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.

Wen-Hang Lin

I do not have a business. May I suggest modifying the question to the following? What was the thought process behind your creativity? The driving force behind being an artist was a deep desire to tell my own story—one shaped by my emotions, memories, and everyday inspirations. I wanted to create a space where I could freely express the unique perspectives I carry, translating them into artwork that reflects my inner world. Beyond personal expression, I also wanted my work to have a broader impact. Read more>>

Rachel Holt

My thought process behind starting my own business was driven by wanting to live a more conscious lifestyle. I started recognizing the ingredients in the products I was using. I changed my routines and daily self-care practices. I realized how much those changes affected my mental and emotional well-being. I wanted to create products using whole ingredients that had a purpose behind them. I gravitated towards the power of plants and I was committed to using organic ingredients and essential oils to help other’s enhance their self-care experience. Read more>>

Kristen Madison | Executive Chef

I started Kale after leaving the toxic kitchen environments I had experienced as a female cook looking to become an Executive Chef one day. While putting myself through culinary school and working in the industry, I soon realized the food I was passionate about and the standards I had for what a kitchen should and can be were above the norm. I was driven to create food from scratch, cooking with the season, and providing guests with an elevated dining experience from a club sandwich to a multi-course plated dinner, my standards are very high. Read more>>

Sharelle Wilbert | Shot By Sade Photography

The idea of starting my business came from a combination of passion, market opportunity, and the desire to want to make people feel beautiful from the inside. From there, I did thorough research to understand the Photography industry, target audience, and competition. I wanted to ensure that my business not only met a need but also had the potential to grow. I also spent time evaluating my own skills, learning new skills and experiences to see how they aligned with what my business required. Read more>>

Taryn Ravi Sandesh | Massage Therapist, Sound & Energy facilitator, Yoga & Dance Teacher

I wanted to offer an all inclusive experience for my clients to dive deep into their healing and embody their radiance. Since 2012, I’ve studied and gained experience as a bodyworker (massage modalities), energy and sound facilitator, yogi and dancer, cultivating an eclectic tool box for anyone looking for somatic healing and embody holistic wellness. My vision is to be a part of wellness and creative retreats around the world, collaborating with fellow wellness practitioners and creatives to bring light and empowerment worldwide. Read more>>

Rachel Beers | Tiny House Retreats & Nature Advocate

Back in 2016-2017, my husband Justin and I were both working long hours at our corporate jobs, living in a 2,300 sq. ft. house in Scottsdale with our 2 boys (our 3rd son was born in 2018), supposedly “living the dream” but we were not happy. We were spending way more time away from our family and working jobs that did not align with our hearts. After discussing the trajectory of our lives compared to what our hearts were saying, we knew the path we were currently on was no longer the right direction for us and our family. Read more>>

Andy Higgins | Musician / Music producer

Well, I prefer working for myself and having at least some control over my destiny, especially since their is intellectual property involved and very personal information that I would like to be in charge of how it is distributed at least to some extent. Read more>>

Leafynoms | Food Enthusiast and Matcha Connoisseur

I had my fair share of ‘small businesses’ in the past with making and selling clay charms in elementary school, clothes and knick-knacks in middle school, and virtual forms of items in high school. All of these eventually faded away due to my decreased ability to dedicate time and of course, education taking the front-seat. Read more>>

Captain David | Beverage Director & Bartender

That’s the next step in my career. I’ve been in Hospitality for over 20+ years. It’s something I have always wanted to do, but I always seemed to find a reason not too. Connected with my Business Partner, Tiki Dan, had ignited my desire again to go for it. We started Sugar Cane back in January and we haven’t looked back. It’s been a wild ride. The feedback and acceptance from the local cocktail scene and the Tiki community has been so supportive. I feel very humbled by this opportunity we’ve created. We wanted to be in control of our events, cocktails, themes, etc. This just makes the most sense to the both of us. Read more>>

Oliverio Balcells | Multidisciplinary Artist

It was freedom of time, space and financial situation. Read more>>

Amy Bartko | PR Expert

When I started Chatterbox, my thought process was centered around achieving a better work-life balance for myself and my family. I wanted the flexibility to be present for my kids while also pursuing my passion for PR and marketing. Creating my own business allowed me to shape my career in a way that aligned with my personal values, ensuring that I could be there for important moments with my family while still making a meaningful impact in my professional life. Read more>>

Paul Popoff | Founder & Chief Strategy Officer

For me, the decision to start my own business came from an innate drive to solve a problem that I saw no one else tackling effectively. I knew there was an opportunity to build something from the ground up, but it wasn’t just about creating a company—it was about creating impact. Read more>>

Joy Steele | Boudoir Photographer

When I first started my own business, it was all about having more control over my work-life balance. I wanted to spend more time with my husband, my daughter, and be able to participate in the activities that really mattered to me. That’s still incredibly important, but what I didn’t expect was how much I’d love connecting with the women I photograph. Hearing their stories, seeing their confidence blossom during a session—it’s truly rewarding in ways I never anticipated. The relationships I’ve built have become one of the most fulfilling aspects of my work. Read more>>