We recently connected with Audrey Ra and have shared our conversation below.
Hi Audrey, thanks for joining us today. It’s always helpful to hear about times when someone’s had to take a risk – how did they think through the decision, why did they take the risk, and what ended up happening. We’d love to hear about a risk you’ve taken.
I started by small business with watercolor in 2017. I had been painting for a year and began posting on Instagram regularly. After a few months of posting, I would receive comments about how I painted this flower or what supplies I’m using. I was happy to share, answer comments, and wrote regular blog posts on my website. But part of me always wondered, would I be able to actually teach watercolor?
I had attended graduate school for education and always wanted to be a teacher. But not a formal, classroom teacher (no shade if you are one! It just wasn’t for me). So I launched an e-book about how to paint loose florals in July 2017. I had a great response and sold over two dozen copies.
It slowly dawned on me that this could be a real thing. However, I felt like I wasn’t reaching enough people. So I started looking into teaching online. I owned a single DSLR camera and no other fancy equipment. I joined Skillshare and recorded my first class and launched it in September 2017.
This was a huge risk for me because I had no idea if this was going to pan out. I had no experience teaching online. I didn’t have the right audio or lighting equipment. I didn’t even have a studio. I used my dining table for my first course! Would people even take my course? I had just invested countless hours doing something way out of my comfort zone. Would it be worth it?
In the end – yes. It was worth it. I became one of the top 10% of teachers within six months and now I have over 20 courses on Skillshare. At one point, it was even my main stream of income (I’ve since diversified, but it is still a source of income).
Now there have been risks that I took that didn’t pan out, but for now I just want to celebrate this win. :)


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 back background and context?
Hi there! I’m Audrey – a teaching artist to over 50k students, lover of plants and nature, and your #watercolorbestie.
I’m a self-taught artist that found my creative voice through a mental health journey that started in 2016. When I was at the lowest point in my life, I found bullet journaling, then calligraphy, and then watercolor. Each opened me up to the wonder of the world around me and I was able to find myself again. I’m living proof that art has healing power. And I want to share that experience with each of you. I enjoy noticing the details, capturing the essence of a subject, and creating pretty things that make my heart smile.
As a trained educator, I like to teach in a constructive way to help you grasp and gain confidence with watercolor basics. But I also promote letting go of perfectionism and expectations and letting watercolors literally wash your anxiety away.
I hope through my online courses, in person workshops, tutorials, and even my shop, you can discover the wonder of watercolors and the creativity in you.
I’m located in the Chicagoland area and proud to be an AAPI and woman-owned small business.
Some fun facts:
– I have three fur babies with my husband – Aslan (beige tabby cat), Rocket (white/grey long hair cat), and Charcoal (pomeranian-poodle)
– My houseplant obsession took over my house during the COVID lockdown
– I love to visit the Chicago Botanic Garden with friends or by myself
– Throughout my lifetime, I’ve lived on three continents and over a dozen cities
– I love to laugh out loud… like really loud
– I only like to take photos from one angle of my face. I’ll let you figure out which side


We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?
Growing up, I was taught to be the best and perfect. Mistakes were not tolerated. A grade of A- might as well be an F. I was the stereotype of an Asian American student with strict parents. And while I understand now that they pushed and challenged me so hard because they wanted me to succeed, it shaped me into a person who was full of fear, anxiety, and low self-worth.
A big lesson that I had to unlearn was that mistakes are okay and that there is always something to learn from it.
Watercolors actually helped me greatly with learning this lesson. When you paint with watercolors, you’re painting with water which is hard to control! So sometimes, watercolors will do things that are unexpected and unwarranted. I’ve learned over the years to lean into that and let it do its thing.
I still struggle with giving myself grace and being proud of my own work without comparing to others. I’m very much a work in progress, but each day is a chance to grow.


Let’s talk about resilience next – do you have a story you can share with us?
When I think of resilience in my business, I think about the fact that I tried to launch a shop on three separate occasions.
I first launched an Etsy shop at the very start of my journey. Around 2017. I had NO IDEA what I was doing. I listed custom work for cheap. I was selling hand painted things for $10. It was pretty ridiculous when I look back. I didn’t know much about SEO. But I’m the type to just go for it (sometimes without thinking), and see how it goes.
Suffice to say, it was a fail and I closed the Etsy shop within a year.
Fast forward to early 2019 or so, I felt the urge to open an online shop again. This time on my own website. I didn’t want to deal with Etsy fees, trying to compete with others, etc. I had always wanted to make my own stickers, so I got a Cricut. But I ran into all sorts of other problems with equipment and my website. There was also a small part of me that didn’t feel proud of my work. I was still struggling with comparing to others. Marketing my shop was another daunting task that I never quite grasped. I burnt out quickly and closed it before the pandemic hit in 2020.
During the start of the pandemic, I was going through some personal trauma, so I took a pause from everything. I didn’t paint for almost six months. But I slowly emerged and began painting again and found myself. It wasn’t easy, but I was finally making things that I was actually proud of and eager to show people.
After a few years, in early 2023, I had that same urge to launch an online shop. I had to really search within myself and ask hard questions before failing possibly for a third time. I sat with the question, “WHY start an online shop?” What’s the point of it all anyway? What sets me apart from others? I was reminded of how I grew up scrapbooking, making handmade cards for friends and family, adding stickers to every little thing, and personalizing gifts to make the recipient feel special. And then it hit me. That’s what I want my shop to feel like. That the customer feels special and that they can help make others feel special, too.
So I launched my shop for the third time in September 2023. I had mostly paper goods – greeting cards, stickers, art prints. I’ve since expanded to include additional products such as washi tape and print-on-demand products like tote bags and tea towels.
I am incredibly proud of myself for not letting past failures stop me from trying again, and learning that when you know your WHY, it’ll fuel everything you do.
Contact Info:
- Website: https://www.audreyradesign.com/
- Instagram: https://www.instagram.com/audreyradesign
- Facebook: https://www.facebook.com/AudreyRaDesign/
- Youtube: https://www.youtube.com/@audreyradesign
- Other: https://shop.audreyradesign.com/
https://www.pinterest.com/audreyradesign/



