Welcome to the first installment of our newest series – Ask An Entrepreneur. We’ve polled an assortment of our favorite lady treps to discover what inspires them, what keeps them going, and the ups and downs of being your own boss. The goal of this series is to help budding entrepreneurs strike out on their own and to provide a place to share their stories and words of encouragement. Feel free to share your thoughts in the comment section below!


When did you realize you wanted to go into business for yourself? What sparked that initial decision?

I realized I wanted to be in business for myself when I got real honest about being a bad employee in the 9-5 world. My “hobby” of teaching and performing comedy started to become more and more of my focus and was the thing that inspired me. Weighing the options of Take A Risk And Do What You Love or Be Kinda Miserable Working For Someone Else was an easy choice after a while, happiness feels much better.

Tami Nelson, co-founder of The New Movement Theater


When I saw the freelancers invoices – they were doing the same job as me and getting paid what I would earn in 3 months for a 2 week job. That was the catalyst! I think that’s probably very specific to my industry though. The idea being that you would earn your stripes in-house and then strike out on your own if/when you were ready.

Jo Coombes, freelancer with RED Diary Service


In college I worked for a small business (a husband-and-wife wedding photography team where I learned everything I know about photography!) but never imagined I would go out on my own. It seemed too difficult – too many moving parts and pieces to always be on top of. So when my husband and I moved to New Orleans, I “went corporate” and only lasted four months. I was astounded at how miserable I was in a cubicle, working the same hours every day, butting heads with the same coworkers, and feeling like I wasn’t getting anywhere or accomplishing anything. I took a long Christmas vacation at the end of those four months and I started panicking when I thought about going back. I decided 21 was too young to be this miserable, so I went back and turned in my two weeks notice and officially launched Sarah Becker Photography here in New Orleans in January 2013!

Sarah Becker Lillard of Sarah Becker Photography


I don’t like taking orders from other people. I feel the need to be in control, but not of a group of people…just in control of my ideas and how they come to fruition. I also need to work on my own schedule. My productivity is at it’s highest when I am not forced to produce.

Amanda de Leon of Amanda de Leon Clothing

I realized I wanted to go into business for myself when there was no one in the industry I wanted to work for.  There wasn’t a design aesthetic that matched mine, so I figured I’d go for it!

Kim Starr Wise, owner of Kim Starr Wise Florals


I had a vision in mind for a certain type of business, and when I realized it didn’t exist I knew I’d have to go into business for myself if I wanted to see it come to fruition. After a lot of planning and strategizing, the final push came when I was in a job that was not the right fit and I was miserable every day. I recognized that the situation wasn’t really changing at all, so I could either stay and things would remain the same or I could jump and everything would change.

Hattie Moll, owner of Hattie Sparks Boutique

I knew in college that I eventually wanted to go into business for myself, but I didn’t know what industry. I initially began Culture Shock as a blog, and used it as a tool for me to educate people about other cultures, but it slowly turned into a business.

Christine Alexis, founder of Culture Shock LLC


I always wanted to work as a creative, but I never really knew what that meant or how to go about it. After college went into the “right path” got a “real” 9-5 (8-10) and a nice little house with a yard. It seemed like it was what I was supposed to do. But after a while I realized that wasn’t what I was looking for. My partner John also was feeling the same. So we decided to change our lives. We sold everything we had. Moved to a small apartment, saved up every extra dollar and set off. We ended up backpacking and sailing across the southern Caribbean from Grenada to Colombia over the next year. During that time we designed and developed a blog where we started sharing our story and our designs. It caught on and by the time we were in Colombia we were freelance designers. At which point we decided to change our lives again, moved back to the U.S. and officially incorporated Hop & Jaunt, our creative design agency. It’s been just about 5yrs now and we’re still growing and learning and following the path that seems right to us.

Aly Kilday, Co-founder of Hop & Jaunt

This post originally appeared on, a website I founded that served as a site to inspire creatives & entrepreneurs to obtain a better work-life balance. The site garnered over 78,000 views. It has since been discontinued.