How to overcome self-doubt and be a creative leader

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“We all have moments when our idea of who we are and our sense of self gets challenged,” says Piera Gelardi. “I had a moment like that when our company started to grow and develop. I felt really comfortable in my role as a creative person, heading up creative projects and expressing myself through creativity, but I started to feel really uncomfortable and almost like an alien in other parts of my role. The executive and creative director parts of my identity were really split – and the executive part just felt so foreign.”

Piera Gelardi is co-founder and Executive Creative Director of Refinery29 – the women’s media brand with teams in New York, London and Berlin. The brand started out in 2005 with a focus on style, offering a guide to New York’s best independent boutiques. It now covers everything from fitness to politics and business and has 500 million users across various platforms.

The business grew quickly – in 2013, it was named the fastest growing media company in the US – and Gelardi says this rapid growth initially left her feeling uncomfortable. Speaking at D&AD Festival, she said: “I was having to do lots of things that I didn’t necessarily have any background or training in. I had to start managing these big teams and thinking out business strategies and doing a lot of negotiations and I felt so uncomfortable in these new roles that I started to think maybe our company was scaling and I wasn’t the right person for the job any more. That was a really painful moment, because here I was – I had built this company from the ground up and all of a sudden, I didn’t feel at home.”

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Use your strengths as a weapon

While she doubted herself at first, Gelardi eventually realised that she could adapt to her new roles by using her strengths to her advantage – for example, using her creativity and listening skills to develop her own unique style of negotiating.

“Before that time … I thought you had to be uncompromising and it felt really unlike me,” she said. “So what I started to do was negotiate something like this: I would start by painting a really clear picture, using my imagination and my vision, so really describing the thing I was going to create with the other person in a lot of rich detail, until that person was nodding along and saying, ‘I want to make that too’.

“Then, I’d take a moment and use my skills in collaboration and listening and say, very transparently, ‘OK, I have x and you are asking for y, let’s talk about how we’re going to get on the same page’,” she explained. “And then I would use my creativity to listen to what they said and come up with different solutions for them. This felt really natural for me and I started to exceed both the goals that were set for me and my own goals for myself in negotiation. That was a pivotal moment because I realised that you can bring your strengths with you – almost like a safety blanket – into new areas. Your identity is not fixed and you can use [your strengths] as a weapon.”

Illustration by Refinery29 senior designer @byisabel to promote Be Bold For Change, an event hosted by Refinery29 to mark International Women's Day
Artwork created by Refinery29 senior designer @byisabel to celebrate International Women’s Day – part of the brand’s Be Bold For Change campaign with Keds

Creating the right conditions for creativity

Gelardi also discussed the importance of identifying the conditions that can lead to great ideas, whether that’s going for a run or making a Pinterest board.

Recalling a time when one of her colleagues doubted herself after struggling to come up with ideas under pressure, she said: “I’ve learned that you need to create the right conditions for creativity. When I have to brainstorm in a pinch, I need to set myself up, so for me, that means surrounding myself with imagery (my office is full of photos, or I’ll open a Pinterest board), it means word association (I’ll open a magazine and go back and forth doing word association) – but the biggest condition for creativity for me is bringing people into the room … who I feel really comfortable with and can be myself around.”

“It’s such an important thing to recognise,” she continued. “So often, we can become fixated on that moment of deficit, that moment when you don’t have the idea or you fall sort but what if [when that happens] you do the opposite – you follow that breadcrumb trail back from when your brain was exploding with ideas and you came up with something brilliant and you figure out ‘what were the conditions that led you there’? Was it music you were listening to? Did you take a walk around the block? Did you have someone in the room with you?


Once a week, Gelardi invites people from across the company into her office to hatch new ideas. Sessions start with basic physical exercises often used in improv classes – such as shaking out each limb in turn while counting down (loudly) from four to one. Gelardi believes this helps put people at ease. “We shake because it levels the playing field – I’m just as silly as you are, you’re just as silly as I am, so let’s just leave our inhibitions at the door,” she said. “We shake because play creates trust and we shake to get ourselves out of our heads so that we’re present.”

During these brainstorming sessions, teams are forbidden from discussing restraints such as budgets or traffic targets. “This isn’t because traffic and budget are not considerations that are part of the creative process – they absolutely are – it’s because in that environment, especially with a mixed group of people who don’t necessarily think of themselves as creative, we want there to be no limitations. We want them to feel that anything is possible,” said Gelardi.

Poster created by Anna Sudit for Refinery29 in support of the Women's March earlier this year. Refinery29 commissioned a series of posters that women could download and print out
Poster created by Anna Sudit for Refinery29 in support of the Women’s March earlier this year. Refinery29 commissioned a series of posters that readers could download and print out
Poster by Refinery29's Art Director Anna Rose Jay in support of the Women's March earlier this year. Refinery29 commissioned a series of posters and made them available for readers to download
Poster by Refinery29’s Art Director Anna Rose Jay in support of the Women’s March earlier this year. Refinery29 commissioned a series of posters and made them available for readers to download

The importance of listening

Asked what makes a great creative leader, Gelardi was reluctant to recommend any particular management style but said it was important to “lean in” to your strengths. “I don’t think there’s a universal or right way [of leading] … but what I’ve found for me is the power of listening,” she said. “I don’t think the leader’s voice has to be the loudest voice in the room. I have got most of my best ideas in conversation with other people, listening to other people’s opinions, and I think creating an environment where other people feel comfortable voicing their opinions [is really important].”

“If you create an environment where people are scared of a leader, or a leader tends to shoot them down, then you have all these smart creative people around you, but you’re not actually utilising them to the best of their ability,” she continued. “So helping other people to understand what works best for them, helping them to create those conditions [for creativity] and having a degree of flexibility in the workplace versus one set way of doing things can help you to work with and leverage people’s unique strengths.”

She also believes that laughter is an important part of the creative process. When working at a magazine in New York, Gelardi says she had some of her best ideas in informal brainstorming sessions where she and her team would fire off one wild idea after another. “I would see this pattern emerge again and again. Someone would say something super ridiculous, we would all bust out into fits of laughter and then boom, a brilliant idea would follow. I truly believe that laughter unlocks a higher level of brilliance.”

Find other outlets for your creativity

Gelardi has what many creatives would consider a dream job. But she also said it was important not to expect to find complete fulfilment in your work. Answering a question from a member of the audience, she recommended finding other ways to channel your creativity outside of work – particularly if you feel constrained in your day job.

“So many people put so much emphasis on living out their whole being and putting all of their hopes and dreams into their career. You think, ‘this is going to be my everything’ – and I don’t think that’s realistic,” she said. “I have my dream job to all intents and purposes but it’s not my everything. There are other places that I need to go to nurture other parts of my creativity and my being.

“I have a friend who’s a really successful artist … and he told me that he got the most fulfilment from creating his art when he worked at a vintage store in the daytime and went home and made art at night,” she continued. “Our culture emphasises that our career defines us – when we meet people, the first thing we ask them is ‘what do you do?’ – but we’re all whole, robust people and you can find fulfilment in other places. I took an improv class this year and I won’t shut up about it, because for me, it was amazing to learn this other skill and stretch this other muscle.”

Piera Gelardi was speaking at D&AD Festival in London, which continues today. More info at

The post How to overcome self-doubt and be a creative leader appeared first on Creative Review.


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