Lessons From Meeting Oprah


In this week's episode of Chill & Prosper, I’m talking about meeting Oprah and how freaking cool it was. 

I’ve spoken about it before but there's some new insights recently about how it changed me. 

It was a very cool experience with some interesting lessons for all of us.

I talk about ...

  • What I said to Oprah when we met
  • The biggest lessons Oprah taught me
  • The unexpected lesson on receiving


Hey, gorgeous. I'm so excited to talk to you today because I wanted to tell you the story about when I met Oprah and how freaking cool it was. I've written about it. I've spoken about it so many times, but even there's just some new nuances for me about how an amazing experience it was. I really think that there, for those of us who grew up watching Oprah every day, she taught us so much. And sometimes I think about like, who am my kids watching after school, who are my kids watching when they're at university sitting round, bumming around like I did. And who are they learning from? Because I learnt so much from Oprah growing up, I would rush home. I'd try and get the first school bus after school, because I knew that if I got that one, I could watch it in full or I have to miss the first 15, 20 minutes of it.

And she taught me so much from my small town on the Central Coast, New South Wales, Australia, about things that I'd never thought about before. I'd never met anyone who was gay before. I never met anyone in my town who, oh gosh, we were all pretty, there was mostly white kids in the school too. And so she taught me so much about different cultures and different experiences. But most of all, I'll tell you about what I told her about what she taught me the most. But anyway, here's the story. Oprah came to Australia, she was doing a tour, a speaking tour, and you could go and see Oprah in a big stadium for like a hundred bucks, or you could buy a VIP ticket for two and a half grand to go to a small meet and greet with her.

And when the tickets came out, I was on holidays with my family. I was right in the back of the car, in the little jump seat, and I had 2% battery. And I saw the tickets came through and I was just like, "Oh my God, I have to do this." And I was like trying to buy the ticket as quickly as I could. And I'm a big believer in this that when somebody you love, who has made an impact on your life, if they come to your town or if there's an opportunity to meet with them, take it. One, you never know when somebody is not going to be there anymore. You never know when someone's going to stop touring. You never know when something like a global pandemic will happen and we won't be able to gather together. So, if you get an opportunity to, to go to a concert, meet your idol, have a VIP day, whatever, take that opportunity.

And I knew for me, I was like, "Oh man, I'm taking, I'm jumping on this." And so was like two and a half grand. That's a lot of money. But I mean, I could spend that on lots of different things. When I think of some of the things that my hubby spent on, I was like, "That is a freaking bargain, absolute bargain." Okay. So what happened was I was like, "Oh my God, I have to get really fancy and dressed up." So even before it, I was like, "Oh my God, I have to, I don't know, I have to make this a cool experience." So I went into a shop and I wanted to buy a Camilla kaftan. And as I went in, I wasn't wearing very fancy clothes. I looked like I just come from the beach. And the lady was like, "These kaftans are very, very expensive." And I was like, "Okay, I'll take two of them then." And she was like, "Oh!" And it was my pretty woman moment. And I just thought, "Oh, already Oprah is teaching me so much about this. This is so cool."

And so I had my fancy kaftan, I got my hair done and all that kind of stuff. And I turned up, because I thought, "I have to maximize this experience. I have to get my money's worth." And so as I was getting ready to go, Mark was like, "You have to take your book. You have to give her your book. You have to make sure you ask a question." And I just went, "Oh my God, no, I'm not going to do any of that." I'm just going to enjoy the experience and just like take it in and receive it.

And that's a really good lesson as well, is that sometimes we just get so caught up in what we have to manifest, that we don't actually take the time to receive things for ourselves. And I just went, "I'm not going to stress. I'm just going to go and just soak in her, her goodness, really. I'm going to soak in her goodness." And so I often, the big lesson on that too, is how much I live my life sometimes for my business. I'm like what I have to get something out of it for my business instead of just receiving it, just being there for myself. And part of that was, I was like, "I have to Instagram this whole experience for my Peeps. I have to do live streams in the queue and I have to make a cute little video."

And I was like, "No, it's okay to do it for me. It's okay to just to experience this in my own skin, through my own eyes for me, even if I never share it with anyone." And of course I'm sharing it now, I've milked it to death since then. But I think this is just such a valuable lesson in like, it's okay to keep things sometimes for ourselves, you don't have to share everything on social media. You don't have to make everything about your business. You don't have to turn everything into your business idea. And so it was okay for me to get my hair and makeup done for me, just to feel good. I think that's kind of cool.

