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Meet Chloe Leonard

Today we’d like to introduce you to Chloe Leonard.

Chloe, let’s start with your story. We’d love to hear how you got started and how the journey has been so far.
I grew up in a small town called Novato, just outside of San Francisco, with a fun, creative, and entrepreneurial family. My dad is a commercial real estate broker, with plenty of other leadership roles on the side, who works with a team but for the most part, is very independent. My mother, on the other hand, is an artist of many niches – painting, fashion, design, beauty, and now skincare! Needless to say, I’m definitely their child. Growing up with parents like them, creativity and entrepreneurship was in my DNA.

On the road to finding my creative niche, I tried a lot of artistic outlets during my childhood and teenage years, like drawing, painting, creative writing, fashion design, and photography. I loved all of them, but nothing stuck. When I went to Chapman University to study Communication Studies and English in 2013, I realized that the last thing I wanted to do was work a … nine to five. GASP! As an introvert and someone who is incredible with time management, this career lifestyle that my professors and friends were all promoting and going after was my own personal nightmare.

Nevertheless, I wanted to keep my options open, so I got myself some internships and part-time jobs. I was a production intern at The Newport Beach Film Festival and Sony Music Entertainment, and I also had smaller jobs, including a warehouse worker at a wine production company in Napa, a hostess at an expensive Italian restaurant in Newport Beach, and a clothing store sales member in Downtown Disney. I’m not going to lie, I was not the best employee, and like clockwork, by the fifth or sixth month, I would show up late half-fast everything, and eventually give up and quit. I never lasted more than sixth months at any job.

In 2016, I decided to study abroad in Florence, Italy for six months of my Junior year, learning about public relations, creative small businesses, art, and philosophy. I think this period sparked my creativity in a new way because when I returned to the States, I picked up a new niche out of pure curiosity and boredness: Web Design. In just one week, I taught myself how to build a fully optimized website on Squarespace and WordPress, as well as how to use Photoshop. It became my new addiction (and in-lecture distraction). It was the creative hobby that just kept on giving.

When starting my last semester of college, I realized I was short a few credits before graduating. Luckily, during the seven-hour drive from San Francisco to Orange County, I was listening to my favorite podcast, Almost 30, hosted by Lindsey Simcik, my SoulCycle instructor at the time, and Krista Williams. On the show, they mentioned they needed an intern, and immediately, I knew it had to be me. Never having any podcasting or recording experience before, I messaged Lindsey while driving (not good, Chloe, not good) and the next day, I had an interview with them.

A week later, I became their first intern and employee. This small internship would change my entire career trajectory … and life. When I graduated in May, I had been doing five months of intern work for Almost 30 and for the first time, I LOVED MY JOB.

I got to listen to amazing interviews with the most fascinating people in many industries – like spirituality, entrepreneurship, business, health, and wellness – when I wrote the show notes weekly, I ran their social media accounts and helped them grow a deeper, more interactive community, and I was able to bring on some of our very first sponsors and guests, like Chelsea Leifken, Jessamyn Stanley, Coola Suncare, Onomie Beauty and Thrive Market! Krista and Lindsey gave me the one thing I never knew I wanted in a job – the freedom and trust to create designs for them and to build their network.

After graduation, I decided I’d keep my job with them working remotely while I lived at home until I found a full-time job in San Francisco. For months I kept getting rejection after rejection during the interview process. To earn some extra cash and exercise my creative side, I started taking on web/graphic design clients who inquired about me through Almost 30. With the help of Krista and Lindsey, who always fed me so much knowledge and encouragement about growing my own business, I was able to create my own design “side hustle” called Leo Creative. However, I still didn’t have the confidence to live and run a business on my own.

So after nine months of “side-hustling,” I got a Community Manager job at a corporate start-up and moved to Los Angeles to be closer to Krista, Lindsey, and my clients. With three jobs – my 9 to 5, the Almost 30 Podcast, and Leo Creative – you can guess, burn out became inevitable. During the six months at my 9 to 5, my client intake had doubled, my skillsets expanded, and my exhaustion grew. I just couldn’t do it all – working before work, during work, after work, and on weekends. I was being pulled in too many directions, doing a job eight hours a day I didn’t care about with no time to come up for air.

One day while I was driving home from work, suddenly a voice that was not my own came into my head and told me I wasn’t going to make it to the end of the year, that this would be the final time I’d work a 9-5 and for anyone but me. I couldn’t have agreed with this intuitive message more. By August of 2018, I decided to quit my full-time startup job of six months and pursue my business and Almost 30 full time. Although it was scary and took a lot of thought and planning financially, I, fortunately, was able to quit and double what I was making through Leo Creative and Almost 30.

