Two years passed since I’d announced to the world I was pregnant. During that time, I had cocooned myself to nurture my now thriving daughter. We had spent a little over a year in Liberty, Mississippi, where I figured out how to be the mom my daughter needed me to be. But I was determined that Maddie didn’t pay for my mistakes simply because I was young. I needed to break the cycle of mistrust, stress, and reconciliation. Casper’s lifestyle sabotaged his ability to be a proper father to our daughter. Once we left Liberty, Casper’s relationship with Maddie started to unravel. I tried to pull myself together and get on with life, but it wasn’t easy for me. Panic started to set in as I realized I was a single mom, wholly responsible for my daughter’s well-being. I went through an unsettling time of profound sadness that often left me listless and unmotivated. My own world had imploded, but Maddie’s was just beginning to open up. Her health and happiness flourished, despite my own dismay. The mother in me took over, and I dedicated what energy I had to being the best caregiver for my daughter. I spent months in an introspective state, working through the emotional chaos of the previous years.
Learning to trust was the cornerstone of my metamorphosis. I had to learn to depend upon not just my intellect, but my instincts as well. Sometimes what appears good for us doesn’t feel right. With the help of family and positive people in my life, I started to establish guidelines on how to trust others and be confident in my decisions. The complexities of being a child living as an adult exacerbated my anxieties to the point where instead of making difficult decisions, I made none at all. Both Maddie and I suffered for that. I also needed to own up to my role in the failure of my relationship with Casper. Although my naivety and youth had worked against us, I realized that holding him accountable for his behaviors, and subsequently my own, was important. I had only started to understand who I was, and even at eighteen, I had a long way to go to becoming a woman.
Being Maddie’s mom and caring for her added a fullness to my life and, in turn, gave it new meaning. But there were many days she was the singular reason I got out of bed. I was relentless in keeping my shit together for her. The smile I used to wear for others was replaced by the one I wore only for Maddie. We laid low for a time to avoid the press, and I instituted an elaborate schedule to ensure that every one of Maddie’s needs were met. I kept calendars and knew when everything had to be done. At the time, I was a self-diagnosed obsessive-compulsive. I never considered it a disorder because the manifestations of it made my life better and Maddie benefited from it too. She wanted for nothing. I sang to her, and we played often. Her well-being bolstered my own. Strength and confidence returned as I demonstrated my competency as a mother.
Slowly and steadfastly, joy returned to my life. The more time I spent with my friends the happier I became, and Jamie was a huge part of that. Jamie completely respected my devotion to Maddie and understood we were a package deal. Before our relationship grew into a romance, we established a deep and abiding friendship.
Diane, Brandi, and I decided to have a girls’ night in. Brandi suggested we go over to Dane’s family home to enjoy the pool and Jacuzzi. Sometime in the early evening, Dane and Jamie showed up. Slowly, everyone went home or to sleep, but Jamie and I stayed up all night talking. When the sun rose and we still hadn’t run out of topics, I was stunned. I’d never stayed up all night with anyone. We didn’t touch or kiss. But we were building a bond. I remember laughing at the thought: My daddy’s name is Jamie. My name is Jamie, and now, there’s Jamie.
Jamie quickly became a staple in my life. Jamie, Maddie, and I usually spent time in the company of friends, even as our feelings grew, to make sure Maddie felt comfortable. We were typically a threesome. We never wanted her to feel threatened by our budding romance. Early on, Jamie put Maddie’s needs in front of his own and agreed she was the priority. Sometimes we would joke that he was really in the relationship for Maddie. The connection they shared was instantaneous. “Kismet” is the best word for him coming into her life. Each of us grew to care for each other, and over time our relationship evolved.
At some point, Brandi insisted that the four of us go on a double date. Everything was new for Jamie and me, and I was excited to be going on a proper date. We drove to New Orleans to see the Christmas scenery and then to a swanky hotel for drinks. On the way home Brandi and I were sitting in the back. I leaned in between the seats to change the radio and when I glanced at Jamie, he kissed me. I thought, Oh, okay, that’s weird. But okay—our first kiss. After that, he really started to pursue me. Casper, who thought my devotion was endless, could feel me pulling away in earnest now. I started setting appointments for him to see Maddie, always with one of his parents accompanying him. Things were getting messy, and it wasn’t an ideal time to start dating. Jamie wanted to take me out and I was fearful Casper would manipulate the truth and accuse me of misconduct. Jamie and I agreed that we would do all we could to keep our relationship out of the press.
