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Conversations with the Inspiring Jessica Ashley

Today we’d like to introduce you to Jessica Ashley.

Thanks for sharing your story with us Jessica. So, let’s start at the beginning and we can move on from there.
I had my start in hair/makeup when I was in junior high. My school was putting on a play for the Wizard of Oz and I did not want to be on stage. Due to my school being small, we all had to be involved so they let me work backstage with costume design. I saw the makeup being practiced and instantly knew that it what I wanted to be a part of. Watching the transformations and seeing the characters come to life was unlike anything I had ever seen happen. We get to see the characters on TV or in movies, but I had never seen the process of it come together.

Fast forward to graduating high school and I knew I wanted to go to cosmetology school, but my mom encouraged I go to college and then, if I still wanted to do hair and makeup, then go back to school for that after I had a bachelor’s degree. I did that and got my Bachelor’s degree in Business Management and Human Recourses. But ten years out of high school, here I am, doing hair and makeup! It goes to show you that it’s never too late to follow your dreams.

After college, I applied for a job with MAC cosmetics. I got through the first round of interviews, but as I was talking with the recruiter I could tell I was not moving forward in the process. Instead of leaving, I asked her what I should focus on, so I could be ready and better prepared next time. She had told me that no one had ever asked her that, and she sat with me for over an hour past my interview time looking at fashion magazines, showing me how to break down the look, looking at textures, and color patterns; storylines and moods. This was the most valuable lesson I had ever gotten, as I really was a self-taught makeup artist at that point. A year later, I was working for the brand. And that launched my career in the beauty industry.

I worked for MAC cosmetics as a freelance artist and as a permanent artist in a freestanding store before I became a freelance artist for myself. I am fortunate enough to work with some of my closest friends with Hannah Elisabeth Beauty as well as continuing to build my personal portfolio.

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?
It was definitely not a smooth road! One of the hardest things for me was knowing that I was not getting passed along my first MAC interview. Now, I realize I had no real experience and MAC might have been a longshot for me at the time, but I took a chance knowing that worst that could happen was that I would not get the job and would be left in the same position as I was starting. Well, the worst happened, but I was not left in the same position. I left with a broader understanding of how to recreate looks, how to visualize my end look, how to understand what other people, whether a client or a photographer were looking for. I was defeated and nervous, but that one conversation set me up for success more than I ever thought it would have at that time.

Makeup is sometimes looked at as a hobby over a career. But the beauty if this industry is it really can be whatever you make it. It is not always glamorous. It is hard work, it is sacrificing your weekends for early morning call times or your holidays spent with your family to get others ready for their event. But it is so worth it to be a part of someone’s special day. To make them feel beautiful, strong and confident. In this industry, we are able to connect with people and become a part of their stories, and in a lot of cases, change their lives. The connection and bond I create with my clients is something I would never trade.

What should we know about your business? What do you guys do best? What sets you apart from the competition?
I specialize mostly in bridal and lifestyle makeup. I love to do more natural, enhancing makeup looks to accentuate the features of the face. I love it when my clients tell me they still feel like themselves. Don’t get me wrong, I love a dramatic smoky eye and a nude lip! That is always a classic look. But I love working with neutral, bronzy colors to create a timeless makeup look. The skin is usually my main focus, to create a flawless canvas to bring out the rest of the makeup look.

Looking back on your childhood, what experiences do you feel played an important role in shaping the person you grew up to be?
For as long as I could remember, I was that little girl that loved makeup. I loved getting my nails done and playing dress up. I love to tell this story to my clients when they ask me when/how I knew I wanted to be a makeup artist. When I was a child, maybe four-five years old, my grandma would sit at the kitchen table with me and with clean makeup brushes, would just brush my face. No actual makeup was ever used, but she would explain the ‘pretend’ makeup looks she was doing and I could sit there for hours with her. Among other things, that is my most fond childhood memory.


  • $150 for Bridal makeup
  • $100 Bridesmaids/Other applications
  • $100 for lifestyle

Contact Info:

  • Phone: 847-778-4547
  • Email:
  • Instagram: @jessica_hebeauty , @jessica_ashley__
  • Facebook: Jessica Ashley

Image Credit:
Maggie DeRolf photography, Autumn and Melinda Photography

Getting in touch: VoyageChicago 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. Donna Smolak

    January 10, 2019 at 7:10 pm

    WOW J-Lo has nothing over your beauty. I read your story and was very impressed and driven by your youth and desire for this industry. It appears your Grandmother had a positive influence on your Life. Best of Wishes on your Business Future and adventure. I will watch for you during the Academy and other Awards for the Make-up Category.

  2. Patricia Mieszala

    January 11, 2019 at 5:09 pm

    Congratulations, Jessica! Your talent and beauty, inside and out, is a gift to family, friends and clients alike in making special times in their lives even more special! Thank you for sharing your story… Wishing you an ongoing journey with continued success in making dreams come true, for yourself and others!

  3. Jane Stanford

    January 12, 2019 at 8:18 pm

    So happy you are seeing your dreams come true Jessica. I admire your talent and determination.


    January 12, 2019 at 8:49 pm

    Your love for the beauty industry is evident in every makeup work of art you create. Your are indeed an artist! Your story proves that hard work and a “not giving up” attitude, leads to success. May you experience as much happiness from creating as those who benefit from your loving, tender care.

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