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During the Covid-19 crisis, we had a (virtual) chat with inspirational woman, business owner, and EnterprisingYou client Sissy Rooney, to discuss starting a business during a pandemic…

Hi Sissy! Firstly, tell us about how you became an entrepreneur?

After being excluded and told I wouldn’t amount to anything, I left school with no qualifications. English, maths, science and French just wasn’t for me, but my textile teacher saw I had a talent for fashion design. She sent me tickets to see a college fashion show, which blew me away and inspired me to go back into education and eventually graduate with a first in fashion design. That was the starting point for my first successful business, Street Style Surgery, which delivers educational workshops to young people across the UK and globally.

Tell us more about Street Style Surgery.

Street Style Surgery has been running for 17 years. In that time, it’s grown so that I’m now employing around 80 freelancers, who deliver a range of workshops in creative skills such as fashion, music, beatboxing and DJing. The aim is to encourage young people to shout about their skills and to be the best version of themselves, which is why we also deliver emotional and wellbeing workshops.

How has Covid-19 changed the direction of your business plans?

Things were going really well with Street Style Surgery until lockdown hit, closing the schools we work in. At first, I spent this time organising my databases, but then I had the opportunity to slow down and reflect on what I really needed in life, which was to be in my creative flow. That’s when I decided to start my new business, I Make People Happy.

Tell us more about your decision to start your new business, I Make People Happy, during a pandemic?

I realised that, although I facilitate lots of people to be creative every week at Street Style Surgery, I don’t actually get to physically create myself much anymore. Lockdown has given me the space and opportunity to relaunch a dream that I’ve had since I was six years old. It’s a dream I’d put to bed at 27 and now, at the age of 44, I’ve reignited that dream again. About two months ago, I started to research t-shirt printers, and I came up with a range of t-shirts that have positive and inspirational messages on them. I’ve just designed a mini range, and now I’m waiting for the samples so I can put them in the shop. I’ve actually made sales, so people like my stuff.

That’s great! How did you hear about EnterprisingYou?

I heard about EnterprisingYou from a friend. I told her about my new business idea, and she said, “you should tap into this programme called EnterprisingYou. They’ve been amazing for me.” So, I googled it, applied, and, someone called me within about a day. Next thing I knew, I was then speaking to my Business Coach, Kirsty. During that first phone call, she told me “you have lots of energy and zest, and I think you can go places.” That was four weeks ago, and within a month I’m now selling my products and designs, and I’ve got the business support coming in. It’s quite phenomenal really, how fast it’s happened. 

How has having an EnterprisingYou Business Coach made all the difference?

Even though I’ve been in business for 17 years, I don’t know it all. By taking my new idea seriously, Kirsty has helped me to realise my passion. I love her; she’s really nice and personable. Recently, I was actually selected to be in Mo2vate Magazine for International Women’s Day, so I emailed Kirsty to tell her, and it was nice to have someone say “that’s amazing Sissy!” - To have someone invested in your business journey is priceless.

Congratulations on being selected as an inspiring woman! How else have EnterprisingYou helped?

I’ve also had a meeting with a finance coach and a wellbeing coach; they gave me some pointers about managing my time better, which I’ve implemented straightaway, and now I’ve been told I can see a mentor within the fashion industry, who can help me with branding. I’ve also been able to access EnterprisingYou’s job portal, which has allowed me to tap into a wide range of training opportunities, including a diploma in digital online marketing, which is exactly what I need to push the business forward. I don’t even think the full scope of what is available has become known to me yet.

That’s fantastic! Would you recommend EnterprisingYou, then?

I have and would recommend it! EnterprisingYou’s support has been invaluable to me, and it comes from people who genuinely want to help make a difference. My experience has been so positive; within a month, the support and wealth of information I’ve received has already exceeded all expectations. I can’t believe it!

What do you love most about being an entrepreneur?

I love having the flexibility and freedom to carve my own day out. I’m a solo mummy, so it works for me… even if it sometimes works against me! I love being able to inspire people to reach for their dreams and to see the creative industries as a viable career choice.

What does the future hold for you?

Now I want to take I Make People Happy further; I want it to be a lifestyle brand that encompasses positivity and making people feel good. I’ve just created t-shirts that say ‘strong women lift each other up’ and ‘empowered women empower women’. I just want women to be empowered with who they are. I can definitely see this growing into something bigger than t-shirts. Street Style Surgery is also starting to take off again now, so EnterprisingYou are going to be advising me on taking on an intern and maybe franchising the business. My future plans are to grow my fashion brand into a well-known label and for Street Style Surgery to keep on reaching out and inspiring young people.

To find out more about Sissy, Street Style Surgery and I Make People Happy, visit the links below:


We provide fully-funded support to the self-employed and gig economy workers across Greater Manchester. If you would like to find out more about EnterprisingYou, register online or email

More information about the EnterprisingYou programme can be found here


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About the author

Michael Ayre

Michael Ayre

Engagement Officer at the Growth Company

With an eclectic mix of experience including recruitment, employment support and over 5 years working within the prison service, Michael believes in the strength of communities and collaboration to ensure that everyone at all levels can achieve their aspirations. Michael is a keen runner and has a natural appetite for success, not just for himself but also for the people, businesses and communities around him.