TRINNY WOODALL: I Wish I Knew THIS in My Twenties | GREAT MOMENTS

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3:12Hello, everyone. I'm Jamie Lang, and this is Great Moments. Hey, everyone. I hope you're well and welcome back to Great Moments. Now, if you're new here, this is the place where I'm going to bring you a standout moment from one of my favorite great comedy conversations. These are the moments that have stayed with me long after the recording, and I hope you can take something away from them. Now, if today's conversation leaves you wanting more, you can find the link to the full episode in the show notes. So sit back, settle in, and here it is.

3:45There's drains and then there's uppers. there's a drain there's a drain but you're the opposite of drain you definitely bring people up have you felt those low moments or do you not allow yourself to get there no I have felt those low moments lots of times radiators drains or radiator so I had that moment Susanna and I had worked together for 10 years where did you guys meet Susanna was working for The Telegraph writing about women's cricket because she just had an affair with Imran Khan for a few years. Or is she still with David Linney? I don't know. Something happened. Something happened. And she wanted to do something else.

4:35So then there was me and I was trying to do business and I hated business. My dad was a businessman and I was just trying to do it but I had no qualifications, nothing. I always felt a fraud. I felt so fraudulent. and it wasn't working. What, because you didn't understand it or you felt out of place? I was so out of place. It was me and many men on a trading floor. I was trying to fit in, so I kind of swore like a trooper. And, you know, we were doing puts and stops and butterflies and options and commodity trading. The arse end of things, really. It is the arse end. Commodity trading can be the arse end.

5:08I did physicals and then future. Just quickly, out of how many people were you? Were you the only woman? There was a secretary in the front room and then there was me in the sales team and then there were about 60 men. How do you hold your own in that scenario? You develop this skill of just becoming one of the boys. In that environment, the only way I thought I could succeed was to become one of the boys. so they were all loutish imagine the most loutish of your friends and that was this collection of people i'm in my 20s and i think i've got to dress like a boy so i get raid my father's wardrobe i come into work in the winter in his covert coat i get um my suits from miss selfridge but i go and take all the buttons off and i go to the button queen in maryland lane i get livery buttons on my suits i then buy you know with my salary i buy ferragamo men's shoes no fratelli rosetti men's men's rogues.

6:07And I just become a boy. It was the only way I felt, because I had never felt sexy, feminine, booby girl. So I couldn't lean into, let's be ultra feminine in this male world, that wasn't me. And I always felt more comfortable to be slightly masculine. So I leant into that. And I even had quite a low voice. A lot of the people who were my clients thought I was a man. On the phone? Yep. I had this client. Because you purposely did that? I've always had quite a low voice. But I had one client who was this Nigerian and you did everything by phone and you were trying to sell them a fund. And I remember I'd chat to him every day and he'd call me up and he thought I was a man.

6:51And I realized only off the second call when he started sort of saying, oh, when I come to London, can you take out some saucy bars? And I was like, oh, fuck. And then the time came when he said, I'm going to come to London and I want to give you 250 grand, this fortune. And I was so excited, but I thought he's going to meet me. And because he's going to discover I'm a girl, this is not going to work. So I took the person sitting next to me, who was my sort of buddy, and I said, you've got to be me. So we went in, you used to record all the conversations then. So we went into the recording room and I went back on all the conversations I had with him.

7:27I said, look, listen to the conversation so you know what we've been talking about. He does that. I said, I'll split the commission with you. Then he comes that day, the day he comes to the office. Philip is in the room with him. I'm the secretary just in case he makes some mistakes and I can pass him notes or something. I'm the secretary. Philip negotiates it and remembers to say the things I said before, signs the deal. But that was the way that I did it. But do you really think if he had realized that you were a woman, he wouldn't have done the deal with you because you were a woman? He was a very alpha man.

8:06And I think that he would have been really embarrassed by the conversations we had. Or would he have been pleasantly surprised? Oh, he would have been embarrassed by the conversations you were having. Yeah, and then realized I was gone. Don't forget, this is the 80s. You weren't even born. 88. All right. This is actually 89. So you were a year old. I was a year old. You're a year old and I'm trading commodities. All right. Yeah. So that's what it was then. And it was quite different. But, okay. But then do you think that in life, because you would have realized at some point that he realized that you were a man and you didn't say anything back.

