The uncertainty of entrepreneurship causes many entrepreneurs to put off starting their business. For others, losing a job or other economic hardships push them starting their businesses earlier than expected. In our conversations with thousands of entrepreneurs we’ve seen so much variety in when, how and why people started their business and so we wanted to share a wide variety of views and reflections on the question of whether these folks wished they had started sooner or waited longer before starting their businesses.

Mia Casanova

For me I wished I would have taken the jump to being a full-time hair and makeup artist sooner. Before doing this full time I was in nursing school, just helping out friends and family that needed to look special on their events. What really pushed me to do the jump was my daughter. Amor was born Exactly at thirty-five weeks and was rushed to a NNICU. Read more>>

Samantha Bryan

Looking back at when I launched my business, I wish I had trusted myself more and launched sooner. My business launched in June of 2022, after years of personal research, and implementing systems into my own life. I knew this is what I wanted to do and I knew I was more than capable of making this a successful business. Read more>>

Tiandra Robinson

I started my marketing business back( then it was public relations) in 2009 out of frustration and necessity. I had just graduated with my Master’s in Marketing Communications and got tired of applying for jobs with ad agencies in the city (Louisville) and not getting interviews. This is when I decided to freelance my services on the side to build up experience, I only did it for that experience so I could look appetizing to those agencies. Read more>>

Jane Fernando

I started my business in 2020 during the pandemic (along with so many others). It was born out of a longtime desire to create an e-commerce fashion business. I just never made the time to sit down and do the research and the work to get it off the ground (or if I did, I would get distracted by the demands of everyday life). The pandemic was a unique period of time where a lot of people began exploring different hobbies and trying things out of their comfort zone out of boredom or simply because they finally had the time. Read more>>

Philippa Channer

I truly believe that I would be so much further along with my business and personal development had I started my business much sooner in life. I launched Channer Consulting in February 2020, right before COVID-19 changed the face of how the world engaged with brands significantly and so much more. I had earned over 13 years of experience in the marketing field as a communications manager at a local nonprofit and decided I wanted to take what I learned to help other nonprofits and small businesses in the area overcome marketing challenges. Read more>>

Taylor Isom

I could say I wish I would have started my business sooner, but I’m thankful for the journey I had nonetheless because it really has given me an appreciation for what I have now. So just as a back story, I did photography as a hobby from the time that I was maybe 15 until I was 21 or so, and I had always said it would be so cool to be a photographer as a job, I was so inspired by a handful of people at the time. Read more>>

Courtney Heywood – Pierce

I launched Care Blackage in under 24 hours, but I honestly think I did it at the right time. It was 2020, we were in the middle of a pandemic, George Floyd had been murdered on camera, and I wanted to do something beyond just sitting with my feelings. I couldn’t go out and protest because of respiratory issues, so Care Blackage became my contribution to the cause. It provided a way for me to raise money for bail funds [I donated 100% of profit from my first two months of sales] while simultaneously giving my peers an outlet to spread joy. Read more>>

James Rodriguez III

Being fully transparent, not starting my business sooner is one of my deepest regrets in business. I personally feel like I lost out on years of opportunities to learn and grow. I always knew I wanted to start a business, but I remained in the side hustle phase for the entirety of my educational journey. I was stuck on this idea that I needed to finish my educational journey before starting my business to obtain enough knowledge to do so. Read more>>

Dawn Parkins

Looking back at it, yes – yes, I would’ve listened to my calling when I was younger. In college you have UNLIMITED access and all the time under the sun. Friends, family, even strangers would ask me, “why aren’t you in fashion, you have a great eye.” But, growing up you’re told art doesn’t pay the bills. Even though I graduating with a Bachelors in Criminology, I still kept my heart in the arts in everything I did. Read more>>

Jamie Rogers

If I had it all to do over again, I would have definitely started my business sooner. I just officially started my photography business last year in June when I quit my previous career in software sales. I was finally burnt out and needed a change. I had been doing photography as a hobby for a few years and I thought it was finally time to make a change and try it as a career full time. I wished I had made the decision sooner as I’m certainly happier being my own boss but I also wished I had started sooner as getting your business ramped up takes time. Read more>>

Maya Lawrence

11 years ago I was fresh out of studying a Masters in Textiles & surface pattern, had secured a job as an Interior Designer in an affluent area of London, and had a clear vision of where I wanted my creative career to take me. Life’s circumstances, changed my path and motherhood, along with the dreaded imposter syndrome prevented me from reaching the goals that I had set myself. Although being 11 years younger would be amazing and allow me freedom to work all the hours under the sun, there is an element of life experience that has impacted my creativity for the better. Read more>>

Dannielle Olliver

Yes! The most difficult idea in the world is to pursue your dreams. We live in a society where money dictates so much of our lives, the idea of anything that isn’t considered a traditional source of income can be overwhelming. I think it is so important to remember that life can change at any minute, and that if something does not work out a new path always shows up. Had I started my creative career sooner I can only imagine the concepts and ideas that would have found me! Read more>>

Brittany Eve

I wish I would have fully tapped into my creative ability and understood its value sooner rather than later. I have always dibbled and dabbled in the arts at a young age from dancing, drawing, writing and creative directing but it never clicked that I could thrive with these talents in the real world. My family, especially my grandparents, always wanted me to get into the medical field or get a “good job with good benefits”. Read more>>

Hao Ding

Starting my creative work earlier is crucial for me as it unlocks my true self. It’s like finding a key that opens a door to a world where I feel free to be who I am without judgment. I have always felt drawn to the arts, and expressing myself through film, game design, and comic art has always been my greatest passion. For as long as I can remember, I have been captivated by the power of storytelling, the beauty of visual design, and the limitless possibilities of creativity. Read more>>

Amy Butowicz

We arrive when we are ready. I don’t believe there is a right, better or correct time to dedicate one’s life to a creative career. I could spend time wishing I would have gone to an art school, achieved a BFA or spent less time in my twenties exploring different passions but all the roads I have taken have led me to the place I am now. All the experiences, adventures, failures, and commitments to different interests enrich my work in the studio and provide my own unique lens to see the world through. Read more>>

Sarah Sneesby

I started my professional creative career quite later than many of my cohorts, so there is a lot of early career networking that I missed out on. However, rather than viewing that as a weakness, I believe many of my strengths come from the fact that I had a career prior to my creative career as a director and movement director. Unlike many fellow directors and choreographers, I did not spend my 20’s on the audition & performing circuit. Read more>>

Shy Johnson

If I could go back in time, I would have wanted to start my creative career sooner, but mentally I believe I started at the right time. I started my creative career during covid. Many people may have done the same, but I needed the freedom that covid gave me at that point in my life. So what I mean by that is, before covid, I was so bound to a schedule of going to work, coming home, and getting the kids and myself ready for that next workday that I couldn’t imagine doing anything else even if I wanted to. Read more>>

Delee Cox

I started my business on a whim. I didn’t put much thought into whether I would succeed or fail, I just started. It all began with a thought: Is there a market for this? I began my career 20 years ago as a hair stylist. I took a long hiatus when my children were little. I have 4 kids, ages 17-9. As they became more independent and started school, I wanted to do something more, something meaningful, something I was passionate about. Read more>>

Amber Clancy

Although I started my business in the midst of the Pandemic. October 4, 2020 was my season to launch my empire. Had I started sooner I never would’ve had to same drive nor determination to see my vision come into fruition. During that time I privately dealt with many distractions that effected me mentally and emotionally. Read more>>