S15, BONUS EPISODE! How To Fail: Trinny Woodall on single parenthood, business failure and the empowerment of her 50s

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Masterclass.com/fail Hello and welcome to How to Fail with Elizabeth Day, the podcast that celebrates the things that haven't gone right. This is a podcast about learning from our mistakes and understanding that why we fail ultimately makes us stronger, because learning how to fail in life actually means learning how to succeed better. I'm your host, author and journalist Elizabeth Day and every week I'll be asking a new interviewee what they've learned from failure. Trinny Woodle was born the youngest of six children and sent to boarding school as a child. She was told she'd make a good secretary and to limit her ambitions accordingly. Although her background was privileged, it was also challenging. Her family went through money issues when she was in her teams. In her 20s Woodle fell into addiction and substance abuse. Largely she says to mask her lack of confidence. She went to rehab and eventually got sober at 26. She started out her career as a city trader before moving into marketing and then into fashion. Along with her friends who's had a constant time, she wrote a weekly style column for the Daily Telegraph before making the leap into TV. And what a leap it was. What not to wear was one of the most influential shows of the early 2000s attracting millions of viewers and I was one of them. And it spawned several best selling books in her 50s. Woodle made another career pivot this time into makeup. She founded Trinny London in 2017 and I own several stackable Trinny eyeshadows and wear her makeup every single day and wearing it right now. It really is brilliant and I promise no one paid me to say that the brand recently expanded to skincare. When asked in a recent interview what she'd say to her 20 something self, Woodle responded, I think she'd say thank God I lost my insecurity and thank God that your 50s are better than your 20s. Trinny would all welcome to how to fail. Thank you. That was very nice. I genuinely love your makeup. It's that's all I'm wearing. Lovely to hear that and I'm gratified that you have because I speak to many people you have or haven't tried it so it's so nice to speak somebody and they've had that experience. Yes and I really, really value how practical it is because recently with all the travel chaos with flying I've been striving to fly everywhere with carry on only and your stackable pots make that so easy. So thank you. Glad to be in love with you. I wanted to start the introduction that way and end it that way because for me it really shows how resilient you are and what a mistress you are of reinvention and career pivots. Have you always been like that have you always been able to change according to the circumstances and to make a success of something that for other people would seem like a really serious failure. I think it's very interesting the difference between reinvention and evolution because reinvention doesn't maybe suggest you're taking what you've learnt into the future and to me evolution dark so when I look at my journey I probably Elizabeth think it's how I've evolved. As a person and to an outside world it's like reinvented she used to fashion now she does beauty that's a reinvention which it is but I think you get to a stage that if something isn't working you've got and you have in you that passion to do something to change the world or to change up people think or to help people you then think what how else can I do it and there are definitely moments where you are so disheartened by what you have not achieved that you set out she even that period. Or you feel like in the instance when I you know stop being on TV in England and nobody wanted to have us on TV in England because there were other more exciting people who felt pressure that kind of picking yourself up and thinking okay what do I still have to offer and what do I need to develop and evolve to be something that's exciting and there's a kind of mix of both. It sounds like you're very honest with yourself then I am I don't know if I am all the time because sometimes you know I can walk around diluted about something so I can be harder myself in terms of what I haven't yet achieved or what I feel I should be doing more of. I can think I'm doing something better than I do until somebody says hey Trinny I don't know if you are so yesterday I was in a situation where I had to really challenge myself on how I was as a CEO you know how I was turning up as a CEO what what can I do to improve how I do that that is an ever evolving journey. When you get to be a CEO for the first time at 50 because you're bringing a lot of experience of life with you and you're learning about managing and delegating to a team whereas up to that point in my life I felt responsible for every action and every thought I had and it comes very different when you grow business because you are entirely responsible for guiding the direction of that business for the execution in the guiding of what you want to achieve. Is done by many people and you're trusting how they do it is integral to how the business grows. That's so difficult then because so how did you have to challenge yourself yesterday you mentioned that there was a specific instance is it to do with managing people because that's something that I really struggle with I very much struggle with the need to be liked but also having to have business boundaries in place. Yeah I think it's about learning to work with different characters and one thing I know I am like one thing that will I'll never not know and it's one of my talents is that I can read a room and understand what somebody's thinking even if they don't want to admit it I kind of know it because when you work for a long time where like interview over 20 years one of the things you've got to learn how to do really quickly. Is to create an intimacy in a relationship so you understand what that person's thinking and not being able to say and you want to try and help them get it out that's kind of like the best skill to have when you do make it and also know how to dress them but it's that fundamental skill if you watch something and it's an engaging program it's because that's in there there's an intimacy created so in this situation yesterday it was about being vulnerable to try and allow somebody else in the room to be vulnerable you know and we want to do that. You know and we will always come across instance like that where we can either just be the kind of strong boss or we can try and show some vulnerability which allows somebody else to open up and that doesn't always go according to plan you know but it's not weakness to be vulnerable and it's really important it was just a very emotional experience yesterday which is a real feeling. It's like you know when you have an unbelievably good cry and it's quite therapeutic or you have an incredibly strong emotional situation and it drains you but you feel like that sort of very heavy day for four days and suddenly it rains and it's much better afterwards it's kind of that great clarity today actually as a result of this and it's about sometimes you need to push those emotional situations so that. The cards are really laid on the table so that you can then just let it out wake up the next day have great clarity and then have the vision like today I have very specific things on which all about the future of the business and something else as a project I'm doing and I need to bring my best brain to the table today in what I'm doing so doing this is nice actually in the middle of my it's really important meetings today because it gives me a chance to remember what I have to offer because that's a little bit of what we're discussing. Yes, Trini that's so beautiful how you just put it and it's everything that I believe about vulnerability actually being the source of strength and connection and solidarity and I think that's very brave of you and you basically described having an emotional hangover and then waking up that day when you're like I'm no longer hungover. Yeah, let's just talk quickly about what not to wear I was a devoted viewer and many of those programs I mean I know we're in a different TV era now but many of those programs were deeply moving because clothes can be so important they can be armor they can be a misplaced defense mechanism what really sticks in your