But the media got ahold of the story and used a terribly unattractive picture of Jamie and a separate one of me on the cover of Us Weekly. There weren’t any pictures of us together, and to be honest, we weren’t really serious at the time. Jamie and his friends had a good laugh at the whole thing. Our friend Peter, who has since become my second daughter Ivey’s godfather, said, “Jamie. We’ve done some crazy shit in our lives. But you’ve really outdone yourself this time.” Jamie’s humor and authenticity were just what I needed to let love grow between us. Such a good man being placed right in front of me after leaving a destructive relationship wasn’t lost on me. I just couldn’t open up my heart again so quickly. But we continued to spend time together and his fondness for Maddie expanded. Feeling skeptical about bringing a man into our lives, I wasn’t sure he was best for us at that point. Jamie’s integrity and goodness were never in question; it was my judgment and missteps that kept me guarded. Our nontraditional courtship stopped and started a couple of times over the first year and a half.
By this time, my artistic soul was also reawakening. The sensation is akin to an itch that has to be scratched. I yearned to create and express myself. My outlet of playing Zoey was no longer available to me, and I knew portraying a character wouldn’t give me what I needed at that time. I was full of conflicting emotions, and I wanted to express them. Although I’d spent years acting, music had always been a way for me to connect to my emotions.
The questions Ms. Lou posed months before came to the forefront of my mind. It was time to start establishing my independence and develop a long-term plan for my professional future. I was certain Casper was incompetent and could not help to support us emotionally and financially in the long run. For a while I had money available from my previous jobs and believed that Casper and I would share all the parenting responsibilities. But now, the enormity of the fiscal responsibility I had of being Maddie’s exclusive provider hit me. I needed to take a step to securing our future. Two things came to mind: storytelling and music.
Growing up in my house, there had been music playing pretty much twenty-four seven. My momma’s love of Elton John filtered down to me, and Daddy’s passion for country music sparked an appreciation for the genre. During my younger childhood, women performers were releasing power anthems and positive songs. Both my sister and I loved Shania Twain—and I was a huge fan of the Chicks (formerly the Dixie Chicks), Mariah Carey, Madonna, and Janet Jackson. All of their music and experiences influenced my life, and ultimately I decided to take my private thoughts and put them to music. Country music felt like a good fit for me. I had great respect for pop music, but my songs felt more in line with my Southern roots. The progression to songwriting felt natural, yet honing my craft was a challenge.
Ms. Lou suggested I visit her in Nashville, where I could explore both my ability and opportunities for songwriting. I used one of her small offices to escape the world and focus on transforming my feelings into words. I treated songwriting like any job. I got up, went to the office, and put pen to paper. I used the quiet, introspective time to share my thoughts. After I showed my talent and dedication to writing, I started to attend sessions with other writers and industry professionals. We’d sit around in an office with our guitars and create material. These short writing trips to Nashville went on until I realized I would need to spend more time there if I wanted to continue developing my music. If I was going to give this thing a real chance, I needed to live and be seen in Music City. I knew I wanted to be taken seriously as an artist and develop strong writing relationships that could only happen if I was constantly available. A move would also mean a fresh start for Maddie and me. It would be my chance to show my daughter I was strong and capable, that I possessed the confidence to start from scratch and build a promising future. Maddie’s dad wasn’t going to hold us back. He was struggling with his own demons, and his visits with Maddie were inconsistent. I was still supportive of him maintaining a relationship with her, but even that wasn’t going to keep me in Louisiana.
Leaving Louisiana was an unnerving decision for me. I was still learning the ropes of motherhood. I struggled with my residual feelings over the decisions and sacrifices of the past few years. My intention had been to provide a wholesome life for Maddie, but the reality was I had been scared of being on my own, and because of that, we both paid the price. That fear kept me in a cycle of behaviors that weren’t good for me or Maddie. Jamie knew I needed a change, and although we would be hours apart, he understood my desire to try. Jamie flew up to Nashville with us and helped Maddie and me get settled in our new home. He continued to be supportive during a time of great uncertainty. He believed in me, and that faith served as a cushion in my life. I put our romantic relationship on hold. It didn’t make sense to try and make a new relationship work with a new career, in a new city, with a young child to care for.
