Have respect for money and success - success isn't what matters, relationships are.


The Female founder Series ~ an inspiring extension of the Win@Work Podcast. We explore the stories of inspiring women who’ve fearlessly mastered career pivots of their own, and more about how they found their version of success and fulfilment.

We’re peeling back the layers to their successes and sharing their winding roads of missteps, lessons, trying moments, and even outright failures that we can all learn from.

This week's spotlight is the incredible Lillian Gray, fine artist & Art school #femalefounder

What have you built & what inspired you to build it............This is a glimpse into Lillian's story.......

Lillian was raised in Jacobsbaai, a small town on the West Coast in the Western Cape, South Africa. The outdoors and nature were her best friends and her surroundings played a central role in her upbringing. The lack of electricity and the remote setting of the town forced her and her siblings to seek alternative means of entertainment and activities. It cultivated an active imagination and love for creativity. She could draw before she could write, and always had her sketchbook handy.

At the age of 9, Lillian started painting on glass and selling her art at local curio stores. When she was 10 years old, she participated in an Eisteddfod and sold her first artworks to one of the judges. Not only was Lillian already an artist in the making, but also a keen entrepreneur.

Lillian had her first solo exhibition as the ATKV’s Regional Artist of the Year for the West Coast at 19. Her first encounter with oil paint happened when she was 24 and this soon became her preferred medium on her journey to find her own artistic identity.

She went on to earn bursaries to study at the University of Stellenbosch and the prestigious Stellenbosch Academy of Design and completed her studies with distinction.

Lillian started drawing like most kids at the age of 5, and like Picasso said : “We all start as Artists and then some of us decide to stop”, Lillian however just never stopped.

Her father was extremely business-minded and, from a young age, herself and her siblings were encouraged to make their own money. By the age of 13, herself and her younger brother won the ABSA Young Entrepreneur of South Africa’s Award for their small business.

She always knew her father would only allow her to study art if she also studied business. So, two weeks after graduating, at the age of 23, she started her own business. After gaining ten years’ experience in the commercial art industry, she decided to follow her passion of being a full-time artist.

Her favourite part of being an artist is the freedom to do what she loves. Creating new paintings in her studio, accompanied by good music and wine, which is her epitome of happiness. Her husband and kids usually sit and chat with her while she paints.

As someone who has had the privilege of being well-travelled, she has always placed a high value on being an international citizen, dedicated to the wellbeing of the planet and all its ethnicities and cultures. She has always had a keen interest in politics and has a strong belief, that we are all here on this planet to help each other and work towards a better future.

As an artist, when you paint a face in blue, green or purple, the work transcends race. It’s no longer a white person or a black person on the canvas, it’s just a human being, a global citizen. In many cases it also transcends gender. She has seen many clients view her artwork and refer to the image as male when the next person experiences it as female. The recurrent themes in her work are hope, empowerment, conquering fear and overcoming trials and tribulations.

In this vein, the abstract brush strokes and textures add another layer of meaning. Her work seem unfinished, because we are all somewhat unfinished, a work in progress. The edges are blurred, and some lines are broken because we are all a little bit broken on the inside.

In the words of her friend Bev :

“Lillian’s art depicts what it is to be fully human, we all have brokenness which is more often than not obscured from others. This is contrasted by effervescent joy (whatever the source) and the ‘bright’ moments, which makes life worth living.

It can also be said that this vulnerable, broken individual has to negotiate life through a world which is made to look flawlessly beautiful by the facade that others create, even though they are not entirely whole.”

Her hope & belief is that her art can contribute towards the ongoing struggle for equality and the improvement of global human relations, even if it is just on a small scale.

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?

I was bright eyed and bushy tailed, an ambitious 20 year old. I made a lot of money early on in my career with my first business - a design agency. After 6 years it failed gloriously and I learnt a lot from that terrible experience. It taught me to have respect for money and success and it also taught me that success isn't what matters, relationships are.

If you could have a gigantic billboard anywhere with anything on it — metaphorically speaking, getting a message out to millions or billions — what would it say and why?

  • I believe that art should be accessible.

  • I believe in breaking down the inaccessible convoluted art world.

  • I believe all people are creative and can learn art as a skill.

  • I believe we all need creativity and art. Beauty is essential and not a luxury.

  • I believe art can, has and will change the world

  • I believe art can be a financially successful and abundant career.

  • I believe creativity is what differentiates us as humans from A.I. and that is vital for the 4th Industrial Revolution

In the last five years, what new belief, behavior, or habit has most improved your life?

Austin Kleon, author of “Show Your Work” and “Steal Like an Artist” says “Find the most talented person in the room, and if it’s not you, go stand next to him.” I fully agree with Kleon. If you have never studied business and you wish you could, find someone that did to guide you. Or find a talented business woman / man in the field and stand next to them.


  • E-Myth by Micheal E. Gerber

  • The Power of Moments by Chip & Dan Heath

  • Outliers by Malcolm Gladwell

  • Be so good they can’t ignore you by Cal Newport

  • Whatever you think, think the opposite by Paul Arden

  • Crucial Conversations by Al Switzler, Joseph Grenny, and Ron McMillan

In the last year, what have you become better at saying no to (distractions, invitations, etc.)? What new realizations and/or approaches helped? Any other tips

Systemising the business so that it can run without me. (E-Myth) Creating moments for our clients (Power of Moments) Expanding the team and finding the perfect crew members. I also split the business in two, one, Lillian Gray the Artist with original artworks and lifestyle products with an international focus and secondly the Lillian Gray Art School with a local focus teaching art to children in Johannesburg.

In this unique time in our history with the Global pandemic, how would you say has it impacted your perspective around business? What would you do differently or change going forward?

2020 will definitely go down in history as a year filled with challenges. However, it is also a year that has forced us to change our ways. It has forced us all to grow digitally and to adapt to a world of virtual learning. It’s amazing to see how skilled 7 year olds have become at handling conference calls and scheduling their Google Calendars. I definitely did not possess those skills at that age.

In short, 2020 has forced us all to stretch our minds and grow into our unimaginable capabilities. Naturally, such a year hasn’t allowed us to have a standard art exhibition. Our usual exhibition norms have changed: the big venue, band, dancers, exhibition stands filled with art and visitors discussing pieces while enjoying refreshments, is not possible. As an art school we could have just surrendered to the challenges that 2020 kept on dishing up, simply shrugged and murmured “Oh well, I guess we just won’t have an art exhibition this year.” That would have been easy. However, our students’ absolute dedication, focus and resilience has been nothing short of remarkable, especially during our country’s hard lockdown and later lower levels of lockdown: we simply couldn’t let them down.

Our team sat down and brainstormed ideas on how to showcase our students’ work and to use this online platform to teach them the business of art, but most of all to give them a platform on which to shine. So we launched our first Virtual Art Exhibition. You can now show our students art online here:


We trust that this new way of exhibiting will have a far greater impact and reach as we are no longer limited by an exhibition’s physical location.

If you loved this weeks Female Founder Spotlight, shoot me and Lillian a DM on Instagram with your favourite part of the feature, because we would love to hear from you & we absolutely love living a life of colour & creating beauty with others who have an appreciation for local artists!

@winatwork.women & @lilliangrayart or @lilliangrayartschool

Let’s Social

Lillian Gray ART SCHOOL

Website : here

Facebook : here

Lillian Gray ARTIST

Website : here

Facebook : here

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