Thinking through whether to start a business – whether to take the risk, whether to go out on your own – isn’t easy. So we asked some entrepreneurs we admire to tell us about how they thought through the process of starting a business.

Jillian Dara | Journalist and Content Creator

I never set out to start my own business. In college, I majored in journalism and anticipated working for a newspaper or magazine—print was my preference but as in-house publishing and editorial teams scaled, I embraced digital platforms. After working as an editor for two years, I decided to try freelancing. I was still relatively a newbie to the industry, despite my previous managerial positions, but I felt like this was the only way to control the type of content I wanted to produce. I jumped in pretty blindly, got comfortable with being uncomfortable and marinated in it until I finally started seeing results from countless hours of hardwork. Read more>>

Sandy Rubin | Alternative Fine Jewelry Designer

I remember splurging on my first piece of fine jewelry years before I ever dreamed of owning my own fine jewelry line. I was fairly new to NYC at the time and decided to go to the Diamond District for my big birthday purchase. I did my research and found the best suggested time to go was a Friday less than an hour before closing, as vendors may be more willing to negotiate with you to get that last minute sale. I also felt dizzy with the amount of information on diamond buying on the web and to calm my nerves, I downed a couple drinks before marching my way over. Read more>>

Taneka Johnson | Business Strategist & Certified Professional Life Coach

The thought process for me behind starting a business is that it typically should be based off of your real life experiences, something that comes to you naturally to do or a skillset that can be monetized and has proven itself monetizable. When you build a business from your real life experiences, you provide the chance for a more authentic brand to be built, which these days is hard for people to find on social media with so much fabricated fluff out there. The authenticity and real life experiences are what helps your brand/business stand out specifically to the magic you bring to the industry. The thing that makes it uniquely yours. This way you aren’t worried about a saturated market in the field of what it is that you want to do. Read more>>

Francesca Lewis, MD, FAAD | Board Certified Dermatologist and Medical Director of Delray Dermatology + Cosmetic Center

As a general and cosmetic Dermatologist, I decided to open Delray Dermatology & Cosmetic Center to provide better Dermatologic care for my community. My goal was a practice where all skin issues could be addressed and patients could feel comfortable coming for both medical and cosmetic concerns. My goal has always been to provide quality, compassionate and comprehensive medical care, as well as to combine safe and effective laser treatments and cosmetic procedures for a natural looking end result. Read more>>

Nicole Lashae Ben | CEO & Design Strategist

I’ve had a few different moments in my life where I started my own business or side hustle. My first official business was a beauty box subscription that curated monthly boxes of hair products. When I started that business, I was thinking of creating a solution for myself and women who had similar pain points. Most recently, I started revamping my consulting business, which I started at the beginning of 2019. The revamp has been almost like something brand new. My thought process was pretty simple this time around. I thought, “How can I use my expertise from my career and turn it into a company that I’d LOVE to work for.” Read more>>

Caitlin Burling | Polymer Clay Accessory Maker

I always had dreamed of working independently for myself and creating products that I could sell to others. When I lost my job in content marketing at the start of the COVID-19 Pandemic, I started making clay earrings as a way to fill the time. However, I quickly knew it had the potential to bloom into a larger business. I started by selling to friends and family through Instagram, and soon after created my own website. Initially, I didn’t place too much pressure on my small business to succeed because I didn’t want to lose my excitement for this craft. I took the time to practice my skills and techniques, and worked to create very high-quality products. Read more>>

Monica Gomez | Artisan Soap Maker & Mother

When I first began making soap in 2016, I had no idea that this would become what it is today! Initially, I started making soap for my family because we suffered from sensitive skin. The commercial products offered in retail stores and products prescribed by a physician weren’t working for us, so I turned to the internet to do my research. I found lots of information online to help with our skin sensitivities, pointing me towards handmade soaps. Initially, I thought, man, this is a lot like cooking, which I consider to be one of my favorite things to do, aside from making soap, of course. Read more>>

Marlor Motchell | Fashion Designer

I always knew that I didn’t want to work for anyone else. I always had an entrepreneurial spirit, as a child I would come up with creative ways to make money. I started freelancing while in college to make a couple of extra bucks and from there the business grew itself. I graduated from college and decided to focus on my business full time and take it to the next level. Read more>>

Delonne Brotherson | Owner and Curl Specialist

After deciding to return to my natural roots in September 2010, the first thing I realized that there was no help for hair care. Styling was minimal as it seems as though when you mention styling and natural hair, it means braided extensions, crochet braids or sew-in. After roughly a year of trying to figure out my own and realizing I was on my own, I started thinking about everyone else in my community and island who have natural hair or wanted to return to their natural hair but no clue how to care for it. All we had was how our parents did it and if you had parents from back then, you know the routine, shampoo, conditioner, dry, a lot of grease and braided for a week or 2. Read more>>

Sarah Stecker | CEO & Founder of Travel Advisors Unlimited LLC

Eight years ago I never thought I would be where I am today. Booking friends and family for fun Disney vacations was all I needed to do. Then I met Annette Youngbauer a franchise owner of Travel Leaders. She burned something inside of me that drove me to want to explore. The need to teach people that there’s so much out there in the world that hasn’t been discovered, turned into a passion of mine. Read more>>

Cori Sue Morris | Founder & CEO, Retreat Foods

Retreat Foods is actually my third business—I’ve been building companies and brands for 10 years. I started with a cheeky little media company, Bitches Who Brunch, which I started, scaled and sold in 2018. Then, I ran a marketing agency helping women-led, early stage brands scale and grow. But, back to Retreat. I was living and working in New York City, and I lead a very health-conscious lifestyle. During a particularly stressful time at work (I was working at WeWork during the failed IPO drama), I started experiencing severe, debilitating pain and inflammation. I just couldnt get out of bed in the morning—my whole body ached, I was perpetually exhausted, and swollen all the time. It turns out, my stress (cortisol) levels were off the charts—my stress was literally manifesting as physical pain in my body. Read more>>