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.

Chamaillerie Simmons

I never imagined that I would dive into doing hair full time. I developed my passion for braiding as a teenager. I would braid my friends hair at school and practice on myself and my two siblings. After graduating high school, i wanted to do hair, but like many others having a guaranteed paycheck and benefits reeled me into corporate America instead. Read more>>

Juliet Baker.

We have loved offering permanent jewelry to our customers over the past 3 years. We have loved the concept since hearing about it around 8 years ago. At the time, we were offering high-end costume jewelry. Our jewelry was worn on the red carpet and by celebrities and we loved being able to see it being worn by celebrities magazines and on TV shows. Read more>>

Chanele Ramos

I don’t wish that I started my business earlier because it took time for me to find the courage to actually start my business. I found out about doulas in 2017 after giving birth to my first surrogate twins. I had a pretty traumatic birth and when I found out about doulas it was like a light bulb went off. I wished I had one, but since I did not I figured I could be a doula and help someone not go through what I went through. Read more>>

Brittany Gutierrez

The question that pops up in every business owner’s mind. When I first started building my business, that question was the first thought that came to mind. Am I starting my business too late? Will this set me back? As I was writing out my business plan, the last 10 years flashed in my head. At that moment is when I realized that I started my business at the perfect time in my life. If I started my business sooner, I would not have had the mindset of a business woman as I do today. Read more>>

Katie Urich

In 2018, I was working at a full-time job that had previously been a dream for me – managing the marketing department at a contemporary art museum. I knew that eventually I wanted to work for myself, and I had started a couple side businesses and projects, but I planned to stay at my job for at least the next five years before making the leap. I ended up leaving rather suddenly, after a case of workplace sexual harassment was seriously mishandled and I didn’t feel able to ethically market the museum. Read more>>

Dani Lynn

Honestly, I have asked myself this question a few times though I am a firm believer in the theory that everything happens for a reason and things will happen when the time is right. Would life be different if I had started my business earlier? Would I be further in my career? What would life look like if I decided to take a chance on myself a little earlier in life? Most of us who are entrepreneurs have found ourselves in this position. Read more>>

Sierra “Sisi” Troup

I feel very lucky in that I started my business at the exact right time for me. It was during the pandemic, so I had extra time at home on my hands. Additionally, I had just graduated with a degree in accounting from the University of Oregon, so I had a lot of the really crucial business knowledge I learned still very fresh in my mind. Read more>>

Kimberly Nesmith-Huger.

Definitely. I wish I would have started my business much sooner. Life has a way of humbling you, so I had to learn to “let my guard down” when it comes to taking risks. In early 2017, I experienced a layoff from my corporate job. For the first time ever I was unemployed and seeking direction. I knew the gifts and talents I possessed but was unsure of how to leverage them properly for a business. Read more>>

Carly Jones

I’d like to say yes, I would have started my business earlier and part of me does. However, I also enjoyed being a phlebotomist and medical assistant before turning my passion and love for photography into career. I also believe God had a plan and everything has led up to me having a job I love so much. Read more>>

Dominique Daniels.

If I could go back in time I wish I would have started my business sooner. I started my business in 2020 from a love of making unique gifts and wreaths. I started making wreaths and gifts for coworkers and it just took off from there. Career wise I was a Medical Assistant working at a Job that after 10years I started to have to rebid for every 6 months which was frustrating to say the least. Read more>>

Emily Miller

I originally started Golden Girls as a way to make ends meet a year after I graduated college, but I wish I would started in college. Spray tanning can be a great way for college girls to make money while learning how to manage business finances, business-to-businsss relationships, and independence. I would’ve been able to gain business experience on a smaller scale in Starkville, MS and scale up faster after moving to Memphis. Read more>>

Raniah White.

I had just took a break from college after coming back from Rome, Italy because I couldn’t find what it was that I wanted to major in and do for the rest of my life. I was good at everything I’ve done in high school, so I went into college as a chemistry major. I soon realized that college chemistry and high school chemistry were on two totally different spectrums! I changed my major twice to special education and then psychology, but nothing seemed to keep me interested enough to want to major in it. Read more>>

Virgil Banks.

If I could go back in time I would have started my business sooner. I started my business on August 8,2020. I was a Independent Contractor for a small Business Agency. If any later I would have never growed to love the business like I do now. The things that I would have had to change was being patience enough to know knowledge is power. So The more knowledge I obtained the sooner I could have started. Read more>>

APIPHANY FULLER.

If I could go back in time I would definitely had started my business sooner, I feared taken risks in the past and I wish I had took them sooner, than to regret wasting time with doubts. Read more>>

Virgil Banks.

If I could go back in time I would have started my business sooner. I started my business on August 8,2020. I was a Independent Contractor for a small Business Agency. If any later I would have never growed to love the business like I do now. The things that I would have had to change was being patience enough to know knowledge is power. So The more knowledge I obtained the sooner I could have started. Read more>>

APIPHANY FULLER.