8:47You just sort of went, okay, I'm going to keep going. Yes, I did. I did. And there was something that made me feel. Yeah. What made you feel? be more successful in this stage if he thinks I'm a man still it just it sounds inconceivable to you no it doesn't sound inconceivable really I really I knew it to be true so much because it makes it makes what happened I okay um when I did Made in Chelsea for many years right I uh realized very quickly I would do a scene and people would find it funny and I went okay I gotta be funny there and then I did another scene and then I would be really loud and they go, God, you're so energetic, so loud, so I'd have to be more.

9:29And so I became this version of myself which becomes exhausting. When you're not being truly authentic to yourself, you become exhausting. You become, you're drained and if you are going into your trading with men, you're becoming more masculine because that's what you feel like you have to. I was swearing like a trooper. I'd go home and my dad would say, what happened to you? What happened to my daughter? The thing is, Jamie, I was never successful in it. I was always, you know, I always say this thing that I went to. In your eyes, that is. No, no, no. In everybody's eyes. Okay. Okay. There was Black Monday and I was the first one out the door.

10:02You know, last one in, first one out. For sure. I would go to the, I thought about this. I'd, you know, go in on the tube in the morning and I'd have the Financial Times on the outside and I'd have the Daily Mail on the inside every day. You know, I pretended, pretended, pretended because I had no idea. You know, I had to do my Series 3 mercantile exams, Chicago Stock Exchange mercantile exam. I looked at it and I thought, this is gobbledygook. You know, I just, how I passed, I don't know. But I really, I really didn't do well at it. In any way you could look at it. And I realised I've got to leave.

10:36Two things here. Firstly, I disagree. I think. No, I was really bad, Jamie. No, I think you were, but you still got it. That's what's so interesting. You still got it. You didn't look at it and you think the 80s, okay I don't fit in here because um you know it's a different time you know all these different things going you thought no I'm gonna go and do that and you you went and did it which which for me that is that's the winner there you actually went and did it yeah again I remember when my mom said to me I was 18 years she said you can't get a job and I said I'll get a job she said no you can't and so I walked up to Byron Burger restaurant yes I remember on Kelly and High Street and I walked in there and I said hi and they went hi who are you and I said I'm here to apply for a job front of house.

11:20And they went, okay, what's your experience? I said, I've had many years experience. You're doing this and this with my dad and all these different things. Made a complete lie. And they went, okay, you start on Thursday. And I came back and I was so bad. I was, there was one moment when my first week where the, I don't know, something happened in the kitchen, nothing was working. These people said to me, where's our food? And I didn't know what to do, so I just walked off because I was so, but the victory is actually getting there and putting yourself in that situation. Did people think you were as bad as you were?

11:49Yes. Did you get fired? No. Well, I kind of gave up. Yeah, you didn't get fired. I got fired. There's a difference. I got fired. All right? So I got a... This is my win. You can try and have the win, but you walked out. You didn't get fired. They thought you were good. You had this thing that what you felt inside was so profoundly different from what people saw. So maybe your trajectory is how those two have come together. Whereas before there was more front than Brighton Beach and it was about your leaning into yourself and actually becoming a bit of something. We went on a tangent, but you were talking about Suzanne and how you became friends.

12:23So how did that relationship form? So we meet and I have this idea for this column in the telegraph, not in the telegraph, but just something where you go and you'd get honest advice as to what to wear. And there was not, you know, it was a very different time from what there is now. There wasn't much to choose from that was in the high street. and it was all in magazines months later and therefore wasn't in the high street anymore. If it ever got, if high street clothes ever got into Vogue magazine, they'd sort of cut something and make it just for Vogue, but it would never be produced. So it was really different from now.

12:55But she loved the idea and I told her the idea and this friend who introduced us, she then called me the next day and said, can I take your idea? And I was like, no, you can't fucking steal my idea, but we could do it together. So we then work on it together and then she has an editor who's saying, I've got this whole page free. I've just moved over from motoring to page three of the weekend section of the Telegraph. You have no history. We have no. Susanna has experience in writing women's cricket. And I have no experience. But I've had 15 years by the stage of every single girl who comes to my apartment ending up in my bathroom, seeing makeup, what they should use, skincare, what they should use, going in my bedroom.

