Almost every entrepreneur has had to decide whether to take the leap now or wait– perhaps they wanted to acquire more capital, experience or connections. Given how common this predicament is, we asked some successful business owners to reflect back on whether they wish they had started sooner or waited for a better time.

Morgan Rogers

I like attribute painting as my introduction to makeup. The very first thing I picked up to create something with was a paint brush, & I’ll bet you’ll find some sort of paint brush in a makeup artists’ kit today. I was working at an art studio through a summer program when I was fourteen. Soon after my mom took me shopping for my first makeup palette and brushes. By mid-school year, I was doing makeup in homeroom at high school. Read more>>

Cody Sheski

Looking back at my childhood, there are times that I wish I would have used my time more wisely in terms of practicing and perfecting my craft. Especially since this was a time with very few responsibilities and obligations. I spent a descent amount of my free time teaching myself guitar, but growing up in a small town, I was unaware of what a music producer even was. I thought that every top 40 artist on the planet made their own music, visuals and did all the marketing themselves. Read more>>

Lauren Rushing

If I could go back in time, I would have created sooner and explored other mediums in art. Since I was young, I felt like everything I saw was a still from a movie. Since then, I knew it was a gift that I should utilize. When I was in high school, I ran a photography business for portraits. I had started my photography journey at 13 by creating self portraits as an emotional outlet. Read more>>

Sammi Bivens

I began my journey of entrepreneurship back in 2011. My first business venture was called Tainted Rose and I sold women’s jewelry, handbags, and clothing. I was very young when I started the business and I had no real goals for it and I honestly did not nurture it in a strategic manner. I had plenty of success, after shipping to almost all 50 states and several countries before retiring from the business in 2019. I decided to pivot to my current business, Digital Marketing Maven and Associates in late 2019, after working with one client who solicited my services. Read more>>

Tyenesha Fields

Jacinths Homeless Foundation (JHF) Was founded in February 2018 by Tyenesha Fields. She started JHF because she experienced the struggles of not having many options while being homeless. She was homeless 2 times in her life traveling from many shelters with her young son.  To qualify for a spot in transitional housing she was required to have been homeless for 2.5 years. This was one of the things that she wanted to change, no one should have to struggle and live on the streets for 2+ years just to receive assistance. Read more>>

Tijuana Green

I have had the thought in the past that I wished I started to pursue my dreams sooner. I was hesitant to start a YouTube channel for at least 5 years, I was always waiting for the “Perfect Moment”. Waiting to have the best camera, the best lighting, a recording studio and etc. I soon realized that the perfect moment would never transpire, that day I decided to make a plan. Once I made that plan, hit my goals I took the leap of faith. Read more>>

Brian Melekian

In 2012, at a turning point in my career, I made the decision to go back to school to pursue my MBA. Looking back on it, it was more of a fear-based decision than anything. I’d reached a certain point in life where I wasn’t sure what came next and school seemed like a dependable, safe route. The road more traveled. 18 months and $100,000 later, I’d memorized a few formulas and had my MBA. And nothing changed. I may have understood Internal Rate of Return and the Time Value of Money, but my phone didn’t magically start ringing. And besides all of that theoretical academic knowledge didn’t mean much in the real world. Read more>>

Carrie Peeples

I spent years working in the Corporate World before venturing out as a solo entrepreneur. I kept thinking I’d never be able to make the same amount of money with a full time job than I would make in my own business. I held myself back waiting for the perfect time to leave and that just never happens. I did finally leave when the company I worked for was bought out but I wish I had started 10 years earlier when I had the initial thought to start working as a professional organizer. There is no right time to start, there is no right time to leave, there is no right path to owning and running your own business. You just have to do it. And not stop. Read more>>