WINNING TO LOSE

By @shantellewrites recorded and transcribed September 7, 2026  Homeless in my car, reflecting on why I self-sabotage after posing the question in my journal a couple of days earlier.

THE QUESTION

“Why try when everything I won or deserved was taken away from me?”

▶ LISTEN — Winning to Lose

Listening time: 10pm

I wrote in my journal a couple days earlier: “Why try for anything when anything I ever won or deserved was taken away from me?”

Losing My Voice

And yeah, so I started thinking about all these moments. I remember preparing for karaoke with Alanis Morissette’s “You Learn.” I sang it perfectly, 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 they 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, in my opinion, couldn’t sing it the way I could—but she looked more like Belle.

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, including Mr. and Mrs. Claus. 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 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 for 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 80, and had still let people into Honors English with lower averages than mine. 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 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? It didn’t matter. The lawyer in the fancy office in New York was suave. He said it was a winning discrimination case and he wanted to take it on. But it was either wait years for the case to go through and maybe finally get paid, or pay my active bills by taking my severance check and agreeing to sign an NDA 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 improvised.

And then there’s the pageant. That’s one of the biggest memories as far as my dad and just feeling unsupported. 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. And somehow I’m still singing to this day.

They don't even know Me.

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.

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 been.

Show Pony 🦄

At my first startup, I told him I was going to Michigan to do the VIP project—the next phase—and he never listened to me. I taught the new white girl under me everything I knew. I delegated the forms and smaller things I used to do to her. He kept it going. Then when I came in on Valentine’s Day to present at the kickoff for the VIP meeting, I got fired. So I guess they presented all my work without me. That sent me into a mental breakdown.

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 handwriting, putting everything in a nice cover for a report about the eye. I knew everything about the eye. Eventually they gave me an old computer. Eventually they started sending a van to the train station when it was snowing. It took so long for anyone to help with the obvious.

They used to do community service in the hood across the street from my actual house. I would take the bus all the way back to school, but when we got to my neighborhood I would run to some random house because mine was the most beat-up one on the block.

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. And I remember another moment when my stepdad had me in the car but 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.

There are little memories like that everywhere. 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 in one shot. I had been playing forever and finally got to the last level, 8-4. My dad had bought me that Nintendo, one of the only presents I remember him buying me, and he said I could get a new game once I beat that one. I believed him. I was really trying to beat it. Then my mom and stepdad were arguing behind me and the TV got knocked over. I never tried again to get there.

Get rich or die Trying.

When I was 26, my dad took me out to get lobster. It’s one of the only times I remember being with my dad around my birthday. 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. 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.

When my mom, my brothers and I were going to live in a homeless shelter, I guess he said I could come stay with him. But why would I leave the people who actually loved me? Even as a kid, I knew I had to be there for my real family.

I probably still 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, and she had three kids, not just one. Sometimes she would lose it, come into my room while I was sleeping, start pulling everything down, get me in the car and say my dad was going to have to take me. We would get to his house. They might look out from the upstairs window of that big house if they noticed us, but I would just pretend to knock on the door. I knew I wasn’t really welcome.

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. I do remember getting lobsters with him and him cooking them. I remember watching kung fu with him. I knew my dad liked kung fu, so I’ve always liked kung fu movies.

And I remember one other time with my dad. I waited all day and called him and called 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. Another time he took me to the movies and we saw Die Hard 3. That’s why I hate action films. I refuse to watch them. Why wouldn’t he pick a movie his kid would like? I hate action films.PERIOD.

“Why try when everything I won or deserved was taken away from me?”

Answer: DON’T Try

Trying admits failure before you start.

 I HATE ACTION MOVIES, BUT MY LIFE IS ONE.