Brandi had just graduated from nursing school, and I offered to have her come to Nashville to help me with Maddie. I thought it was a perfect opportunity for both of us, but she opted to stay in Louisiana and make a life with Dane. I hired Erin instead, who was terrific. Soon after I paused my relationship with Jamie, Erin called to say that dozens of roses were delivered for me and Maddie. Jamie and I were both upset about the break, and a different kind of relationship evolved. We decided not to decide. We continued to talk regularly and saw each other from time to time.
Daily life in Nashville was a great kind of busy. We lived in a beautiful home in the Governors Club, and I devoted my time to Maddie and music. Maddie’s days were full, and Momma came often to help out with her care. I was a sponge soaking up musical knowledge. I took guitar lessons, and I learned scales and chords and the Nashville Number System, a method used to understand chord progression. It makes playing by ear easier. I wanted to be able to comprehend the nuances of recording in the studio and working with musicians. For example, I wanted to know what “on the two” meant, and how chords were transcribed into numbers. It’s similar to learning a whole new language. I practiced the guitar until my calluses developed and I became proficient in the number system. Being a part of that community of musicians brought professional purpose back into my world.
The move was a good change for us in so many ways, and starting over motivated me in all aspects of my life. I decided to challenge myself and studied for the ACT. With the number of quality schools in Nashville, I knew going to college was a real possibility. I studied for several months and felt confident that I would score well on the test. On the day of the exam, Momma and Maddie dropped me off at the local high school where the test was administered. It was a bizarre experience. I walked in with my pencils in hand and sat at one of the desks. There was only a year or two between me and the other test takers, yet I felt out of place. Within minutes, several people were turning around and staring. I heard the whispers. “Is that Jamie Lynn Spears?” “Are we on a television show?” “That’s her, right?” “What is she doing here?” The sensation was surreal. Soon the proctor came in and the focus went to the exam. When the results came, I tore the envelope open with childlike enthusiasm. My score revealed I was capable of getting into a decent school. I contemplated the idea of a full-time college experience while managing Maddie and a budding music career, and just didn’t see how I would be able to do everything. Maddie and music were my passions, and that was the path I chose. I believed in the value of education, but still, I had a toddler and bills to pay.
Jamie and I continued our version of a long-distance relationship for a few months, but the pressures of motherhood and working in Tennessee proved too much for me to manage. I broke it off. Jamie remained my close friend and I knew no matter what the future brought, he would be a fixture in our lives.
My assistant Erin needed to move on and my friend Kayla, who had just come out of a sour business deal, came to work for me. I loved having a friend who I could trust be there for me and Maddie. She was also friendly with Jamie, and she gave me little updates about what he was up to.
Maddie and I would make weekend trips to Momma’s house in Kentwood so Casper could continue to be in Maddie’s life. Casper said he was trying to get ahold of his destructive habits, and he’d sought out the professional help he desperately needed. Still, considering his past missteps and unreliability, I found it difficult to leave her with him. At this point, we agreed to supervised visits, closer to where he lived in Mississippi. Over time, Casper proved to me that he was ready to resume a healthy relationship with our daughter. I wanted so much for Maddie to have a closeness with her father I ignored the warning signs. We visited Louisiana for the holidays and Casper acted the part of father and showered us both with attention. He wanted to visit us in Nashville, and I didn’t see the harm. Casper came full of enthusiasm and spent quality time with Maddie. He was helpful with Maddie and was actually acting like the father she deserved. We went to the park and had meals together. Maddie seemed happy. Initially, I saw how being a family would be good for all of us. But there wasn’t a true connection between Casper and me. In fact, I felt, if not marginalized, then self-conscious around him. Despite all that, I had this thought looping in my head: Maddie deserves a family. After the first trip to Nashville, he talked me into more visits and, ultimately, into giving us another chance. I was once again manipulated into a place where I thought we could make this work for our little girl. He moved in with us, and within days I began to feel the same old doubts. Casper slowly revealed his true nature. He was reluctant to find work and made excuses about not being able to get a job. Almost immediately he began to undermine my rediscovered confidence. Casper would tell me how things needed to be done and would criticize the way I did things. I paid for everything, and his petty excuses for not getting work continued.
