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.

Lenise Robinson

I often wish I had started in the beauty industry much sooner because I didn’t have the technical skills that my peers had since they had already been assisting in salon settings. I realize I probably could have had I not let fear cripple me for so long. But what I also appreciate is all the skills I’ve been able to bring into my business because I didn’t start it sooner. I may not have been able to do amazing hair, but I had the structure and discipline needed to sustain the business side of things. Read more>>

Darlene Wiliams Roberts

Yes I wish that I has started my business early on. The business was a hobby for my husband he was running and maintaining the daily task of the vineyard. While he was maintaining the vineyard I was busy running my business in health and wellness along with my Spa. My cousin would say Darlene you need to learn and understand what it takes to maintain the vineyard, I did not pay her any attention and went on about my business. Read more>>

Jaime Saunders

As a child, my aunt was a photographer and always stressed the importance of memories. She lost her battle with cancer in her 20’s when I was only 13, but the pictures she took have provided memories that will last forever. In my late 20’s my mom brought me my aunt’s camera and told me to capture every memory I could, just like her sister did. I truly wish, in that moment, I had taken the chance to start my own business and follow my love of photography. So, looking back, that’s the only thing I’d change. I would’ve taken the risk sooner. Read more>>

Shaquil Martin

If I could go back I would’ve never stopped creating art as a hobby. I got back into art in 2020 after moving to Kansas City 6 months prior. I hadn’t even done a sketch since 2014 so I had fairly little optimism in my capabilities. Woodburning was my first venture and looking back I realize had I kept drawing/sketching on the side not only would my skills be more technically sound but my confidence would be up! It took about 2 years in until I really had that feeling of I AM AN ARTIST. I can almost see a timeline that would put me at the level I’m at now about 3 years ago. Read more>>

David Carrington

I think theoretically, I would start my business sooner because I would be further along running the company. But I will say that all of my experiences up until now, I wouldn’t change that for the world because Everything I’ve done in my career has led me to this point. To Start this business and run this business the way I’m doing it now, with the experiences that I’ve had so far of my career and life. I started COMPASS last year in January 2022. Read more>>

Nahvi Phouthakhanty

I wish I would have started my business way sooner, although I’m still pretty young to start this business at the age of 18. I was a young girl who grew up in the suburbs and just graduating high school. Throughout high school, I was also helping with my family business that a few of my aunts owned. I didn’t have plans to attend college like the average person, because I wanted to go my own route. Read more>>

Nykisha Banks

If I could go back in time, I see both ways of wishing to have started my career sooner or later. Sooner because I would’ve loved to enjoy the life I have now, To be creative without judgment of Corporate America, or serving under someone who doesn’t value the work or feel like something was taken from them when the heart was pure and only being authentic without any strings attached. Read more>>

Christineh

I definitely wish I had started out sooner. Like, way sooner. I started about 3 years ago at 33 and when I think about it, I wish I had started after high school or even in my earlier teen years but it was definitely a different time then and not as easy to put a song together as it is nowadays. I definitely would not have had the resources that we have today, like social media, all the apps that help artists, Read more>>

Kimberly Gutierrez

I think if I were given the opportunity to start my creative career sooner, I would take it. I didn’t have much of a creative career until a few years ago but I do wish I had started taking my art more seriously earlier in my life. I knew I wanted a creative career since I was child but I had never really known how I would achieve that. Much like my older brothers, I didn’t start considering that until I was a senior in high school and was confronted with college applications. Read more>>

Brendan Fallis

My career as a dj started in 2008. I moved to NYC and quickly realized that surviving on my daytime job salary of $21k/yr was quite limiting. A friend of mine at the worked as a manager at a bar/restaurant, so on slow nights we thought we’d teach ourselves how to DJ and I could also eat a free meal. That one night turned in to 2 nights and suddenly many more. I used it as a platform to launch in to a creative space, while still working my daytime job for a few years. Read more>>

Sarah Gavin

For quite a few years before I started my cookie business, I was pursuing art and hopeful I would find a niche that could turn into a business. I’ve always loved art but never committed to one medium/style/etc and so nothing ever really took off. While working full time and before becoming a mom, I always struggled to commit time to pursing the business dreams I had. In slight desperation, Read more>>

Gareth Hunter

Never had an issue with when I started but more so with slowing down the process because of fear of risks involved. I wish I would have stayed strictly on my creative path. Over the years (during financial hardships) I would take time, sometimes up to 3 years to venture into a 9-5 job that appeared more stable or safe. This was due to becoming a father and in one case becoming a husband(that didn’t last long). Each event occurred right when my career slowed and the stress as well as lack of support to push through became too much- so I would take on a 9-5 job for a few months that some times turned into years. Read more>>

Jamie Zerr-Lockwood

If I could go back in time, I would have started my art journey right out of high school instead of finding a full-time job right away. I look back at my life and always ask myself that question as I’m sure most artists do. The thing that always held me back was being told that being an artist isn’t a real job. True, I would have struggled at first but don’t we all? Read more>>

Michael Galyean

So I have always been a part of the arts, just enough to scratch the itch, but never giving it the attention it needed. I moved to Tennessee to attend the University of Tennessee with plans to be a UT Cheerleader. I completely chickened out, and moved on with regret my whole life. Why didn’t I try out? Why did I even come to school and not move to a performance town? Read more>>

Destiny Shivers

I have been a creative and “free spirit” for as long as I can remember; uncertainty and doubt come with the territory. After almost two years of blogging and content creating inconsistently, I wish I would have taken advantage of the time I had at home-not working or needing to-when my daughter was small to really focus on and build my followings. While I do not regret focusing on my child and my own mental health, I do often wonder where my content would have taken me by now. Read more>>

Alice VL

Looking back, I’ve always written and always wanted to give life to my stories. I wrote the outline of my first book as a teenager, and kept it hidden while growing up, starting a family and through the years in my career as a Recruitment Consultant. I would lay awake at night and be bombarded with stories running around in my head, keeping me from sleep. One became two, then there were four and at one time, as many as a dozen. Read more>>

Autumn June

My name is Autumn June I’m a local singer- songwriter performing for the past 8 years along Pinellas County’s beaches and threatus County. I also perform in my hometown Old Orchard Beach Maine in the Summers. In 2013 I began to attend open jams in the surrounding area particularly at The Daiquiri Shack with Mad Beach Mafia and the highly respected John Spinelli with Spinelli Drums. Read more>>

Jakena Spencer

I feel that I started my business at the perfect time. This is actually my second business the first is a trucking business with my husband. I started Empowering Scrubs Company October 2022. I was blessed to be able to be a stay at home mom for a little over a year at the time. We had moved from Illinois to Arizona the year prior. Perfect timing for a fresh start. Read more>>