So one thing that was really fun, there was like a VIP line and all that kind of stuff and a VIP a special entry. And I met two Lucky B's in the queue, which was really cool. Of people who said, "Oh my gosh, I loved your book. You've like, you've helped me." And I'm like, "Ah, this is beautiful." So one thing that we had to do before we went in to meet Oprah is we had to sign a waiver. We had to sign an agreement that we weren't going to give her any presents, any gifts. And I was like, "Hmm, why would we even be doing this? How weird?"

But it was really good experience. And then I've learned a ton of stuff around this myself, because a lot of people often send me gifts. And from learning that experience of her saying, "Please don't give me any presents." I have had to make that a boundary and say, "Hey, please don't send me stuff." Because it really adds up. Like every time I went to my postbox, I would have 30 presents there. And you might think, "Oh, lucky bitch, Denise, why are you even complaining about this?"

But I want to live a minimal life, I want to be really intentional about the things that I bring into my life. And people would just randomly give me presents or give me their books and things like that. And so even just seeing how she set up that event gave me some permissions around boundaries. And I remember hearing that after her show, she used to always let people just talk to her or go back to her office with her. And someone was like, "Oh, Oprah, I want to talk to you. And she went, "Yeah, okay." She took this lady back to her office, and she said, "Oh, can you buy me a house?" And then from then she was like, "You know what? I'm going to set some boundaries around this and I'm not going to burn myself out, do too many shows in one day." And things like that.

Anyway, so what was cool is that, so we got into the VIP experience and she just wandered out. There was no like fanfare, there was no music. She was just like, "Hey guys, Hey y'all." And I was like, "Oh my God, it's Oprah." Super casual. And I was like, "There she is." She's exactly like how she's on TV, but she's just a normal person. And then, this is why I love talking about money too, because she was just like, "Hey, so I heard you guys spent a lot of money to be here." And I was like, "Oh, she's talking about money." And I love talking about money. I love just saying what it is. Right? And so she was like, "Why would you do that?" And already I'd put myself off the hook. I was like, I'm not going to have the pressure to ask her a question. I'm not going put pressure on myself to do anything. But she looked at me, she pointed straight at me and she said, "Why are you here?"

And then she goes, "Hang on, wait, are you wearing a Camilla?" And that's when I said, "Oh my God. Yeah. I bought this specially, I wasn't going to wear target to Oprah." And she was like, "Excuse me, Tajai. I would Tajai stuff all the time." I mean, "Ah, of course." But then she was like, "Why did you come? Why did you spend so much money to come and see me?" And I was like, "Oh my God, I've been watching you since I was a teenager. I've gotten so much value out of everything you've done." I've never spent a cent with Oprah up until then. I watched her show for free. I got her wisdom for years for free. And I was like, "Well, I just wanted to come and meet you and say, thank you." And she goes, "Well, how long have you been watching me?" And I said, "Well, since primary school." And she went, "Ah, so I raised you." And I went, "Oh my God." She just, she knows the impact that she has made. She knows it. And she owns it. She owns that, "Oh, you're just one of my girls that I've raised." "Yes!"

And then she said, "What's the biggest lesson I taught you?" And I said, "To break the cycle." That's it. I knew that to live a bigger life, to do the things I wanted to do that I had to break the cycle. And I learnt so much from her about dysfunction. And like red flags, I obviously saw them in my own family's life, but she really taught me to look for red flags in relationships. She really did teach me so much. And so that was my interaction with her, that it wasn't the end. That wasn't the end of my interaction, but that was ... I just sat there and went, "Oh my God, I just got to talk to Oprah. That was so cool." And that was for me just going, I'm not putting the pressure on myself to make this anything except to just receive it. All right. I learned so many more lessons from that interaction and I will share them with you straight after the break.

Hi, my name is Janet Baretto, and my business name is Primary Formed. My website is Anyone Can Craft With A One.com and I live in New York and I can officially say that I am an inventor. And one Lucky B. I downloaded that book off of Audible and everything changed. I got cleared and went for it, I had no funds to join the program that would help me manufacture my invention when I signed up anyway. Guess what? The money came, magic. If you don't understand what that means, read the book. Thank you Denise.

My name is Melanie Huestis and I'm an intuitive energy coach with a big heart and a mouth to match. I live in London, Canada with my three kids. One of which I just happened to be married to. When I read, Get Rich, Lucky Bitch, I found Denise's authenticity so refreshing. I dove into the part about money beliefs and discover that I believed I could do what I love or I can make lots of money. I had no idea that this powerful thought was affecting pretty much every business decision I made. This book helped me discover that I really can have it all and without sacrificing what matters.