Jamie and I spoke periodically, and I owed him a phone call to let him know that Casper was back in my life. I’d put off telling Jamie because instinctively I knew he was going to disapprove. The idea of disappointing him nauseated me. Finally, I knew I had to tell him. I couldn’t get him on the phone and decided to text. It started off pleasant enough, but the second I shared the news, the tone of his words changed in a way I had never experienced. Jamie’s opinion meant everything to me. Anger and disappointment suffused every word. “Do you realize the mistake you are making for yourself and Maddie? He’s trash. He’s proved it time and time again. He’s not reliable. Being with him, Jamie Lynn, is just bad! He’s trash and you being with him makes you trash too. It makes me question everything I know about you.”
I was hurt and his judgments caused me a lot of pain. Jamie had never been that harsh before, but ultimately it was just what I needed to hear. This time around it only took a few weeks for me to realize that Casper was up to the same old tricks. I saw through his parasitic nature and finally realized how bad he was for us. Things in the house were tense. I grew uneasy but Jamie’s words gave me the confidence to end things for good. Casper said he was going home for a quick visit. I decided we would have “the breakup talk” once he returned. But within days, I knew something was wrong. Casper didn’t answer when I called, and he never contacted me. I saw a posting on the social media page of a girl I followed—and there he was. Casper had returned to Mississippi and slid right back into his destructive behaviors. I didn’t need to wonder about what happened any longer. More pictures and stories about him stepping out on me followed. I was relieved by Casper’s departure, but the lingering humiliation cemented the end of our relationship.
I knew something drastic would be required to eradicate Casper from my life. For years I’d hidden behind a false smile and convinced the world that everything was great. Now I needed to admit to my family that nothing was what it seemed. I called Momma and said, “Casper is gone—and he is never coming back.” She listened as I described some of the shrewd and twisted ways Casper had manipulated me, how I allowed behaviors that rendered us vulnerable to go unchecked. I confessed that for months I fought against every warning bell in my head to try and keep us together for Maddie. Momma told me she didn’t realize until recently that Casper had grown to be utterly unreliable. She called in the Spears troops, and Maddie, Kayla, and I joined Britney on her Femme Fatale Tour. I spent the time sharing the difficult details of my life and isolation with her. Daddy, who had stepped up to help Britney during her difficulties in the past couple of years, was on the tour too. He helped get rid of the extortionists and conspirators in her life and had even committed to his sobriety in support of Britney. The conservatorship was just a small piece of his commitment to helping her. They stayed sober together, and seeing my father put Britney’s needs ahead of his own desires helped my old resentments fade. For a period of time, the conservatorship mandated that Britney be drug and alcohol tested on a regular basis. My father volunteered to do it with her in solidarity. This was the first time in my life where someone was holding them accountable for their behaviors, and the perpetual anxiety I lived with for so long finally subsided. I could stop worrying about their sobriety.
We started to spend some time together and heal our battered relationship. He apologized to me for the years of humiliation and embarrassment he’d caused. He said, “Jamie Lynn. I know I don’t deserve to be in your life or in that of your child. But I am hoping you can let me earn your trust again.” Moving past my experiences of the previous two years helped me see Daddy was trying his best to do the right thing, and for that alone, I slowly let him back into my life. I didn’t just forgive and forget. There were stipulations that included healthy behaviors and absolutely no drinking. For the most part Daddy manages his end of the bargain, until he doesn’t and I have to kick him out of my life for a while.
Spending time traveling with my sister, and the people we called family, was the best medicine. The steps to be the woman I wanted to become began on that tour. It took time to stop chastising myself and start thinking in a more positive way, but somewhere out on the road I realized I’d tried everything in my power to make it work with Casper, and that simple fact made moving forward easier.
I returned to Nashville with renewed vigor. Jamie was happy to hear that Casper was gone but questioned whether I would make the same mistake again. I said, “Nope, this time it’s game over.” Our friendship was back on stable ground, and I focused on my life in Nashville. Jamie dated another woman, and friends set me up with men they deemed “perfect” for me. They were often professional athletes, and the dates always showed me a good time, but their notoriety didn’t give us the connection my friends believed it would. One night a guy I had been out with a few times called. I asked what he was up to, and he said, “I’m out with a friend.” Turned out that friend was another guy I had been out with. I thought, Only in my crazy life. I quickly realized going out and being seen by the public didn’t thrill me in any way. I became absorbed with motherhood, writing, and singing.
