It’s a bit of a mind game when preparing to interview a media personality. Particularly so when the person is a career interviewer. On the one hand, they get it. But sometimes it actually raises the stakes.

But there’s something about Elizabeth Day – a writer and broadcaster, best known for her podcast How To Fail With Elizabeth Day – that immediately creates a safe space. Maybe it’s because her dulcet tones have soundtracked many hours of flying, driving, walking or simply sitting in my apartment over the past five years. But the familiarity runs deeper than a regular parasocial relationship.

The premise of her wildly popular podcast is to celebrate “the things in life that haven’t gone right” and what can be learned from these experiences. Over the course of 20 seasons, Day has amassed more than 220 intimate conversations that explore themes ranging from rejection, grief and addiction to friendship, fame, sexuality, parenthood and happiness.

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Episode one, which aired in July 2018, featured Phoebe Waller-Bridge on turning terrible dates into award-winning television, female anger and finding love in her friendships. More recent episodes see Miriam Margolyes, Dan Levy, Elliot Page, Bear Grylls, Geri Halliwell and Margaret Atwood on the mic. Day invites her guests to share three failures from their life, exploring what they’ve learned from each moment and how the frustration, floundering and fear surrounding these events ultimately led to their individual successes.

Day doesn’t have to coax anyone into vulnerability. She speaks candidly about her own failures – including divorce, fertility struggles and friendship break-ups. She shares these in the podcast episodes, but also in her book How To Fail: Everything I’ve Learned From Things Going Wrong.
“When I first started [recording] I had to rely on people taking a bit of a risk with this slightly strange concept. I got really lucky with my guests,” Day tells Broadsheet.

“But I think it helps that when you’re asking someone to be vulnerable, you’re able to share your own vulnerability too,” she says. “I’d come from a very old-school journalism background where I was taught not to put myself into interviews, but I realised that with this specific kind of conversation, there was such an intimacy to it … it felt like the power dynamic was off if I wasn’t sharing too.”

A self-proclaimed recovering perfectionist and people pleaser, Day has found a niche in creating community with likeminded people. Reframing success helped Day to be kinder to herself about understanding what failure really is. “The premise of How To Fail is not ‘fail fast, fail often’ in that Silicon Valley ideal. We should absolutely try our hardest. But if we’ve tried our hardest and we still fail, it’s about what happens next. The true test of character is how you respond to failure,” she says.

Day believes that our experience of failure can be boiled down into two distinct categories: your garden-variety mistakes, like failing a driving test, and cataclysmic events that feel completely out of your control.

“Sometimes people think they need to dust themselves off immediately and bounce back the next day from something really difficult because that is the definition of resilience. But it isn’t. There needs to be time to grieve and sometimes that process will take a lifetime.”

For Day, more than a decade of fertility challenges, miscarriages and ultimately accepting that she doesn’t want to carry on fighting a losing battle has caused enormous sadness in her life. But it also taught her how to be compassionate with herself.

“I do think that even sadness can teach you something. If nothing else, it teaches you about the breadth of human emotion. The texture of life. We cannot all be relentlessly happy all of the time, unless we understand what it is to be the opposite. I’ve discovered that you can live at peace alongside the sadness and there’s no right way to feel.”

Day cites Mo Gawdat and Chimamanda Ngozi Adichie as two of the most influential guests for her personally. “When we see people [we admire who] have felt like terrible failures, have had moments where they felt like they couldn’t go on but are here sharing their wisdom, that’s where I feel a great source of connection,” she says. “There’s so much power to be had in that solidarity.”

Accumulated wisdom is the theme of another of Day’s books, Failosophy: A Handbook for When Things Go Wrong. “Mo has taught me so much about not being our worst thoughts. Our anxious brain exists separately from our soul and being able to challenge it is important,” she says of Gawdat’s impact on her work. “Our anxious brain has our best interests at heart but only a limited set of skills. Mo suggests giving your anxious brain a name, separating its identity from you.”

Day acknowledges that failure can feel very personal, like a rejection of sorts. Her advice is to always interrogate that feeling. “That feeling isn’t you, it’s just something you’re having,” she says. Day believes that any type of failure can be a source of data acquisition about yourself and a chance to learn and ultimately grow.

“If I fail again, which I undoubtedly will, and have done since starting the podcast, I now know two things: I’ll survive it and because I’ve decided to look at it this way I will acquire some necessary data about myself or about what to do differently.”

Failure has also helped Day think about success differently. “It’s not about dollar bills and private jets, although that’s obviously nice. It’s about being able to show up as my authentic self in every area of my life.”

An Evening With Elizabeth Day at Sydney Opera House is on February 26 and her talk at Melbourne’s Hamer Hall is on February 28.