Okay, welcome back. So I'm talking about when I met Oprah and how freaking cool it was. So after she pointed to me and just said, "You, why are you here?" And I went, "Oh my God, thank God. I've spoken to Oprah." Something really interesting happened after that, that I actually got a little bit more like I was sitting there thinking, "God, I really want to ask her another question. But I can't like what if it's too greedy to ask another question?" And so it's just a really interesting experience of like how much I hold myself back from things sometimes, because I think, "Well, I'm already lucky. I'm not allowed to have more. Well, I'm already blessed. It should go to someone else." And so often I don't apply for competitions. I don't apply for awards because I think, "Well, I'm already blessed. That should be someone else's chance." And realizing that even recently I was thinking, "Oh, I don't have to market my program anymore. I'll let other people sell their programs." And it's like, "Well, what? There's always room for more abundance."

And imagine a long time ago when Oprah was doing her show and she was one of the first people to like make a million dollars from her salary and she's super abundant, right? And then she wanted to own her show. And imagine how many people said to her, "But you're already making a crap ton of money from doing this. Why would you even want more. Now, why would you want to expand this?" You're already number one or you've already done so well, why would you need more? And then even thinking about like, because I used to just be on Oprah.com all day, all day long at work. And I remember she'd always have these house tours where she'd be like, "Oh, have a look at my Hawaii house. Have look at my guest house or whatever." And imagine if she just was like, "Well, I already have a house. I don't need more houses." And how often does she go to her house in Hawaii? How often does she go to her house in Montecito? Montecito, is that what it's called?

And so she's really taught me that it's safe to have more, it's safe to have bigger dreams for your life. And I don't think, I don't consider her someone who's really greedy or ostentatious, but she has a ton of just beautiful abundance in her life. So anyway, I was sitting there thinking, "Oh, I'd be too greedy to have more interactions with Oprah." So it's like, I'm allowed to have more than I need. I'm allowed to have enough. I'm allowed to have a lot.

So I loved seeing how she role modeled boundaries. So in the first section, I talked about how we had to sign a waiver to say that we weren't going to give her any presents and how that gave me permission to have boundaries around it, to say to people, "Hey," people would ask me for my address or they'd ask my assistant, "oh, I want to send Denise a thank you gift. And I'd start to say, "Hey, look, I so appreciate that. But you know, I'm doing Marie Kondo, Marie Kondo decluttering ... and actually, no, it's good. So you can donate money on my behalf or just send me a good wishes or buy something for yourself or whatever, or give it to someone else."

And so what happened next is that some people would get up after I'd asked my question, I was just sitting back. People would get and go, "Oh, Hey Oprah. I just want to let you know something like how much you changed my life." Or whatever. And then they would have brought a gift with them. And they were like, "Oh, I put together the scrapbook for you of like all ..." There was one person was like, "Oh, all the articles in Australia that have ever been written about you, I've put them all in a scrapbook and I want you to have it." I could just see her face just going, "Oh, what am I going to do with this? This is great." And then there'll be like, but your team said, "I couldn't give you your present." And she was just like, "Uh, that's okay. You can give it to me." And so it was, yeah, it was really tricky to see sometimes you can set terms and conditions. You can set boundaries and people will still try and overstep them, even in a situation like that.

But what was really cool is the way that she had boundaries around her time. So someone would stand up on the microphone and they'd go, "Oh, Hey Oprah. I just want to let you know how much I love you ..." and going into the story and she'd be like, "So what's your question?" And they would just go, "Oh." They just wanted to talk. And I've also seen this at a conference. I've seen a few people do this really well. Kendall Summerhawk does this so well, she's a great money mentor. She's a business coach. And at her conferences, she'll actually say to people, "Hey, I don't want to hear your life story. Just tell me your question." And it's like, "Oh yeah, cool." And Oprah was just like, "Yep, what's your question? What's your question? That sort of question. What's your question?" And it was so brilliant just to see her role modeling boundaries like that. It was really, really cool.

And I don't know where I saw this. Aw, sorry. I don't know where to attribute this. But someone was saying that after events, before you ask for questions from the audience, give people a chance to chat amongst themselves so they can get that out. And then when they get up, they can ask a question rather than just say stuff. So it was so much fun to see that. And even seeing some of her really honest and practical down to earth advice. So someone was saying, "Oh, I'm setting up a charity. I want to set up a charity, helping people in these particular country, because there's lots of poor kids, lots of orphans. What do I do?"