Ms. Lou suggested a therapist could help me sift through the trauma of the past couple of years and my residual anxiety. I wasn’t completely invested in the idea and believed I understood my depressive episodes. In the past, I’d had bouts of sadness and disillusionment that would manifest in different ways. I attributed these episodes to changing hormones and the stress of everything I endured. Until I saw some of my sister’s struggles, I thought most of it was part of growing up. I was still so young, only eighteen, and until then I didn’t realize the severity of the problem. There were days when getting out of bed was nearly impossible. During other periods of distress, I would completely lose my appetite and my weight would drop drastically. Talking with someone seemed to help, but the cycle would eventually return. I managed to cope the best I could and found that my creative outlet was a powerful antidote for my emotional challenges. Aside from the joy of motherhood, I’d always found it difficult to maintain a true level of happiness. Looking back, I think I spent so much time trying to be what everyone else needed, I never discovered what brought me genuine pleasure. That discovery would come a couple of years down the road.
Work brought balance back into my life. I found that living in Nashville was a big asset to a budding music career. My commitment was obvious to anyone who met me. I spent hours with musicians and other writers. I learned that there were several approaches to songwriting. I attended writing rooms, where two or more music professionals worked together for hours at a time. I had the pleasure of working with several songwriters, including Chris Tompkins. Throughout my life, I’ve met hundreds of famous people, but never felt starstruck the way I did when I met brilliant songwriters like Chris. Coming face-to-face with someone responsible for some of the greatest songs ever written was awe-inspiring and left me speechless. Chris cowrote award-winning songs for Carrie Underwood, Martina McBride, and Luke Bryan. He has written and cowritten “Before He Cheats,” “Blown Away,” and “Drunk on You.” I could fill an entire page with his illustrious résumé. But like many others, Chris made me comfortable almost immediately. He sat with a guitar and asked me to tell him a story. He’d strum a few chords, take my words, and make magic. He told me my story was worth telling, like it was for anyone willing to share their journey. “If it happened, you can tell it.” My history was the soundtrack to my life. I spent months sharing parts of myself and writing music that exposed the most vulnerable sides of me.
I also worked with Liz Rose, one of the most respected and celebrated songwriters in country music. She had written award-winning songs for Taylor Swift, Miranda Lambert, and Carrie Underwood. She had won an Academy of Country Music award and been nominated for multiple Grammys. I was honored and humbled she saw potential in me and was willing to work with me. Liz was knowledgeable and I found the experience inspiring. She was wonderful to work with and encouraged me to continue when I got dismayed. Until I started writing, I didn’t realize how some songs could come in minutes and others would force me into a journey of profound self-discovery and challenge me on an emotional level. With making music, it’s all me—the raw, blemished, and imperfect me. My fans hear the finished song, but they don’t know the inspiration or the hours of writing and recording that went into it. Once the song is released, it becomes subject to others’ interpretations. My song becomes theirs, and if my vision gets lost along the way, well—it’s a natural consequence of sharing music with the world. Music transports all of us to another place and time. It evokes memories and emotions in a way no other medium can.
When I wasn’t caring for Maddie—nurturing, having playdates, or attending to her needs—I was laser-focused on writing and performing. Like all Nashville musicians, I paid my dues playing gigs at small venues. I shopped my music around to a few labels, who indicated I should keep at it—so I did. I kept writing and performing. I sang at a few of the honky-tonks and bars on Broadway.
In between performances, Maddie and I traveled home to Louisiana to see family. Visitations between Maddie and her dad dropped off month after month. It is well documented that Casper struggled with drugs and alcohol and encountered difficulties with the law. He couldn’t make child support payments. His interest in her waned. The parental bond between father and daughter was collapsing, and I felt compelled to do everything necessary to protect my daughter. I appeared in family court a few times to safeguard Maddie’s interests and was eventually awarded full custody. I continued to encourage supervised visitation between Maddie and her father. The judge ordered him to be drug tested before spending time with his daughter. He balked at the concept, and at times didn’t bother to visit at all. His parents wanted to maintain a healthy relationship with Maddie, but their son always came first. I came to distrust their ability to put Maddie’s safety first, and over time that relationship began to dissolve. I was determined to provide opportunities for Maddie to see her father, but only if everyone adhered to the court-mandated guidelines.
