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.

Tawanna Houston

If I could go back in time I would not change the timing of when I launched my business. Read more>>

Taquesha Jones

I started Kwees Kitchen in February of 2021. As time progressed and I started to gain more clients and experience, I started to wish I did this at a much earlier age. I do understand things happen when they are supposed to, but I just feel I would be much further if I had started in my early 20’s. I am currently 33. Read more>>

Lauren Bodwell

Growing up I had a lot of passion for photography and were eager to pursue it as a career, having no idea at the time I could work for myself and make it a viable business. I also felt some uncertainty and doubt about my abilities and experience. I felt hesitant because I didn’t feel qualified or have a clue how to run a business. Read more>>

Jaila Kaleisha

My passion for dance has always been there. I feel that I have known my purpose for a long time. I knew that I wanted to dance and teach dance but as a kid I had no idea how to make a business out of it. Read more>>

Rachel Antone

If I could go back in time I definitely would have started my slow fashion brand years before I actually started. I wouldn’t have changed my experience at all and I have no regrets for when I did start the brand, but for years friends and family told me I should start my own brand. Read more>>

Millicent Compton

I started my own virtual assistant company, Transcend Solutions LLC, in October 2020, during the Covid-19 pandemic. It was a challenging time for me, as I had lost my previous job due to the lockdown. However, I decided to take this opportunity to pursue my dream of running my own business. Read more>>

Alejandra Marez

Do I wish that I started my business sooner or later? No. If I would have started sooner, I would be a bit lost. I use to work for another waxing salon and I’m thankful for the things I’ve learned there. Starting straight out of esti school wouldn’t have worked. You learn from experience, and I’m glad I did at that salon. Read more>>

Kim Petitt

I launched my online store last year. I sometimes wish I had started my business sooner when I think back on it. Meeting demands and feeling stressed for the sake of someone else’s business had reached the point to where it was starting to take its toll on me. Read more>>

Spencer Bell

I was fortunate that I found a job out of school that gave me the flexibility to grow my freelance career. Once I was at a point where I was earning a living freelancing it became an easy and safe choice to quit my other job and pursue my video work full time. Read more>>

Radomir Jordanovic

I started really young with just any software I could get, and before that I was editing with tapes. When I was 13, my dad said, “I see that you like this audio and video stuff, so let’s go get some real software for it.” We went to Circuit City, if you remember those stores. Read more>>

Nicci Sevier-Vuyk

I’m often asked if I wish I had started my career sooner or later, and it’s a question I’ve thought about a lot. On the one hand, there’s a part of me that wonders what my life would have been like if I had pursued art from a younger age. Read more>>

Danielle Doetsch

This is a fun question. There is definitely a part of me that thinks about what if I had pursued art sooner. I was in my mid 30’s before I started to pursue art as a career. But a bigger part of me thinks some things happen in their time and when they are meant to happen. Read more>>

John Hartt

I started being a “real artist” after I turned 50. I could have started in my twenties. Recently, I was looking through some old sketchbooks (20+ years) and realized, I had the chops to be an artist back then. Why didn’t I? I was pretty immature and was prone to do irresponsible things fairly regularly, but the main reason I waited so long was that I lacked the courage and confidence needed to create the life of an artist. Read more>>

Brittany Quickel

Before I started learning about filmmaking and reading tarot for clients, I had an entirely different career as a sign language Read more>>

Santiago Villegas-Giraldo

I wish I had started sooner. Before I took art seriously I was pursuing a career in science, hoping to become a mathematics and physics teacher and investigator. I was going to college for that and realized that art was my real passion and what gave me the strength to keep going during the hardest times. Read more>>

Leah Thompson

This is one I think about often. I struggled so much in my younger years (and still do, really) with self esteem. I knew I always wanted to do something creative, but never thought I was good enough or was a “real” artist. Constantly, I would compare myself to others and always thought my art and my voice was “too weird”. Read more>>

Helen Louise Stiver

If you could go back in time do you wish you had started your creative career sooner or later? Give us the backstory – when did you start, where were you at life-wise/career-wise? What would starting later or sooner have been like for you? What would have changed about your experience and looking back do you wish you had started sooner, later or at the same time? Read more>>

Gin Blanton

Yes, I used to believe in following the conventional path of earning income by going to college and getting a good job, working five days a week, and taking a week-long vacation once a year. But over time, I realized that this routine was slowly draining away my happiness. Read more>>

Kalondria Gregg

Sometimes I do wish I had started doing hair & attending cosmetology school as soon as i graduated high school some years back but I took a year off trying to find my purpose . Though I had always been an A/B student growing up, I knew going to college wasn’t for me. Read more>>

Jacqueline Reagor

Honestly, no. I feel like everything I have experienced up until this point has only benefited me in my work as a creative. By working in the hospitality industry, I have learned that achieving a standard of excellence in any endeavor requires preparation, integrity, and commitment. Read more>>

Clay Carter

They do say “better late than never”, which is true, but yeah, there’s definitely a part of me that wishes I had started sooner. Now obviously I had other musical projects before, but I was always in a supporting role, not really a driving force or leading. Read more>>

Lee Ann Lander

Yes. I wish I would have had the courage to follow my creative path right out of high school. I wonder how much I could have already accomplished. But I doubted myself. Wrote off my callings as irresponsible pipe dreams. I know now that I am absolutely wired for creativity and always have been. Read more>>

Mel Dalton

In a sense I definitely wish I had gotten serious about writing music and playing guitar years ago. Like, 25 years ago would have been great! I think about the catalog I could have by now and yeah, maybe there’s a little regret at what could have been. Read more>>

LJR

Sometimes I wish I had started learning the music industry earlier, because I imagine how much farther along I would be with my vocal training and fanbase, and how some relationships I had then might be in better shape now. Read more>>

Shannon Chatmon

I definitely wish I had started my creative career sooner. When I was younger, I wanted to be a sports commentator because I love basketball. My initial major in college was communications, but I was shy and doubted my ability to pursue a career in the industry. Read more>>

Asha Mae

I’ve always been very creative but I became a single mother at a young age. I felt that I owed my child stability and the best that I had to offer. Of course, for me, that meant getting a traditional 9-5 and working my way up. I did that just that but ignored my true, creative self. Read more>>