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.

Xenia Mateiu | Gift Store Owner

I wanted to have a flexible schedule that I cam make work with my life style, also a very important part of the decision to own my own business was to be able to have the freedom to grow it the way I wanted to and be in charge of my own success. Read more>>

Julia Kestner | Hand Letterer, Designer, & Mental Health Advocate

I wanted to start a purpose-driven business where I can create art and also help raise awareness on mental health. As someone who lives with mental illness, I know firsthand how difficult it can be. Hand lettering and illustration have been extremely therapeutic for me, and making art has brought me joy when joy seemed impossible. I wanted to to give back through my art, and that’s how my business came to be. All of my products have messages that spread mental health awareness, and I also give back a portion of my profits to mental health organizations. I believe that art has the power to heal, to educate, and to spread hope, and through my business I strive to help others realize that they are not alone. Read more>>

Lenila Batali | Executive Director

I think life takes you on journeys that you weren’t planning on. I was a designer and watercolor artist enjoying a successful business. But because we have had to raise a daughter with autism, life started taking me to a different direction. Being very active in our daughter’s high school life, I was asked to be on the Workability Program as the artist work experience component of their program. Since 2013 I have enjoyed working with our special population and teaching them design/artistry. In 2017, we planted a vineyard and started our non-profit organization, D’Vine Path. We are dedicated to creating a safe and dynamic community providing life and vocational skills in agriculture, hospitality and the arts. Read more>>

Meg Flanagan | Educational Advocate & Consultant

When I first launched MilKids Ed, now Meg Flanagan Education Solutions, I was motivated to serve a deep need I saw in my community: the lack of parental support during the IEP process. Too many parents weren’t aware of their legal rights or how to negotiate with the school district for the supports and services their child needed. As a special education teacher, I understand educational data and how the “system” works from the school point of view. As an advocate, I’m able to take that insider knowledge and use it to help families and children get everything they deserve for an equitable education! I chose to build my advocacy business as an entirely remote operation in order to serve clients around the world. So far I have been able to help families in Virginia, North Carolina, Indiana, Pennsylvania, California, Maine and Japan. Read more>>

Erin Warfield | Holistic Health Practitioner

After giving birth to my first child almost 19 years ago I knew I needed to be an inspiration to my children one day. I was working as a caregiver for a quadriplegic at the time. This was Very rewarding work. Radanath was his name. He had a Massage Therapist come and see him a couple times a month. I was very impressed with her and knew that was the line of work I wanted to add to my skillset. Read more>>

Ashley Pagliuso | Vampire and Owner of Straight Outta The Coffin

It was a giant leap of faith….I really had no idea what I was doing when it came to starting or running a business. I had previously worked for a company named Jungle Tribe shipping orders, doing stock, organizing photo shoots and working on their social media. I loved it but I decided id be moving to Australia part time to be with my then boyfriend. I didn’t have any friends in Aus and a lot of down time so I decided id start my own online shop. It was horribly scary and expensive to get things off the ground but very freeing and exciting at the same time. I finally had something that was my own! Read more>>

Stacy Lederman | Artist

I started my own business so that I could meet the needs of my family as well as follow my passion and earn an income. I used to work/paint from home when the kids were younger and now I have my own studio space. It is important for me to set my own hours and be flexible so starting my own thing seemed like the best way to meet the needs of myself and my family. Read more>>

Peter Dingli | Sculptor

After graduating form Art School in Melbourne Australia, I was very optimistic about practicing Sculpture. This lasted for a few years. However, there came a time when I had to make a choice between securing a stable income for my then new family or pursue an unstable Art career. I chose to enter the teaching profession. I taught Art for many years but didn’t have the opportunity to also have an Art outlet. I have since stopped teaching, the children are now independent and moved to San Diego where I can now put all my efforts into my Sculpture. Read more>>

Lalo Saidy | Underwater videographer/photographer, White Shark Guide, Dive Instructor

As a kid, I dreamed of seeing a Great White with my own eyes and promised myself that one day I would. Little did I know that promise would become a reality and better yet actually become my profession and lead to the start of my own company. Today, I consider myself very fortunate, after 17 years in the industry as an underwater videographer/photographer, white shark guide and dive instructor, to be in a role that allows for that passion, experience and knowledge to be shared on a daily basis with people from all around the world . In return, I wanted to create a company/ brand that embraced all the shark lovers out there and made them feel included and provide an opportunity for them to contribute to shark and marine conservation projects as well as trying to help Marine Biologists focused on shark research get the tags and equipment they need to continue their work. Read more>>