Doing business, playfully, with Emma Worrollo

27 Apr, 2021 | Podcast, Season 5

This week on The Whin Big Podcast, Katie speaks with Emma Worrollo, founder of The Playful Den – an online community committed to making life more playful.  They talk about Emma’s decision to leave the agency she founded to do something new and how the pandemic affected her decision.

In this week’s episode, you’ll hear Katie and Emma chat about making the Instagram switch from doing it for fun to doing it for business and the commitment it takes to make content meaningful, authentic and strategic all at the same time.

Today's episode is sponsored by the Instagram MOT. This 20-point checklist and free training are freshly updated, so get stuck in to find out if your profile is fit for purpose or needs some attention! Click on the big yellow button below to get started right away.

Emma’s business journey

Emma’s transition from her previous work life to her current one is still very new and fresh, so when Katie asked her to share where she is right now Emma described it as ‘very much TBC’. Ten years ago Emma Worrollo founded an insight strategy agency for global brands and as such was a leading thought leader in emerging generations, looking at ways to think and communicate with the future consumers.  

At the time of recording this podcast, Emma had only recently stepped away from leading the agency towards building a community of parents around the idea of living playfully. Through the research she carried out for her strategy role, she developed a keen interest in the relationship between playfulness and mental health. 

Turning an online community into a business venture

Emma used her Instagram account as a creative outlet, using Stories as a way to try out new ideas and experiment with her knowledge. She used it as a therapeutic ideas journal and enjoyed the engagement with her community. 

For Emma, she’s achieved everything she wanted to with her agency and felt a strong pull towards the rewards she experienced when she’d get positive feedback from her audience. 

Using Patreon for a creative business

During maternity leave, Emma had more space to play with her new ideas and joined Patreon. On this crowdfunded membership platform, followers pay for additional content from their favourite creators. 

It exceeded her expectations and had a hugely positive impact when people were willing to pay for content from her. She had never planned to become an influencer, but Patreon gave her a final push to accept she could turn it into a business.  

Emma polled her followers on Instagram before setting up on Patreon. The response was huge, and that gave her the confidence to go ahead and try it out. A year later and she still loves creating Patreon and the community she’s built up through it. 

How to leave your business to start a new one

Katie was curious about how Emma managed the emotional exchange between the excitement of building a new business while exiting from an old one. Was there a strong emotional pull between the two? 

Emma describes the experience as being similar to grief. 

“I went through anger, sadness, and so many emotions I wasn’t expecting. Once I’ve made a decision, it’s made. It was about untangling the logistics of making sure the business is well set up, the team are in a good place and handing everything over. It was massive.” – Emma

Emma made steps to leave the agency in Summer 2020 so it’s taken quite a long time to get through the untangling. 

How the global pandemic became the catalyst for change 

Emma had a huge set of challenges in front of her by the pandemic hit the UK. She had a baby three weeks before the first lockdown, and having that kind of lifestyle change on top of the restrictions from the pandemic, gave Emma a chance to reflect on the importance of feeling fulfilled in work and family life.  

This gave her the clarity to recognise the agency wasn’t meeting her needs, despite loving the business and team she’d built. 

“There’s a perception that, as a woman, as a mother, if you reach a certain level of success and you just shut up. Be grateful you got there! You do not rock the boat; you do not ask for more.” – Emma

The beginner’s mindset

Katie and Emma chat more about how the pandemic gave them the window to imagine how different work can be, and Emma shared her insight on a term known as the beginner’s mindset.

She described it as the idea of forgetting everything you’ve learned and already knew and re-imagine what life could look like. For Emma, the pandemic enabled this shift in her life. She focussed on the beginner’s mindset and moved forward in that space.

Moving on with a new business

Emma’s had an idea for a lifestyle brand for a few years now, and it was by experimenting and playing in the online space that she turned dreams and visions into plans. She recognised the first step was to build a personal profile and engaged audience to give the brand energy.