13:36So people followed me for that. So I knew amongst a very small group of people that people came to me because they knew I would know, which is the kind of one first time ever I felt confidence in my ability. I was going to say, yeah. Just quickly before we go, because do you not see the pattern? I don't know. I'm not a therapist. No, I know. Tell me the pattern you think you see. I honestly see the pattern. The pattern with you is this. It's like it's I think success is driven by risk and the ability to be brave. And there are these pockets throughout your life where something becomes a problematic and you go or you go, OK, that needs to stop or that needs to change.

14:23People don't typically change. They don't move. They stay doing the same thing forever because they like the monotony and the routine of it. and you don't you're constantly whether good or bad for you you stick at it but then if you sort of go oh no I'm not going to do that I'm going to move here I'm going to move here I'm going to move here I'm going to move here and you're figuring out the whole time what works for you most people don't do that what I used to do which I don't do now this is the big difference and I've got two people living with me right now who are in their very early 30s and they're starting two new businesses and I noticed it in them and I challenged them on it, which is in my 20s, I'd always, if one thing wasn't working totally, I'd move on to the next because I wasn't prepared to have the patience to make it work.

15:08Because there's a big difference between what you deem to be people who are being monotonous doing the same thing and somebody who's being dynamic. There is that in between where, or the extremes where you'll just change because you don't like what's in front of you. So instead of actually proving to yourself, you can succeed at something, you just change to the next. And I did that with, I had this business called Socket to You. And, you know, the socks started to, you know, disintegrate and I just moved on. You know, I didn't think let me resolve the problem. So, so there were moments when I had these little businesses.

15:37And then when I felt I had another business called Mission Impossible, which would have been called now today, quintessentially, but it was, you know, what are the best things in London to do? And you would retain us and we would book you rest a concierge service. And I got stationery made for it. You know, that's the first thing I always it because i got the stationery because because this feels proper because it feels proper it made you think it was proper because then the imposter syndrome goes because i've got a card i've got a card those unlimited i have a card mission impossible i have a card socket to you company i have a card all right it was always so important but it was that slight when it doesn't work, leave it.

16:20And with Trini London, when I have a challenge, I work through it. So there's been a shift in how I look at things now.

16:48Pro Football is back, and so are the predictions. Trade yours on CalShe, America's number one prediction market platform. Indy takes on Kansas City, with Indy currently trading at 28 % to win. A$100 trade pays out$336 if they win. Download CalShe. Use code AUDIO25 to get$55 when you trade$25. K-A-L-S-H-I. CalShe. Trade what's next. 18 plus only. Restrictions and eligibility requirements apply. Event contract trading involves risk and may not be suitable for all investors. CalShe products are not available in all jurisdictions. Prices, values, and available markets may differ from those mentioned.

17:20For more information, see calshe.com slash regulatory. 500 orders a month was manageable. 5 ,000 is madness. Embrace intelligent order fulfillment with ShipStation, the only platform combining order management, warehouse workflows, inventory, returns, and analytics in one place. What used to take five separate tools, ShipStation does in one. Automate fulfillment and rate shopping to ship up to 15 times more with up to 90 % savings. Go to ShipStation.com and use code AUDIO to try ShipStation free for 60 days. Hey everyone, it's Chris Guillebeau here, host of the Side Hustle School podcast. This episode is powered by AT &T Business.

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18:41I'm ready to make a splash with clearer skin thanks to SkyRizzy, Rizinkizumab RZA. SkyRizzy is a prescription-only injection for adults who are candidates for systemic or phototherapy. At four months, most people saw 90 % clearer skin when measured from head to toe, and many were even 100 % plaque-free. People also saw significant improvement in psoriasis symptoms of pain, redness, itching, and burning. Don't use if allergic to SkyRizzy. Serious allergic reactions, increased infections, or lower ability to fight them may occur. Before treatment, get checked for infections and tuberculosis. Tell your doctor about any flu-like symptoms or vaccines.

19:16Now there's nothing on my skin, thanks to SkyRizzy. And that means everything. Ask your doctor about SkyRizzy, the number one dermatologist prescribed biologic and psoriasis. Visit SkyRizzy.com or call 1-866-SKYRizzy to learn more.