Alright – so today we’ve got the honor of introducing you to Jessica Papineau. We think you’ll enjoy our conversation, we’ve shared it below.

Jessica, thanks for joining us, excited to have you contributing your stories and insights. What’s the backstory behind how you came up with the idea for your business?

People that don’t know me would never guess how I started in fashion.

I grew up in the backwoods of Maine with my mom, as my parents divorced when I was 5. My mom and step-dad chose for us to live off the land, growing our own fruits and vegetables for our meals. We had no electricity, no running water, no TV and had to use an outhouse. We had one very small wood burning stove to heat the house in the winter. I used clothes as a way of pretending I was somewhere else, that I was someone else. Mind you, my clothing was from the Salvation Army, so I had to be creative in how I used these articles of clothing to create beautiful outfits. Some of my earliest memories include me trying on my Salvation Army outfits, looking in my full length mirror and pretending I was at parties having so much fun and feeling beautiful and powerful. I remember my imagination was so vivid that I truly felt like I was actually there at these parties with all these amazing people that loved spending time with me. It truly felt magical. At this time in my life I was an only child and had to use my imagination to entertain myself.

When I was young I hated growing up in the backwoods of Maine and always wondered why God put me with this family that was nothing like me. I remember always feeling different and I never quite fit in. I resented my family for making me live without all the things that most normal children had and felt so resentful that I could live what I perceived as a normal life. It wasn’t until I was much older that I realized I had to grow up the way that I did so that I could serve women to be the best version of themselves through how they were physically showing up in the world.

It wasn’t until I was much older that I realized that my imagination was my super power and having this super power allowed me to help women imagine for themselves what they never thought was possible. This realization didn’t fully resonate with me until I was about 40. I had been working in a local high-end clothing boutique in Sarasota, Florida for about 8 years as the sales manager growing annual sales to multi 7 figures over the course of me working there. In the boutique I would help women shop in the most purposeful way and create incredible outfits that made them feel beautiful and like the best versions of themselves. My side hustle was going to these women’s homes and curating their wardrobes to align with their lifestyle and who they authentically were. Over the course of these years I was beginning to see beautiful transformations in the women that I was serving. I noticed that after a short time of working with me they would begin to feel better about themselves. They would lose the weight that they had previously never been able to lose, their relationships would improve and they would begin to have more success in business.

During these years I always had the feeling that I was meant for more, but I always questioned that I was capable of creating a business on my own that would be profitable enough for me to leave my current job.

One day on my way into the boutique I was listening to my favorite podcast at the time which was Tony Robbins. In this podcast Tony said something that stopped me dead in my tracks.

He said “If you know you have a gift that needs to be shared with the world and can make a massive positive impact on others lives, then it’s selfish not to share your gift with the world.” When I heard Tony say these words I finally understood. It wasn’t selfish to want something more for my life. It wasn’t selfish to go for my dreams. It was selfish not to. Something shifted in me at that moment. The only way I can describe it is that the whole world began to open up for me. My narrow view of my small everyday life that once had seemed so significant, no longer felt significant at all. I became curious, I started to see things that I would’ve missed before, because my view had been so narrow. I began giving attention to everything that unfolded around me, and I began to see opportunity all around me. I started to feel like something bigger than me was leading me to something greater, something bigger than me. I had a knowing that I just needed to lean in, to and have faith that I was being drawn to serving women in a deeper way than I previously had.

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?

People often wouldn’t guess how I started in fashion. I grew up in the backwoods of Maine without the conveniences most people take for granted—no electricity, running water, or TV. For me, clothes, which were from the salvation army, became a way to dream of a different life, to imagine myself in places where I felt beautiful and powerful. My imagination was my escape, and over time, I realized it was my superpower—allowing me to see possibilities beyond my surroundings.

Years later, I found myself in Florida, working as a sales manager at a high-end boutique. I loved helping women find pieces that not only looked good but felt right for them. I noticed that when I took the time to curate outfits that truly aligned with who they were, it sparked something in them—confidence, joy, a sense of empowerment. This passion grew beyond the boutique and turned into my side hustle: going to these women’s homes to curate and edit their wardrobes, ensuring their clothing reflected their true selves and fit their lifestyles.

Through these home visits, I began to see real transformations. Women would not only look great but also start feeling better about themselves. They’d shed old insecurities, build stronger relationships, and even find more success in their careers. That’s when I knew my work was more than just styling—it was about helping women step into their full power.

Still, I struggled with the idea of leaving my stable job to turn this side hustle into a full-fledged business. But one day, while listening to a Tony Robbins podcast, something clicked. He said, “If you know you have a gift that can make a massive positive impact, it’s selfish not to share it.” In that moment, everything changed for me. I realized my calling wasn’t just to make women look good—it was to help them feel their best, to use my gift to make a real difference. I leaned into that purpose, knowing that it wasn’t about playing small but about showing up fully and helping others do the same.

We’d love to hear a story of resilience from your journey.

When I was 16, I moved from the backwoods of Maine to Winnipeg, Manitoba, believing it would be my chance to break into fashion. Excited for a new beginning, I put on my nylons, black skirt suit, and pumps, and for the first time in my life, I took a city bus with my resume in hand, typed on an old typewriter. The bus ride itself was daunting, and I was nervous, but determined. I headed to the largest mall in the city, ready to hand out my resume to every women’s clothing store.

