Sara Annapolen’s Stories, Lessons & Insights

We’re looking forward to introducing you to Sara Annapolen. Check out our conversation below.

Sara, so good to connect and we’re excited to share your story and insights with our audience. There’s a ton to learn from your story, but let’s start with a warm up before we get into the heart of the interview. What is something outside of work that is bringing you joy lately?
A new routine this summer is playing Mahjong at our pool club weekly with friends and all of our daughters. The girls swim and play, and the moms get to connect. It’s an amazing special moment in time, where the sun sets late, and the air is warm, there is so much laughter. And there is space at the end of the evening for a mother daughter connection too. A special late bedtime. Knowing fall is coming ahead makes us enjoy every moment of this.

Can you briefly introduce yourself and share what makes you or your brand unique?
Hi! I’m Sara Annapolen, artist and Founder of Sara Joy, a brand built on spreading positivity through my colorful artwork. I spent 5 years building a Resort wear clothing line using my own artwork on fabric. I transitioned away from fashion and into full time art in 2024. I add joy to playful community settings through my large scale wall murals, my most recent being art at a community pool club! I also create custom paintings for peoples homes. And I am most passionate about Judaica art – celebrating Jewish heritage and generations to come – Hebrew graffiti on canvas, and modern playful hamsa paintings. After October 7th, 2023 and the attack on Israel I channeled my anxiety into a series of Judaica paintings called the Simcha Series. The collection has since grown and is now a whimsical fun representation of Jewish Joy!

Great, so let’s dive into your journey a bit more. What breaks the bonds between people—and what restores them?
This question feels so important right now, as our world is very divided. I think not being able to accept change can break the bonds between people. The only constant is change, and we are all evolving. If you have a willingness to learn about other people, be empathetic, and compassionate, and forgive, bonds grow tighter. And I do believe bonds can always be restored with more listening, less talking. More compassion.

What did suffering teach you that success never could?
Failure and suffering shaped my drive for mental peace. At a point in my fashion journey I started to hate what I was doing. And I was so conflicted in that emotion – I was living my dream – I had my own clothing line. I was sad, anxious, and so confused how I could hate something that I built on my own. I realized I had to change course – and I realized how important my mental health was to me. In making this change to pursue full time art instead of continuing manufacturing coverups I was choosing myself over my ego and my pride. A year later I see how incredibly worthwhile of a decision that was. I am so much happier. I had to hit that low to make that decision and move on.

Next, maybe we can discuss some of your foundational philosophies and views? Is the public version of you the real you?
YES. Most definitely. I’m emotional in private and public. I say what I think, always, and I’m always the real me. I believe in kindness always. And I’m an artist with paint on my hands who loves to make people smile!

Okay, so let’s keep going with one more question that means a lot to us: If you knew you had 10 years left, what would you stop doing immediately?
I would stop worrying about opinions of my paintings, of my website, of my Instagram, opinions of people overall. I would stop worrying about success. I’m already successful doing what I was born to do – but it’s hard to remember that! I would stop worrying about what other people think and I’d truly create without limitation. I’d also stop doubting my worth in any capacity.

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