Meet Bailee Wolfson

Bailee, can you briefly walk us through your story – how you started and how you got to where you are today.
I have always wanted to be a makeup artist since I was really little. I was doing my own makeup for dance recitals and I was always really interested in trying new products from a young age. I remember having a huge eyeshadow palette that my mom gave me to play with and used the blues and purples to give my brother a black eye. Growing up as a millennial in Minnesota in the 90s/00s, I did not have YouTube tutorials to learn from. My age bracket was clearly behind on the learning curve.

I remember mentioning to my parents in high school that I wanted to be a makeup artist but their idea of a makeup artist consisted of the people working at a counter in a mall. Their response was, “you gotta go to college and get a “real job”, so I did. I’m very happy about that decision, as I actually loved my college experience at the University of Arizona. I got a degree in Communication and Art and Art History, studied abroad in London and two weeks after graduation, I moved to New York in 2008.

I arrived in New York just in time for the economy to crash. I was doing online editorial for Coolhunting.com and interning for Elle.com, Jetsetter.com, hostessing, working for Soho House, etc., and then I got a huge opportunity to work for the luxury watch company Audemars Piguet doing Marketing and Events. I really believe our life is a journey and I think all of my work experiences have been so beneficial, as I have learned a lot and met a TON of people along the way.

I did come to a point where I needed a change. I either was going to look for another events job or pursue makeup. I thought to myself… there is no better time than the present and I will always regret it if I don’t try, so try I did! The long story long is that I was trying to figure out the best way to go about breaking into the industry while gaining experience in the most efficient way. The universe sort of fell into place for me when I randomly met Jenny Smith, a Global Artist for NARS Cosmetics while I was shopping at Bloomingdales in Soho, NY.

After chatting with her, I decided to take a six week intensive course at the Makeup Forever Academy and then followed back up with her. She became my mentor and I was her first assistant almost right away. I gained invaluable first-hand experience working with her. I got to assist her on editorial shoots and was able to be on her team at New York Fashion Week in my first year as a Makeup Artist. She really taught me so much about the makeup industry and was truly selfless in giving her time and energy to me. I am extremely grateful, as so many people tend to just look out for themselves.

I think because I was a bit older when I started on my journey to become a makeup artist (late 20’s), I was lucky to have a lot of connections and friends already in the creative industry, i.e., photographers, stylists, content creators, creative directors. I was freelancing and getting my own jobs, as well as assisting all during the last three years of living in NYC.

After almost nine years of living in New York, I moved to Los Angeles. Since moving to California three years ago, it’s been hard being a freelancer and having to start over. I have had to grow my network slowly over time, and work hard at making new friends and contacts. My passion for makeup and the art of creating beauty is worth the struggle. I do look back on the nice salary of my previous job sometimes and get frustrated but then I think to myself how I never wanted to end up in a desk job and there I was.

Being a Makeup Artist allows me to express myself. I remember the quote from Oprah that always stuck with me. “If you do work that you love and the work fulfills you, the rest will come”… and I think I’ve found that. It’s not always easy to freelance but for now and the foreseeable future, it’s worth it!

Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
There are always challenges when it comes to getting work as a freelance makeup artist. The most challenging thing for me is having work come in waves. It seems like its all or nothing. When it rains, it pours but when it’s not raining, you are stressed and feel like you will never work again. It feels like a dramatic thing to say, but ask any of my freelance makeup artist friends and I bet they would all agree. So I would say the inconsistency in work and the inability to plan ahead is the biggest struggle. 

We’d love to hear more about your work and what you are currently focused on. What else should we know?
I work on editorial, fashion, beauty and personal clients. I love enhancing natural beauty, perfecting skin, highlighting people’s best features and making people feel good about themselves. My work reflects my attention to detail and my ability to listen to the client and bridge their vision with my own. In many cases, less is more.

What is “success” or “successful” for you?
That is a big question. I feel successful just by being asked to do a job I love. Seeing an end result where the client is happy and knowing my work is well received is also very rewarding. A lot of times it’s easy to start comparing yourself with others, but I like to try to remind myself that everyone’s path is different and we are all where we are meant to be.

Contact Info:

• Website: www.baileewolfson.com
• Phone: 612-702-4742
• Email: [email protected]
• Instagram: https://www.instagram.com/bailerina/