How To Fail With Elizabeth Day

SPECIAL EPISODE! How to Fail: Henry Holland on business failure in the time of Covid-19

April 22, 2020

In the last of four special episodes specifically designed to help you through lockdown and Covid-19 anxiety, I welcome the fashion designer Henry Holland onto the podcast. This week, How To Fail returns to its usual format of discussing three failures but I've chosen to make this a special episode because one of Henry's failures will speak directly to a lot of people right now. It is the failure of his business, House of Holland, a failure linked to the impact of Coronavirus and which has left Henry having to call in the administrators and let beloved members of staff go. It's a failure he is still coming to terms with and I'm so grateful to him for choosing to talk about it. 

We also discuss growing up in Ramsbottom, with childhood friend (and future supermodel) Agyness Deyn, and going to a school which stifled his individuality and where even the female teachers were called 'sir'. Later, Henry became a fashion journalist on teen magazines in London before he started making slogan t-shirts as a side-hustle. The t-shirts proved so popular they rapidly became a sought-after fashion item, and Henry's future in fashion was assured. It was a life that took him onto the world's catwalks and into some of the most glamorous parties (keep your ears tuned in for the Kanye West anecdote) but, last month, he was forced to acknowledge that his business was no longer financially sustainable.  'The emotional turmoil of closing a business was one that was heavy to bear,' he wrote recently in a piece for British Vogue. 'But now, on the other side, while unemployed in the craziest economic time we’ve experienced in a generation, I can’t help but feel a sense of relief. Relief I am no longer letting people down. Relief I am no longer pretending everything is perfect when in fact it’s not. And relief most of all that I have space and time to think about what it is I want from my working life.'

Thank you Henry. We'll be back in June for a brand new season with a truly fabulous line-up of guests. Until then, stay safe and I hope you all enjoy the episode. 



If you really can't get enough How To Fail content and are looking for something to read during lockdown, there is a book! How To Fail: Everything I've Ever Learned From Things Going Wrong is out now and available to order here



How To Fail With Elizabeth Day is hosted by Elizabeth Day, produced by Naomi Mantin and recorded, edited and mixed by Chris Sharp. We love hearing from you! To contact us, email

Social Media:

Elizabeth Day @elizabday

Henry Holland @henryholland


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