship—especially when their talents overlap? It’s not as if one daughter excelled at opera and the other played the drums; both of Tina’s daughters wanted to sing, dance, and act.

“I’m the youngest sister too, so you always have that fight in you as the younger sister, especially when your older sister is extremely successful and beautiful. It’s not really about jealousy, it’s just about, like, ‘I want to show them that I can do it too,’ you know? I never looked at that as a competition between the two of them. I looked at that as more of, you know, they’re two personalities shining—and give them both an opportunity to shine where they shine.”

In 1999, Jessica’s debut studio album dropped and the whole family moved to Los Angeles. Tina oversaw the girls’ costumes and the set designs for their shows, while Joe was their manager. “We weren’t laying by the pool,” Tina says, explaining that everyone had a role. And while none of the roles were easy, “It was just a beautiful time.

“We hit the road like the Partridge Family, one bus with, like, five dancers. We just did it, you know? I wouldn’t have done it any other way. I’m so thankful that I had all that time with my kids, and that I was there to watch over them and protect them, and make sure they were okay.”

Eventually though, Tina would learn, as all mothers inevitably do, that we can’t protect our children from everything, especially once they are technically grown.

Having made her mark in the music industry by age twenty-one, Jessica married fellow singer Nick Lachey, popular in his own right as part of the chart-topping boy band 98 Degrees. In 2003, MTV offered the popular pair a reality show, Newlyweds: Nick and Jessica .

Viewers couldn’t get enough of the young couple, myself included! The marriage lasted just four years, but their ups and downs were daily watercooler conversation throughout the show’s three seasons. Their family members, despite varying degrees of comfort with the exposure, sometimes appeared on the show. Tina, who, along with Ashlee, prefers more privacy than her older daughter and now ex-husband, says she quietly asked herself, “Do we really want to do this?” Apparently, the girls did. Before long, Ashlee was also headlining her own reality show.

“Back then, it was the real deal,” she explains. “It wasn’t scripted, this was happening in real time, and it was being taped. Kudos to the Kardashians ’cause I don’t know how they did that, it just doesn’t fit my personality. But soon, you just kinda let your life flow and let it go.”

In the midst of that “flow” came the moment that went viral, before viral was even a thing. Jessica, while eating a can of tuna on camera, questioned if it was actually chicken because the brand was Chicken of the Sea. Viewers—from the average teen to late-night talk show hosts—pounced. Jessica was humiliated, but Tina insists she just laughed it off. As a mom, I would have felt devastated for my child, but she says Jessica always had an offbeat way about her. “You know, even as a kid, she would just crack me up,” Tina says. “Her way of thinking, her thought patterns and stuff, are so funny to me.

“But those were real moments,” she adds, a bit less lightly. It’s one thing when your kids mess up and not too many people hear about it. Jessica didn’t have that luxury; her “slipups” became national entertainment news. And, with two daughters in the public eye, Tina has dealt with more than her share of public relations nightmares.

In 2004, when Ashlee released her debut album with the lead single “Pieces of Me,” she snagged a choice spot as the musical guest on NBC’s Saturday Night Live . As her second performance was set to begin, the vocals from her first song were accidentally broadcast, revealing that she had lip-synched her previous performance. Mortified on live TV, Ashlee ran off the stage. The backlash was quick and dirty, with Ashlee having to explain that she was advised not to sing live after losing her voice due to acid reflux. She said of it all, “I made a complete fool of myself.”

The moment was painful for Ashlee, and painful to watch— especially for her mom. But Tina knows what all seasoned moms know: that challenges can build character, that mistakes are necessary tools for learning, and that this too shall pass , no matter how big or painful or embarrassing your “this” is.

“I really taught them to be fighters, and to pull from within themselves and within their faith in God,” Tina says. “That’s how I dealt with stress, actually. A lot of prayer, trust in the bigger picture and in God’s protection, and knowing that they were going to be okay. And teaching them, the world is not always going to be easy, people are going to say negative things about us, but, you know, you rise above it by loving others and sharing that love.”

Revisiting the SNL experience on a podcast in 2023, Ashlee said that she should’ve had just said no to performing when she lost her voice. (No judgment on my part; I can certainly relate.) I think we all learn, sometimes the hard way, that we must own our power and just say no when our gut tells us that something isn’t right. That goes for managing our children’s lives, or our own. No , as they say, is a complete sentence —yet it’s not a universal solution for every problem.

