Winning to Lose
WINNING TO LOSE
@shantellewrites • Recorded September 7 and rewritten September 8, 2026
Written while homeless in my car, reflecting on why I self-sabotage after posing a question in my journal a couple of days earlier.
Voice Auditions
And yeah, so I started thinking about all these moments while entertaining myself with car karaoke, singing Alanis Morissette’s You Learn. As I sing the words you live, you learn, I remembered that I sang it perfectly when I auditioned for it back in the day, but the girl in my a cappella group looked more like Alanis Morissette. They made us try out back and forth, back and forth, back and forth all night, and then finally gave it to her for the look—even though I grew up singing that entire album.
One of my teachers said I didn’t look like Belle, and that’s why she gave the Beauty and the Beast solo to a girl who couldn’t sing, but she looked nothing like Belle, actually. Belle is not blond and pale with freckles, but she is white.
Then there was the fifth-grade Christmas show everyone waits for because the fifth graders actually get to host it. There are skits in between each grade’s songs, and Mr. and Mrs. Claus are the stars. I had waited since kindergarten to try out for Mrs. Claus, and I won it fair and square against everyone. After I won, they decided they needed to split Mrs. Claus into three Mrs. Clauses. She starts off white, then in the middle she’s Black for the blues song I killed, and then the third one is white again. I won it. Too bad.
My tenth-grade English teacher didn’t like me. I was so surprised when I saw I wasn’t in Honors English when my schedule arrived over the summer before eleventh grade. It ruined my entire summer. My mom saw how distraught I was, so we went to the school and investigated. It turned out the teacher had changed my grade and made it an 88, and had still let people into Honors English with lower averages than my fake average. I fought my way into the class I rightly deserved.
Then I killed Honors English with one of the best English teachers I ever had, and I killed AP English with my favorite English teacher in the world. I would never have gotten there if I hadn’t fought to get into the class I deserved. (I scored almost perfect on my verbal SATs without studying!) I still saw that teacher walking around every day. Later she went on to be a headmaster at another school, I think. What was her punishment for changing my grade?
Make sure you’re not the only one who actually values the connection.
I was number two on the sales team before they fired all the Black people—even the guy who was still in training. What could he possibly have done wrong? Nothing. The new COO said she “wanted a different look.” The lawyer in the fancy Armani suit in the fancy office in New York said, “that’s the definition of discrimination.” He wanted to take it on, but made me aware that I could wait years for the case to pay, so I had to make a choice. I chose to pay my bills with my severance check. To collect the check, I had to sign an NDA agreeing not to sue.
I want to lobby for that to be illegal. There’s no way that should be legal. If you did something wrong, I shouldn’t be forced not to say anything just so I can keep living and protect my livelihood. How unfair is that?
Sometimes survival looks Impoverished, I mean Improvised.
And then there’s the pageant. That’s one of the biggest core traumatic memories in addition to my dad’s neglect. My mom and I studied. We practiced. I sang The Greatest Love of All, by Whitney Houston, so many times. When I got there, we didn’t even know all the different things we were supposed to contend with. I’m reading the program and kids are backstage doing karate and backflips. All these white girls seemed so prepared, and I was completely intimidated. I didn’t have the business outfit. I didn’t know there was an interview.
Then I got onstage in the biggest auditorium I had ever seen in my life, and no words came out. No song came out. My mom cussed me out so badly in the car. She has apologized for it, but it’s something I’ll always remember.
I can always imagine myself in the back seat with amber lights cast over the parking garage, waiting for the gate to lift as my stepdad pushed in the validated ticket. We ate KFC that night (maybe cuz I was chicken). And somehow I’m still singing to this day.
I realized in another journal entry some time ago that I probably don’t feel completely safe sleeping at night because another core memory is being woken up at three or four in the morning. I understand where my mom was coming from because I have breakdowns at that time too, raging on everyone I love, and she has three kids, not just one.
