We were lucky to catch up with Ana Tskhomelidze recently and have shared our conversation below.

Hi Ana , thanks for joining us today. One of our favorite things to brainstorm about with friends who’ve built something entrepreneurial is what they would do differently if they were to start over today. Surely, there are things you’ve learned that would allow you to do it over faster, more efficiently. We’d love to hear how you would go about setting things up if you were starting over today, knowing everything that you already know.

I am starting over right now, beginning from ground zero. For the past eight years, I worked in the tech field. I started as a front-end developer and later transitioned into a product manager role. My job provided a sense of security—at least that’s how I felt. There was a distinct company culture, along with benefits and a steady paycheck; however, I have always been more interested in pursuing a creative career, but I was driven by the desire to get back on my feet soon and have a secure job.

I was managing a complex and important project, overseeing multiple teams across different time zones. The emotional stress from my job was significant, and I felt dissatisfied with what I was doing. I realized I wasn’t a technical person, and I wasn’t unleashing my full potential. However, with such a demanding schedule, I didn’t even consider learning something new, taking courses, or pursuing a different degree.

At the age of 32, I had a turning point in my life, when everything seemed to crash down, I felt an inner urge to make a profound change. I decided to leave my life in New York City and start anew in Florence, Italy, where I enrolled in a BA program in Graphic Design.

I want to emphasize that it is never too late to start over. I once read a quote that resonated with me: “How old will I be when I learn to play the piano?” The answer was, “The same age if you don’t.” Starting over, especially at a time when you want to feel “settled,” can bring feelings of uneasiness.

At this stage of my life, I thought I would have my own house or apartment, possibly a husband, and maybe even a dog. Yet, here I am, single, in a new country, learning a new language, and sitting at a desk with Gen Z. (By the way, I have made amazing new friends and truly enjoy spending time with them.) I feel stronger and I’ve learned to rely on myself.

So, what do I do now that’s different from my 20-year-old self, who didn’t know what she wanted, was a bit naive, and pursued a career that felt “right” or “smart” to secure a job? One thing I’ve discovered is that I now possess a great creative hunger, more life experience, and a stronger ability to learn. I understand that everything begins with that first scary step, but each step we take toward understanding ourselves is always gradual and requires patience.

One thing I am doing differently is stepping out of my comfort zone and addressing my imposter syndrome. I’m attending creative events and meeting professionals in design, art, and fashion. It can be intimidating, especially when they are my age and I am just starting. However, I’ve learned not to rush the process. In other words, putting myself out there, being curious about others, checking out the trends and being more present and rooted in my current life.

I think this is one of the most important lessons I would have applied differently in the past. Previously, I always rushed to reach a finish line, believing that once I achieved XYZ, I would feel successful and happy. This mentality caused me to overlook the importance of the journey itself and to question how I felt at that moment. I’ve come to realize the importance of asking myself: Does this feel right? Is this the right path for me? Are these the right people for me? How do I feel in this environment?

And last, but not least, being able to sit at the shore of my own life without wanting to lead someone else’s life. Taking my life’s circumstances as they are, looking into “my plate”, and allowing myself to transform into the new woman that I am becoming. Creative, energetic, vital, and hopefully inspiring to some.

Ana , love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

I’m Ana, I’m from Tbilisi, Republic of Georgia and lived half of my life in NYC. I am a graphic designer and illustrator specializing in branding, packaging, web design, and print media, including brochures, postcards, books, and magazines. My background in web development and product management gives me a comprehensive understanding of how design decisions impact user experience, engagement, and overall business success and I help clients bridge the gap between technical and creative aspects, ensuring seamless collaboration and alignment.

For you, what’s the most rewarding aspect of being a creative?

I think it’s the freedom to be yourself. As I see it, an artist cannot be caged in. He or she cannot create from a place of restriction. It is being authentically and unapologetically yourself.

Any resources you can share with us that might be helpful to other creatives?

Yes, two books that helped me in my creative journey are The Women Who Run with the Wolves by Clarissa Pinkola Estes and The Artis’s Way by Julia Cameron.

Contact Info:

• Instagram: https://www.instagram.com/ana__tskhomelidze/
• Linkedin: https://www.linkedin.com/in/atskh/

Image Credits

All images are designed and illustrated for me. The bear illustrations were done for a client — Wirestock.