mind from those programs. Is there one particular exchange that you always remember there's more than one actually because you know the original what not where we made in England for BBC and it was a three or four seasons I can't remember and it was kind of very sharp edit have a hierarchy 360 mirror well secret filming lots of kind of points that you push in TV to keep the attention of the viewer. So quite sort of black and white undress I made with ITB and it was about going into a couple who had had difficulties and working out if they could learn to love themselves again totally different story maybe one that people want ready for but I so enjoyed making that because you felt you had an impact and all of those stories I remember every single one because they were once you know husband or wife wife gets breast cancer. Can't then undress in front of our husband for the five years after and it's the journey of how can you allow yourself to feel your husband still loves every part of you and how can we help you get that and how can we help the husband let the wife know that it's so relevant to him what's happened to her you still love so profoundly those things move you and they stay with you so I do remember those a lot and I remember that the most important thing for me with somebody would emotionally move forward if they decided when we were going to be in the middle of the world. So I decided when we did a revisit show on what not to wear and they were wearing 50% of what they used to if I felt their head space a change I felt we've succeeded. And then after that when we stopped working in England we had a magic nigger company we had a spank's company and the company in front set who you know we worked with said can you make a show in Belgium Suzanne and I were like well nobody's working with us in England will do it so we made this tiny show it was really stressful to make. They had a sponsor for the show that was clothing sponsor compromise our creative integrity it was really challenging on many levels we did the show but anyway the people who distributed it took it to mipcom and 14 territories bought the rights and you know our agent called up so they bought the rights and I said fine do we get any money and they want you to go to those countries to make the shows. And because we weren't making anything in England we thought why not and also we had more just pay we were you know main breadwinners in our family and we needed to go out and money and at the moment in England we weren't earning money so. We did the shows and that journey for me was the most interesting journey of all the makeovers I did and it was the most of the knowledge I gained that I brought into the business of Trilly London because. What it did is it took me to many countries with different cultures and skin tones and ages and attitudes towards women from India to Poland to Australia to Israel America Scandinavian lots of countries and in each of those countries whatever the religion might be or you know an India I dress a lot of Hindu women Muslim women in. Israel I was dressing also Jewish women and very liberated women there was this common theme of we get to a place sometimes in our life where we get stuck and how can we move forward and so I've always carried that and thought how can you move somebody forward it might be the smallest thing that a girl was the star of her class university and she goes into a job and she suddenly feels tiny fish and huge pond and who is she you know you might have a woman who. Has got to a station life where she has many people around her who all want her to be a certain type of woman and in that she loses sight of who does she actually want to be and present this after the world and so. So many of those women were incredibly powerful stories and stories I will remember always because they were women having to make a huge shift in their life and where do you think this. Drive of yours comes from I mean if I were going to play cod psychologists for a minute the fact that you were sent to boarding school at such a young age I think you were six you were also the youngest of six children was there part of you that felt. A lack of confidence in your own space in the world that wanted to feel better and that therefore wants to make other people feel better would that be fair. I would say that's because yeah I'm going to school it was a very different year this is a six years but I didn't have a close relationship with my parents because they had a very old fashioned approach to bring up children. And one of those was also the boarding school is an option that quite a young age would you look back on that and I think I thought of like six and a half what I ever said school you got to be kidding. I don't blame my parents act how it was but it did definitely make me feel what can I do to make people like me you know and at school I wasn't academic at school and I was quite good at acting I wasn't really good at anything else. I got very bad at level and a level results and I was terrible at sport and I was sick of it so I couldn't be in sports so at school you're kind of there's kind of academic sport or sort of drama so drama. I had a win on but I wanted people to like me there was probably an element of being rejected by elements of my life and so I found this first years of school quite painful I had to when I moved school I stayed down a year so I kind of struggled to really make friends at 10 11 when I moved to another school that my sister was at and and then because I am I academically was really bad the people I painstakingly for the first time in life made friends with move to the next year up and I had to start over. I remember that time I felt very challenged by that and and working out who my friends were and and to begin with it was just to have a friend and then it was actually getting that little bit more of confidence thinking is this the friend that I'm really getting on with or actually is it just for the sake of having a friend you know so there was a lot of quite lonely feelings until I was probably about 15 there was a feeling of loneliness my all my brothers sisters had kind of left the home you know so I see them in holidays but not really. During school that much so I did want to always have something that people would like about me so I was quite good at sort of looking at people and saying oh if you tweet that your uniform and put a bit of makeup on and then people would say "I'm really trying to make sure what you think and I loved it it gave me such a kick to feel somebody needed my opinion that literally that basic." "Are you shy? I'm confident and shy and they can be two linear things because I will go to a big event and love to spend time with the new if I feel I don't know if I've said anyone to talk to you to hear you know just because I just feel uncomfortable to stand and look for people I know and sometimes you know I'm really tall so it's easy to be able to get a good feeling. I always wear very high heels when I go out now not so much because I know I'm going to take it but it would help me see people in the room that I would know. You know I was when I was up to about you know in my 20s I was really shy but I'm also confident I also will and this is probably in the last few years if I go somewhere now. I will just go up to people and say hi I'm Trini who are you and I just sometimes my daughter is embarrassed by my awkwardness when we're in a place or standing next to somebody I've never met for and I'll just chat to them and I think you do that having come from a sort of TV world because you just begin conversations and she can't understand why I'll just begin conversations with strangers but I enjoy it. I enjoy seeing what makes people take a lot and and every time you start a conversation with somebody you just learn something else about human nature and I like to always be doing that so those two run linear. I love that I think we're so similar in that respect I'm also tall so I'll see you at a party hovering above the heads of everyone else. Exactly. Let's get on to your failures. Your first failure was the launching of your 1999 business tell us what that business was and what happened. It was something that I used to write a column in the telegraph for years and then we did a show for Grenada which then didn't get picked up and then I was just really interested in the internet Susanna not so much actually. She loved writing and doing the column