On the few nights she would lose it, she came into my room at witching hour, violently waking me from sleep, pulling my clothes down from plastic hangers. (No wire hangers! lol), get me and my bag in the car, venting, “My dad was going to have to take me!”
As she drove to the suburbs, we would get to his house and I’d be ordered to get out of the car and knock on the door. My dad and stepmom might look out from the upstairs window of that big house if she was still venting loudly when we pulled up, but if she quietly waited, I would just lift my fist, moving it in a knocking motion, stopping just millimeters from the red wooden door. After pretending to knock on the door long enough, I’d turn to my mom and shrug. I knew I wasn’t really welcome.
When my mom, my brothers and I were going to live in a homeless shelter, I guess my dad said I could come stay with him. But why would I leave the people who actually love me? Even as a kid, I knew I had to be there for my real family. My mom’s love is real and present, even when she makes mistakes. She always let me know her feelings were not my fault. She taught me to be brave enough to apologize to my daughter, or anyone really, and go seek help. She always says, “We’re just souls leading each other home.”
We used to do school community service in the hood school across the street from my actual house. I would take the bus all the way back to school, but when I didn’t want to commute an extra 1.5 hours, I’d stay in my neighborhood. My classmates would ask, “Which house was mine?” and peer through the windows of the school van as it drove slowly down the street, and I would run to some random house as the school van slowly drove down my street. I couldn’t go to my house because it was the most beat-up one on the block.
One morning at announcements, the class president stood up in his bow tie and blond hair and told the class not to waste lunchmeat in the cafeteria because people in my town, the community service town, didn’t get a pound of food to eat each day.
I’m a Unicorn 🦄 NOT a Show Pony
At my first startup, I told my VP I was going to Michigan to do the VIP project—the next phase—and he never listened to me. He’d been very influential on my development as a speaker, passing on books and enrolling me in Toastmasters. I flew out to Michigan and I got on my knees on the hotel carpet, petitioning God for help with a foxhole prayer at 1 a.m. He answered me and I confidently wrapped up the most entertaining presentation at 4 a.m.
I successfully led the launch, gathering research requirements and setting milestones to achieve success faster in this new VIP phase. When I came back, he acted surprised that I’d gone, like he’d never heard me in our one-on-ones.
I taught the new white girl under me everything I knew. I delegated the forms and the smaller things I used to do as a junior analyst to her. I managed the project at a high level. Having started when the startup was just eight people, I’d naturally learned to get the doctors’ and academic scientists’ needs understood by the engineers, QA, and the CTO if I needed new capabilities.
Then when I came into the office on Valentine’s Day, anxious to present at the kickoff for the VIP meeting, I got fired. I was relieved from overworking, but thinking of the junior analyst I trained presenting all my work without me sent me into a mental breakdown. She definitely had the look. Blond and pretty with a smile. Easy to trust.
I’m worthy even when they don’t think I’m worth it.
And some of these memories go all the way back. In fourth grade, when it was finally my birthday and my turn to sit in the birthday chair, there was an excuse for why I couldn’t. I hand-wrote all my papers while other people had computers. I remember one time we had this weird typewriter machine and I tried to use that. I ended up staying up all night, drawing and writing in perfect cursive till the wee hours of the morning. I put the pages of my report on the eye in a laminated clear book cover. I knew everything about the eye. I could see my disadvantages.
Eventually the school gave me an old computer. Eventually they started sending a van to the train station when it was snowing. If it showed up, I didn’t have to watch my friends fly by in Audis and Range Rovers, listening to them happily shout through the window that they’d see me at school. They seemed oblivious to me trudging in snow, and I could never count on a pity ride during any storm. It took so long for anyone to help with the obvious.
I studied French so hard and had the best accent. I was at the top of the class because the headmaster I grew up with always took care of me and had said I would get to study abroad. But the new headmaster said I had to earn my way. How was I supposed to earn my way? My mom didn’t work, and I had never learned how to save for something like that. So I just didn’t get to go. I tell people it’s because I got mono. I did get mono—but I was never going. I took that language because I wanted to go. I still haven’t.
