How to think through whether you should start a business

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.

“I started my business as a wedding planner and florist because I’m deeply passionate about creating meaningful, beautiful experiences. After working in the industry for a few years, I realized how much I loved both the design and the planning sides — and I saw an opportunity to offer couples a more personal, customized approach. Read More>>

The idea didn’t stem from a traditional entrepreneurial ambition. I didn’t dream of launching a business for the sake of building one. Life pushed me toward it—or rather, an inner fire that kept growing over the years. It was fueled by the silent injustice endured by millions of people living with excess weight, and by the glaring absence of humane, effective, and compassionate solutions to their suffering. Read More>>

Starting my salon was deeply rooted in a desire to create more than just a space for beauty, it was about building a sanctuary where people feel seen, heard, and confidently transformed. As a hairstylist, I’ve always been passionate about helping others express their identity through their hair. Over time, I realized I wanted full creative freedom to shape the entire experience, from the energy of the environment to the standard of care clients receive. Read More>>

I’ve always been interested in entrepreneurship, but this business came about in a somewhat unexpected way for me. I decided on a whim to try creating watercolor house portraits as holiday gifts for my family. They were made for the fun of it, but after posting a photo on Instagram I had someone ask if I could paint their childhood home! This gave me the first inkling that this business had legs, and I leaned into it on the side of my full-time job as a UI/UX designer. Read More>>

Growing up in Savannah with two entrepreneurial parents made owning a business feel normal. I watched them solve problems, take risks, and stay accountable, so creating something of my own always felt like an eventual step, not a dramatic leap. After three years coaching and then managing inside traditional gyms, I kept seeing the same gaps: generic “one‑size” programming, clients cycling in and out with little long‑term change, and almost no integrated system tying training, nutrition, daily habits, and accountability together. Read More>>

I grew up in a family of business owners, freelancers, and entrepreneurs, so it was never a foreign thing. There were always conversations about the businesses they ran, what was going well, what wasn’t, lessons learned, etc, and I heard it all growing up. Being exposed to those conversations and feeling like it was “normal” helped me feel like it was something I could do. Read More>>

I started Odd Modd Works because I wanted control over my own work. I make what I want when I want, and that’s the best way for me to create. There are so many more tools now for artists who want to go their own way, and I’m all about it. It may take longer to get where you’re going, but you don’t have to compromise your art to get there, and that’s an important factor for a lot visual artists, musicians, and writers. Underground hip hop artist Pro Dillinger calls it ‘taking the stairs’, and it’s worth the extra work. Read More>>

I founded Touched by Teaa Makeup with the purpose of illuminating the beauty and confidence that already exists within each of my clients. My goal has always been to create a meaningful, personalized, and unforgettable experience that not only enhances their appearance, but also empowers them from the inside out. Read More>>

I decided to delve into music full time after a great career in my day job in the tech world. While I enjoyed that side of things, I reached a point where I didn’t want to juggle days and nights any more. My personal situation gave me that freedom. A huge part of that decision was having the support of my wife, #1 fan, fellow musician and best friend, Barbara. Read More>>

If I being quite honest, I never thought about starting my own business. I owe that credit to my family & friends, if it wasn’t for them G’sM3diaProductions wouldn’t exist right now. I’ve always enjoyed working with cameras, but they are the ones who pushed/motivated me to take what I love to do professionally and make a career out of it. So there wasn’t really a thought process for me starting my own business because I was afraid of not being good enough or maybe this is more of a hobby than an actual career, but thankfully to my support system I was able to make that first jump and start my career that I love dearly. Read More>>

My thought process behind starting my own family cleaning business was driven by a desire to create jobs and make a positive impact in the community. I wanted to build something that not only supported my family but also opened doors for others to earn a living with dignity and stability. By offering reliable cleaning services, we could help improve local homes and businesses while providing honest work to those in need. It was about giving back, creating opportunity, and making a difference one job and one clean space at a time. Read More>>

I started THE WILD in 2020, during the height of the global pandemic. That pause, both global and personal, forced me to truly reflect on the kind of space I wanted to create and be part of.
My early years were multidisciplinary by nature. I studied architecture early in college, then pivoted to video/film production and photography. I also worked in broadcast journalism space for some time, which sharpened my ability to chase and tell stories that wanted to be discovered. Music was always present: Reggae, Calypso, Hip Hop, Classical, Rock, R&B. I was often told to choose one lane, even though the work that moved me most lived in the intersections. Read More>>

The thought process of starting my business, Thanx A. Mills, LLC, came from a strong realization: silence can be harmful. Growing up, I followed the unspoken rule that “what goes on in this house stays in this house.” But I soon found that keeping silent only caused me internal pain and sadness. Breaking that silence helped me discover my true purpose—helping others find their own. Read More>>

My thought process behind starting my own business started when I was a little girl, between the ages of 8-10, and I learned the definition of the word entrepreneur. I chose it then. I remember feeling, several times throughout my life, that I did not want to spend many years of my life working for someone else to achieve their dream. Read More>>
The foundation for my entrepreneurial journey was laid by my Godfather Joe L Franklin, a successful business owner since the early 1980s. He operated his company for over 40 years, and it was through his mentorship that I was given the opportunity to launch my first business at the age of 19. At the time, I was still young and not fully prepared for the responsibilities that came with business ownership, so I made the decision to focus on college instead. Read More>>
I had just graduated from the Conservatory of Music and I really wanted to make a living out of music. But in the process, I realized that the platforms conventionally used to start a carreer in music were very selective, unreliable and I would spend most of my carreer struggling to survive. Especially because I don’t have the safety nets others have to succeed in the industry. So, I made the choice to make my own business as a wedding and events singer. That way, I could make a living out of my passion. Without having to rely on producers, directors, labels, and others deciding wether I was worthy of success or not. I decided to make my success as a singer my choice and not someone else’s. Read More>>