Today, working for myself has secured that longtime freedom and independence I’d always been craving. It proves that I can create my life and success however I want. It’s an unconventional and more challenging path to take at such a young age, but it means much more to me than just designing amazing things for amazing people. As a millennial, I feel we are changing the way society thinks about what a “real job” is.

It’s simply not about waking up, going to work, leaving work, going to bed, and doing the same thing the next day anymore. The stigma of having and not having a 9 to 5 is deteriorating with the rise of start-ups, influencers, YouTube stars, and trending entrepreneurs. People are holistically evolving in their efficiency and worth because it’s not necessarily about working harder anymore, it’s about working smarter. Count me in.

Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
I run a one-woman show every day, and for once in my life, it depends and thrives on me being different! However, growing up, I always felt like being different was a bad thing. I was bullied for my appearance from grades 1st-8th and was a very shy, independent kid as a result. When I attended a private Catholic High School, I began to suffer from severe depression and anxiety.

I missed so much school because of anxiety attacks and therapy sessions that I was one absence away from not graduating. During that period, I had two choices: accept that I’m different and make the most of it or bathe in my sadness and live with a dark cloud over my head. With a little help from my therapist, medication, my family, the few friends I had remaining, and listening to Lady Gaga’s Born This Way album on repeat, I owned my differences and ran like the wind with them. I credit a lot of my confidence today for that period in my life.

For entrepreneurs, like myself, anxiety comes with the job. It pairs really well with self-doubt too. The biggest struggle is not letting those fears, and false situations come into your head because it takes up space that could be used to create your best ideas. I still struggle with it every day, some days are better than others. I find that meditation, turning off social media, exercising mid-day, and hanging out with people at least a couples times a week (#introvertlife) helps keep me inspired and refreshed to stay as positive as possible.

We’d love to hear more about what you do.
I am the owner and designer of Leo Creative, a Los Angeles-based creative design studio. I specialize in web design, logos, branding, prints, eBooks, decks, labels, wedding stationery, and social media management. I’ve been lucky to work with clients and brands like Tori Spelling, Elevate The Globe, HUM Nutrition, SoulCycle, Y7 Studio, and more. I’m also the Creative Director of the Almost 30 Podcast, a top 100 iTunes podcast hosted by Krista Williams and Lindsey Simcik. For Almost 30, I manage their social media, website, online products, design all of their marketing collateral, and provide art direction for any campaigns, tours, or events.

With these two jobs, I’m able to take what I learn from Almost 30 – strategic marketing and targeting mass audiences – and bring it to my Leo clients, and take what I learn from Leo – self-motivation and digital creativity – and bring it to Almost 30. As a designer and creative, I’m always searching for inspiration and something that brings me back to my purpose. Having these two outlets reminds me that design is not about creating something beautiful, it’s about figuring out what you want to say, how you want to say it, and, ultimately, building a unique image that will be shared with the world.

Do you look back particularly fondly on any memories from childhood?
Anything my imagination was capable of creating.

During my childhood, I would …
– draw houses, people, towns, and flowers
– build my own clothing brands with my Barbie clothes and pretend I was in charge
– make an absurd amount of collages with cutouts from my mother’s InStyle and Vogue magazines
– direct and choreograph my own rendition of Cat’s The Musical (I probably had over 50 renditions)
– be a makeup artist or hairdresser for the day and use my little sister as my model
The list could go on, but I think you get the point.

As a child, our imagination is 99.9% freedom and .01% fear, and as a result, it created some of the best days of my youth. It’s an undeniable source of inspiration for me.

Contact Info:

Image Credit:
Stef Villers, Dreylon Vang,  Lindsey Simcik, Krista Williams

Getting in touch: VoyageLA is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.

1 Comment

  1. Lori Sheron

    December 21, 2018 at 08:37

    Hi Chloe,
    It’s Lori Sheron (aka Cameron’s Mom lol!). We just received your family’s holiday card in the mail today and I councidentally logged on to Facebook (which I rarely do) and read this article shared by your proud mama! I’m so incredibly proud of all you have accomplished (as if I had anything to do with it!) and wish you much success in the future. You clearly wear your heart on your sleeve and all I can say is you are an inspiration to your generation…and mine as well. It warms my heart to know that you followed your ambition and took that leap of faith; I admire your courage and hope you continue to thrive! Sending warm regards on behalf of the entire Sheron Family!

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