and but she was also becoming a mom and things and I kind of was obsessed by it and I just felt it was exciting and I I'd always been a bit techie. Like my very first job I had an apple literally a few years off they were made you know when I was up 20 I was obsessed with the whole modern technology element and I remember some I made a connection that there would be e-commerce online that I wasn't by the stage. But I felt there's going to be what I did know and understand compared to writing a column in a newspaper is you could do something and it could be seen around the world and I love that that your audience was global in a flash and that was not at that stage something that was present. So I kind of felt if you could have a portal and I remember one long weekend I did some weird cleanse I never do cleanse is I didn't give a shit about diets but I just for some reason did this thing but it gave me great clarity I drunk this disgusting stuff out of a bottle. I don't know why I did it but I did it. I think I was doing a thing of trying to have a child and that I was trying all different things you know cleanse your body of sugar you will be able to give me more fat out whatever it was I was trying. And I kind of had this real epiphany I felt I want to create a destination I had such a clear vision of what I wanted it to be I felt I wanted it to be all areas for women I knew I'd have a focus on things that people knew must for like clothing and makeup and style. I knew that the biggest frustration for women was that they would buy things and they wouldn't fit or where could they find things that was the lack of where can I find something so I had the idea I wrote down 20 pages and I said Suzanne I think we should do this and then we took it somewhere we took it to Cape Le Whilers who were only because I read they were doing ecommerce platforms. I had a marketing person though we co-could them they at the time were wanting to do things for women online they didn't know where they were heading and she said what you need I said 500 grand because she's only kicked me on the table saying are you insane I had no idea. Two weeks later sends me an email the woman and says I don't think you got the right amount I think you need 650 grand. So they give it to us and then with that I think oh my god so this is the point by which I then did things very differently today with Trinny London but I thought immediately I've got a great idea but I have no idea. I have no idea how to execute this idea so I need to find people who know things better than me so I also my brother who is good as finance to be CFO I was founder I got a woman in from Barclays to be CEO because I thought I don't have run a business I'm sort of creative and founder we then raise 7 million from to the seas in two and a half months quickest raise I've ever done and hired women very quickly predominantly female we had hard coders we did poll code here at the time so we had a lot of people in tech writing the community. We developed technology that would show women's body shape and you could change it was really advanced technology I remember game see sex sites sex club yock dot code UK because they have the best animation in England on online and I'm getting to his office and you know they were literally other rooms I said what's in those rooms I saw polls you know it was so funny but it was the thing that the sex industry then were the most visual animation of anything online and I just found interesting so I thought that was a good place to go. I talked to them anyway the ideas were big and the execution did not allow for a lack of e-commerce starting in there for no way to monetize and after about a year we then went into sort of dot com boom went to dot com bust 2001 and it was really changing the industry the reinvestment was really challenging we had no path profitability and we had to close it so I had to close it after about less than two years and it was so painful because I had become during that process it had become my life. Susanna had children so she was in the business not probably as much as I was because she was pregnant having babies you know I would be calling her at eight I didn't want to say where are you said I'm breastfeeding. I was able to come and quickly please I had no comprehension of what it was like to be a working mother because I was so obsessed and it then I had to wake up the fact that we wouldn't be able to get financing and we had to close it and I had to close it by myself Susanna was having a baby and her second baby or I don't know and I just remember moving the office tried to negotiate the contracts all the big players who've worked in the business left so it was kind of then suddenly up to me to do all the things my seat. I do all the things my CEO and CFO had done and I want to make sure the team had a good severance pay so negotiating with our investors it was really challenging and I remember I sat in this tiny office with two people in the business thinking what next what am I going to do and I'm feeling at that stage what have I got to offer because I did still did the columns the telegraph but I made my my vision of what I my life should be so much bigger than that the telegraph didn't seem much it was great I had a bloody income. So it was really great but my vision had been popped so you know I went abroad and I went on a retreat in Arizona at this place called cottonwood which did you know retreats people in recovery and I did a week retreat and what I learned for the first time then which I try and do more of now is that I had to bloody well live in the moment. You know I live so much in what I've done what I got yet to do that I hadn't cherished the present and I hadn't really made the present weighty to give me that feeling of a grounding to not have that sort of imposter syndrome I'm going to be found out moment so in that week it was not believed in intense weeks I came back Elizabeth and I was like I'm open to whatever is going to happen next not like let me grab around and try and you know make something have which might not be the right thing for me and then I got a call from BBC so fascinating there are so many questions I want to ask you because I've never gone through that kind of business experience I wonder what it feels does it feel like grief or does it feel like heartbreak does it feel like humiliation like what what other experience would you relate it to or is it just entirely unique. I'd say the thing at least felt like what's humiliation because humiliation is a public condemnation of what you're doing and you know I had to do an article on the after you say we've gone into a nation. I just felt so sad it hadn't succeeded because I really the thing was Elizabeth I still believe the vision was right so I think that's what saddened me the most that I had put my faith in people I'd employed who are really qualified and they had glided in the business and hadn't grafted. So I actually looked at all the things I would do differently if I ever did it again even at that stage I thought that so when I came to start Trinny London I thought I'm not going to hire really over qualified people too early who would take me on a journey of where they think they visions should go and I need to have the face of myself that I know our consumer and I know where the business should go and that I will hire those people when I need them to help me execute getting it there on my vision. So that was a biggest change and that I knew I needed to not want to be all things to people which we wanted to do too much at once then starting eight channels but start with a core so in terms of verticals you know then we were doing clothing make up cookery home where everything it was just you know what you folks on this a consumer so to me I knew I had to start with one I have six verticals I wanted to do for Trinny London but I had to start with one I had to prove that vertical to myself into investors before I started on another. And well the business that way so there was so much I learned but at the time when you talk about what was my core feeling it was just heartbreak it was like having to break up with somebody or in love with and not one of you is leaving the other but knowing you have to break up which is the most painful way to break up. Yeah and you mentioned that you went to cottonwood and that you were an art in recovery were you ever worried that the pressure or the stress of that situation