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Conversations with Kathleen Benjamin

Today we’d like to introduce you to Kathleen Benjamin.

Hi Kathleen, so excited to have you with us today. What can you tell us about your story?
My interest in beauty started as a child with my own dry, curly hair and growing up in the 70s, straight hair seemed to be the look everyone wanted. I was naturally drawn to learning how to straighten and style mine.That personal curiosity became the beginning of my lifelong interest in hair and beauty.

We all face challenges, but looking back would you describe it as a relatively smooth road?
My journey hasn’t always been a smooth road, but I’ve never questioned my love for the beauty industry. I actually chose to study cosmetology in high school against my parents’ wishes. I followed my instincts, stuck with it, and became a licensed cosmetologist shortly after graduation.

Over the years, I found myself wanting more creatively. After spending time working in salons, I decided to venture into freelancing. It was a scary step, especially while raising my children and worrying about the financial uncertainty of working for myself.

One of the biggest challenges in my life came in 2009 when my former husband passed away, shortly after our divorce. At the time, I was raising two teenage children and suddenly faced the responsibility of supporting all three of us financially. It was an incredibly difficult and uncertain chapter in my life. I had to find the courage to become financially independent and create a secure future for my family. Looking back, that experience taught me resilience, determination, and just how much I was capable of accomplishing, even when I doubted myself.

I think one of my biggest obstacles throughout my career has been getting out of my own head and overcoming the fear that I wouldn’t succeed. I knew I had the creative skills and experience, but running a business was an entirely different challenge. Taking a business course helped me understand the fundamentals of running a business and gave me the confidence I needed to move forward.

Along the way, I discovered a new passion for bridal hair and makeup. That led me to launch On Site Hair and Makeup in 2016. This year, I’m celebrating 10 years in business with a talented team of approximately 20 artists.

What started as a leap of faith has grown into something I’m incredibly proud of. I’ve learned that life doesn’t always go according to plan, and sometimes the most difficult experiences push us toward opportunities we never imagined. Most importantly, I’ve learned to trust myself, embrace change, and never underestimate what I’m capable of achieving.

Alright, so let’s switch gears a bit and talk business. What should we know about your work?
What I love most about my work is the ability to make someone feel beautiful and confident in their own skin. I’ve never believed that beauty is about transforming someone into a different person. For me, it’s about enhancing what’s already there and helping people see the beauty in themselves.

I’m best known for my natural, softly enhanced makeup and romantic hairstyles. My philosophy has always been that you should still look and feel like yourself, just a little more polished and confident.

This year marks 50 years since I first stepped into the beauty industry at just 16 years old. I think that experience is one of the things that sets me apart. I’ve watched trends come and go, but my approach to beauty has remained consistent. I’ve learned that listening to people, understanding what makes them feel comfortable, and building trust are just as important as the technical skills.

What I’m most proud of is my perseverance. There have certainly been moments when I wanted to give up, but I’ve always found a way to keep moving forward. Building my own bridal hair and makeup company and surrounding myself with a talented team of artists has been incredibly rewarding.

After all these years, I still genuinely love what I do. There’s something very special about watching someone look in the mirror and smile because they feel like the best version of themselves.

What’s next?
Looking ahead, I want to continue growing my bridal hair and makeup business and doing what I love most—helping brides feel beautiful and confident on one of the most important days of their lives.

A few years ago, I also started a YouTube channel, which has opened up an entirely new and exciting chapter in my career. My focus is helping mature women navigate the changes that come with aging, particularly when it comes to skincare and makeup. I want women to understand that beauty doesn’t have an expiration date, but sometimes our techniques and products need to evolve with us.

After nearly 50 years in the beauty industry, I find it incredibly rewarding to share what I’ve learned with women who may be struggling to feel confident in their changing skin.

My goal is to continue growing both sides of my business while staying true to what has always inspired me—helping women embrace their natural beauty and feel good about themselves at every stage of life. Im looking forward to spending time with my family too!

I’m excited about this next chapter because it reminds me that no matter how long you’ve been doing something, there’s always room to grow, learn, and discover a new passion.

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Four women in wedding dresses holding bouquets, smiling and talking indoors with a window in the background.

Bride and groom in wedding attire sharing a moment indoors with large windows and greenery outside, smiling and embracing.

Group of women, some in matching blue shirts, gather outdoors around a smiling woman in a white dress holding her dress's sides.

Young woman in wedding dress outdoors, smiling, with trees and grass in background.

Young woman in wedding dress with veil, smiling, standing indoors against a plain wall.

Group of seven women in elegant dresses, holding bouquets, standing indoors in front of a window and chandelier.

Bride and groom stand beside a vintage white car outdoors, with white columns and lanterns in the background.

Five people smiling together indoors, dressed in formal attire, standing close, with a fireplace and decorative items in the background.

Smiling woman in wedding dress holding a bouquet outdoors, with trees and greenery in background.

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