Store by store, I was met with polite refusals—my resume showed no experience in retail. Finally, I reached the last store, tucked away on the second floor at the far end of the mall. Exhausted but determined, I walked in and handed my resume to the manager. She saw I had no experience, but when I spoke passionately about my love for fashion, she decided to give me a chance and hired me on the spot. I was over the moon, despite the sore feet and nerves from my first city bus adventure. This was my first real opportunity to style women beyond myself.

When I started my first shift, I was thrilled, but I soon realized I’d been hired at a plus-size clothing store, and the women shopping there didn’t want help from a tall, lanky 16-year-old. Each time I greeted a customer, they would brush me off, some even raising a hand to signal they didn’t want my assistance. I watched them frantically grab clothes, hide their bodies under oversized layers, and leave without buying anything, looking defeated. It was heartbreaking to see these professional, confident-looking women struggling with body image. I felt helpless and frustrated, knowing I could help them feel beautiful if they would just let me.

After a month of facing this rejection, I decided something had to change. One day, a woman came in and, as usual, when I offered to help, she put her hand up and said, “I do not need your help.” But instead of stepping back, I approached her differently. As she was about to leave, I said, “I know you said you didn’t want my help, but you must have come in today with a purpose. You drove all the way to this mall, to this store, in the dead of winter. At this point, what do you have to lose? Why don’t you give me a try? I know I can help.” She paused, relaxed a little, and said, “Okay, fine, I guess you’re right. I really don’t have anything to lose at this point.”

Her name was Kathy, a high-level executive who needed an outfit that made her feel professional and confident for an upcoming conference. I carefully chose pieces that I knew would flatter her, and she reluctantly agreed to try them on, saying, “I don’t think these pieces are going to work on me, but I’ll try them on just for you to see that they won’t work.”

When Kathy stepped out in a fitted silk top and slim navy pants, she focused on her perceived flaws, especially around her midsection. I gently added a long cardigan, accessories, and nude pumps, and asked if I could help her put them on. When she looked in the mirror again, I saw her eyes move from her midsection to her legs, then up to her eyes, where they stayed. Her eyes filled with tears. She turned to me and said, “Thank you.” She took a moment to compose herself, then added, “I never thought this was possible… For the first time in my life, I actually feel beautiful!”

At that moment, I felt the same magic I used to feel as a child, creating outfits in front of my mirror. But this time, it was even more powerful—seeing another woman feel beautiful because of my help. That day, I realized that fashion was more than clothes; it was my gift to help women feel confident, powerful, and envision a better life for themselves. It was the moment I knew I was meant to share this gift with the world.

What’s a lesson you had to unlearn and what’s the backstory?

Growing up in the backwoods of Maine with my hippie parents, who were committed to living off the land, I was surrounded by a belief that anything related to fashion or beauty was superficial and unnecessary. Our home didn’t even have electricity, let alone any emphasis on appearance. Yet, I found myself drawn to it all—spending hours creating outfits from my Salvation Army finds, trying on every combination in front of a mirror, imagining myself feeling beautiful and confident. But I always wondered: was I worthy of a nice outfit? Was putting on makeup every day just vanity?

For a long time, I wrestled with the idea that my passion for fashion was somehow frivolous. I felt guilty for wanting to look good, as if it contradicted the values I was raised with. It wasn’t until much later in life, when I started working in a high-end boutique and curating wardrobes for clients as a side hustle, that I began to see the truth: fashion and beauty were not about vanity; they were about empowerment.

Working closely with my clients, I saw firsthand how transformative fashion could be. I remember helping one woman, Kathy, who reluctantly let me style her after initially rejecting my help. When she finally looked at herself in the mirror, her eyes moved past her perceived flaws and settled on her own reflection—tears filled her eyes as she said, “I never thought this was possible… For the first time in my life, I actually feel beautiful!” That was the moment I realized that fashion was about so much more than clothes. It was about helping women see themselves differently, feel confident in their own skin, and step into their true power.

I had to unlearn the belief that caring about how we look is superficial. Through working with so many women, I’ve discovered that when they feel beautiful, they unlock a part of themselves that’s ready to take on the world. I’ve seen women’s confidence soar, their relationships improve, and their careers flourish simply because they started to embrace their own beauty and style. They stand taller, speak more assertively, and feel more connected to who they authentically are.

Now, I understand that beauty and fashion are tools for transformation. They allow women to express their authentic selves and share their gifts with the world. It’s not about the clothes or the makeup; it’s about the freedom to show up as who you are and feel deserving of everything you’ve dreamed of. When I let go of the idea that this passion was superficial, I found the real purpose behind it: empowering women to see themselves as they truly are—worthy, beautiful, and powerful.

Contact Info:

• Website: https://www.csjstyling.com
• Instagram: @thejessicapapineau
• Facebook: Customized Styling by Jessica
• Linkedin: Jessica Papineau
• Youtube: Customized Styling by Jessica

Image Credits

Rana Tierney