Women Who Make Waves: Issy Von Zastrow From Kiteboarding to Watercolor

Issy Von Zastrow is one of those people who quietly lives down the street and totally blows your mind once you get to know her. I had no idea what a badass she was until we started spending more time together in Todos Santos, and I’m still in AWE. You really don’t know someone’s story until you ask.

A former world-class kiteboarder and now a full-time watercolor artist, Issy has spent most of her life connected to the ocean. Whether she’s out surfing her local break or painting pieces in her studio, water is at the center of everything she does. Her story is one of independence, reinvention, and finding freedom through both movement and art.

Here’s what she had to share:

When did you first fall in love with the ocean?

I was in love with the water and ocean since before I could walk and when I could, I would run straight to the deep end and jump in without a second thought. It has always felt like home, and I made the easy decision of living on the beach when I was 17. I was on a trip to Tanzania and fell in love with the time scale of the beach life and decided it was it for me.

How has your connection to the ocean shaped who you are?

It shapes who I am completely every single day. Being able to spend each morning playing in the waves sets me up for a great creative day. Living next to the ocean for years has brought me peace and kept me out of the rat race.

What’s something you wish more people knew about you or your profession?

I grew up in the wildness of Africa with wild parents who loved nature and all the ups and downs that come with that life. It’s about not sweating the small stuff and surrendering to the bigger picture. I love creating paintings out of water and pigment and paper—it’s fully surrendering to the greater.

What first inspired you to pursue both kiteboarding and art?

I fell in love with kiteboarding straight away on the most beautiful of beaches in Zanzibar. I found independence and freedom in the ocean, and that struck my heart immediately. I’ve always had a focused attitude, and I was determined, so I dropped out of university and moved to Zanzibar to pursue the sport—and ended up 3rd in the world :)

Watercolor came much later when I was completely and utterly burnt out from kiteboarding after 5 years on the World Tour. I was desperately looking for a new creative outlet. It was during 2020, and I started experimenting with watercolors and was supported by my community to continue into the unknown. Now I have my own business and I’m selling and showing internationally. It’s amazing what can happen in a few years.

Did you face any significant challenges or obstacles along the way? How did you overcome them?

Oh, yes of course. So many. But the key is to keep the eye on the prize. I know what I want my life to feel like and that keeps me going every time. It’s my big dreams that get me up off the floor and I continue on.

I’ve been robbed many times, stuck with no money, lost without a phone, alone somewhere new, and had my ideas rejected constantly. It’s just about deciding if you can keep going—and that belief has to come from within.

What motivates you to keep going, even when things get tough?

I guess deep down, it’s a belief in myself that anything is 100% possible. I’m much easier on myself now when something doesn’t work out or art doesn’t sell. It’s all part of the process, and it’s all about continuing to put yourself out there.

What are some of your most memorable underwater or marine experiences?

Oh wow, well recently, I had a gray whale swim within 10 meters of me in the surf lineup, and that was a truly magical day. She was massive and powerful yet extremely graceful and kind. I went home and directly painted her in watercolor :)

I feel really grateful to have a long list of magical ocean moments from over the years, and each one holds a special place in my heart and has changed my perspective on reality in some way.

What advice would you give to someone looking to follow in your footsteps?

Don’t follow in MY footsteps—make your own trail. I wish I had been told this more often when I was young, as I constantly tried to follow others’ paths to success, and it was never genuine to mine. My best advice is to follow YOUR joy and be brave in your endeavors, but we each have our own path to cut even if the prize may be similar. Do what works best for you.

How do you define success?

This came up a lot in my career as a professional kiteboarder and now again as a professional watercolorist, and I believe the definition is changing constantly. Personally, I measure success by obtaining my personal goals and dreams, but also break it down into the daily life. If I didn’t enjoy the daily process of obtaining said goal, the prize isn’t worth very much.

I know because I’ve been there—where the trophy seems like everything, but really it’s just a moment like the one before and after. It’s how you get there and what you do after you get it that define your life.

If I’m happy, grateful, and peaceful, then I consider myself very successful.

What’s next for you in your artistic journey and your connection to the ocean?

I’m not going to pretend I know the exact plan, but I have goals of increasing my painting sizes and showing my watercolors in a few favorite cities around the world. I’m also planning a ladies surf trip to warm tropical waters with some of my girlfriends.

If you could describe your art in three words, what would they be and why?
Free, Loose, Bold—because it is all freehand. I don’t sketch or practice, I just start.

Lessons from Issy

Issy’s story is a reminder that success isn’t about following a perfectly mapped path, it’s about choosing your own and being bold enough to trust it. From standing on podiums as one of the top kiteboarders in the world to starting over with a paintbrush in hand, she’s shown how reinvention, creativity, and a connection to the ocean can carry you into your next great chapter.

To see more of Issy’s work and adventures, follow her on Instagram at @vonzastrow.art and @isabelvonzastrow, or check out her latest pieces at vonzastrowart.com.

And if you know someone else who’s out there quietly making waves, send us their story—we’d love to feature more incredible women like Issy!