Carol “Lyssen” Blakely-Oscar’s journey is inspiring. She had a strong work ethic from a young age and a desire to create a better life for herself and her family.
Blakely-Oscar’s parents divorced when she was 10, and her mother moved her from the south side of Chicago to San Diego, California. In middle school, Blakely-Oscar took charge of her future, pursuing any opportunities that came her way. Her first job was in the city administration building, and she loved to dress up and go to work like an adult.
“I wanted to afford nice shoes and clothes and the kind of Oreos I wanted, so I worked hard to have a more comfortable life than my mom had,” Blakely-Oscar says. “I was a mature kid. When I was 16, I convinced my mom to let me move to Arizona and live with my cousin for half a year. I ended up staying.”
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DOWNLOAD NOWWhen she arrived in Phoenix, Blakely-Oscar started working at the Burger King next to her new school. She graduated a year early with a near-perfect GPA and wanted to attend college to become an engineer. Yet, she couldn’t afford it.
She still lived with her cousin and wanted to pay her own way, so she took a job at an amusement center, Jungle Jim, and then at the child daycare center KinderCare.
“I got my motivation from people I crossed paths with,” Blakely-Oscar says. “I’d notice when someone seemed confident or kind, and I grabbed a little piece of that. I wanted to take something I admired from everyone I met to become the person I wanted to be.”
Before she turned 18, she found a job as a fabrication technician making Nokia phone cases and later joined a semiconductor company. One of her colleagues also worked at the University of Phoenix and told her that if she got a job in administration, she could attend college for free.
Blakely-Oscar became an admissions coordinator in the registrar’s office and was quickly promoted because of her strong problem-solving skills.
“I love puzzles, so I figured out a process to get transcripts in 24 hours instead of six months, and that helped me move up fast,” Blakely-Oscar says. “Before I turned 20, I was in a managerial role.”
She balanced a full course load, work, and family responsibilities, all while advancing her career and becoming financially secure. By 22, she had paid off her car and bought a house. Yet, she wanted to find balance by pursuing her passion for poetry.
“I remember my first poem was about a bad relationship. I wrote it in about seven minutes,” Blakely-Oscar says. “I loved dancing and performing on stage as a child, so I was comfortable reading my poems before an audience. One night, I was performing at an open mic, but it was actually a competition—and I won. I decided I needed a stage name. ‘Carol’ is pretty, but not the name of a star. I chose ‘Lyssen’ because I wanted people to listen to my words.”
The name stuck, and her family and friends still call her Lyssen today.
Around the same time, she left the University of Phoenix to take an executive leadership role for a financial firm, Ameriprise Financial. Her boss supported her side gig, and her colleagues convinced her to use her gift at work. She started writing poems about leadership and speaking at leadership conferences, first at Ameriprise and later at other organizations.
Her ultimate dream was to take her talent to New York City, but Ameriprise’s first transfer opportunity was in Philadelphia, so she made the move. She continued writing poetry alongside her corporate work, which evolved into motivational speaking. Blakely-Oscar became a certified life coach yet still had bigger dreams.
“In high school, I took a broadcast radio course,” Blakely-Oscar says. “In Philly, I wanted a larger microphone for my poetry, so I started a talk radio show called Lyssen and Be Heard. I was the favorite poet of people who didn’t like poetry. It led to performances with diverse audiences, from popular poetry clubs to elementary schools, colleges, community events, political banquets, and NBA pre-game shows.”
To get to New York, Blakely-Oscar transferred with Ameriprise to Connecticut.
“I lived in Manhattan so I could continue entertaining on an even bigger stage,” Blakely-Oscar says. “One of my greatest acts was at the Apollo Theater. It was my high point.”
She found her “calling” and a unique way to inspire others. She used her skills and stage presence to engage with a broader audience, sharing her words of wisdom and promoting her personal and professional growth.
The next move was to Chicago, still with Ameriprise. Being with family she hadn’t seen in several years was great, yet she grappled with finding balance. She had exciting opportunities to incorporate her poetry into plays, perform at museums, and distribute a poetry album, and she was making enough money to pursue it full-time. In her 12 years at Ameriprise, she learned a lot about business and was ready to apply it to her own venture. She could no longer do both.
Blakely-Oscar met and married her husband while in Chicago. His day job was in insurance, but his passion was music. They decided to move to California for music and television opportunities. Before they moved, she found out she was pregnant with twins. It was a shock, but it didn’t derail their plan.
“During the final week of moving from Chicago, my mother had a heart procedure, and I was told it would be best if she lived with family to help monitor her health, so we had to make a pit stop in Arizona,” says Blakely-Oscar. “The babies came early and were born in Arizona. Afterward, I struggled with side effects of pre-eclampsia and what I believe was postpartum depression.”
She adds, “I had always been such an independent woman and go-to person for friends and family, But at that time, I couldn’t do it. I had shows and music videos lined up in California, but they had to wait.”
They eventually settled in Palmdale, California, where Blakely-Oscar applied her years in operations to create an assembly line to manage her own life. She needed to figure out how to juggle caring for twins and her mother while figuring out her next career step.
Blakely-Oscar and her husband started a marketing company to pay the bills. It allowed them to take turns working with clients and caring for their family.
“I started to reach out to old contacts from my motivational speaking work, and they remembered me,” Blakely-Oscar says. “Some said they still quoted my work and wanted me back. It felt good that there was still a demand for my services. It helped me rebuild my confidence.”
At the start of the COVID pandemic, her twins were six, and, to her surprise, Blakely-Oscar learned she was pregnant. Their baby girl, Peace, brought the family more love and joy when they needed it most.
Peace was born around the same time Blakely-Oscar enrolled in her first Harvard Business School Online course, Sustainable Business Strategy.
“I took the course because I needed to figure out my path post-COVID,” she says. “My motivational speaking had purpose, and the course helped me realize that I could balance building a business with purpose and being successful.”
She enjoyed the experience so much that she enrolled in a second course, Entrepreneurship Essentials.
“It was really challenging,” Blakely-Oscar says, “but it woke up the other side of my brain. I learned how to build a business for the long- and short-term, raise money, and map out an exit strategy.”
Since completing her courses, Blakely-Oscar has continued building her speaking business and focused on giving back to the community. She and her husband started a nonprofit, My T.O.T.A.L. Me, which stands for “Time Out to Always Learn.” It focuses on building confidence and leadership skills in youth while helping parents develop and engage. They offer courses for parents to understand and navigate social media with their children. They also run a travel youth basketball organization that teaches kids how to build character, be confident, and persevere.
Blakely-Oscar is the president of the Parent Teacher Association unit at her children’s school, is writing a book, and producing her own iHeart Radio podcast. On top of that, she’s the Organizer for the HBS Online Community’s San Francisco Chapter, creating events and promoting networking opportunities for professionals throughout southern California.
“I look back and smile at how far I’ve come and how much I’ve learned,” Blakely-Oscar says. “I want to teach kids they can go to Harvard, just like me. I’m now building a program for inner-city kids who don’t have a path to college. I want to help them create a plan and show them how to execute for success regardless of their circumstances.”
Blakely-Oscar’s determination, passion, and commitment to lifelong learning will continue to drive her success.
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