would cause a lapse in your recovery never never I mean I feel that when I was in very early recovery I quite a few like four of my very good friends didn't make it and I had a really profound sense that I have one life it really like you know that has never left me so the recovery I have now is my interpretation recovery but I have a spiritual path I have a sense of I need to have that time to have a sort of meditation in my day I need to write a gratitude list of you know things I am grateful for as a person I need to challenge myself and my character traits to know if I'm living my life with integrity some days are really good some days I'm shit at it so those elements I carry with me now but at that time I just think I've never ever thought for a second in you know I was 1990 that I would go and let's become you know cocaine addict no. I have to say I'm finding it so calming speaking to you I find you very calming and wise and I'd expected a lot of things in this interview but I hadn't necessarily expected that sense of calm I've got my because of what happened yesterday well yeah it's so interesting that it's I mean I suppose it's part of that linear duality which is actually complimentary that we were talking about that being confident and shy you are calm and wise and considered and you are also training on Instagram who is this ball of fantastic energy makes me want to buy everything in Zara and get it tailored I don't really have a question there I just wanted to comment on it but my question on this failure my final question on this is about money because it strikes me having done my research and read a bit about you for this interview you've gone through several times in your life where you have lost everything or almost everything that must have felt I imagine very insecure and uncertain so what's your relationship with money like does it scare you it's complicated I was going to say to you because you said to me at the very beginning if this is anything you need to change or take out let me know and the one thing was that when you say things and interviews over the years they get this interpreter so my dad didn't lose all his money when I was 18 but what happened was we had this very very privileged lifestyle of living between a few countries and then when I was 16 17 there was a big change you know you still own to home I would say I would say the height of my father's business success was sort of 30s 40s and then 50s there was some changes in his life so what was very interesting in that is I saw that you know in my life and I saw the effect had on him and the changes he had to make to his lifestyle as a result from what he had achieved very early I took that in I've taken that in Elizabeth and it affects some decisions of how I think about things today there are a lot of people who have success certain stage and we might know this and know that we have parents who you know are at a stage where if they're alive they've had to compromise the life they had because they're older and their financial planning was different and so you know the ability to leave a consistently great life that you want to have for yourself whatever that entails for you as a person financially or just moralistically or whatever you know I want to have the freedom to do that and when I was younger you know there was a time when my parents never pushed me to get a university or to do anything and my sister you know had a lovely apartment in central London and so when I was 18 I kind of knew I just had to start work and most people start work at 18 when they go to university but I sort of first I didn't have smart enough to go to university but I kind of knew I also had to go in our money I had a Saturday job when I was 16 to 18 cutting meat in parched it you know I did that because my memory is always really bad but I know I needed to do my pocket money because I wasn't necessarily getting pocket money for my parents so and I would start businesses at 16 at school I started a business you know called Bose unlimited so there was this part of me that knew I wanted to be an entrepreneur but I also knew I need to earn money and when I started my first job you know I paid 8000 pounds a year as a salary that's probably what most people paid if they didn't go to university so I've always wanted to live beyond my means in so much that I love lovely things I love clothes you know I love to waste my money away on clothes whatever it might be I just love them like people might love to buy themselves a nice sofa or telly or a car or I just like clothes and that's something that doesn't earn money as you as you buy them so I've had periods of my life where I've had lots of money and I've been the sole breadwinner and I've been supporting quite a few other people in my life and there's been periods of time where I've no money when all my friends around me have been earning quite good money and I've had to kind of work that one out for myself so it's very interesting our relationship with money you know to me when I look at the possibilities of financially where Trinny London could take me there are some founders who have a vision which is a very financially driven vision and some founders who have a vision which is a sort of spiritual vision and my vision is one where I want to feel at some stage where I'm not too old Elizabeth where I feel that full financial freedom that if I could work from tomorrow I wouldn't be changing how I would like my life to be it's not that I'd suddenly like to take a private jet or feel I always travel first class around the world it's just literally kind of sort of basic things I think when you're 20 or 30 you might think I want to be a billionaire and the value of a company to be a billion and I have a vision for Trinny London which is about I want it to be an incredibly successful company because then I feel it has an impact on so many more people so the bigger it is the more impact it has and I know that as a business you know to many people who are customers of Trinny London we're more than a beauty brand we bring them something else and I love that there are a lot of not-for-profit businesses and our concept of not-for-profit is that we want to be more than just a product for people that we just want to make them feel better about themselves and even if they never bought a product from us that halo effect of what myself and Trinny London represents to women is something that I want to be global, fully, fully global as a concept money is a complicated thing yeah it's fascinating here you talk because I recently had a realization and it comes from the freelance life which I know my background is also print media and I know you'll understand this it comes from that fear that if you say no you're never going to get an offer again and I realise that actually the bulk of my stress and anxiety comes from that mindset and I had this moment where I thought how would my decision making be different if I chose not to worry about money and just as a sort of hypothetical exercise how might I change my answer to that thing I'm being offered and it was a revelation because it suddenly became so much clearer what did you then do for that to get yourself to that mindset and do you think you're successfully there it's a process the reason that I got to that point and this is something I'd love to talk to you about during the course of this conversation is because I'm on a fertility journey that has lasted the best part of 11 years and as you will know only too well that someone who did lots of IVF yeah and I salute you for that like stress is one of the major things that you keep being told you know you've got to get ready and you've got to calm and you've got to be ready so that's where the thinking came from I was like I need to make a change in my life because I can't operate this level of adrenaline stress so then it was about working out why I was stressed and I was like well I'm so busy and I feel like I got and that came from fear that it might all go away tomorrow and it did change like I quit a job after I had that realisation because I thought okay if I'm not going to worry about money what out but does it bring me what does it bring me and that actually it didn't bring me enough spiritual sustenance to do it for that reason so I think I'm getting there but I don't think I'm there yet I mean I the same things to one side because I feel that I remember when I was on that IVF journey and you