ON AMBITION… With GILLIAN ANDERSON AND MUNROE BERGDORF

2 Mar 2026 · 12 min · 4 chapters

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In short

Podcast Summary: How To Fail With Elizabeth Day - Episode featuring Gillian Anderson and Munroe Bergdorf

Podcast Overview Title: How To Fail With Elizabeth Day Description: A podcast that celebrates failures and explores the lessons learned from them, featuring guests who share three significant failures and their outcomes. Episode Title: ON AMBITION… With GILLIAN ANDERSON AND MUNROE BERGDORF Episode Description: This episode discusses the duality of ambition—its driving force and potential pitfalls—with insights from actress Gillian Anderson and model Munroe Bergdorf.

Key Themes The Nature of Ambition

  • Ambition as a Motivator:
  • Can propel individuals forward and sharpen focus.
  • Encourages dreaming bigger.
  • Ambition's Drawbacks:
  • Can create a relentless cycle where self-worth is tied to achievements.
  • Raises questions about the cost of chasing ambition.

Gillian Anderson's Perspective

  • Work Ethic and Guilt:
  • Identifies as a workaholic driven by the need to earn her place.
  • Experiences guilt associated with stepping back from work to focus on motherhood.
  • Balancing Act:
  • Discusses the importance of setting boundaries to prioritize family time.
  • Acknowledges the joy found in her work while recognizing the need for pleasure and balance.
  • Pleasure as a Right:
  • Considers pleasure often seen as frivolous, advocating for its recognition as a source of power and transformation.

Munroe Bergdorf's Journey

  • Impact of Rejection:
  • Shares experiences with gatekeeping in the fashion industry, which fueled her ambition.
  • Transitioned from being a token gesture to a leading voice for representation.
  • Resilience and Representation:
  • Highlights the evolution of the fashion industry towards inclusivity.
  • Speaks on the importance of perseverance and paving the way for future generations.
  • Envisions a future where trans individuals are celebrated equally without being pigeonholed.

Key Takeaways

  • Ambition's Dual Nature: While ambition can drive success, it can also lead to a detrimental sense of self-worth based on productivity.
  • Guilt and Balance: Both guests discuss the guilt tied to ambition, especially for those balancing work with family responsibilities, highlighting the need for boundaries and self-compassion.
  • Resilience in Adversity: Munroe's narrative underlines the importance of resilience and the impact of representation in achieving success and normalization in industries historically dominated by exclusion.

Conclusion This episode of "How To Fail" dives deep into the intricacies of ambition through the lenses of Gillian Anderson and Munroe Bergdorf. Their discussions illuminate the pressing questions around ambition's role in our lives and its potential to both empower and overwhelm. The episode serves not only as an exploration of personal struggles but also as a call for recognizing the value of pleasure and representation in the pursuit of success.

Links and Mentions

  • Elizabeth’s Substack: [theelizabethday.substack.com](https://theelizabethday.substack.com/)
  • How To Fail Community: [Join Here](https://howtofail.supportingcast.fm/#content)
  • Gillian's Episode: [Listen Here](https://swap.fm/l/7NyZMzkfVOpGyDtlB6k0)
  • Munroe's Episode: [Listen Here](https://swap.fm/l/tu153m3gHYreWBZSrcY1)
  • Podcast Subscription: Available on Spotify, Apple, and other platforms.

Follow Elizabeth Day

  • Instagram: [@howtofailpod](https://www.instagram.com/howtofailpod/) | [@elizabday](https://www.instagram.com/elizabday/)
  • TikTok: [@howtofailpod](https://www.tiktok.com/@howtofailpod) | [@elizabday](https://www.tiktok.com/@elizabday/)
  • Website: [www.elizabethday.org](http://www.elizabethday.org)

Listener Engagement

  • Share Your Failures: [Get in Touch](https://howtofailpod.com)

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Gillian Anderson on Workaholism

3:25 to 8:00

Gillian Anderson discusses her work ethic, ambition, and balancing work with family.

“First up, let's hear from Gillian Anderson.”

Munro Bergdorf on Ambition and Representation

11:00 to 14:00

Munro Bergdorf shares her experiences with ambition in the fashion industry and the importance of representation.

“I think I'm an extremely ambitious person.”

Embracing Our Authentic Selves

14:00 to 14:35

Learn about the importance of self-acceptance and the power of authenticity.

The Power of Truth

14:35 to 14:51

Gillian Anderson emphasizes the strength found in personal truth and expression.

“final word for me would be powerful you're so powerful you're powerful in your truth you're powerful in your words on the page, you're powerful in person.”
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Transcript

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0:00Munroe Bergdorf:Masterclass is the streaming platform that makes it possible for anyone to watch or listen to hundreds of video lessons taught by more than 200 of the world's best. Whether it be in business and leadership, photography, cooking, acting, music, sports and more, Masterclass delivers a world-class online learning experience. The classes that excited me the most were the ones on writing. So there's a session with actual Malcolm Gladwell, author of Blink and the Tipping Point. He's done 24 classes on how to find, research and write stories that capture big ideas. And it's totally inspiring. I love that you can turn your commute or workout into a classroom with audio mode so you can listen to a masterclass lesson anytime, anywhere.

