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

Tiffany, appreciate you joining us today. Can you talk to us about a risk you’ve taken – walk us through the story?

Taking risks has truly shaped my journey. One of the biggest risks I took was resigning from my teaching career in 2020 to go full-time into business. At that point, I had already been running my first business since 2018, but leaving behind a career that I’d spent years building, especially in a field I was passionate about, was a major leap of faith. I knew it would mean letting go of financial security, the comfort of a predictable routine, and the support system I had as an educator.

But I was driven by a deeper calling. I wanted freedom—freedom of time, freedom to pursue my passions, and the freedom to make a bigger impact on the world. I also wanted to create a legacy for my children and for generations to come. The decision wasn’t just about me; it was about setting an example for my kids, showing them what it looks like to chase your dreams, take risks, and build something meaningful.

I remember feeling a mix of excitement and fear as I submitted my resignation. The fear was real, but the excitement of creating something that would not only allow me to have the life I wanted but also help others was stronger. The early days of going full-time in my business were challenging, of course—there were doubts, tough days, and times when I wasn’t sure if I was making the right decision. But looking back, it was one of the best decisions I could have made.

Starting my second business, Taylor & Jessie, in 2022 was a reflection of that same determination. It’s a brand that speaks to the heart of who I am—helping women set and crush goals while prioritizing mental well-being. The risks I took were not just about entrepreneurship; they were about designing the life I truly wanted and making sure I built something that would continue to give back to others. So far, it’s been a journey of incredible faith, growth, and impact, and I know it’s just the beginning.

Tiffany, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I’m Tiffany Lewis, the Founder and CEO of Taylor & Jessie, a stationery brand on a mission to help women crush their goals while protecting their mental health. My journey into the business world started in 2018 when I launched my first business. But even before that, I spent 15 years in education, teaching and leading in various roles, which deeply shaped my approach to entrepreneurship. Coming from a family of educators, I was always passionate about empowering others, especially women, and helping them realize their full potential.

In 2020, I made the bold decision to resign from my teaching career to pursue my business full-time. I was craving more freedom—time, financial, and personal—and I wanted to create something that would leave a lasting impact, not only on my life but also on future generations. I launched Taylor & Jessie in 2022, a brand dedicated to creating everyday stationery that combines functionality with self-care, helping women organize their lives while also nurturing their mental well-being.

At Taylor & Jessie, we offer a range of products designed to streamline daily tasks, encourage self-reflection, and foster goal-setting. Our flagship products include undated planners, notebooks, notepads, and sticky notes. This year we will launch, Pen Pal Packs, which feature curated stationery items to spark creativity and connection. Everything we create is designed to not only enhance organization but also inspire a mindful approach to the everyday hustle.

The problem I’m most passionate about solving is helping women feel in control of their goals AND their mental health. So often, we’re juggling multiple roles—career, family, personal growth— it can feel overwhelming. My products are designed to be tools for those women, giving them the structure they need to stay on top of their tasks while also providing moments for self-care, reflection, and recharging. At the heart of everything I do is the belief that success and well-being go hand in hand. You can be ambitious and driven while also taking care of yourself.

What sets Taylor & Jessie apart is our unique approach to blending productivity with mental health. So many brands focus solely on productivity, but we recognize that being effective in life requires balance and self-care. Our stationery isn’t just about staying organized; it’s about creating a positive, intentional space where women can prioritize their well-being while pursuing their goals.

I’m most proud of the impact we’ve already had. Every day, I hear from customers who feel more empowered to take control of their goals and prioritize their mental health. Knowing that I’m creating something that’s making a difference in people’s lives is incredibly fulfilling.

To potential clients, followers, and fans, I want you to know that Taylor & Jessie is more than just a brand. It’s a movement dedicated to helping women achieve their dreams while prioritizing their mental health. Whether you’re looking to organize your life, set new goals, or just need a moment to reset, our products are here to support you on your journey. My goal is to help you design a life that you love—one that’s full of freedom, purpose, and, of course, self-care.

Have any books or other resources had a big impact on you?