know for the first few years of it I was very stressed I remember being on set at what not to wear and you know two times I lost a baby on set and it was quite a lot of the right experience and that was probably many reasons Elizabeth Y1 does Miss Carrie and I remember always my very nice IVF doctor said that embryo is like it's in a hot avenue you know it's so protected it's not falling or it's literally but there is something that we feel that causes through our veins of that feeling of when you're stressed and that causes all adrenal release and I know inherently that's not great for getting pregnant I just know that whatever a scientist might tell you there's still that part of that thing so releasing ourselves from pressures that we put upon ourselves like that kind of our vision of what we feel every August I had what you had you know because I had TV contracts and book contracts and column contracts and every August it will be will I be renewed and I remember August was never a time I could go and relax and have a full sum of holdings I was waiting to see would that contract be renewed and I lived that life for 18 years in the industry of that your any as good as your last book as your last column as your last TV show so it's a very difficult way to live but it also the more feared you are the less faith you have in yourself to know that you're good at something and it's about how do you go it's like there was a wonderful book called Fear the Fear and doing it anyway which I read and read many years ago written in the 50s or 70s I got and it is that feel it is like when you do meditation you know the thought comes in and just acknowledge it and let it go where it's going and that's my when I'm on doing healthy days around fear it's about okay I'm feeling fear that's okay but that is that voice inside my head which is not the core of me you know because as soon as it articulates itself it's no longer me when it's just me laying I feel it's me but when it articulates into negative messages that's when I think can you shut up now and just go and be quiet because that's not me and I have to remember that until days I do and some days I don't but that you know thing around money and thing around the fear of financial insecurity which is what we're really talking about is days that I can be really like you know I kind of already have what I need in a way I sort of think I don't because of some weird circumstances but yes I could have a life at this place so why can't I let go of what that need is or that amount in my mind to have that total financial freedom it is above a certain financial point totally a state of mind You know those times late at night when you're scrolling and you see something online that you've been looking for and you just need to buy it right there and then you click on the link you add it to cart before hitting check out but then that sinking feeding as you realize you don't have your card anywhere here and don't want to get out of bed but that's when you see it that purple pay button that has all of your information saved making checking out as simple as a quick tap of your screen Shopify is the commerce platform behind millions of businesses around the world and has so many benefits you can set up your own design studio use Shopify's AI tools that write product descriptions and even enhance your product photography you can get the word out like you have a marketing team behind you easily create email and social media campaigns wherever your customers are scrolling or strolling see fewer carts go abandoned and more sales go sign up for your one-pan per month trial today at Shopify.co.uk/fail go to Shopify.co.uk/fail I don't want to move on to your second failure without acknowledging your loss and how traumatic and difficult that must have been to go through two miscarriages on set at a time when your friend and co-host is having babies seemingly with ease I haven't had that direct experience but I've had a lot of experiences that I can relate to that on a cellular level so I just want to acknowledge that and I know that we're going to get on to your beautiful relationship with your daughter in your third failure so I'm going to park that for now and go on to your second failure which is your failure to commit to yourself which is a fascinating one and you mentioned that business that you started at school Bose are limited and this failure relates to that tell us how. Because at the beginning of any sort of entrepreneurs journey or when you have an idea you just see everything you want to do and when you were with somebody else you're harving the dream and harving your responsibility but you're making it conditional upon somebody else too but you know we had this idea I don't even know who had the idea first actually it was just to do these hair bows for instance Diana was around she had these lovely hair bows we went to Porto Valermarca got broken we got lots of fabrics made these bows you know walked around London selling them we were still at school and it was a sort of era where it was a fad but we sort of bought into it and I really wanted to do it and I liked it and then my friend who would want to go to art school when she left school selling and to go to art school so I'm not going to go with you anymore and I gave up on it because I just felt do I myself have the ability to follow through on this and I decided I didn't there was lots of good learning in that but I just let go of it now it would have been a tiny business which probably would have just stopped anyway if you later because it was just a one trick pony and I didn't have enough life experience to then think what else could it be and I was very good at starting things not finishing them and my mother in her life started so many things I never finished them I did actually think of that I'm just like my mother the amount of writing paper I'd find of my mother's with different little company names on it you know my mother was magnificent but also she had some traits in her that I didn't respect very difficult things say that but I or I didn't understand or appreciate because I think different spectres were really harsh say about your mother it was easier to say oh it's not going to work because I kind of my mother was like move on to the next there was a little bit of being my mom in this I don't know I did do a few more than one you know because I did another one called Socket you when I was then from one great yeah I'll Socket you I did it with this other girlfriend who was kind of a trust fund girl and I wasn't kind of thing you know I had to earn the money but she sort of so we did that with her flat and it was about socks I went to butter in the East London we got these socks made and I got all these lovely girls and they went on the trading floor I had lots of friends who are on trading floors and they would go around with the baskets of socks and I just what do men need the most that they have time to buy it socks and so you know they went and bought the socks of these girls and the girls I made sure all pretty and flirty you know I was a real feminist at the time but it was just they were lovely girls you know just kind of naive sweet girls and all the men fell in love with them and said let me buy 10 socks instead of 20 so they could chat to them five minutes longer so really really pleased me and correct now and you know I love that business and then because I wasn't experiencing business there were lots of problems came up like the socks really ran in the wash the elastic of the box I went so you know I had all these disgruntled calls you know we didn't have customer service department I was a customer service department and it was like you know I want to refund on my socks I'm working or you know and it just then peaked it out but we by the stage in that midst of the success it ordered so many socks and I remember for like 20 years we kept finding another bloody box of socks in an attic or back of a garage I was saying something and it was like the reminder of this failed business God, normally God that was one of my worst ideas really I mean you say and you say this quite frequently actually that you're not clever and I beg to differ I think you're super clever and smart to have these ideas and that creativity and just be brilliant at ponds but what do you think that those experiences taught you about imposter syndrome? Do you still have imposter syndrome? I'd have maybe two days a month