After Jessica’s reality show and high-profile marriage ended, she remained front-page fodder for tabloids—especially years later when she remarried, got pregnant, and struggled with her weight. Throughout it all, mother and daughter remained close. In fact, Tina was the maid of honor at Jessica’s second marriage in 2014.

Jessica credits her mom for being the mastermind behind the Jessica Simpson Collection, which launched in 2005. At the height of her reality show, brands would contact Jessica to give her clothes to wear and Tina noticed that whatever Jessica wore would then sell out in stores. What some would see as a mere bragging right, Tina saw as a business opportunity. So, she took a bet on her own family to monetize their influence. Tina had Joe find someone to do the licensing deal so they could make the clothes themselves, and both sisters got involved. It seems common now when, with the help of social media, many stars have found ways to expand their personal brands through products. But back then, it was brilliant out-of-the-box thinking. No one would have predicted the company’s extraordinary success. Two decades later, it is the most successful celebrity brand to date.

In February 2020, Jessica released a memoir, revealing how she overcame her battles with addiction, her self-image, her parents’ divorce, and other dark chapters in her life including sexual abuse she experienced as a child. As a mother to her own three children, in Open Book , Jessica directly addresses other moms who may face similar struggles: “I hope you can be proud that your body created life. I was not strong enough. It touched all my insecurities, and I couldn’t handle it. I can tell you that plastic surgery does not fix what’s on the inside.”

The book, like my conversation with Tina, reaffirms what we all know: life happens. We’re all human. Inevitably, life knocks you down. Being a mom, even the best mom, doesn’t mean that our kids—or we—will be spared those blows or immune from their pain. The question is, how are you going to get back up?

“To me the hardest thing with Jessica has been the weight,” Tina says. “We had many moments of, like, guttural crying about the pain, what people would say and how mean people are. But through that, it’s like Jessica has been this amazing, shining example of, you know, ‘I’m not gonna let this get me down.’

“I will be honest with you. Body shaming is a terrible thing, and [watching that happen] has been the most painful thing, as a parent, that I’ve been through. I would just tell Jessica, ‘We can’t let these people dictate our lives. So, let’s just love ’em, move forward, be the best we can be, be an example for your children.’ That’s really all you can do.”

The advice has served their whole family well and, she says, they are now all in a good place. Tina and Joe’s thirty-four-year marriage ended in 2012. Jessica and Ashlee both remarried in 2014. Jessica, now in her mid-forties, has two daughters and a son. Ashlee (married to Evan Ross-Naess, son of icon Diana Ross) has a girl and two boys—one from her previous marriage. The sisters are very popular on social media and, in addition to their thriving fashion and home goods business, they continue to pursue artistic projects.

As for their mom, or “Gigi,” as she’s called by her six grandkids, life’s incredible, she says, and she feels so blessed. “It’s like doing it all over again, and being a young grandmother is actually really fun too. Like, one of my favorite things to do is my grandson Bronx comes over and we play football. For Valentine’s…he wrote me on a card, ‘to the most athletic grandma I’ve ever known.’ ”

From teaching “Jump for Jesus” classes in church basements to making costumes for her famous daughters to running a billion-dollar company, I think it’s safe to say Tina did okay.

“Athletic grandmother,” I repeat, “you don’t hear that very often.”

“I know!” she says, clearly proud—of her daughters, and herself. “I was talking with Ashlee, because her kids are getting older. You have to make sure they have a solid foundation, you know what I mean? You have to be standing on the rock. ’Cause if you’re standing in sand, you’re gonna sink. I do believe we built that for the kids growing up. We have a firm foundation of what we stand on, and that is our faith and the strength in that and knowing that tomorrow’s gonna be okay. Today may be really tough, but we’ll get through it. I do believe that the seeds planted young really do manifest themselves as you mature, one hundred percent.”

There is a quote I love, “Your greatest contribution to the universe may not be something you do, but someone you raise.” Tina, who, at twenty, set out to be the best mom she could be, says she can always look back knowing she gave it her all: “Meet ’em where they are, encourage them, and be their rock. Just be that rock.”

I was born Ethiopian, adopted as a young child by a Swedish family and raised there, in Sweden. My mother taught us that when we leave the house, as the only Black kids in town, you leave with three things: confidence, work ethic, and knowing we were loved.

—Marcus Samuelsson, chef and entrepreneur