The chaos back home wasn’t going to sabotage all the hard work I’d put into making music. I’d dedicated the past couple of years to fine-tuning the art of songwriting. I was introduced to many music professionals and decided to work with a producer who put together a fantastic band for me. I was proud of the music and began to perform the songs live. In the beginning, I was skittish about baring my soul to the world night after night. Each song takes me to a specific place and time in my life, that sometimes leaves me feeling raw and exposed. As weeks passed, adjustments were made to the arrangements, and I just accepted the changes. They were still my songs, but something felt off. The music professionals I thought understood me began to make additional changes to my style and how I carried myself onstage. I had immense respect and appreciation for the advice given to me by the people around me. At an earlier time in my career, I may have been able to agree to these changes. But now, I’d had a fundamental shift in how I wanted to present myself, and I just couldn’t be what they envisioned. I began to feel like a puppet or that I was participating in a country music star summer camp. Nothing felt right. My irritation grew, and I became very robotic in my response to the environment around me. I felt like a product, not myself—a doll designed to look the part. It left me hollow and uncomfortable. I couldn’t reconcile their creation with the very personal nature of my music. None of it felt authentic to me. Was I not enough?
I began to doubt myself, and that triggered a heightened state of anxiety. I once again lost control over my own decisions and felt adrift. The time and money I poured into the production wasn’t yielding the results I wanted. More importantly, I felt stifled and uncomfortable in my own skin. This all came to a head when a performance was scheduled for a number of industry insiders, select fans, and invited guests. Originally, I was told that many of my fans, both domestic and international, would fill the venue. There is nothing like walking out onstage to a crowd of supportive people. But at that point in my life, I was already feeling vulnerable, and as I approached the mic, the lack of positive energy in the room disarmed me. I felt like the attendees were waiting to be wowed. The pressure was overwhelming, but I was trained to push through and be the best I could be in these moments. My band and I started the first song. I had to stay hyper-focused to get through it, when historically performing was automatic and fluid. The crowd warmed up a little, but internally I was unraveling. Something was happening. As the music for the third song began, the words and timing dissipated like smoke rising into the air. I managed to fake my way through the performance. However, for the first time, I rushed—quickly closing the end of the song. The expectations placed on me as a child performer had always motivated me to be the very best in everything I did. I am a Spears, and nothing less than perfect would do. That pressure, which many times had served me in a positive way, began to undermine my confidence and ability. I was scared. Thinking about what went wrong after the show, I convinced myself that the appearance was poorly planned and hadn’t been what I had expected.
Sadly, the panic grew with each passing day. The tipping point came when the band and I were practicing in the studio. The producers and my dad were there as we ran through the songs. The pressure of having Dad in the room may have contributed to my already building anxiety. I always wanted to be the best at what I was doing, every time. The session should have been easy, fun even. But I was too much in my own head, second-guessing what felt right. Here I was, singing my own words, sharing my own stories in a way that felt all wrong. In the midst of singing and knowing I was being evaluated, a sudden and powerful sensation overtook me. A crippling stage fright like I had never known struck me. I never really had anything like it. The closest thing I experienced to that was the overwhelming self-consciousness I felt during high school whenever I played sports, anytime I took the field or got on the court. I was like a human lightning rod. I didn’t want that kind of attention or to be ridiculed for my performance—so I became a cheerleader. This was different. My brain felt like a computer going dark, everything shutting down. The anxiety of the moment manifested physically, and I grabbed on to a table, fearing I was going to pass out. I made my way to a couch and Dad sat alongside me. I was still dizzy and couldn’t remember if I had anything to eat that day.
My dad looked me in the eye and said, “Jamie Lynn, you should go home and get things right.” I knew he was correct. I needed to slow things down. I desperately wanted to go home to Louisiana as soon as possible. I learned early on that a strong woman, a courageous one, recognizes when she is in over her head.