where I have imposter syndrome as a CEO in terms of as a founder and a vision for a business I have no imposter syndrome I know exactly what I want to do I know exactly what I want to off people I know exactly what I want to create for them and I'm sort of most unwavering in that I have most of my belief in that and sometimes it will help me then feel a better CEO so oddly in this meeting I was in this morning after this you know post monsoon of yesterday I was quite quiet in the meeting and then it was talking about you know lots of people about things future of the business and I just you know started to talk a lot about my vision for the future which I hadn't for a while because I'd just been so caught up in day to day stuff and afterwards some people who work with me just were like really excited you know and I just thought I have it in me here it's here that's what I'm really good at and then that allows me to acknowledge that makes me a good CEO because you need you know CEO notes to have vision of where that company is going to be in 5 or 10 years and I have that I know that it's just the little bits in between on a few days a month that just like I question am I doing the right thing here and I think if I ever met a CEO who never questions themselves I'd be really worried about their ability to CEO I'd say that because you need to question your decisions but then once you commit to them you need to commit and sometimes when I'm just a bit flaccid about my commitment to a decision that's when I need to like hey Trinny give yourself a kick up the ass what about Instagram Trinny because I feel like you know yourself completely in that form so do you I'm assuming you never get in post-acindrome when you're doing those star videos that have amassed you over a million followers B.L. yeah never very different audiences too because like we have an Instagram one which is a million Facebook is two million actually and Facebook is really interesting because Facebook you have the ability to have a two way conversation much more than Instagram what I find most exciting about social media is that I started doing it and I went straight to kind of video like in 2017 because I didn't know you know take a nice picture I did that for a few weeks on Instagram and then I just actually thought I just want to chat and it was I think I was quite early to do video and as a result you know when you were going through the feed suddenly this woman's jabbering away about something it arrests your attention so I think that from that especially on Facebook which is all just posting pictures of dogs and cats and memes in its early stages it was kind of like we got this very big following and it creates an intimacy it's a place one can be very intimate and it sounds such an oxymoron but when I do do lives and we accelerate a lot during lockdown so I'm going to be at home and they were consuming social media more and I just have a conversation about what I was feeling at the time and you know if it was a shit day I'd go on say shit day I didn't want it to be too contemplation as the belly because I think you need to be there to give something to other people and I see the purposes to give something and share things with other people that help them there are very few days when I went on to home myself because I was feeling shit and I knew having a good conversation people I'd never met across the world but who I talked to consistently for a year during lockdown was going to help me too you know but I've always felt in my life that if there's something I discover that I feel is interesting and helpful to other people I want to tell everyone about it you know there are people in life who want to keep it themselves and I'm somebody who I want to share it and sometimes I overshare those things but I do feel passionate about things I love and I think are useful or make you feel happier and so I think that I never plan or rehearse and as a result when people watch they know that's just literally a stream of consciousness it's not edited or filtered or anything and I think in the world when so much is edited and filtered that maybe that's broken through and that people feel that's going to be a you know whether I like her opinion or not it's going to be a conversation I might listen to a couple of minutes and I enjoy doing it too and I think that you know we have a very unique community at Trinny London because a lot of communities when you build a business are manufactured by the business or it was a community was then turned into a business but our community is very different and it's our harshest critic and our biggest champion and there is no money that exchanges hands and there's just giving them tools to make them feel better it started with a little woman in North West England called Kelly and she started this fan page on Facebook and she followed me and then it was at the time I was starting Trinny London so you know she said anyone else following Trinny and what she's doing and she got so grouped together and then all these other sort of groups appeared and then when we were the business was growing and one of the people who were at social media said Trinny I'm finding all these other sites did you start them yourself what are they you know we found all these sites so we got in touch with the people who admin the page and we said look this is great you're posting all this stuff and you're taking a little bit of Trinny's phase or a bit of the logo do you want a logo you know we can give you a logo so you can all talk to each other so we created this logo they call themselves a Trinny try we wrote Trinny try and then we started communicating with the people who run them but we said do you want to have a kind of charter you know have some premise by which you post and don't post so we created this charter of what we wanted these pages to be that they would never ever put down any other woman then nobody would try and sell their sort of home bait cookies on the side that it would be a place you encourage and support other women and you talk about stuff you are liking and so it is that and you know it's a place where we now have 33 around the world they're in 16 countries some have 500 members some have 12,000 members they post every day I look at them every day all of them there's a global Trinny try and there's lots of local ones but you know I see people saying I've never posted a picture myself before but I feel safe enough to do it here and I put this out for Don because I want my husband to love me again I mean you get the most intimate stuff there and it's an incredibly special community and I feel very privileged and so pretentious I feel so happy that community is there and that as a result of something I'm started that community has blossomed Trinny it's like everything that you wanted at school on social mass level you've now got these two million it is that it is that and then there's people on there that you know there are thousands and thousands of members of this community as well as social media followers and I see them there's a crossover but there's definitely a difference in the depth of their connection with us but you know some of them are really following some very special journeys as a woman in Holland who was totally agrophobic and never left her house and through following and engaging with myself and the community she now has full life you know endlessly we will get messages from people and I think that also when you're building it we have a team now of like 200 people at Trinny London and there's a very big team that look after community and we get 10,000 comments a week through the different channels when we answer every single comment we're very rare as a brand that we will answer every single comment that people send and that takes a big management of a community team but it gives us a sense of what are women thinking and feeling and what's worrying them and how can we help in this situation and you need that barometer whatever you're making as a product or selling to people you need to understand the barometer of how people feel at that moment in time and what you're doing for them so it's invaluable to all the people who work also at Trinny London because they then hear these messages so just for their some days it's a really tough long working day at Trinny London other days we have the county flush of ceaning so we launched new product and it's like a carnival but when they hear this