Q&A with Olivia Herrick Design

Olivia and I go way back to our early golf competition days. While Olivia is an extremely talented competitive golfer, she's equally as talented in the design world, operating her own business, Olivia Herrick Design. When I decided to start Optimistic Millennial, I naturally reached out to her to help create the logo for the blog, which I absolutely love. It has captured the crisp, clean and professional look I've always wanted for this blog. Olivia's design has been featured in print, billboard, online, and most visibly on trendy Love Your Melon clothing. She has paved her own path to follow her passion. Any millennial with a dream for their own business can learn a thing or two from her path.


Q: Tell me about your design business. How did it start?

A: I have been freelancing for almost 10 years, but I opened my design studio full time in July of 2015. I grew up with a strong passion for art and design and always had a strong feeling that I wanted to pursue a career in the design field. I was designing logos in Powerpoint at 14 years old!

Q: What kind of clients do you work with?

Photo Credit: Olivia Herrick Design.

Photo Credit: Olivia Herrick Design.

A: I specialize in graphic design for independent and private schools. I spent four years working as a graphic design and marketing professional in an independent school setting, and absolutely fell in love with the industry. Despite that specialization, I serve very diverse clients on a daily basis, in industries from manufacturing and fashion to golf and nutrition.

Q: Have you always wanted to have a design business of your own?

A: For as long as I can remember I have felt as though my true calling was to run my own business. I come from a family of entrepreneurs and my parents definitely passed the genes on to me. I am so grateful for the opportunity to provide my clients with a valuable service — I am incredibly passionate about my work. It's a joy every day. 

Q: What were the biggest obstacles to owning your own business?

A: Some freelancers are comfortable being free-spirited when it comes to finances — I am not that way at all. Before I quit my job, I needed to have clients lined up, contracts signed, and a 100% guarantee that I was going to be meeting or exceeding my previous salary. That was very important to me and I am still that way today. One other challenge is how deeply emotionally invested you become when you work for yourself. When you have an employer, frustrations can be left at the office. When you work for yourself, every obstacle is yours alone which is both rewarding (when you overcome them!) and exhausting at times. 

Q: What are the best benefits to running your own business?

Photo Credit: Olivia Herrick Design

Photo Credit: Olivia Herrick Design

A: Running your own business is incredibly fulfilling. At my best, I feel empowered, capable and confident. Entrepreneurship fosters all of these emotions. Running your own business also offers a level of flexibility that is nearly impossible to find in a traditional work setting. Ultimately, it is an opportunity to spend each day doing what I love, which I never take for granted!

Q: Do you have any favorite stories you would like to share about something that has happened with your business? 

A: In 2012 I started working with two college kids who had just completed a class project that was gaining a bit of momentum and turning into a real business. I reached out to Zach and Brian, the founders of Love Your Melon, to let them know I would be happy to help them with a logo for free because I loved the work they were doing. Five years later, Love Your Melon is a $50 million dollar business with over 25 employees, selling hundreds of thousands of products with my original logo on them every year. They are still a client of mine and dear friends as well. One of the most common pieces of advice people give to young designers is “never work for free” but I would say — know when to work for free! 

Q: What advice would you give to millennials who want to do something similar to what you have done?

A: One of the best pieces of advice that I could give would be to work hard. Really hard. I mean really hard. Running your own business can be a grind — you have to have an appetite for your craft and a desire to put in the time and energy that it will take to be successful. You have to be willing to give 110% all the time, because no one else is going to pick up your slack. It is so rewarding, but it is not easy. Stay focused, stay the path, and I have no doubt that you will achieve your goals. 

Q: What are you dreaming about for the future of your business?

Photo Credit: Olivia Herrick Design

Photo Credit: Olivia Herrick Design

A: I would love to expand my work in the golf industry, which is a passion of mine as I play quite a bit of competitive golf. I would also love to do some guest blogging within the next year, and continue to expand my client base. I am constantly dreaming up ideas. I never know exactly what the next week or month will hold for me! 


Hopefully you gained a good sense for what a true small business owner faces to realize success by hearing from Olivia. If you'd like to see more of her work or contact her, you can find her over at Olivia Herrick Design.