We were lucky to catch up with Taylor Montgomery recently and have shared our conversation below.

Taylor, appreciate you joining us today. We’d love to hear the backstory behind a risk you’ve taken – whether big or small, walk us through what it was like and how it ultimately turned out.

Recently in June of 2024 I took the plunge to move across the country from St, Louis, Missouri to Los Angeles, CA. I had been visiting more than a few times throughout 2023 and 2024. Seeing how much the arts were expressed and appreciated I knew this was the place for me, .

Since Covid began in 2019 I had dropped out of college at University of Missouri Columbia (Mizzou). Discouraged with the way school was going I had tried to just move and essentially start over. I had been trying to find my new home in Chicago, Arizona even Florida but nothing ever stuck or felt like home. I always felt like I had left a chapter unfinished. In 2023 I decided to buckle down finish my degree in Health Science with an emphasis in Rehab Therapy. As a first year college graduate on both sides of my family I had to finish to start a new tradition. Although I loved what I did working as a behavioral therapist I was never fully fulfilled. After work I would spend hours working on murals around St. Louis or personal projects I had at home. At that time I was hosting my own pop-up paint n sips about once a month around St. Louis and essentially forced my friends and anyone they knew to attend so that I could share my love of art with others.

In 2024 I started traveling a lot more to LA so much that it became like a second home as my best friend lived there already. Spending so much time in the city, seeing how much they appreciate self expression, I felt like my life was changing before my eyes and I didn’t do anything but prioritize what was fun and what made me happy. In April of 2024 I shipped my favorite pieces across the country and see if they were as good as I thought. I attended my first art show and sold two paintings within the first couple hours of opening. I was in shock but not surprised I just had to find my people. I knew they were always out there. It was then I knew this was the place for me. When I was in LA I was actually doing the things I said I was going to do. No thoughts, no waiting and definitely not asking for permission. I think that is the key to making things you want actually happen as fast and thoughtless as you can. You can make it good later. I knew there was nothing to do but make the change. I didn’t have a job, car or home to move in – just determination and will power.

I had started dating my boyfriend in August of 2023 and he knew that LA was where I wanted to be. We went back n forth of if he would come with me as soon as I left or wait til I got settled. Unfortunately, I gave the man an ultimatum, I told him to just trust me and I would make him proud. And today May of 2025 I am a full time Paint n Sip instructor on Sunset Blvd and he is an engineer at Crane Aerospace. We are both pursuing our dreams and no one had to give up anything in the process. Now I that I have been here almost a year I am planning to go back off on my own to hosting my own Paint N Sips and my own solo art show coming this early fall. I could not be more blessed and happy with the way my life is going.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

My name is Taylor Montgomery I am 27 years old and I am a Libra.
Covid is how I started painting. I was essentially painting canvases for decor in my future apartment that I never got, I was posting everything I did on Instagram and Snapchat and it took off from there. I began doing a bunch of custom canvases for friends, family and strangers. Once I felt comfortable repeating projects I began painting my own stuff adding my own spin to it.
I work with acrylic paint but I have experience in all paint mediums. I create custom clothes, canvas art, murals and Paint n Sip instructor. I am most proud of my personal art and being able to see my creations with others.
As far as problems for others I work extremely closely with custom orders I don’t think I will ever be upset with people asking for exactly what they want or how many things they want to change or add. I try to add my own flare and people usually gravitate towards it. I want future followers and fans to know how excited I am with each and every project and that I will pour my heart in soul into it.

Is there mission driving your creative journey?

My goal is to be in my home with my art studio attached getting ready for my monthly solo show. I want to be creating for brands and designing products to share with their customers. I want to be able to take my paint n sips city to city so that others can enjoy at least a day of being creative and tapping into a side they have not explored yet. I want to be able to sell coloring books with my paintings on them so that all ages can enjoy my type of art.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

I had to unlearn that it was going to be handed to me. There is nothing that I have ever done that just came from me waking up and doing nothing. You have to put yourself out there to receive anything good in this world. And you have to network and talk to people. Tell others your dreams, goals and plans you never know who will make them happen. Speak yourself into existence.

Contact Info:

• Instagram: taylormontgomery__ and paintedbytay__
• Linkedin: Taylor Montgomery
• Other: [email protected]

  taylormontgomery__ tiktok

Image Credits

The pink hair pictures were taken by Makaylah Meredith she was the one who recommended me to you guys