Never Doubt Yourself

with Isy Obi

Introduce yourself! Who are you?
My name is Isy Obi and I’m the CEO and designer for Isy B. Cayman, an inspirational accessories and resort wear brand in the Cayman Islands.

What is one thing no one really knows about you?
I love and cherish my connection with spirit. In my non-fashion other life, I am trained as a medium and a reiki healer.

What’s the best advice you’ve ever received?
“Give yourself permission to change your mind. You’re always allowed to change your mind.” I remember this if I ever feel stuck or I’m unsure about which direction to move in or what decision to make. Sometimes when the road ahead is unclear and I find myself holding myself back or freezing because I am afraid of the consequences, this advice helps me take that next step, no matter how small that keeps me moving forward.

What would you say to 16 year old you?
Worrying never solved anything. Don’t worry, and don’t give up.

What is your greatest fear?
It’s not a fear as such, but I would hate to get to the end of my life and wonder “What if…”. I want to live my greatest potential. The funny thing about that is no one ever really knows what their greatest potential is except in the moment. Which is why it is important to me to try make choices in which I can offer the best of myself in every moment. I know it doesn’t always work, but I can try!

Have you ever had anyone doubt you? How did that make you feel?
Being doubted only makes me more determined because I am naturally stubborn! Anyway, I have found that most people’s doubts are just a projection of their own fears. The challenging thing for me is to remember that and not have my fears triggered by others because that’s where the self-doubt comes in, and that to me is more damaging than anybody’s else doubt.

What message do you think every woman should hear?
YOU ARE BEAUTIFUL. I think this is the message that should be sung to every girl and woman every step of the way as we get older because too often we forget the truth of how beautiful we are, and we make ourselves small and allow others to do the same to us. Let’s not do that anymore. You are a beautiful creation, and you need to remember it. This is the message I want to promote at Isy B. If you understood how special you are, you would never doubt yourself, or your place in the world. 

Have you always had confidence in yourself?
No I haven’t. I was the tallest person in my class at school and I struggled with sticking out and being seen because I was so unsure of myself as a teenager. Luckily, my mother absolutely insisted that my siblings and I stand tall, metaphorically and literally. We’re all tall in my family and posture was a big deal but so was having pride in ourselves and standing up for what we wanted! I’m thankful for the love in her teaching. I also went on to become a model for a short time so the thing that I most struggled with became a gift.

What is your favorite thing about where you live?
I live in the Cayman Islands and absolutely love the Caribbean sunshine and vibrant colors. I live in paradise and It inspires my work and my life, and I am grateful for it every single time I look outside my window.

What do you love most about yourself?
I love that I am never ever bored. I am excited by life, and for there is always something interesting to see or do or learn. I find the world a magical place.

How do you manage your work-life balance?
I travel a lot with my husband to give myself the space I need to come back into balance. There’s nothing like exploring other cultures and seeing how other people live to give my back my perspective on a healthy work-life balance!

What is your favorite meal?
I love any meal that is made with love because I can taste the love when I eat it. My husband makes me breakfast in the mornings while I go through my morning meditations and Reiki practice. It’s simple but he is a naturally meticulous person and sets it up so beautifully that it makes me smile when I see it. That makes it my favorite meal.

What do you do on a daily basis to grow and move forward?
I maintain a regular meditation practice and I write in my journal. I need to take that time for myself throughout the day so that I don’t get lost in the all little things that I have to do each day that take up all my time and leaves me wondering how the day slipped away. I also love reading inspirational books to shift my mind into a different gear from the day-to-day tasks and give me the mental space to see the road ahead and understand where I have been. 

Did you always know what you wanted to do as a career?
No, I haven’t always known what I wanted to do as a career. I started out with a career in finance, working in banking and insurance in London. At that time, it was important for me to prove myself in a competitive, largely male dominated world. I loved strutting around the financial district in my sharp suits, heels and briefcase, playing at being one of the boys so much that I suppressed my creative side for many years. However, as I grew older, that success began to feel a little hollow and my soul wanted something more. My mother had been a fashion designer when I was a kid and so I had grown up around fashion. I have enjoyed designing clothes for fun since I was a kid, and it was something I always thought I would like to do one day but I never really allowed myself to consider it as a serious career, after all, work wasn’t supposed to be fun, was it? It took a long time for me to admit to myself that this was something I would love to do more than anything else.

Were you scared to start the process? 
I was terrified. The most difficult part of the process was letting go of the person I thought I was. I’d created a successful career for myself, and I was going to give it all up to pursue a deeply held dream, but I knew if I didn’t try then this might be one of those things I would regret forever. 

If you weren’t doing the job you have now, what would you be doing?
I would be doing a job that combines all the things I love, creativity, travel, and all things beautiful, but for it to be truly fulfilling for me, it would also allow me to bring joy and lightness into people’s lives, no matter how small. I try to bring this philosophy to the Isy B brand.

What is something on your bucket list?
I have a dream of establishing a wellness retreat somewhere in the mountains where people come to rest, recharge and rediscover themselves. It’s a future dream but it features hugely in my bucket list.

Who is your biggest role model? Why?
I celebrate the women who have overcome adversity and other people’s doubt to forge their own paths in the world. I love Oprah. Both her epic triumphs and her struggles in her life have been very public but I also feel humbled and inspired to have watched some of her journey to the woman that she is. She continues to use her numerous gifts to bring joy into people’s lives. She also embodies the idea of courage and having faith in myself.

Where do you find inspiration?
I find inspiration everywhere! I love beauty in all its forms and find inspiration from being surrounded by beauty, but I particularly love and cherish the inspiration that come to me in my dreams because I know that these are coming from the very deepest purest part of myself.

isy obi

Designer Isy Obi is the Founder of Isy B., the award-winning fashion brand from the Cayman Islands

Scroll to Top