My entrepreneurial philosophy has been shaped by a blend of mentorship, coaching, personal experiences, and my faith. One of the most significant influences on my journey has been the Milestone Circles program hosted by the Nasdaq Entrepreneurial Center. The mentorship and coaching I received there provided not only practical guidance but also the encouragement I needed to push through the tough times. It was a place where I could tap into the wisdom of experienced entrepreneurs and leaders who have walked the path before me, and that sense of community has been invaluable.

Another major resource that shaped my thinking is Simon Sinek’s “Start with Why”. His idea that successful businesses are built on a clear, compelling purpose really resonated with me. From the start, I’ve made it my mission to create a business that goes beyond products—Taylor & Jessie is about empowering women to achieve their dreams while prioritizing their mental well-being. Having a “Why” that’s rooted in my values and the legacy I want to leave has helped me stay focused on what matters most.

I also draw a lot of strength and perspective from my faith. Tapping into my relationship with God through church and my Bible has been a constant source of guidance, especially during challenging moments. “Keep the faith and trust the process” is a mantra I remind myself of regularly. Faith has been central in helping me trust that the path I’m on is unfolding as it should, even when things aren’t moving as quickly as I might like.

I’ve always been inspired by industry leaders and entrepreneurs who have paved the way, but I’ve learned that the most important influence is my own confidence. Leaning into my strengths and trusting my instincts has been crucial in building both my marketing business and Taylor & Jessie. The confidence to move forward, even when faced with uncertainty, is what has propelled me to take risks and achieve the freedom I’ve always dreamed of.

Lastly, my educational background in Communications from Xavier University of Louisiana has provided a solid foundation in messaging, branding, and connecting with people. My years in education as a teacher and leader have also played a role in shaping how I approach business—strategically, with an eye on long-term goals, but also with compassion and an understanding of how to build meaningful connections.

My philosophy is simple: “See it, want it, own it.” You can truly have the life you dream of if—and when—you do the work. It’s about staying committed, trusting the process, and always believing that the vision you have is attainable. With that mindset, I’m able to navigate the ups and downs of entrepreneurship, knowing that everything aligns when you stay focused and stay true to your purpose.

Any insights you can share with us about how you built up your social media presence?

Building my social media audience has been a journey of learning and evolving. When I first started my marketing business, I was caught up in the allure of growing my follower count quickly. I got roped into those “follow for follow” pods, and while my numbers grew fast, I realized I wasn’t attracting the right people—just bots and non-ideal clients. It was a valuable lesson that social media success is much more than just numbers.

Over time, I learned that the key to building a loyal audience is through authentic connections. When I started Taylor & Jessie, I made a conscious decision to lean into storytelling, both online and offline, and to build relationships with people—whether they were customers, other business owners, or just like-minded individuals. I also ran scrappy campaigns, focusing on creating content that was real, relatable, and aligned with my brand’s mission. The goal was to connect, not just collect followers.

One of the biggest shifts in my approach was realizing that social media is not about the numbers. It’s about the people. I’ve focused on quality over quantity, always asking myself, “Am I connecting with the right audience? Am I providing value to the people who are following me?” For me, social media serves as an initial touchpoint that leads my followers to shop with me, build trust, and eventually become loyal customers. It’s about nurturing relationships, not just making sales.

My advice for anyone just starting to build a social media presence is this: show up as your most authentic self. Share both the wins and the losses, the triumphs and the failures. People want to connect with the real you, not just the polished version. Be consistent, but be real. Engage with your audience, listen to them, and always add value through your content. Social media is a long game, so don’t get discouraged if you don’t see immediate results. Focus on building relationships and creating content that resonates with your community. The numbers will follow naturally when you’re consistent and genuine in your approach.

Contact Info:

• Website: https://taylorandjessie.com/
• Instagram: https://www.instagram.com/taylorandjessie.co/
• Facebook: https://www.facebook.com/people/Taylor-Jessie/100089767743977/?mibextid=LQQJ4d
• Youtube: https://youtube.com/@influencedbytiff