stuff from women that could properly because we have a very young team to an extent of Trinny London compared to you know our consumer is 35 plus and our team is you know I'm the oldest by many years in the company and then there's maybe a token few people who are 50 and most people are 40 a lot of 30 and many many are 20 that they feel this could be their mother or their aunt or their older sister and it makes them feel great that there's a purpose here that isn't just whatever their job remittance extraordinary let's move on to your third and final failure which I found this tremendously moving even to read so I don't know what it's going to be like to talk about and as you put it it's failure as a single mother tell us why you chose this I think that you question yourself more as a single mother because there isn't somebody else in the room to share the joy the pain the worry the torture whatever it might be of bringing up children so you will maybe say more often to yourself have I done the right thing you know and there's a few instances in bring up Lila where I've questioned did I do the right thing and is it a failure it's more I've questioned whether I've been a failure in it so with the relationship I have with Lila now and the girl that she is I think I'm really lucky that she is where she's at you know it's more than luck it's also that I've done something right but there have been times when things happen where people would look and think she shouldn't have done that that's been when I've really questioned to myself whether I made the right decision because you're I mean you're a single mother twice over aren't you because you split from your ex and then he died by suicide so that must feel profoundly alone profoundly single yeah it does I think when you when you get separated because you got separated before he died he wasn't so well in other areas Johnny but there were times when as a separated couple we were the best parents when you was well and I really thought how lucky am I that we are so close that we can be incredibly supportive to each other in bring up Lila so when you make a decision to separate it's the hardest thing to do when there's nobody else involved which there wasn't either of us but it was just something that I I felt that had to be done the loss then of somebody dying that way when you didn't expect it and then the removal for that child of their dad in a very harsh way and also my stepson who lost his dad too you know he was 18 19 even though you might have many friends and you know lots of little things that were there like I have a brother and you sort of think the uncle will be like the dad but he then was it living in Australia so I kind of thought who's going to be the man that I feel Lila needs in her life at that time was feeling more traditionally that every child should have a mother of father then you can actually know it doesn't have to be a mother of father what it has to be as two people in that person's life who will offer them different things and when Lila was since she was born she had a nanny she was returning that's called Jenny Jenny then every year I also stay because I was when I stopped working in England I worked abroad and I had to go and leave on a Sunday come back on a Friday so Johnny would look after Lila at home but then when we split up he would have her two nights a week and then not have her at the weekend it was very kind of weird raw reversal of husband and wife but Jenny was constant she was there Jenny is weirdly like Lila sort of grandmother mother and my mother had Alzheimer's so towards you know when Lila was growing up she wasn't a grandmother grandmother and I was sort of mother father but what it meant was Lila had that kind of unconditional I know what food you need to eat now and I think that's the only thing which was not me she had life lessons unconditional love a little spoiling and dad kinds stuff from me and so it has allowed her to be really well rounded she's in a way an only child and I think the one thing of an only child even though she has her brother who's like 10 years older is that they have this self-confidence I don't think if you're one of a few you have always kind of measuring yourself up or being measured up or you know it might mean then that you don't try so hard to so much in life but I know many single kids who are very successful but I look in wonder at Lila at the age she isn't think you so believe in yourself because when I might say you're so what ever she goes I know mommy and I'm like okay even though it's the weirdest upbringing you had and the most profound things happen to you and sometimes I think you know you didn't have that classic let's all sit around the table as a big family with lots of kids and a mother and father I said this somebody last night and discussed politics and and life stuff that might have been boring when I was a kid to listen to but it gave me a certain amount of education but she has not had because we didn't have that upbringing but she said other stuff and you know having the impact of something really big when you're younger makes you in some ways grow up a lot and in some ways remain a child for longer was she eight when her father died? she was nine she was nine yet that must have been such a difficult conversation for you to have with her yeah it was it was I was very lucky because when it happened she was at school two policemen came around to my house and told me and sorry now I'm so sorry I'm so sorry my sister came out very quickly and she was very offensive Julia Samuel who's fantastic grief therapist and wrote wonderful books called this two shop hours and two books on grief and she came around before my daughter come back from school could she tell me what to say she gave me the words "trenny I'm so sorry I'm so sorry you are amazing what an incredible mother mother father as you put it for Liars to grow up with you are clearly such tremendous father apart from anything else and we see the love between the two of you on those Instagram videos a joy for us all to behold you are so incredible for what you've got through and who you are and how all of this trauma that you've been through has shaped your extraordinary outlook on life it is honestly a privilege to witness and I'm so honored that you shared that with me thank you so so much and I wonder if I can ask you something else which is more for the people going through fertility issues right now and a lot of them I know listen to this podcast yeah partly because I've spoken about my own and I know that you went through nine rounds of IVF before Lila and another seven afterwards and I just again want to pay tribute to the courage that takes the Titanic level of courage but for any of us you need little hope is it worth it Trini like when you look at Lila now all of the pain and all of the courage that that took do you think oh my goodness thank goodness I kept going the time in which you decide you want to be a mother or what makes you think you want to be a mother and that's a profound thing to think about because I didn't think in my 20s I'd never burning sight of your mother in my early 30s I'd never burning sight of your mother Susanna was being a mother and I found it in convenience to the growth of our business but did you find it painful as well it must be well I found it irritating okay let's be honest I really can't did I found it irritating then I sort of woke up on day whether we call it biological clock or whatever I just thought of 35 and I thought I really want to be a mother maybe it was when I sort of let go and got over all my mother issues whatever it was but I just had this I want to be a mother now and I had that object sex for like 10 years okay I'd never got pregnant so I sort of knew I couldn't get pregnant actually for years but I never thought how much I want to be a mother so when I made that decision I went literally that day to IVF because I knew there was a problem and I didn't know what the problem was but Johnny and I had never conceived so we went and you know we had really like one day Johnny's sperm would just look like they were dead the next day they were swimming the parking time you know the channel so it was like okay I think he's fine but it would be very different one rating for the next and this is also like 2003 so fertility has come a long way but they said you have unexplained infertility, such a very casual isn't it and so I just started doing it