And she was like, she actually said, "Starting from the ground up is a bitch." She said that. I was like, "Ah. Yay, Oprah said Bitch." It was so cool. I was like, "Ah. She's so normal." And she was like, God, if Oprah can't set up a charity from scratch, which she's had so many problems when she set up her school in South Africa, she was like, "Find experts, find experts who are already doing the thing and partner with them or hire them." And I just thought, "Wow, that's just such good advice." Even Oprah with all her resources, it still comes down to not, don't be everything to everyone. It's okay to get help. It's okay to partner with people. It's okay to get support. Yeah. I thought that was really, really cool.

So what happened next was really fun as well. So we got to have a photo with her and even just seeing how the photo line ran was really good with the way they did the boundaries. So it's like everyone has to line up. And then they said to us, let me take ... I think they had a professional photographer there. So we just lined up, they took the photo and then we went. And I actually noticed this. I went to see JoJo Siwa in concert with my daughter Willow. And they had amazing boundaries around that as well, where they had a production line. And I think, that's a lesson for all of us is that systems really work to move things along and to make things really easy. Because if you just leave it up to people, people are confused. If it was like, "Oh, where do we go? How do we do this?" And it was just like, "There's a photographer here, you line up here. You go one by one, you take a photo, blah, blah, blah."

And so we lined up and I walked towards her and she goes, "Hello, darling." And I was like, "Oh my God, this is just the best." And she looked at my belly because I was actually quite pregnant with baby number two, I think I was like seven, eight months pregnant, but she didn't say anything. And I since have heard that in her early days of her show, she would get it wrong all the time. And she'd say to someone, "Oh, congratulations." And they'd go, "What?" And she'd go, "oh, your baby." And they'd go, "Oh, I'm not pregnant." And so I could see her like eyeing my belly and just going ... and I should have just said, "Oh, hi, I'm Denise. And this is George in my tummy." Because I thought, how cool would it be for my son to name check by Oprah? I think that's really cool.

But I was so excited to get the photo by the way back. And when it came back, I had big old preggo nipples that were like super prominent in the photo and the lighting was a bit funny. And so I had to actually hire a friend of mine who's a photographer to do photoshopping. I had to get her to Photoshop out my nipple because I was like, "I can't share this!" I was so excited to get the photo. And then I was like, "I can never share this. All you can do is see my nipple."

And yeah, the other lesson that I learned from this actually was around the gift bag. I pissed myself laughing when I saw the Oprah gift bag because it was filled with the most random stuff and I know Oprah had nothing to do with it. It was the promoters, blah, blah, blah. But I see this all the time that I do it. My clients do it. You probably do it. When we have an event, we just over deliver, we stuff things full, we over-give just to fill the bags. And so there was a signed copy of one of her books, What I Know For Sure. And this is a treasure for me, I keep it at my rose farm. It's just, it's so meaningful for me. And I mean, now I'm an author. I'm on the other side of it. I sign books and I'm just like, uh, my arm wants to drop-off. But I was like, "This is so cool." Like even if she'd just given us that I would have just been like this was worth it.

And I was there to see her. I wasn't there to get a gift bag. It had like this random gray scarf, you know those cheap knitted scarves with sequins on it. There was a mug that said, I spent a night with Oprah. Kind of cool. There was an Oprah pen and like a notebook. There was a program which is lovely, but I never keep programs, but that's lovely. And then there was some weird stuff. There was like a branded universal charger. You know when people just always giving away USB sticks and things like that. And then there was like a plastic hair twist thingy that you could make like a French roll out of, you know just those cheap things you get from like a $2 shop. And then there was just like some sample stuff that probably promoters put in like face washy thing, just some weird stuff. And then there was a pair of earrings. And I was just like, "Why are we doing this? Why is she doing this?" But I do it all the time.

My first event that I really did in London, in my gift bags, at some point it was going to be like blue nail polish and fake money. And I still, I did branded calculators, branded pens, branded notebooks. Recently at my rose farm retreat, they got like three different notebooks, a coffee cup, a cool rose bag, some honey, some candles. Just like all this stuff and Mark's like, "They're there to see you. You're the prize. You're the prize." But I just thought it was really funny that still Oprah, still didn't think she was the prize enough. Oh, gosh, it's so funny. You know what, by the way, if you do give bags, edible stuff is always really fun and I'm not talking edibles as in like CBD, marijuana stuff. I think giving people candy or lollies and water, I think that's always still good, but just resist the urge to give away all that kind of crap.

Okay, one other cool thing happened is that the designer of the kaftan I was wearing, Camilla, she was there and it was so cool that even Oprah was like, she recognized that I was wearing a Camilla kaftan and Camilla was there. So I went up to her and I was like, "Oh, can I get a photo with you?" And normally I'm so shy about stuff like that. I would never ask, but I was just in the mood after meeting Oprah that I was like, "God, if I can get a photo with Oprah, I can get a photo with any random now." So I asked her and I said, "Hey, how did you get so involved with Oprah?" And she was just like, "Manifesting, like I had her on my dream board. And then I told everybody that I wanted to meet her. And then we did a boatload of work for it." And I just thought that was yeah, really, really cool.

