We’re excited to introduce you to the always interesting and insightful Judith Gaton. We hope you’ll enjoy our conversation with Judith below.
Judith, thanks for taking the time to share your stories with us today How did you come up with the idea for your business?
I originally went to college to become a Fashion Designer. But then, I received my first critique of a collection I designed. My professor told me “You are technically perfect, but boring.” So like all budding artists, I decided to become a lawyer. It wasn’t until years later after I had been in practice for about five years, that things began to change for me. It was always on my heart to go back to style & design. I always had a desire to help women feel more confident and dress the body they are in, it just looked a bit differently than I had imagined.
I was driving home from Coachella and I put a little prayer out there. I prayed that I would find a way to help women, with style, and coaching them on confidence. I had no idea what that would exactly be, but knew I had to at least admit that desire out loud.
Then I met two women who would later become my teachers and mentors, Brooke Castillo & Kara Loewentheil. They are life coaches. Kara was a former Harvard lawyer turned life coach. They both have this view that anything truly is possible. That you can make up a job or profession when you see a need, and actually help people.
So I made up a business that combined all of the things I loved best AND actually helped women. Stylists were putting outfits together for women, but not coaching them on their confidence or their brains. I had a unique understanding of high-achieving women who have been operating like a brain without a body their entire education and careers. I wanted to do more than slap a cute outfit on women. I wanted to create something that helped them have lasting transformation and changes.


Judith, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
We work with people in two ways: small high-touch groups and an online private social club. In both programs we walk women through a framework that helps them EDIT, DESIGN, AND CURATE a style & wardrobe that feels like them. We provide a mixture of life & confidence coaching with personal styling services.
Our clients are high achievers who typically struggle with a few key things. They are at the top of their work game but feel like their outsides don’t match their insides. They are smart cookies, but they don’t feel like their style reflects that. Even if they are getting dressed for work, it doesn’t quite feel like them. They are getting dressed for work, but their style in off-work hours is very inconsistent. If they don’t have a meeting or nobody sees them daily, then they think “why bother.”
We address each of these in our programs. We shop for them and eliminate the common barrier of “I hate shopping.” We help them create a personal style so that they are dressing in a way that feels more like them. Then we work on consistency, so they are showing up more regularly as the woman they envision.
Underlying all of my work is the Motto: Confident Women Leave Legacies. We teach confidence through style.
What else should we know about how you took your side hustle and scaled it up into what it is today?
I got to where I am today business-wise because of a lot of consistent small efforts that built up over time. I started my business while also being a full-time managing partner of a law firm. My business started as a passion project, then became a side-hustle, turned jobby. I made a pact with myself that I would start with a minimum of one hour a day on my business and Saturdays. Then it became two hours a day and Saturdays to serve clients. It was a slow and steady burn.
The biggest challenge was to make sure I was serving all of my clients (style and legal) at a high level of excellence while also making sure to take time off and not get burnt out. It really came down to being disciplined with my time, focusing on what and who was in front of me, and setting boundaries when I was not working.
The lessons I’ve learned along the way.
1. It is okay to be scrappy in the beginning and learn to do everything yourself, but as soon as you are financially able begin to delegate tasks and hire contractors to help you. There is no badge of honor for burn out.
2. It is okay to admit you hate doing a task in your business. There is probably someone out there who loves to do the task you hate. Find them, delegate to them, and pay them well.
3. Surround yourself with people that you can enter into reciprocal relationships with. Perhaps they have some knowledge you need and vice versa. How can you share that knowledge and expertise with each other so that everyone wins.


We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?
I still set quarterly and monthly goals, but I don’t have the expectation that my growth has to happen in perfect little daily chunks.
Contact Info:
- Website: https://www.judithgaton.com/moderncharmschoolopening
- Instagram: www.instagram.com/judithgaton
- Facebook: https://www.facebook.com/StyleCoachJudithGaton
- Youtube: https://www.youtube.com/channel/UCLtfJvACCPxoc5zOFhMfyLQ
Image Credits
Teresa Earnest Briana Leyva