straight away and at the time I was earning quite a lot of money so I do it it failed I do it again I mean I did like five in a year oh my god like you know the gonal F was like in my five and I was like the professional I mean when I very first did it it was like Johnny got the surgical gloves on with the dead the injection you know by the time I was doing the fist time I was like oh you know whatever so it became mechanical and I remember when I once did an interview then when Johnny was alive and they said did it for you were mainly and I was like a bit and Johnny was like so fucking much I think it was properly unattended to a really hormonal cow and I think I was very very difficult to be around and each time it didn't work so the first time it didn't work the second time I got pregnant then that one I just lost lost and then I waited like a month and then I did another one and then it didn't take and then I did another one and it didn't take and then I did another one so within 18 months that was properly and then I got pregnant again and I then had to give birth because it was you know I don't know why I had to give birth I had to give birth and sorry was that a no? because there was some problem but he just said I can't do a DNC you have to give birth I can't remember why but I just remember this kind of I have to say I have night to bed at the start list because I just think you can surprise you just kind of then like you just like on the poster and then I did three more full IVF and then I had frozen some of Johnny's sperm we're getting really detailed here but if everyone listens to this for an element to the day I'm sorry to the boys who were like whoa but this is like a girl's track and fight the boys tap because they have to go through it the other side if you're in a relationship with a man so Johnny was away Johnny was away at a rehab you know that's where our marriage was at and I remember Dr. Ren called me up she said Trini I've got some of Johnny's stuff do you want me to throw it away or not and I was like I don't know what's going to happen in life I said I'll come in just shove it in you know so I remember went in put my legs in the stair shopped it in and I left and I literally left and stopped thinking about it I was like and then you know months later I bled I thought there we go again you know I was just like because things weren't great on lots of levels I was like and then I remember I get to the next month and I think oh I didn't get my period and Marry Ren called me up she said Trini why haven't you coming because usually I was like day 11 I was like can I come and stay when you go to wait till day 13 you know and she called me up to Trini it's day day 100 and I know it was really later what the fuck's going on and I was like I've lost it she said just come in and I was pregnant and I was like oh my god and she said okay and then she said if there's man in Wimbledon because she said you have to go and do all this anti-miscarriage thing so I take this horrible steroid injectors every day I hate you taking and they stung me and I was like off I really thought I don't know if I'm going to be able to keep it but I then went to America and I did the Oscars with Susanna were both pregnant and I immediately called my obstetrician and I said I'm bleeding and I really thought I'd lost Liner and I remember I came back from America and I went straight to Samaritan and he had one of those mobile outer sounds I think I had that inevitable feeling I've lost the baby just like this sort of flat feeling and then I heard her heartbeat and then I was like oh my god you know I so didn't expect to hear her heartbeat I think I had a scan every two weeks because I she was also the wrong way round and upside down and she was born with with tallies and both her feet so she didn't push her feet out that much because she had very you know that all her feet had to be broken when she was born and she didn't kick so most moms they always hear the kick and feel the kick and so she that kind of I never knew she was inside me easily and then she was born early because I lost water and she was born sort of Martin Ard Valley I didn't know what kind of mother I'll be like when you spend that long and Elizabeth you don't quite know will you be that natural like I had Susanna as a role model who to me was this most incredible mother earth mother the kids came first she was but she didn't sort of treat them preciously she was like sort of get on with it country style upbringing of don't be precious you know brilliant mom and she taught me a lot about being a mom I mean she had three by then and I had one so I was obviously always going to be more precious with Liner yeah she taught me a lot I think what made me feel fully maternal was that I breastfed Lila for a year and I did start working after three weeks of having Liner and when I look back I think do I wish I'd spent longer not working but I kind of didn't have the option because I need to earn money and I was the main breadwinner but there were times when I was in America doing a TV show living in this house and there were cables everyone genuinely would come up it's like go breastfeed and take her away and it's just like the weirdest thing but that breastfeeding of Lila that moment of intimacy at the beginning of the end of the evening which I had for a year of just whatever else and however full life was because of the circumstances of our life I think made me so close to her in that very very raw level when you just look at your baby as it's feeding so I learned to be a mother in that first year because when you're not ready to be a mother and then you think you want to be a mother and then you you try to be a mother and you can't be a mother you let go of the fact can you be a mother I totally totally understand that and you think so much about it and you hear so much about it from other people that it becomes stressful in and of its own right thinking I'm fighting for this thing so hard and I don't even know whether I'm going to be any good at it yeah exactly that and if you're somebody that by nature is such a fighter you're a fighter I'm a fighter it's so hard to then decide do I let go or not because this is fight for the sake of I need to fight for this because I feel this is a fight I should have not is this a fight I want and the hardest decision is for those people who decide IVF is not the right route then there's a route of is it that I really want to be a mother so there are many other ways of being a mother and what does that look like and then you sometimes don't know do I want to be a mother or do I want to be a blood mother and how different are they to me as a concept I have friends who are all those things they're surrogate then nothing to do with the baby physically they didn't have it even inside them they're all are mothers I look out to all mother in a different way who are really love and respect and it's a choice it's just your choice of what you want to do with your life because it is going to be what life you give somebody else but it's also what you want to do with your life oh Trinney thank you so much for what has been a really beautiful interview and the last thing I want to ask you about actually because I'm not sure whether it's urban myth or not but it's the fact that your nickname Trinney comes from an early experience of meeting someone involved in the film Centriniens is that right? So that was a guy called Frank Norder and he was either the producer of Centriniens because a friend of mine was all the writer of Centrini's one or the other I didn't know but I was very naughty at school when I was very young I was about five and I went to a day school and I cut a platt off of a girl in needle class because she'd done something and I'd just cut this platt off and she's in my hand very bad when I have scissors in my hand and I was sent home and my dad was there with this guy and he said you are just like these girls that I'm writing about I think he was a writer Frank Norder God it thank you so much I am really really honored and pleased you came on how to fail that's one of my favourite ever and thank you so much for all that you are all that you do and Trinney Woodle thank you so much for coming on How to Fail Okay darling, thank you If you enjoyed this episode of How to Fail with Elizabeth Day I would so appreciate it if you could rate, review and subscribe Apparently it helps other people know that we exist