Readers often email us asking us for advice about new businesses they are thinking about starting and we often find that many of them don’t have a framework for thinking about a more fundamental question: why should or shouldn’t you start a business?

Below, you’ll find how successful entrepreneurs from across the city thought about this very question when they were considering whether to start their businesses.

Borja Zamora

When I started my career, I actually went to law school and worked in IT law, advising software companies and startups. These weren’t your stereotypical corporate clients—they were entrepreneurs building incredible products, running lean teams, and always chasing bold ideas. I quickly fell in love with their energy, ambition, and way of thinking. Read More>>

Bianca Cruz

Taking a leap of faith in 2022, I embraced my creativity by developing my company through photography, videography, and directing. By starting a freelance media business, I was able to break free from being limited to a single art form. I’ve always been passionate about media production and storytelling, so by going freelance, I’ve been able to combine my interests and career path without limiting myself to one specific art form. Read More>>

Athena Livadas

After a decade immersed in advertising and marketing, I found myself craving something more meaningful. I spent six months traveling the world and getting inspired. While considering what to do professionally upon my return to ‘reality’, I yearned to channel my love for travel into a purpose-driven endeavor that would not only satisfy my wanderlust but also enrich the lives of others. Thus, Páme Travel was born. A venture born from my passion for travel and natural skill for planning & organization. Enabling people to travel confidently with a custom itinerary built just for them brings me so much joy daily. Read More>>

Melanie Kowal

Essentially I was looking for a gift for my sister and couldn’t find anything that wasn’t mass produced so it was all the same. At the time id began making simple items of jewellery but I also had a huge passion for vintage and antique pieces, they were so unique and collectible. Sometimes made with very fine skills in ways you just don’t see anymore. So I opened my shop and began to showcase their quality. Read More>>

Karin Gallo

I’ve always been passionate about creativity—whether through landscape design or visual art—so starting my own business felt like a natural step. I wanted the freedom to bring my unique vision to life, blend artistry with nature, and create spaces that inspire people. It was less about following a traditional path and more about building something that truly reflects my passion and values. Read More>>

Nik Boivin

I started my art business out of a deep need for creative expression. By day, I work in finance, but once the workday ends, I crave the tactile experience of creating—working with my hands, playing with color, and bringing ideas to life on canvas. Painting professionally and developing my business felt like a natural next step. As a proud gay artist, I also draw inspiration from my community, incorporating LGBTQ+ culture, identity, and storytelling into my work. Beyond just making art, I wanted my work to have a purpose, which led me to start Bee the Change Foundation—a nonprofit that uses art to drive social change and give back to causes that matter. Read More>>

Ryan Thaxter

I started playing music with my friends long before the thought of it being a business occurred. We grew up together and had formed many bands, but at the end of high school, in 2009, we decided to crystallize all our bands into one group that we called Dubbest (pronounced “duh-BEST”). The vision was to recreate the sounds of early reggae the way it sounded in Jamaica in the 1970s, but with the mindset and equipment we had as 18 year olds from Bridgewater, Massachusetts. Over the years it developed into something much more serious, and we are celebrating 16 years of being together this year. Read More>>

Sydney Thofehrn

My thought process behind starting my own business as a nail artist was driven by my passion for creativity and the desire for independence. As a graphic design student, I’ve always had an eye for visual aesthetics, and nails became another way for me to express my artistry. I wanted the freedom to bring my creative vision to life without limitations while also building a brand that reflects my unique style. Being my own boss allows me to set my own schedule, connect with clients on a personal level, and continuously push my skills to new heights. I saw an opportunity to turn something I love into a career, and I knew that with dedication and consistency, I could create something truly special. Read More>>

Mariana Pantoja Redondo

needed fresh start. I had been stuck in an abusive job as a graphic designer in Spain, feeling creatively drained and struggling with anxiety. I knew I needed a change, something that would truly fulfil me as an artist and professional.

Once in Norway, reality hit—finding a job without speaking the language was a challenge. And then, life threw me the most beautiful curveball: I found out I was pregnant. Suddenly, the idea of carving my own path became not just appealing but necessary. So, I took the plunge and started my own business—a one-woman creative studio dedicated to art and crafts. Read More>>

Jordan Lunderville

I am a very ambitious and independent person by nature, and I have always been that way. Im an INTJ on the Meyers-Briggs scale, a personality characterized by intense ambition, passion, aggression, and leadership, sometimes to a fault (just ask some of my former employers).

So, when it came time for me to graduate high school and find a career, I kept feeling very unsatisfied at the jobs I would get hired at. I would get these unexplainable urges and inklings in my heart that there was something bigger that God wanted to do with my life, and for while, I would just ignore them. Read More>>

Margie Woods

For the past 30 years, art has been my way home—to myself, to my emotions, to a sense of grounding when I am going through hard times. I’ve experienced firsthand how creativity can regulate the nervous system, process emotions, and create space for deep healing. I wanted to share this magic with other women who, like me, needed a way to reconnect with themselves.

I saw so many women struggling to prioritize themselves, feeling stuck, disconnected, and unsure how to access their creativity. I knew the answer could be found using art as a tool for self-awareness, self-care, and healing. Read More>>