The Pretty Boss Mom: Meet Kelly Cookson

Motherhood is one of the most rewarding and stressful balancing acts. It requires pouring your heart out to a little human being while waking up every morning to make sure they have everything they need.

In this series, we highlight a few of those women who are in the middle of their greatest balancing act; pouring their hearts into their children while pouring their hearts into creating a legacy for their families.

Kelly comes from humble beginnings:

The daughter of two bus drivers, a tradition that went back on both sides of her family, and was already continuing with her brother, as a teenager Kelly didn’t expect to go to university or become an entrepreneur. There was every chance she would follow the same family tradition herself.

Leaving school after mediocre A-level results, she took what she describes as a soul-destroying job in a tax office, where she only lasted 6 months before leaving to work in the local library as a part-time library assistant.

Whilst Kelly’s dad was content being a professional driver, it was her mother who provided the inspiration and confidence to change her life. After getting divorced when Kelly was 8, Mum decided to go back to school to get her A levels, a degree, and then a Ph.D. in Organic Chemistry, all whilst bringing up Kelly, her younger sister, and then baby half-sister.

“I watched my mum transform herself and set out on this mission to succeed, and it filtered down to me!” says Kelly.

Leaving her dead-end job, Kelly got a place at uni to study aged 23. Alongside her sister, she becomes the first member of her family name to go to university. Kelly thrived, gaining a first-class honors degree in Business Information Management.

After landing a marketing role a week after handing in her final year project, her career went from strength to strength, as she continued to climb the career ladder, becoming a Marketing Manager for an international software company, and earning well. But after having her daughter in 2017 and returning to work part-time, she became aware she was going to need more flexibility and time off when her daughter

eventually started school.

Inspired once again by her mum, she was determined to find a better work/life balance and embrace a way of working that was more aligned with her personality and values. She craved a role where she could spend time with her family, but also the financial rewards of a full-time job.

So, leaving the security of her corporate role, Kelly decided to go freelance, to set up her own company, Cheer Up Marketing in January 2020 and has never looked back.

Kelly refers to this as her ‘Sliding Doors’ moment, as she could clearly see two paths for herself, one of which involved struggling to balance a corporate career, the school run, and holidays, and the other, the path she actually took, leading to career success and a salary to go with it.

Achieving career success Using her marketing and business expertise, she has managed to grow her online marketing business to achieve a 6-figure annual turnover, with more time to herself than she’s ever had.

Kelly puts her success partly down to being a risk taker because she took the leap from her secure job and salary to a life of self-employment with no savings and some debt from living on a part-time salary after maternity leave. This risk-taking has been a consistent theme as Kelly invested in her own development and in the business to scale as quickly as she could. In 2022 she trained as a Positive Psychology Coach, which alongside giving her more mindset tools to support her ambitions, also helps her clients to realize their dreams. 

Alongside her husband backing her to follow her dreams, it’s her hero mum who inspired her to make a big change because her confidence in her ability to succeed gave her the push to make bold moves to scale her business quickly. Kelly is the perfect example of how you can break the mold and change your destiny and find your own unique path. Using her own experiences and marketing expertise to help others achieve business success, she is passionate about helping her clients supercharge their businesses. Using scientifically proven positive psychology interventions, she helps them to show up with confidence in their marketing and achieve their business goals. All whilst feeling better than ever!

What is It like to run a successful brand while running your home as a Boss Mom?

It’s exciting! My motivation is my daughter. I started this business to spend more time with her and to be available to take her to and from school every day and be at home during the school holidays. Every time I walk her to school, I feel like I’ve achieved success. I’m extremely grateful that I run this business and don’t have to use childcare. 

In terms of running my home, having a successful business means I can finally afford a cleaner! Which is a big help and frees me up to do the money-making tasks in my business. 

I don’t think I’ve achieved the perfect work/life balance – I look at it more like an integration. I’m extremely efficient and can get so much done in the pockets of spare time I manage to find.

What has been your biggest challenge in balancing both career and motherhood?

The biggest challenge has been making myself slow down the business side because I’m very ambitious and have great plans for where I’m taking my brand! I constantly come back to my “why” which is my daughter and spending time with her. This helps me to dial things back a bit when I find work is starting to take over more time than it should. It perhaps means I’ve not scaled my revenue as quickly as others but I’ve hit a 6-figure annual turnover by myself just ⅖ years into my business and I only work 20 hours so I’m very happy with where I’m at.

Behind every great woman is a group of other great women pushing her into greatness, who is your circle made up of?

My mum is a constant source of inspiration and encouragement. She reinvented herself in mid-life with 3 young children to look after and she is my cheerleader. 

I also have a small number of close female friends who aren’t entrepreneurs themselves but are also ambitious and they inspire me to be the best.

I’ve found business masterminds to be instrumental in helping me push myself outside of my comfort zone to try new things and take my business to the next level. I always earn more money when I’ve invested in business coaching and external support. 

 What advice do you have for new moms wanting to jump-start their own entrepreneurship journey?

At some point, you are going to have to make the leap from whatever your current situation is into running your own business. It’s a bit like deciding to have a baby – there’s never the perfect time! You’ll likely struggle to do the day job, be a mum and grow your own business alongside all of that – something will have to give. For me, it meant leaving my secure job and salary with zero savings to start my own business. I’ve never looked back. 

What does being a Pretty Woman Who Hustles mean to you?

It means I’m completely myself – I don’t have to pretend to be anyone else to succeed in business. It also means I’ve created the time freedom to look after my health and my family as well as being an entrepreneur.

Social Media Handles:


Jakia Cheatham - Myles

CEO/Founder of Pretty Women Hustle Magazine

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