Interested in starting your own entrepreneurial journey in beauty and cosmetics but unsure what to expect? Then read up on our interview with Dawn Bliss, owner of Dawn Bliss Beauty, located in Chicago, IL, USA.

What's your business, and who are your customers?

I am in the business of Glamsformations, a term I coined to mean Glamorous Transformations. Taking in as much preliminary info as possible regarding the client, event, venue, lighting, clothing, and (often overlooked) desired feeling to achieve at said event, I lift, brighten, and feminize the face to various degrees of drama, depending upon the client’s personal style and request.

Tell us about yourself

I say that magazines raised me because I spent most of my upbringing memorizing every fashion magazine I could get my hands on. Every day after school, from grade school through college, I’d go to the library for hours, studying and coveting the images looking back at me. I especially loved the vintage magazines in the archives because they added another dimension to all the early Hollywood films I admired. I was most influenced by the Supermodel Era of the ‘90s, including the star photographers and designers because collectively, they celebrated unabashed femininity and glamour.

I majored in Fashion Marketing at ISU and went on to work in the Couture Salon & Designer Sportwear departments at Neiman Marcus, where I interacted with beautiful garments and the fabulous women that wore them. When I modeled in a fashion show, Mario Tricoci Salon & Day Spas was doing the makeup, and that was my first introduction to working in the makeup industry outside of a counter.

I worked at the OakBrook location for almost 19 years, where I did thousand of applications on women of all ages, skin tones, and ethnicities for every occasion imaginable. There I also learned about custom blending, skincare and makeup ingredients and production, beauty retail, merchandising and marketing, public speaking, makeup for tv, runway, & print, and how to lead, as I was the Makeup Department Manager for 12 years. I learned to work fast on my feet and, most importantly, to listen.

I’ve counseled thousands of women over the years, as does happen when you’re “in the chair,” which has given me a greater purpose beyond just applying makeup. I have found that everybody needs healing and being heard, and making people feel beautiful for the day is one way, but it’s also my platform to get in front of them and be a positive light.

My fascination with the mind and human behavior has led me to study hypnotherapy. I’m currently enrolled in the year-long online program at HMI Institute LA. My vision is to create a business around Total Transformation whereby I provide products, services, and wisdom to assist my clients with changing their minds, appearance, reality, and maybe even destiny. As a 50-year-old who looks and acts much younger, I feel that it’s never too late to improve, grow, expand and try new things. I subscribe to the philosophy of “It gets greater later,” and I chose to live out loud and by example.

What's your biggest accomplishment as a business owner?

My biggest professional accomplishments are:

  1. Doing makeup for live nationally syndicated show Windy City Live on the hosts and guests for 2 yrs. That definitely scared me because it was baptism by fire. Whatever I created was not only seen immediately on tv (I’d watch from the Green Room) but also criticized by viewers via social media, and the producers would provide feedback. I was constantly on my toes, and each day was unique.
  2. Getting paid to travel the world to be myself basically. I have traveled to St. Barths, Playa Del Carmen, Cabos San Lucas, Hawaii, Miami, LA, NY, and Boston to do makeup, even flying private! The exposure and experiences my career has afforded me have been life-changing. These opportunities arise as a result of me being authentically myself and trying my best on each client no matter the occasion, their role in it, status, etc. If there is one good compulsion I possess, it’s doing my best in all instances. I also have found that people not only hire you for your talent but also for your energy. Are you fun to be around? How do you make your clients feel? What do you bring to the table? I treat all clients like old friends I just met, so the vibe is, “My fabulous friend is stopping by to help me get ready.” My knowledge and love of fashion and glamour automatically put me in the position to direct the entire look head to toe while sharing a laugh or having a meaningful conversation.
  3. Received the 3 Best Rated Award for Best Makeup Artist in Chicago 2022 by and for achieving The Knot Best Of Hall Of Fame Award by for winning Best Of awards for many years.

What's one of the hardest things that come with being a business owner?

The hardest lessons I learned were:

Don’t be stressed. Take action. Where focus goes, energy flows, so if you are focused on lack and the potential of not having any business, the business will slow down. Conversely, if you interact with your social media, website, and clients by posting more, creating new content (new or recycled), text/tagging clients/vendors, and even meditating on abundance and calling it into existence, you will see an increase.

Trust in your talent. It got you to this point and won’t fail you now or ever as long as you keep going and keep growing. All you have to do is browse Instagram to see thousands of images of what’s happening in the beauty around the world. Watch some videos and try out the techniques on yourself and your clients. It’s that simple. Get out of your head and back into your body.

Discipline is self-induced. Artists tend to lack structure, which can be tough for us. I am the poster child for Forever Young because I always want to play, but without the business component, you just have a hobby, so I carve out time daily to return emails, interact with Instagram, and post on the sites I advertise on. Unfortunately, there’s no getting around the office work, so you just have to get through it so you can play some more.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. You are selling yourself, so the closer you stay to your personal aesthetic while utilizing all of your gifts, the more effortless and satisfying your career will be. Your inspiration and execution will organically be unified into a sellable cohesive package. You are selling YOU 2.0!
  2. Specialize! Create a niche for yourself to stand out in a sea of vendors. You will have more business if you are the only one doing it or one of few. Follow your passion, zoom in to discover what makes you different, and market THAT!

Is there anything else you'd like to share?

The most important tool you have as an entrepreneur is your mind. It can work for you or against you. Lean into the positive aspects of owning your own business like having a flexible schedule, the ability to control your income, and the gift of doing what you love for a living because like attracts like, and a positive mindset not only attracts more business but makes the entire journey more pleasurable.

I spent the first 2 years of my freelance career “white-knuckling it” and worrying about “generating business,” and that absolutely worked against me and caused me unnecessary self-induced suffering. I built a following and was in demand regardless of whether I worried about it or not. When you are in a funk, step away from the business obligations temporarily and immerse yourself in what you love. Whether going for a walk in nature, taking inspirational photos, going to a museum, or out to dinner with friends, get those vibes up by doing what you love, and while in that space, recognize, “I have a pretty great life!”

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

Turn your craft into recurring revenue with Subkit. Start your subscription offering in minutes and supercharge it with growth levers. Get early access here.