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.

Sandy Fernandez

It seems as though the answer would be an obvious “of course I wished I started a business sooner-who wouldn’t?” Yet, the truth is life is about timing and I wasn’t ready any sooner. I had a successful and tenured 22 year career in Banking and Finance, at the height of my career I was managing a 90mm portfolio with a team of 5 and I was making a nice six figure salary. Read more>>

Prof. Ona Miller

I wish I could have started my business much earlier. I have to say that even as a child or as children, we are not always encouraged initially to create our own business or become an entrepreneur. Usually, we are encouraged to immediately go to college, become a doctor, lawyers, astronauts, career executives, bankers, etc. We are also encouraged to be the best wife and mothers and have children. Still, no teachers, community leaders, parents, etc., ever promote, motivate, or push for their children to become business owners or entrepreneurs. Read more>>

Kelly Merkur

I try not to live with “what ifs”. I always knew I was going to do something creative. School was never easy for me, but I always thrived in my art classes. I thought I wanted to go into interior design then ended up changing my major to textile design. The best part about a fine arts degree is that I had the opportunity to study a variety of mediums. The one medium that I shied away from was painting. Read more>>

Jamal Brown

I wish I could say my story started out as something grand and amazing that they’d want to make a movie out of one day, but I’d be lying. Myself and the guys who’d later be known as the ignant crew were just hanging out one day and Coop said ” Bro we need to say this on a podcast.” For someone bold and stupid like me, that’s all I need to hear. At that time I was working the graveyard shift at a radio station slaving away for next to nothing. I was still recording audio and doing my creative thing, Read more>>

Carolyn Kay

I started writing when I turned 39. It was an escape for me. My marriage was falling apart and I felt unappreciated and burnt out at work. On a whim, I decided to participate in NaNoWriMo – National Novel Writing Month. In that one-month sprint, I completed over half of a fan-fiction novel, and I was hooked on writing. Over the next six months, I finished that novel, posted it on FanFiction.net, and started working on other stories. Read more>>

Big Cam

My career started during Shaq’s Big & Tall Model Search with JCPenney & Wilhelmina during the summer of 2019. From that audition I was scouted by a JCPenney executive and signed with Kim Dawson Agency in Dallas, Texas. I strongly believe that everything happens for a reason and everything happens in our lives how it’s supposed to happen. Therefore, I’m glad that I started my modeling career later in life because it gave me an opportunity to mature and truly understand the industry. I had a chance to figure out my purpose and what I really wanted to do in life. I’ve had so many major accomplishments and success stories that built and fed off of this one experience. Read more>>

Aimee Palifroni, CPCE

If I could do it all over again, I honestly don’t think I’d change a thing. I’ve told my story many times of walking out of my last corporate job to finally go at my dream full-time and that story makes me feel more empowered every time. In the hospitality industry, there are a plethora of positions that exist under the events umbrella. Early in my career, I (like many many others) bounced around from restaurant to hotel to venue to catering company before I finally knew where I was meant to be. I was self-conscious of going to networking events and telling people I had moved onto a new venture already. And I heard the comments and whispers from colleagues like, “Oh where are you now?”, and “Oh I can’t keep up with you!”. I took those comments so personally back then. What I realized from that time is that moving through tho Read more>> 

Juno

That’s a good question, If I could go back in time with the knowledge that I have now as an artist. I think I would have definitely took music more seriously at a young age. I started singing when I was 3 years old. Truthfully I think I always knew that I wanted to do music in some way. I just wasn’t sure what I wanted to do back then. I remember my mom used to take me to Disney channel auditions and put me in choir. But it wasn’t until I was high school that I started actually writing and learning to record my own music. Read more>>

Ashley Gallegos

Honestly I can’t really say that I wish I had started sooner or later. I feel grateful for the experiences and opportunities that I’ve had along with the people that I’ve met through them. I started about 2014/2015 which I personally loved for myself because that time frame was one in which I was very much navigating so much curiosity, excitement, confusion, etc. as I was getting older and preparing to graduate high school so it really made me put many things into perspective and slowly start understanding myself in various ways as I was getting older. Had I started sooner or later, I definitely wouldn’t have those experiences and relationships in my life and that’s a bit difficult and strange to think about. It does make you seriously wonder how different life would be. Read more>>

Allura

If I could go back in time, I would have started working towards becoming an artist sooner. I hate that I allowed myself to completely let go of that dream at such an early age because I was told it was unattainable. I did not aggressively pursue my career as an artist until after I graduated from college, but I often think about how much better I would be had I started sooner. Although, pursuing music after college did come with some pros. For example, because I was not worried about studying for exams or going to class I was really able to focus on and perfect my craft. Read more>>

Dr. Valerie Gillespie

If I could go back in time, I would have definitely started my creative career sooner. Without a doubt! I had always been interested in the arts. I started painting from a very young age as my mother often sketched and designed my clothing. I learned the beauty of creativity at a young age through her brilliance. I feel like being a visual artist was always a part of my being and still is today. When it comes to opening our gallery, alongside my husband, Emmanuel, Read more>>

