We recently connected with Tiffany Vivaldi and have shared our conversation below.

Hi Tiffany, thanks for joining us today. Risking taking is a huge part of most people’s story but too often society overlooks those risks and only focuses on where you are today. Can you talk to us about a risk you’ve taken – it could be a big risk or a small one – but walk us through the backstory.

As a mom of three, starting over was a huge risk — and not an easy one. Learning a new trade while stepping into a childhood dream felt both terrifying and thrilling. Art has always been a part of my life, but turning it into a career was a different kind of journey.

I wanted my girls to see firsthand what it looks like to chase a dream with everything you have — to work hard, stay passionate, and build something meaningful. As a homeschool mom, it was even more important to find something that could fit into the life we already loved. In the beginning, balancing it all felt overwhelming, but over time, I realized that balance is the secret.

Taking this risk has been one of the most fulfilling decisions I’ve ever made. I’m building a life that allows me to create, to grow, and to show my daughters that it’s never too late to follow what sets your soul on fire.

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’ve always dreamt of becoming an artist. Tattoo artistry, though, once felt so far out of reach — like it was a dream meant for someone else, or something I couldn’t be successful in. One night, driven by the desire to build something more for myself and my daughters, I took the leap. Becoming a tattoo artist has been one of the most transformative experiences of my life. It’s not just about creating art — it’s been deeply healing for me and, through my work, I’ve been able to help others heal too. Tattooing truly feels therapeutic on so many levels.

I specialize in fine line tattooing, but I’m not limited or intimidated by trying new styles. I believe that growth is continuous, and with time and dedication, there’s always room to get better. Because of that, I spend a lot of time reading, studying, and practicing different concepts and mediums within the art world, pushing myself to evolve as an artist.

What I’m most proud of is the progress I’ve made in such a short amount of time. Tattooing is an intricate craft — there are so many layers to learn, and it can be overwhelming at times. But knowing yourself, staying true to your style, and having confidence in your vision makes all the difference.

My clients are at the heart of everything I do. Building real relationships, listening to their stories, and helping bring their visions to life is what drives me. Every piece I create is deeply personal — not just for them, but for me too.

My aesthetic is a little different from the typical tattoo artist. I love blending storybook elements, fine line work, and touches of realism into my pieces. It’s delicate, detailed, and meant to feel like something timeless and meaningful — something that tells a story and leaves a mark far beyond the ink.

At the end of the day, my goal is to create art that feels like a true extension of my clients’ journey and to always continue growing, both as an artist and as a person.

We’d appreciate any insights you can share with us about selling a business.

Yes, I have sold two businesses.

The first was a jewelry business that I started right in my kitchen. What began as a small passion project grew into something much bigger — eventually leading me to own a studio space, sell through local boutiques, and ship products worldwide. It was an incredible journey, but at that time in my life, I realized the commitment and sacrifices it required weren’t sustainable while I was raising my young children. Selling the business wasn’t an easy decision, but it was the right one for the season of life I was in. It taught me that success isn’t just about growth — it’s also about knowing when to pivot to honor your values and your family.

The second business I sold was a portion of my event company, specifically the glamping services I offered. It was such a rewarding experience — creating unique outdoor stays that helped people reconnect with nature, right in their own backyard. Letting go of that side of the business gave me the space to focus on new passions and opportunities while trusting someone else to continue bringing joy to those experiences.

Both experiences taught me valuable lessons:
• Build with intention, but stay flexible.
• Know your “why” — and don’t be afraid to walk away when your “why” shifts.
• Value relationships — whether it’s with your clients, partners, or buyers, people matter more than products.

At the end of the day, selling a business isn’t a failure — it can be a powerful, strategic move to open the door to your next chapter.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

One lesson I had to unlearn was believing that everything had to happen all at once. I’ve always been the type of person who wants to take 10 leaps ahead instead of small, steady steps. In some ways, that drive has served me well — it’s pushed me to take risks and chase big dreams without hesitation. But in business, I quickly realized that this mindset can also create unnecessary pressure and lead to burnout.

I had to learn (and am still learning) that success doesn’t happen overnight. Some of the most meaningful growth happens slowly, one intentional step at a time. It’s okay to take things slow, to build thoughtfully, and to trust the timing of your journey. Every season of growth serves a purpose, even if it feels like you’re moving at a crawl instead of sprinting.

Contact Info:

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