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.

Donte Davis Sr

I founded my mentoring program, Leaders In Training in 2018. The vision at this time was to help young men that were dealing with life or simply needed direction. Looking back. I wish I would have started it sooner so as to help more young men. Read more>>

Jenniffer Omaitz

I officially started JC Marbling and Book Arts and 2016. This was after a year and a half of study trial and error in the practice of marbling. I wish I had started the business earlier because the practice and art of marbling is such a great fit/balance for my lifestyle and my energy. It was also a tremendous benefit financially as I it learned how to become more entrepreneurial and start to build my brand. There are plenty of art business books that I’ve read over the years but to really just dive in and put something like this in practice was a huge learning experience. Read more>>

Carly Williamson

I launched my photography business in 2025, right after I began photographing my college’s athletics team. I was eager to transform my lifelong passion into more than just a hobby, even though I was juggling the demands of college and schoolwork at the time.

Had I started sooner, I might have gained more experience early on—refining my style, building a clientele, and mastering the ins and outs of running a business. However, I also might not have had the financial stability or life experience needed to navigate the challenges of entrepreneurship. Read more>>

Mindy Wiseman

If I could go back, I would have started my business straight out of high school. I am middle aged (I think – is 35 middle aged?). When I was in high school, it was when social media was just beginning – Tom was my first friend. My generation ALWAYS had a camera, because our phones didn’t take selfies then. I found myself, even as a junior and senior, taking photos of more than just my friends. I was extremely drawn to landscape photography and I did some of my classmates senior photos. When I was at the age where I was looking to my future, we were made to believe that art could be a hobby – but not so much a career. Read more>>

Corey Pressman

I started my creative career at the right time, though I’ve sometimes wondered what would have happened if I had begun earlier. I never saw myself as an artist when I was younger. Creativity was always part of my life through writing and music, but I didn’t feel visual art at the time. Looking back, I can see that all of those experiences shaped my current creative practice, even when I wasn’t aware of it. Read more>>

Marc Santamaría

I truly believe that the path we follow is always the right one. That’s why I think I didn’t start my creative career early or late, I started at the right time when I had to

The life of someone important to me suddenly changed and I didn’t want to be left behind again. I know what it’s like to have everyone continue with their lives except you. That’s why I had no choice but to start moving and lose the fear of sharing my art with everyone else. Read more>>

James Tupling

I had always been creatively sensitive. As a kid I was drawn to stories and would often write my own little short stories or poetry. Language became a way to imagine and create my own worlds. What I wish I understood then, that I understand now, is the powerful connection between the written word and visuals. Visuals can manifest as their own form of thinking but I truly believe that a good idea still forms from being thought through and written down. To be able to articulate the vision through words opens up doors to explore visual motifs and ideas with greater clarity and intention. This becomes even more relevant when we consider the variety of generative art and coding tools that are flooding the market. Read more>>

Will Ward-Ambler

I’m someone firmly believes that we make choices in life moment to moment day today.That we are doing the best we can do at the time. I was drawn to this question because I don’t live from a place of.’ I wish I had of…’ or ‘ if only I’d… Things would have been different.’ Read more>>

URIEL BRG

I released my first full song when I was 21, but it wasn’t because I lacked interest or passion—it was mainly because I didn’t have the right connections, access to instruments, or knowledge of music theory. Sometimes I wonder what it would have been like if I had started my music career in 2015—perhaps I’d be much more established by now. Read more>>