Contrina Jenkins

If I could go back in time I would have started my creative career sooner. I didn’t start producing stage plays & films till I was in my late 30’s. Sometimes I feel like I’m playing catch up to everyone else. But at the same time, things happen on God’s time, not ours. If I was to go back and start sooner things wouldn’t be the same. I wouldn’t have the same team as I have now and it’s a strong possibility I wouldn’t value the lessons I’ve to learn to get me to this point. Read more>>

Lisa Scott

No I don’t wish I would have started my career sooner. I started my career in modeling at the age of 16 as a plus model in NYC. I was one of the first Junior Plus Models in the late 80’s. I went on to work as a model in all areas for the next 3 decades and travel the world. I still work as a fit model for Campbell Agency. I have worked fit, shows, informal, print, commercial, runway as a plus model. In the early part of my career I was signed to Ford Models. Ford had a Television Division that would occasionally get a call for a large size woman. Large size back then was size 12 and above. Read more>>

Michelle Koster

I absolutely wish I would have started my creative career sooner! I leaped into my creative career in early 2019, after working 25 years in a career that was not fulfilling my soul. In fact, the corporate world was slowly sucking the life out of me. I was not happy, and not taking care of myself the way I should have been. I felt stuck and deflated. After returning to school for photography, one of the true loves of my life, I started a business. I began traveling more and loving my life. Read more>>

Ashley Sierra

I one hundred percent wish I had started my career earlier! I was about 22 when I did my first fashion show, and that’s really when I began my modeling career. I was in college, studying elementary education with every intent of becoming a teacher one day. I had the opportunity to walk in a fashion show, which led to photo shoots, which led to getting published and eventually getting signed with an agency where I started taking on real modeling jobs. Read more>>

Stephen Austin

I never thought of myself as a performer. I started doing YouTube videos about 12 years ago. I just talked and told stories. Then apps came along with the ability to do short videos and it changed the way I would do my videos. I did Vine which was a lot like TikTok but before TikTok. It died and TikTok came along. I started doing that and before long I had a following which grew to 1.7 million people Mind you this was at a very late time in my life. I’m 83 years old and had never had this many followers on social media. I’ve done TV interviews, been interviewed by leading magazines, newspapers all over the world. It had been a very unreal experience for me. I wish it had been when I was younger but it is what it is (I hate that expression ) but it’s true Read more>>

Nancy Breiman

I often wonder if I had followed my original plan as an artist out of high school what my life would look like today. At 62 and now retired from a corporate job of 35 years and working as a full-time artist, the answer is obvious to me. It wasn’t always. Life is full of twists and turns and choices you make along the way. I made several defining moment choices and some choices were made for me, starting with my decision on where to go to college. Read more>>

Renee Edd

I actually sang before I spoke. So my earliest memories are hearing my dad sing (he was a fabulous tenor) and singing along myself – to Caruso of all things. A little later, I’d find Judy Garland then move on to Olivia Newton John! So while I started early creatively, I wasn’t allowed to pursue it professionally as a child or young woman. My dad wouldn’t let me. Mom and I tried to sneak me to a Broadway audition but dad found out and nixed that right away. I do regret it, absolutely. But what can I do? Read more>>

Carlos Harleaux

I believe everything happens for a reason and at its appointed time. My first book, Blurred Vision, was released in 2011. Prior to that time, I did about two years of independent research online. Although there was information available, there weren’t nearly as many resources as there are now. At that time in my life, I was 26 and it was honestly a perfect time to start. You can’t write about life experiences well without going through some of the experiences yourself. I’m not sure I would change anything about my experience because it probably would change the person I am today (and possibly not in a favorable way). Read more>>

Silky Hart

My art adventure began eleven years ago. Being a woman of a certain age, one might believe I began my life as an artist late in life. However, I prefer to view the timing as right on schedule. At the time my art journey began, I was working as an expressive arts facilitator in healthcare facilities. I used art forms including dance and theater to help my clients cope with their lives. Read more>>

Jeremy Janus

At the start of February 2022 I left my corporate gig after 5 1/2 years and almost 18 years in the beer industry. My entire education, career, and network was in the industry that my family has been a part of collectively for over 100 years. However, I do not regret waiting until now to make the leap into my creative endeavor. I was not ready to do so at the previous points in my life and I truly believe everything happens for a reason. Read more>>

Harmony Jones

I have always been an artist, but I do wish I had started my creative career sooner. I was always enrolled in an art class from elementary through high school. I would paint, draw, sculpt, and learn about different artists and their creative styles. It was not until my Junior year of college that I started creating art to sell. I was used to designing posters and making artwork for my room, but never posted it for others to buy. The first piece I created for purchase, which is a part of the Embellishment series, Read more>>