We caught up with the brilliant and insightful Kara Winslow a few weeks ago and have shared our conversation below.
Hi Kara, thanks for joining us today. Often the greatest growth and the biggest wins come right after a defeat. ther times the failure serves as a lesson that’s helpful later in your journey. We’d appreciate if you could open up about a time you’ve failed.
When I was 20 years old I was working that summer at a Tony Award Winning Regional Theatre along side celebrities and top industry people. I made two massive mistakes that could have changed the trajectory of my career but I used them as learning experiences.
First off I had a director I was working with that was major in the industry. He directed the original staging of a broadway show we all know. He and I had lunch one day and he told me to contact him when I graduated from college in two years cause he wanted me to work with him. I didn’t understand networking or building relationships. I go zero contact info for him and didn’t stay in touch. Lo and behold when I graduated I had zero clue how to contact him and realized I let that connection drop.
Second I was working with a celebrity actress who was on a hit show at tget time and I was her assistant stage manager, running lines with her and such that summer. All summer she kept asking if I was an actress. I kept saying to her confused I was her stage manager. The thing was I was an actress but I was intimidated by her. And took that summer a tad too literally. Years later I watched the show she was on at that time and realized the season that was filmed after we worked together many of the actors came from that theater festival. If only I had said yes.
So years later I had no plans of becoming a makeup artist but because of learning the importance of building relationships and saying yes I ended up starting this amazing career,
As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
I accidentally because a makeup artist over a decade ago. Back in 2008 I was cast in a small independent film. My main job in the film – to scream and die. First day of filming I show and the makeup artist had just a bag of drug store makeup. I’m allergic to a lot of products so asked if I could do my own makeup. Three days into filming the makeup artist stopped showing up and the director asked if I would help the other actors. I said yes because he was cute.
A year later his brother who produced that film called to tell me he gave my number up someone but wouldn’t tell me who. The next day I got a call from MTV asking me to put together a styling team with myself as the makeup artist for a AXE commercial they were filming. I had zero clue what I was doing but jumped at it and thought it would be a fun one time blip on my resume.
But between those two instances I was cast as a cosmetics model for a makeup line on HSN. Again I thought it would be a one time thing but ended up being with the brand for a decade and promoted to their official USA makeup artist,
All of this snowballed and in 2012 I quit my real job to do makeup full time,
How did you put together the initial capital you needed to start your business?
Honestly I had zero startup capital at all. I was working 60-80 hours a week at a professional theatre bring home only $1,700 a month when I launched my company. I had zero savings. The highest credit card I could get was $500 and they were maxed out. I had buy each set of lashes at $1.99 per client as needed cause I couldn’t afford to buy in bulk. I had to turn down jobs because I couldn’t afford the gas to get there. When I quit my job to do this full time I figured I would either make it work or become homeless. Here we are 12 years later still going,
What do you find most rewarding about being a creative?
The best part of what I do is bringing joy to others. To see a woman look in the mirror and start crying because she’s next felt beautiful before is amazing. To be able to go in a children’s hospital and work with the patience and have their parents tell you it’s the first time their sick child has smiled in days, weeks, months is a true blessing. To be invited into someone life for their milestone moments from weddings to births and everything else. I love the joy my jobs allows me to deliver.
Contact Info:
- Website: https://Karawinslow.com
- Instagram: https://www.instagram.com/karawinslowmua?igsh=MWtvaWltZnJ2eno0aA%3D%3D&utm_source=qr
- Facebook: https://www.facebook.com/profile.php?id=100063624581112&mibextid=LQQJ4d
- Youtube: https://youtube.com/@karaslipstickdiary?si=QkJZOlRmvVzFbGlo
- Other: https://maps.app.goo.gl/PAMisusaMa8P4eZn7?g_st=com.google.maps.preview.copy
Image Credits
1. Photo on white background – Adrienne Fletcher Photography
2. Doing bride in robes makeup – Barbara Ann Photography
3. Doing makeup tv behind client – Tiffanyleigh Photography