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2:20Munroe Bergdorf:After you purchase,

2:21Gillian Anderson:they'll ask you where you heard about them. Please support our show and tell them we sent you.

2:26Munroe Bergdorf:Welcome back to How to Fail. This week, we're talking about ambition, the engine that drives us forward, the inner voice that tells us to keep going, and the shadow side that asks whether we've ever done enough. First, actor and Emmy winner Gillian Anderson reflects on being a self-confessed workaholic and the belief that she has to earn her place through constant effort. Highly relatable. We discuss pleasure as power, the guilt of not working, and how she balances fierce professional drive with parenthood and presence. Then model and fashion icon Munro Bergdorf shares how her ambition was forged through rejection and gatekeeping in the fashion industry.

3:08Munroe Bergdorf:From being treated as a gimmick to witnessing real change on the runway, she speaks about perseverance, representation and widening the path for others.

3:17Elizabeth Day:This is an episode about striving, self-worth,

3:20Munroe Bergdorf:and it asks whether ambition liberates us or quietly runs the show. First up, let's hear from Gillian Anderson.

3:32your final failure is your failure to not work are you a workolic yeah and where do you think

3:41Munroe Bergdorf:that comes from why do you feel that you need to work in order to earn your place on this planet

3:47Elizabeth Day:i don't quite know but i do have so i mean it's a like a protestant work ethic i'm not quite sure where it's come from. But what I do know is I feel incredibly lucky on the one hand. I mean, on all hands. I don't mean on the... Yeah, I'm incredibly lucky, incredibly fortunate, privileged, all of that, to have the choices that I have had both in my life and my career. And part of it, I think, is showing myself that I deserve it because I'm doing all these things, If all these good things are happening, then I'd better be working for them. You know, it's not coming lightly or it's not frivolous.

4:32Elizabeth Day:That's another thing, actually, that I wanted to talk about in terms of pleasure that I'm starting to realize, too, is that so much of pleasure is perceived as being frivolous. Yes.

4:45Munroe Bergdorf:Trivial.

4:45Elizabeth Day:Yeah. And why? Why isn't it as much of a sense of power, you know, to lean into that, to properly embrace pleasure and make space for it and make time for it and give it to oneself as it is the other things that we. And so I'm, you know, I'm trying to have more of that in my life, but also realizing the degree to which so much of what I'm involved in, whether it's, you know, this drink or one of the shows that I work on or etc. is about pleasure and the joy and pleasure. Anyway, I digress. I think you're so right about pleasure because why can't it be as ennobling, as transformative, as suffering or sadness or pain?

5:33Elizabeth Day:Yeah.

5:33Munroe Bergdorf:Because it's the same thing, but the different end of the spectrum.

5:36Elizabeth Day:Yeah, exactly. I mean, actually, I do feel like even though I am a self-described workaholic, I do get pleasure from it. I do get pleasure from that. When I'm clear, it turns out when I'm not eating prawn crackers and drinking Coca-Cola, I think quite clearly and things come to me. I'm in a moment right now where, and I'm sure that a lot of it has to do with my age and it's none of wanting to leave a mark. It's none of that. It's just it is feeling like, hang on, I've still got some things to do. I've still got things to do that I didn't even know I wanted to do. And that is, of course, in roles and building a company that I'm building.

6:20Elizabeth Day:But it's also just in terms of realising that I do have a few things that I want to share with people.

6:26Munroe Bergdorf:And have you ever regretted working too hard or taking on a project?

6:34Elizabeth Day:There have been a couple moments when I haven't been able to stop around my kids. You know, that had more to do with not in terms of my work as an actor, but stuff on the side or with other projects and stuff where I have felt the guilt of choosing to focus on those things instead of having time with kids. And I feel like there's a good balance right now. I feel like when I'm with them, I'm with them, you know, and that has become more and more meaningful to me. It's been really important to me in terms of my acting work to always have them as part of the priority in terms of this is when I'm available, this is when I'm not, etc.

7:23Elizabeth Day:but this is different. This is in terms of what happens with meetings and with Zooms and all those other things that end up in our days today taking, sucking that time. And I've got some pretty strict rules around all of that so that my workaholism is something that my boys can look at as being beneficial to them because they can see, you know, not just in terms of what I bring home at the end of the day but in terms of seeing me effectively building things and they both have an interest in that and I think it's been really great that they get to see and I think they would say that too that to see a mum who is entrepreneurial and making things and they're teenagers aren't

8:12Munroe Bergdorf:yeah and you mentioned two of them are and then I have one who's yeah 28 okay

8:23Munroe Bergdorf:So I want to talk about glasses for a second. I need them for long distance and increasingly as I age, I sometimes need them for reading too. I know it's happening. And somehow buying them is always way more complicated and way more expensive than I think it should be. That's exactly why I love Warby Parker. They've nailed the combination. Great quality, fair prices, tons of styles, and actually helpful customer service. It just feels super smooth and easy. And they have this thing called virtual try-on. It's a total game changer. You can try on frames straight from your phone before you buy. It's honestly kind of mind-blowing how accurate it is.

