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.

Gemali Martinez

Looking back, I wish I had started my business sooner. Initially, I was hesitant due to fear of the unknown and financial responsibilities. Read more>>

Paige Burns

I’m so glad I started my business when I did. I didn’t feel necessarily feel prepared – or qualified – to start a business, but I know that’s a really common feeling among first time entrepreneurs. Read more>>

Elise Kwenin

I actually think I started my business right when I should’ve. I taught for 10 years in a public school setting and I had so much time to understand the several local school systems, understand how to create lessons and how to work with many different types of students and educators. Read more>>

Sam Baker

I often think about the 10 years I worked in corporate before finally starting my own business. During that time, I spent a lot of time thinking about the entrepreneurs I knew who left college and started working for themselves right away, and wishing I’d done the same. Read more>>

Sophia Whitewater

I really started doing photography professionally while taking photos for 3 Exits to Hattiesburg. While taking their photos, I would go up to other bands performing and offer to do their photography, and then that transitioned into portraits for them or for coworkers at my day job. Read more>>

Haley Kristovich

You know I actually feel that I started my business at the exact right time in my life! I have worked many jobs over the years and always continued to do weddings on the side helping friends and family, but it was not the right time for me to dive in full force until exactly when I did. Read more>>

Emily Wysocki

I think this is such an important question for me. I have always been drawn to working for myself but it took until recently to actually believe that I could. Read more>>

Bridget Jenkins

If I could go back in time, I wish I would have started my business sooner. I started my business back during the Pandemic in April of 2021. Read more>>

Damaris Santana

I was exposed to beauty and makeup in a classroom setting in high school, the course was Apparel Marketing. We had covered parts of the beauty industry and I was so captivated by what we learned. Read more>>

Jeanne Jones

I believe that my creative career happened at just the right time. I was not ready to fully embrace the time that I needed to study and perfect my skills until I was in my 50″s. Read more>>

Kourtney Cannon

I wish I started my art career sooner rather than later, but I also wish I knew that I had the passion to paint. Unexpectedly painting came out of my new journey and motherhood. Read more>>

Janine Krantz

I wish I had embraced what I knew I really wanted to do rather than getting pushed along the path to vocational school and cosmetology in high school. Read more>>

Paula Alves

Yes, I certainly would have loved to have started earlier as an artist, I should have listened to my instinct but I also believe that with maturity we understand many things and everything takes the necessary time to happen. Read more>>

Nancy Murty

I have been drawn to drawing and painting since I was little. But, my upbringing discouraged me from pursuing art as a career and instead pushed me to pursue practical vocations like nursing or physical therapy. Read more>>

Drin Lezhe

A couple of years ago I hit a point in my life where I felt rushed when it came to my artistry. People around me told me that I was getting older and wondered why I had not released any music. Read more>>

Brandi Victoria

Part of me wish I would’ve pursued my creative career sooner. I go back and forth with myself on this topic regularly and can think of many reasons both options benefit me. Read more>>

Slab Osiris

I would actually say it’s not about when I started, since I began officially recording in 2012-2013, but actually how consistent I could’ve been when I started. Thats the thing I wish I did earlier in my career so far. Read more>>

Altaire Gural

Altaire Gural I’m a novelist, playwright, screenwriter and professional acting coach for film and television. I came to my multihyphenate career rather late in life (I’m now fifty three), Read more>>

Ipsita Govender

Yes and no. I initially started studying Architecture, but as cliché as it sounds I had just gone through a bad break-up and I wasn’t in the right headspace to focus on what I wanted. Read more>>

Stephanie Miller

When I started working in advertising at 22, I planned to become an art director. Advertising is (and was) a very competitive business. I didn’t believe my work was good enough and that intimidated me. Read more>>

Andrea Jones

Sometimes I wonder where I would be if I had found my confidence in my voice sooner. or known someone in the music business early on. Read more>>

Lorena Noeto

“There’s a quote from the ancient Chinese philosopher Lao Tzu that I really like, which says: ‘When the student is ready, the teacher appears.’ This can be perfectly applied to this question because if I didn’t start earlier, it’s simply because I wasn’t ready. Read more>>

Bill Karaffa

My carrier in art started very late in my life. As a child I always had a strong interest and talent for art. I was sent to pre-college art classes at the Carnegie Mellon University of Fine Art at the age of 12. Read more>>

Christine Tarquinio

I arrived on the music scene quite late in life. I first started really working on my voice and learning vocal technique in my mid twenties. Read more>>

Uguntaye

I definitely wish that I had started my “creative career” sooner. I didn’t really start getting into music and creating it until I was 16 or 17 and I had a lot of catching up to do. Read more>>

Shanovia Gillard

I definitely wish I had started sooner. Had I known that helping people repair their credit would generate so much revenue I would have quit my dental assistant job way sooner then I did. Read more>>

Tiffany Clemons

I absolutely wish I would have started in my career in real estate sooner. I was first interested in real estate when I was in high school. I knew I wanted to be involved in real estate I just want sure in what capacity. Read more>>

Joyce Carlisle

I wish I had started my business sooner It is such a rewarding job. I worked in corporate America for over 30 years and this is so much more rewarding. Read more>>

Sukia Akiba

Looking back, I wish I had merged my real estate experience with my environmental passion sooner. Maybe then, I could have made a bigger impact during a more critical window. But here’s the thing – better late than never! Read more>>

David Čáp

Often I think about the fact that I lost a lot of years by not being creative and that my path was not traditional in that I didn’t study at an art college and I was in a non-creative profession. Read more>>