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Oprah Winfrey
Oprah Winfrey
American host and television producer, Oprah Winfrey
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Oprah Winfrey class questions 😆☘️.

📅 Oct 09, 2026 Back Of The Class Podcast 9 MIN 45 VIEWS 44 SEGMENTS · 2 SPEAKERS

What Oprah Winfrey said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Oprah Winfrey told host Ben that she did not chase a dream but did her best in each moment, starting her career at age 16 when a radio station employee asked if she had heard her voice on tape, leading to her first job. She explained that she was so impressed by Ben's actions that she agreed to the interview, recalling how at 21 or 22 she waited backstage to ask Maya Angelou (whom she had read at 14) for five minutes, finishing the interview in four minutes and 58 seconds. She identified the hardest obstacle as not listening to her inner voice, which she equated with instinct, intuition, or God's voice. Winfrey credited her religious upbringing, where she believed God was her father and Jesus her brother, for her confidence. She advised the younger generation to focus on their hearts, not social media, and to get still to hear the soft voice of God. She shared a manifesting story: seeing six trees at a friend's house at 27 or 28, later noticing six trees in her own yard, now living in a forest, and concluded by urging listeners to ask the life force what dream it has for them.

Key takeaways

  1. Oprah said she was not chasing a dream but doing her best in every moment, and she started in radio at age 16 after a spontaneous offer to read on tape.
  2. She credited her religious upbringing, believing God was her father and Jesus her brother, for her confidence.
  3. She told Ben that the hardest obstacle is not listening to your inner voice, which guides you to your best future.
  4. She advised the younger generation to focus on their hearts and get still to hear the soft voice of God, not social media.
  5. She shared a manifesting story: at 27-28 she saw six trees at a friend's house, and later had six trees in her yard, now living in a forest.

Numbers and commitments

FigureWhat it refers toTypeAt
16 Age when Oprah was hired for her first job in radio timeline 1:01
4 minutes and 58 seconds Time she took to finish the interview with Maya Angelou metric 2:45
21 or 22 Age when she asked to interview Maya Angelou timeline 1:34
14 Age when she read Maya Angelou's book timeline 1:50
72 Her current age other 4:20

Chapters

  1. 0:00Starting in radio at 16
  2. 1:34Interview with Maya Angelou
  3. 3:03Hardest obstacle: inner voice
  4. 4:00Confidence from religious upbringing
  5. 5:11Advice to the younger generation
  6. 6:36Manifesting the six trees
  7. 7:56The life force's dream for you

Questions asked in this interview

5
  1. 0:04Oprah, first question I have for you is, if you could see the steps that you took when you first started to get to where you are today, do you think you'd still chase that dream and take all the same steps again?
  2. 3:03What is the hardest obstacle you've had to overcome in your career?
  3. 4:00Where did you get your confidence or your self-belief from?
  4. 5:11And what advice would you give to the younger generation out there?
  5. 6:07Like I was only in Spain there two months ago and I was thinking, wouldn't it be mad if I ended up being over two months?
Ben 0:04 ↗
Thank you so much. Oprah, first question I have for you is, if you could see the steps that you took when you first started to get to where you are today, do you think you'd still chase that dream and take all the same steps again?
Oprah Winfrey 0:19 ↗
Well, I actually, Ben, I wasn't chasing a dream. I was just doing my best in every moment. And this is what I, you know, try to share with everyone. Um, you can have a dream and a big dream and a vision and that's a wonderful thing, but I didn't have a big dream for I was going to be a fourth grade teacher and because I was excellent at as as a reader when I was in this contest for being misfire prevention. I went back to this radio station where it sponsored us and I was sitting there and the guy offered me an opportunity to read. He said, "Have you ever heard your voice on tape?" I was 16. I was 16. How old were you?
Ben 1:00 ↗
I did.
Oprah Winfrey 1:01 ↗
Okay. So, I was 16. And he said, "Have you ever heard your voice on tape?" And I said, "No." He said, "Come here and I'll and and read this for me." And I started reading, but because I'd been reading since I was like three, four, I read so well. He then called everybody else in the room and said, "Listen to this kid read." And by the end of the day, I was hired at 16 in my first job in radio. So I didn't I didn't have a big dream to be in radio because I thought it was
I took a step. But I will say that what Glenn did today one of the reasons why I was so impressed.
One of the reason the reason why I'm doing this interview is because when I was 21 22 there was a very famous poet author named Maya Angelo. She wrote a book called uh
Ben 1:46 ↗
I po I rise. Yes. Very good.
Oprah Winfrey 1:50 ↗
Very good. Very good. That's good. Okay. So, she wrote that, but she her book was called I Know Why the Cage Bird Sings, which I read when I was 14 years old.
And she was in Baltimore. Okay. And I by this time I was now in television and I asked my news director if I could go to interview Maya Angela.
So, I didn't have an appointment with her. I'm just waiting backstage.
Ben 2:17 ↗
Dor stepping on it.
Oprah Winfrey 2:18 ↗
Yeah. Yeah. Yeah. Waiting backstage for her to show up. She comes out of the door and I did the same thing that you just did with Gail today.
I said I said, "Miss Angelou, Miss Angelou, may I please have an interview?"
Ben 2:33 ↗
Funny thing is, over I didn't like I was telling that Gail was over with you, but I didn't know it was Gail I was talking to. That's why I was shocked after someone was like, "You know, you were just talking to Gail." And I was like, "No, you didn't even know it was Gail."
Oprah Winfrey 2:45 ↗
No. But I did that thing where I waited backstage for her, waited outside the stage when she was coming out. And I said, "Could I just please have five minutes of your time? Could I just have five minutes of your time?" And she said, "Yes, you can have five minutes." And I finished the interview in four minutes and 58 seconds. Okay.
Ben 3:03 ↗
What is the hardest obstacle you've had to overcome in your career?
Oprah Winfrey 3:06 ↗
Um, this is the hardest obstacle anybody has to ever overcome is not listening to the voice inside you that guides you to the future. You have that voice. You have that voice. That voice told you to come here today and get this interview and to go to hotel after hotel to try to figure out where I was. That's what that voice told you. That voice that guides you will guide you always to the best place for you. If you're listening to your inner voice, which some people call the in your instinct, some people call it your intuition, some people call it the voice of God, but everybody has it. So my biggest obstacles have come when I did not listen to that voice, but I listen to my head or I listen to my friends or I listen to what society say or I listen to that. But as long as you are listening to that voice, you cannot go wrong.
Ben 4:00 ↗
Where did you get your confidence or your self-belief from?
Oprah Winfrey 4:03 ↗
Well, I was raised very religiously. Were you raised with the religion? So, I was rel I was raised to believe in God and you know, not only was I a a little girl growing up very poor. I loved you saying we have the same background.
Ben 4:19 ↗
Yeah, we have the same background.

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Cite this transcript

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APA

Winfrey, O. (2026, October 9). Oprah Winfrey class questions 😆☘️. [Interview transcript]. Back Of The Class Podcast. CEOInterviews.AI. https://ceointerviews.ai/interview/3020072/

MLA

Oprah Winfrey. "Oprah Winfrey class questions 😆☘️.." Back Of The Class Podcast, 9 Oct. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3020072/.

BibTeX 
@misc{winfrey2026_3020072,
  author       = {Oprah Winfrey},
  title        = {Oprah Winfrey class questions 😆☘️.},
  howpublished = {Interview transcript, Back Of The Class Podcast. CEOInterviews.AI},
  year         = {2026},
  month        = {oct},
  url          = {https://ceointerviews.ai/interview/3020072/},
  note         = {Speaker-attributed transcript with timestamps}
}