Meet Ana Peña

We were lucky to catch up with Ana Peña recently and have shared our conversation below.

Ana , so great to have you with us and we want to jump right into a really important question. In recent years, it’s become so clear that we’re living through a time where so many folks are lacking self-confidence and self-esteem. So, we’d love to hear about your journey and how you developed your self-confidence and self-esteem.

Confidence is a quiet satisfaction that comes from knowing you did your best in the moment, with the belief that, with hard work and faith, each step forward will only get better. Confidence comes from practice, the people you surround yourself with, your gratitude habits and your self-talk. I’ve learned some of these principles through my personal journey, and here are a few of them that underline this very theme.

Confidence is a Muscle
I learned this first-hand when I was a salsa performer and dancer. I had rigorous training that often involved being in the studio every day of the week, and late into the wee hours of the night. And, on top of that, we often had to perform in front of a lot of people. Every rehearsal, I would hear this from my teacher, “Smile! Pretend you are on stage! It’s all muscle memory!” We would drill the routine over and over on the 7th floor in a peach-colored studio in Midtown Manhattan, pretending we were on-stage, even though we definitely had no stage makeup on, and were practicing in socks and heels. Whatever you practice in private is the way you will execute in public. I’ll forever be grateful for all of the life lessons being a salsa dancer taught me, especially with confidence. The lesson: Confidence comes from practice. Hours of behind-the-scenes work prepare you to shine and be “stage-ready” when it counts.

Model Excellence
They say confident people are “born” with it. While this sounds lovely in theory, most of us know that oftentimes, confidence must be learned. Thus, one must surround themselves with groups and people that are practicing confidence at a high-level. As a calligrapher, I think about how important this has been in my journey. Some examples come to mind – I have a couple of business coaches that are modeling excellence day in and day out (hi Tammy and Rosie!), and have been blessed to work with some great calligraphy mentors (hi Holly!) that support my entrepreneurial journey. They have paved the path to excellence ahead of me. Confidence is a road, and some people are just a few miles ahead. Why not ask them to share the landmarks and bumps they’ve passed along the way?

Growing Confidence
Regularly practicing gratitude or prayer can be a powerful confidence booster. It’s hard to stay down when you focus on the magic moments or God in your life. While it’s not always easy, it’s a kind reminder that you have people and things rooting for you. And if you don’t feel that way, it’s a gentle nudge to seek out a supportive community. Confidence grows by celebrating the small wins and comparing yourself to who you were yesterday, not to others. Remember, every step forward, no matter how small, is progress. Just like a flower needs water and sunlight to grow, you can nurture your confidence by feeding it with faith, gratitude and the support of others.

The Impact of Words and Surroundings
Your subconscious is shaped by what you consume—whether it’s books, music, or conversations. While motivational quotes might seem cheesy, they plant seeds of positivity in your mind. Similarly, music and media influence your thoughts. Choose what you consume carefully. As a calligrapher, I believe in the power of words and aim to use them to inspire and improve the world. The words and people around you matter—they help shape the confidence you build.

Thanks, so before we move on maybe you can share a bit more about yourself?

My name is Ana Peña, and I am one of the calligraphers of Handsome Ink, a creative studio that I founded with my husband that
specializes in all things calligraphy. Our work centers on creating bespoke, live activations with you guessed it—calligraphy! We work with brands to bring their upcoming event to the next level, by personalizing items on-site through hot foiling, engraving, or the beautiful art of writing. We also love working on personal commissions. While “Handsome” is in our name, it’s not a nod to our appearance, but rather an homage to our incredibly good-looking dog, Handsome. He says *woof* (hi!).

Our mission is simple: to bring people closer together through the art of calligraphy. We love personalizing gifts for loved ones, crafting heirloom-worthy poems, and connecting with those who appreciate this vintage art form. We have the honor of connecting with people that appreciate the artistry of this vintage art. Everyone needs calligraphy, and through our work, we seek to glorify God and spread joy to the clients and brands we have the pleasure of working with.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

I’ve always had a strong desire to learn and a passion for taking classes. A significant part of my journey has been about learning to be a leader. Before diving into calligraphy, I spent many years as an art director, eventually becoming VP of design, where I led teams. Along the way, I focused on developing my leadership skills—reading about leadership, attending conferences, and embracing growth—so I could apply them not only in my role as a team leader but also in my personal life as a mom.

Ability to add structure
They say the only constant is change, and that was especially true during my corporate tenure and agency years. A big part of my interest in leading teams came from the ability to bring clarity and structure to often vague briefs or uncertain projects. Organization takes many forms, and discipline plays a huge role in that. By learning to add structure while staying flexible—a key lesson I picked up from being a parent—things start to feel more manageable. So learning about discipline and organization, has been so helpful in my career as an artist and entrepreneur.

Creative thinking
I’m very grateful I was able to go to art school. Though our classes focused on technique-heavy deliverables, the biggest lesson came in backing up our creative with conceptual thinking. Creative thinking can be applied to anything! It makes your writing, your cooking, your art, that much more compelling. I would encourage others to think of ways to add meaning to their creative pursuits, by looking introspectively.

For me, much of this work has come through self-reflection, along with the support of my loving family and husband. They’ve encouraged me to look inward and find meaning in my journey, which has made it even more fulfilling. For those of you just starting your own journey, people, but also books are invaluable treasures. Find what sparks your interest and dive in!

Okay, so before we go we always love to ask if you are looking for folks to partner or collaborate with?

We’d love to add personalization to events (whether galas, weddings or activations) with calligraphy. If you are planning an event, and want to add a memorable touch, consider our calligraphy studio Handsome Ink.

Contact Info:

• Website: https://www.handsomeink.com/
• Instagram: @handsomeink