9:05Munroe Bergdorf:And it's really helped me understand what flatters my face shape rather than what I think I want to wear. Plus, Warby Parker isn't just about prescription glasses. They've got contacts, online eye exams and sunglasses too. Basically everything you need to keep your eyes happy. Bottom line is you get high quality, great looking prescription eyewear at a fraction of the typical price. Our listeners get 15 % off and free shipping when they buy two or more pairs at prescription glasses at warbyparker.com slash fail. That's 15 % off when you buy two pairs of glasses at warby, that's W-A-R-B-Y, parker.com slash fail.

9:48Munroe Bergdorf:After you purchase, they'll ask where you heard about them. Please support our show and tell them that we sent you. 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 checkout. But then that sinking feeling as you realise you don't have your card anywhere in 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.

10:24Munroe Bergdorf: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£1 per month trial today at shopify.co.uk slash fail. Go to shopify.co.uk

11:04Gillian Anderson:I think I'm an extremely ambitious person. I have a drive that I think is my biggest attribute. I've really had to live a life of discipline and a life of tenacity and constant setbacks, constant people that are gatekeeping, people that are withholding and, you know, coming into the fashion industry nobody wanted to hire me and it took some of the biggest photographers just taking a chance on me like Nick Knight like Rankin who wanted to work with me when you know I was constantly having doors slammed in my face because they were like why would we work with a trans person almost and it's you know I know that a lot of black models from the 90s felt the same way as like we're you know I watched a documentary the other day where they're like we're just not hiring black models this season it's exactly the same so why would we work with a trans person there's not that kind of campaign it's not an LGBT campaign and like now we're seeing that change we're seeing trans people be in shows and it's not a thing that they're trans it's just you know I mean it is a thing because the visibility is incredible and you know when I see a trans model on a runway if it's like Alex or if it's Maxim or if it's oh god India or if it's all of these incredible people that are within the industry that means so much to me but it is not exploited that they're trans anymore and for so long it was I have done shoots where my transness has been you know almost like a gimmick and I'm really glad that I've opened doors for so many people I've been in this industry for almost a decade now.

12:49Gillian Anderson:But if it wasn't for, you know, hearing the stories of, you know, women like Naomi Campbell and Joan Smalls and Jordan Dunn and Leomi Anderson talking about, you know, being exploited from like the ages of 14 and being told that there's no Black models this season or being on set and not knowing how to do Black hair. If it wasn't for those stories and seeing their tenacity and that they could get through it, then I could apply the same kind of work ethic and be like, okay, well, one day, there's going to be more than one trans person on the runway, or there's going to be a trans person on the runway.

13:25Gillian Anderson:And, you know, I have faith that there's going to be multiple trans people on runways one day. And then that's going to filter out as well. And then we're going to see more trans people in all sorts of campaigns. And then the beauty standard is going to change. And then trans beauty is not going to be seen as any different from any other beauty, just like black beauty is now getting the respect that it didn't once upon a time and that's really you know what the book is about as well is everything does change and I've really got faith that one day trans people are gonna be able to navigate society in the same kind of freedom that other people that experience the same kind of oppression in yesteryear did and we'll just be able to be ourselves without having to constantly be so aware of the fact that we're different

14:13Munroe Bergdorf:you gave me four words i'm gonna let you off the final one oh i'm sorry i forgot that i was um maybe the last one's long-winded it's such a beautiful place to end and if i can i would like

14:26Gillian Anderson:to give the final word you're like this is quick fire i think no i never wanted to be quick fire

14:30Munroe Bergdorf:with you honestly i could do this for hours but i know you've got a fabulous lunch to go to the final word for me would be powerful you're so powerful you're powerful in your truth you're powerful in your words on the page, you're powerful in person. I am so grateful to you for finding time to do how to fail. Honestly, it's meant the world to me.

From the publisher

Ambition can be a powerful force: it propels us forward, sharpens our focus and pushes us to dream bigger. But it can also whisper that we are only as good as our latest achievement - and these two brilliant former How to Fail guests explore what it really means to live a driven life.

Gillian Anderson reflects on her lifelong drive to prove herself, the guilt she feels when stepping back from work and the tension between motherhood and a demanding career.

Munroe Bergdorf shares how rejection and gatekeeping in fashion shaped her ambition. Once treated as a token gesture, she has become a leading voice for representation, speaking openly about resilience, self‑worth and creating space for others to follow.

An episode about striving and self‑belief – and about whether ambition truly supports us, or whether we end up chasing it at our own expense.

Listen to Gillian’s full episode of How to Fail here: swap.fm/l/7NyZMzkfVOpGyDtlB6k0

Listen to Munroe’s full episode of How to Fail here: swap.fm/l/tu153m3gHYreWBZSrcY1

🔗 LINKS + MENTIONS:

Elizabeth’s Substack: https://theelizabethday.substack.com/

Join the How To Fail community: https://howtofail.supportingcast.fm/#content

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👋 Follow How To Fail & Elizabeth:

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Website: www.elizabethday.org

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How to Fail is an Elizabeth Day and Sony Music Entertainment Production.

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