If I could go back in time I would definitely had started my business sooner, I feared taken risks in the past and I wish I had took them sooner, than to regret wasting time with doubts. Read more>>

Shelby Susnick

I started making short form video content starting in February 2020 and quickly realized I was good at it. It wasn’t until this year that I started landing bigger partnerships and consulting. I also didn’t realize my worth until later this year. Going back, I wish I priced myself accordingly for my services. Knowing your worth is so important these days. Read more>>

Dominic and Serena Fournier.

We always talk about how we wish we had started our business sooner. Our business was started out of necessity. Serena had just been let go from a corporate job and Dominic was working at a non-profit. With 3 small children, we had to get creative. With our background in events, Dominic decided to start DJing again on the weekends. It took about a year for him to leave his full time position and pursue the business. Once we both jumped in full time, the momentum was astonishing. It does make us think, “where would we be if we had started sooner?”. Read more>>

SHARNICE WALKER

I began Colorful Scissors, LLC in 2008 when I was 12 years old. I had an idea visit my clients at their homes and style them because a lot of people did not have transportation or was bed bound. I knew bringing the salon experience to them was a golden idea because my clientele started with senior citizens. Read more>>

Gabriela Ramos

I have always been fascinated by jewelry. As a kid I often got teased by my family for wearing “too much jewelry” also as an adult… and I always knew that it would be something that maybe sometime in my lifetime I would pursue but honestly it took me forever to decide if it was something that I truly wanted. It wasn’t until the pandemic as most things were right.. that’s when i finally decided to take the risk and play with the idea. Read more>>

Jerica Lovings

If I could go back in time, I would’ve definitely started my creative career as a music artist sooner. Only because, I’d have more knowledge and experience in the music industry. I started my music career in 2020, during the pandemic. With the whole world on lock down, my creative juices started flowing, and I started writing raps. It started off as a hobby and turned into a career for me. Read more>>

Bruce Fraser.

I’m glad I started my creative career later in life. I learned so much from each of my careers and interests. They all contributed to the career I have now. I didn’t have the range of skills I had when I encountered ceramics. From the moment I started in the field I had an unexplainable confidence. That was very unusual for me in my life. Having said that I don’t think I would have liked the work when I was younger. Read more>>

Brandy Seville

I se many of my peers and they are starting at 20-25 years old and then I see how young people in this industry who have “made”, how young they started and I can help but think who do I think I am? If I had started earlier though I would be one of the actors with no life experience. Performances would fall flat because I wouldn’t have experienced anything honestly in order to depict it. So while I maybe “behind” I think it only allows for me to be more authentic on screen. Read more>>

Alexandra Wuyke

Creating has always been an important practice in my life. It wasn’t until a few years ago that I decided to take my passion for acrylic painting from hobby to small business. As a teenager, I had pursued smaller selling opportunities like creating clay earrings and even offering custom embroidery on jeans when that was a trend. Read more>>

Gayle Davidson

I have always wanted to be a performer, actor, singer-songwriter, author, etc. I don’t think there was a moment when I wanted anything else. I worked for many years doing various acting jobs and singing in bars, and clubs. After I had my daughter, I started getting more into the business side, starting in film and TV sync which led me into booking and then management. I think if I hadn’t had the first-hand experience myself as an artist in the industry, I wouldn’t have had the capacity to use that to help others. Read more>>

DeAngelo Ervin

Yes I wish I would have started sooner in my music career because I’ve always had a passion for music and growing up I’ve always had people giving me broken promises to go to a studio and start my music career but it didn’t happen. Then when I started my music career I was going through a rough time in my marriage to the point I was getting a divorce. Read more>>

Lee Watts

As a 50-something new CEO, I have always kicked myself for not starting my business sooner. Although I started my company as a side hustle in my 40s, I often wish I would have gone more fully into my business much sooner. Without my employer asking me to choose my path and career commitment, I believe that out of fear, I would have still continued to juggle a full-time career and my growing side business. Read more>>

Anio Leaks.

I believe in God’s timing. I believe Ivan and I are here now for a reason and God chose now to be the time for us to shine our light on the world. Funny thing is at times I could be very impatient but with KLQ it’s something I knew when we get the green light it’ll take off and that required patience. KLQ clothing was an idea from 2018, I was working at ADT at the time as a Security Advisor, there were many of us, Read more>>

Aubrey Wilde.

There were so many moments in my life where I wanted so deeply to run after my dreams of creating the brand I had dreamt of for so long. But life has a way of showing us what’s most important in each chapter and timing and patience meant everything in this story. After years of working in the fashion industry and being a mother to two little ones I eventually found myself in a place where I knew if I didn’t take the leap, I would regret it. Read more>>