I put on my own baby shower and planned it to perfection. Then my daughter’s dad and I got into an argument. He stood at the door and knew how to work the police situation, and I didn’t get to have any of the stuff I had collected for the baby who would soon be born. My mom didn’t come to the hospital. Surprisingly, my stepdad came with the most refreshing orange juice, but he was also the stepdad that pulled over to the drive thru with me and my brother, and only got McDonald’s for his biological son. That was when my mom told me I didn’t have to call him Dad anymore.
Yeah,
No dad.
I deserved to have a dad who said “Happy Birthday!”, but my birthday is the day after the child he had five years after me. She lives in that big rich house, and I don’t get a happy birthday. I wait forever.
My dad had bought me one Christmas gift, but it was major—a Nintendo! He said I could get a new game once I beat that one. I believed him.
My mom and stepdad were arguing in the kitchen while I was playing Super Mario Brothers. You couldn’t save games back then—you had to play it all in one shot. I had been playing forever and finally got to the last level, 8-4, with the shortcut in Worlds 3 & 4 and the trick to get 10 lives (it shows up like a crown if you bounce the turkey-turtle against the steps before the flag). I was really trying to beat the 8-4 castle, a maze, when my mom and stepdad knocked over the TV.
I don’t know that much about my dad, really. My stepmom never really took to me. Maybe I’m not takeable. I would be with them, but my dad would usually be out. Only once did he stay, and we went to a real dock to get lobsters. Their claws were rubberbanded as they rustled in the big brown paper bag at my feet on the car ride home. He cooked them and ate his with mayonnaise. Gross! But the next morning I also learned he ate ketchup on scrambled eggs, and I think of him when I do it when someone cooks me unflavorful eggs. I think, “My Dad likes ketchup on eggs so we’re alike.”
That one unbelievable daddy-daughter day, we watched kung fu. The woman could swing her long hair to cut and kill people! At the conflict in the plot, they cut her hair like Samson and she lost her powers.
Now I knew my dad liked kung fu and long hair, so I braved hot grease as my mom cooled the hot comb on the hottest day of the year; hoping my dad would grace the annual Fourth of July cookout at Seaside Park—and compliment me like everyone else and love his daughter with long beautiful hair.
Nosey Jamaicans, old buddies who know how cool my dad is, will ask me, “When last you see your father?” I’d shrug my shoulders, knowing it was one or two years to date.
It was such a surprise to me when I started hanging out with my late grandma and learned that he didn’t just come to town once a year. He came every day to visit his mom, my grandma. It also surprised me to see my baby photo on her dresser at ninety years old!
Get rich or die Trying.
When I was 26, my dad took me out to get lobster. Red Lobster (where I’d worked a few years before). It’s the only adult birthday with my dad. I was being evicted at the same time and I told him about it. He owned rental property in Connecticut, so the advice he gave me was that it was almost impossible to get people evicted there. That actually helped me figure out how to extend the process. You can’t really do that the same way down here in North Carolina.
At that dinner he also complained that he didn’t have a lot of money. I never asked him for help with the eviction. I would never ask for help no matter how much money he has.
Then he pulled out this huge wad of money—the biggest wad of money I had ever seen. I remember wondering what “No money” looked like for him.
I was always waiting for my dad, even almost missed my own birthday party at the Discovery Zone, till my mom pried me from the window. But that night, after the party, I returned to my post and courageously kept calling him until he finally came to take me to Walmart to look at bikes. We didn’t get the bike he had promised for my birthday.
My Dad took me to the movies once and we saw Die Hard 3.
I hate action films till this day! Why wouldn’t he pick a movie his kid would like?
BUT MY LIFE IS ONE.
I’m going to have to pick my own movie that I like.
Get rich or die Trying.
Watch Pastor Mike Jr. right after.
Starts at the important part — 22:28.
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