She used the example of Glossier’s success through social media as her inspiration. Still, she admitted it took a while for her to stop comparing herself to other startups and tracking numbers as a measure of success.

“I stopped focussing on growth and started to think more smartly about what my audience actually want from me.” – Emma

Emma wants to set up a lifestyle brand that sells consumer products but knows the route to getting there is to build a strong philosophy and set of values, so her strategy is to get paid for doing that. 

She’s in phase 1 of building the community and focus on learning what her community actually needs before moving on to phase 2, which is more about offering services, courses and products. 

Keeping brand values at the core of business 

Emma currently runs a parenting course, teaching parents how to grow a playful mindset. The course covers each of the characteristics of the mindset, which are: 

  • Joy 
  • Curiosity 
  • Creativity 
  • Open ness

When she sat down recently to work on her business plan, she realised that those characteristics are the same as her brand values. By matching content with these values, she will build up a strong philosophy that can take her into a consumer brand. 

A week in the life of Emma’s content 

When it comes to content – like so many of us – she’s keen to move away from a random approach to content and into something more planned and focussed.

She’s still grappling with the idea of scheduling out an entire day to work on writing blogs or creating content but knows it’s something she wants to start doing. As a result of not doing this, her Instagram output has been sporadic.

“I’ve had the attitude that if I have something really good to say, then I’ll say it, and otherwise, I don’t want to take up other people’s space. I’m trying to find a balance between standing by that because I know people value my opinion and expertise, but I realise I have to play the game more than I am if I want to build out my profile.” – Emma

Emma’s figuring out her content plan right now but knows she needs to carve out 1 – 2 days a week to plan social media, write blogs and create Patreon content. To kickstart her content discipline, she’s committed to building a business audio diary every day on Patreon. By doing this, she hopes it will get her into daily practice.

Authenticity vs Strategy

Katie can relate so much to Emma’s points about content discipline. As you know, Katie doesn’t enjoy planning everything out, so she had her challenges when it came to creating a plan and sticking to it.

Katie made an intentional decision to carve out time and create a plan. For her, the word ‘authentic’ gets overused because of the struggle between creating really valuable content that has to feel authentic, so people relate to it, but doing it on a schedule that feels anything but.

For Emma, the biggest struggle is around how in-depth she goes with her content. When she does get involved in creating content, it’s about topics she feels passionate about, and so Instagram Lives and blog posts go into more depth than other content might go.

Katie has some advice for this:

“When I get an excellent idea that’s got a lot of meat to it, I don’t give it away all at once. I want to get ahead of myself by using the idea to create five pieces of content instead of one and a half. Then I can work to a schedule because I already have the stuff – rather than being lead by the schedule to come up with something new.” – Katie

Emma’s most successful content to date

Emma ran a pep-talk series on Instagram Stories and followed it up with a grid post and blog post. The theme was on lockdown and came from the stories she heard about parents and young children at loggerheads with homeschooling.

Emma’s personal beliefs about childhood learning and structured academia before the age of 7 meant she could talk to parents about their unrealistic expectations of what they should achieve in this setting. The pep talk helped parents negotiate between child, school and employer to create a more playful, creative learning experience.

It was from the heart, and quite a radical approach and, as a result, was very successful. She chose Instagram Stories for this content, which she regrets now as it disappears from her account quickly. Next time she’ll choose something with more longevity, like IGTV.

What’s on Emma’s bookshelf?

Emma doesn’t’ have time to read business and development books and instead consumes content through magazines and podcasts. 


  • Courier Magazine is the only business magazine she reads. She enjoys the case studies and stories about new brands.
  • Two mindset magazines she enjoys are called Flow and Breathe. They focus on topics as diverse as mindset, philosophy and life in the pursuit of wellbeing and happiness. Emma compares reading these magazines as healthy food for her brain.
  • New Philosopher is another favourite.


Keep the conversation going with Emma & The Playful Den.

The Playful Den on Patreon
The Playful Den on Facebook
The Playful Den Website
The Playful Den on Instagram

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