And then the event in itself was amazing, but I just felt like meeting Oprah was just such an incredible moment for me. It made me feel good about just showing up and doing, doing my stuff. And if Oprah teaches us anything, it's that we can break the cycle. We are enough, that's it. So, thanks for listening to my Oprah story. I would love to hear what celebrities you have met and what celebrities have changed your life. So definitely tweet me a picture. Oh my God. When I got started on this, I was like, "I've seen this celebrity and this celebrity." But Oprah was the one for me that just stuck out so much, but I would love to see your pictures with your celebrities. So I'm on @DeniseDT all across the interwebs on Facebook, Twitter and Instagram. That's my social media handle, @DeniseDT. Post it publicly. Talk your story about what meeting your celebrity meant to you and please tag me. Because I love, love hearing about it. All right, gorgeous. I will be back with my final thoughts after this short break.

Hey Denise, it's Mariah with Bare Heart Boudoir on the Central Coast of California, just got done listening to Get Rich, Lucky B for the second time. And my biggest takeaway is when you talk about taking care of your skin, when you first start to take care of it, you're really excited. And then you get a little blemish and you just have to push past that and keep it going because that clear skin is going to happen. Well, we have been manifesting great things this year. I manifested myself a free facial, which was phenomenal. Our ideal clients. And then we had a little blemish. My husband was in a very severe paramotoring accident and he broke his paramotor in addition to breaking his neck. However, he was quite lucky. And he walked away from that accident. Now, yes, a little bummed because he broke his paramotor, however he's walking and talking and breathing, which makes us so happy. Now I knew that he would be a little bummed with not having a paramotor, but we sent positive energy. We manifested it. And two days ago, all of his friends got together and bought him a new paramotor, which is worth thousands of dollars. Now, yes, we got past that blemish and I ready for clear skin and positivity. Thank you so much, Denise.

Hi, gorgeous. Welcome back. Thanks for sticking with me. And here's my final thought for today. It's something that sounds like I'm being a dick, but I'm absolutely not. So having money doesn't mean that bad things are not going to happen to you in the future. Right? You'll still, your car will still break down sometimes. Things will break. There's no magical place you're going to get to where everything's perfect. And so now instead of like complaining or going, "Oh God, the universe doesn't like me or again. I say something again, please don't think I'm being a sick. I'll go, "Lucky we're rich." And I know it sounds funny. So the other day, like our air conditioning broke down and it was like super, super hot. And so we had to go for a drive and our Tesla battery didn't kick in. These are all like Lucky Bitch problems, I know.

                                                And we were driving around and our tire burst. Right? And then Mark was fixing it and it started raining. And I was just like, sometimes when a string of things happen like that, you can really see it as a sign from the universe that bad things are happening or your luck has run out or the universe doesn't like you or whatever. And so I just say, "Lucky we're rich. Lucky we're rich." And it really, it really turns things around for me. But what if you're not rich yet? One thing that I did in my very early days to remind myself how lucky and blessed and abundant I was, is to put it into perspective that if you are listening to this, if you've got a phone, if you've got a place to live, you are so lucky and abundant and blessed.

And all of us are pretty much in the 1% already in terms of luck and abundance in the world. And yes, you might be struggling sometimes, or you might not be as rich as you like, but just try it and see what comes up for you. Again, it's not about me. And I'm not being a braggy bitch on this, but just try it. Next time something happens where normally you'd complain or you'd feel the lack or you'd feel like a bit fearful. Just try it and say what it feels like, "Lucky we're rich, lucky we're rich." Oh, I can't wait to hear the comments on this one because I can imagine for some people that sounds really tone deaf, for some people it just brings up some stuff for you. So totally tell me what you think. My social handle on this is @DeniseDT all across the interwebs. I want to hear what that brings up for you, lucky we're rich. Try it, try it and see. Okay my gorgeous one. Go forth, chill and prosper, peace out for me. And I will see you on the next episode. Bye.

About the Show

Chill & Prosper is your weekly dose of money mindset, marketing and humour from best-selling author and entrepreneur Denise Duffield-Thomas.

Denise's philosophy is that there is ALWAYS an easier way to make money and that's what she's here to help you do. Each week, you'll get actionable advice to help you make more money, with less work. There's no need to hustle - let Denise show you how to embrace the Chillpreneur way.

Be sure to hit subscribe so you don't miss an episode!