We caught up with the brilliant and insightful Cassandra Hess a few weeks ago and have shared our conversation below.

Cassandra, looking forward to hearing all of your stories today. Risk taking is a huge part of most people’s story but too often society overlooks those risks and only focuses on where you are today. Can you talk to us about a risk you’ve taken – it could be a big risk or a small one – but walk us through the backstory.

I have always enjoyed the arts. Being creative with my hands and with my thinking is just who I am. When career day happened in high school, back in the 90’s, it wasn’t acceptable to choose the artist path. “You can’t make money being an artist.” Those words were far too commonly heard amongst anyone who desired to take the artists path. So, I felt it was appropriate to pick business as my ultimate career path. However, the problem with that for me was that I made terrible grades in school. I found it very hard to focus or to find interest in anything other than creating art.

After thinking a bit more on this, I had learned that college was not my only option. Trade schools had become more and more desirable amongst a lot of students. For me it was the answer. I decided to go to Cosmetology school and then ultimately the goal would be able to work my way through college. The dream was to one day be able to own my own business/salon. This was the plan that started me on my way.

After I received my cosmetology license, I got an apprenticeship job at a very high end salon. After assisting and going through their education program, I was able to get behind the chair and see paying clients. At the age of 19, I started really making a good income. I bought my first home at 21. I loved it. Living alone and making it on my own was an extremely important thing for me to be able to do.

I grew up with a single mother who struggled raising 3 kids without any financial assistance from our father. Despite being extremely educated and making a decent income as a nurse, it seemed that money was always a stressor. My mother showed me how important it was to be able to support yourself and never to expect handouts and so I never did.

After working in the salon and deciding that I absolutely loved my job, I made the decision not to continue my education. I felt I could build the life I wanted with the income that I was making, which was more than I could have ever imagined it being. I was an excellent hairstylist, but as time went on, I decided that the salon environment just wasn’t for me anymore. There had been some changes in the company that had me second guessing what I really wanted. So, after 8 years, I packed up my things and went on my way.

It was super risky to leave such a well paying job, but to all that knew me, they didn’t question if I was making the right decision. They knew my determination would land me on my feet. I decided for the time being to do hair out of my home. The demand became so high that I made even more money being on my own. I continued working as a hairstylist out of my home for 15 years.
In that 15 years, I got married, had a baby, and finally started my art career to fulfill the dream that never went away.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your background and context?

Being an artist was a title I never fully understood, until I actually saw myself as the artist I had always been. People would tell me all the time what a great artist I was and I would say thanks, but I’m not there yet. The reality is, being an artist is a practice. Always experimenting with different techniques and mediums. Making beautiful art pieces and then the next not so beautiful. Each piece is a lesson and a masterpiece all in itself. The masterpiece is the knowledge that is gained with each creation.

I never went to art school. I think I was too intimidated by all the “real artists” that would be there. Plus, I couldn’t see paying for something, that I believed at that time, would never actually make me money in return. Insecurity in myself was not lacking. So I painted and painted and painted. I would take a workshop here and there and then I would take whatever beautiful piece of knowledge that I got and incorporate it into my art. I started to get requests from people for commission pieces. Then people started buying my own creations. Then I was able to open an Etsy shop and sell art that way. It was so exciting for me. I felt validated and I felt like maybe I was finally an artist. However, I struggled because I felt like I didn’t have my very own style that made me stand out from the rest. So, I kept painting anything and everything.

Once I had made the commitment to myself to become a full time artist, I knew I couldn’t let myself down. And I knew to find my own personal style as an artist, I had to keep going. As my journey continued, I discovered that I love painting the feminine figure with a lot of color and natural elements. I started to lack resources for references, so I began to photograph myself in costumes and fun poses. Then I started to evolve that into painting my face and body to match my wardrobe. This was incredibly satisfying for me. It became a type of performance art that I used for my paintings. Once I started this, I began to make a name for myself as the woman who paints herself and then paints herself on canvas.

I feel very proud and excited of the journey that led me to where I am. I am nowhere near complete as an artist, in fact I feel I am just getting started. What excites me the most is that I have discovered for myself that I do not have to put myself in a box to be taken seriously as an artist. In fact the more I do as a creative the more I become exactly the artist that I want to be, or even better, the artist that I am.

My business has grown from being a painter on canvas to now painting on people for a body canvas experience. This includes fun photographs and poses to really show off the painting and the human figure including an option of having a painting made of self or loved one that was painted on.

I think my background of doing hair for over 20 years has given me an advantage in knowing how to style people. Making a painting is one thing, but painting on people is a whole other thing. People want to be transformed, but yet feel attractive. This has been my life’s work and I’m proud to be able to now achieve this as a practicing artist.

We’d love to hear the story of how you built up your social media audience?

When I first started creating art, I knew the ultimate goal for me would be to go public. Once I started to feel more confident with painting, I opened an instagram account and would post a new painting everyday. I had enough paintings that I had completed to be able to do this for a bit. At first, my immediate friends and family were so surprised and supportive of my art that they helped me spread the word. However, just like a lot of things, after a year or 2 my momentum started to fizzle out. I started creating more fun videos of me painting or just silly videos for fun, but I felt like it wasn’t capturing what I was trying to communicate.

Eventually, I started sharing more of me and getting more personally connected to my following and was able to develop more momentum again. But the real growth happened when I finally figured out what I was saying and how I wanted to say it. I began to be more true to myself and not worry about how it would be received by the public. The reality is you can’t please everyone and there will always be negative with the positive. My takeaway at this point is as long as you are true to yourself and your goal/purpose, the rest will fall into place.

As an artist that wants to survive on purely just creating, it is important to make a name for yourself. It is important to remember that what you have to say matters. Even if you feel like it’s insignificant and shouldn’t even bother mentioning or posting it. Post it anyway. It will matter to someone and probably more than what you think. Honestly, I am nowhere near where I want to be, but I am also exactly where I need to be. Growth is the destination.

Have you ever had to pivot?

Being an artist to me means creating. It also means practicing constantly. When I first started, I painted anything and everything. If I saw something and I thought it was beautiful or interesting, I painted it. I also got caught up in thinking, what will more people like? I noticed as I did that, I became unsatisfied with my art and I felt like I had to explain why everything was so different and why I didn’t have a style. I didn’t feel very proud of my creations and it was because it wasn’t from my heart. It wasn’t saying what I was trying to say. When I figured that out, I pivoted to creating all my own inspiration photos and painted what interested me. During this transition I started to sell less paintings and began to doubt myself as an artist. But as I continued to stay true to my visions, my paintings also began to build more momentum and more interest. There will always be lulls in business, but my greatest lesson I learned is the lulls offer a chance to step back and make sure you are still in the same mindset you were when you started. If not, pivot.

Contact Info:

• Website: https://cassandrapainting.etsy.com/
• Instagram: @cassandrapainting
• Facebook: Cassandra Hess
• Youtube: @cassandrapainting