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.

Amaya Lorè

If I were to go back in time, I would say that I’m exactly where I’m at and should be when it comes to my art and how I express it and where I’m growing and how I am expressing it, and the consistencies in the discipline that I’ve cultivated over time to express my art in the way that brings it into the world and the light that I truly feel is honest and true to what I truly am trying to capture. when it comes to my images and even my words, I would say that being 25, I am definitely just starting and Where I was at with my art in the past, that’s where I was at in the past so I would say where I’m growing I do feel like my art is in the space of where it needs to be, which is why I’m in the space of wanting to share it more and give it its time and it’s moment and not have it be in the shadows and hidden so silently and quietly. Read more>>

Allison Atkisson

I shot my first solo wedding in 2012 and knew immediately that I loved it—deeply. But back then, I didn’t believe “photographer” was a real job. Not in the stable, responsible, adult-sounding way I thought I needed. So, like many people chasing security, I chose a different path: I became a dental assistant. I spent eight years bouncing between offices and doctors—working hard, learning a lot—but always feeling like I’d left an opportunity on the table at that very first wedding. Read more>>

Kaseu Fraley

If I could go back in time, I wish I had just trusted my younger self and started right out of high school. I’ve loved photography since I was around 14, but back then, it felt like more of a dream than a realistic career. So I did the “safe” thing I went to college, tried to follow the traditional path. But when I got pregnant with my daughter, something in me shifted. I realized I didn’t want to spend my life building someone else’s dream. I wanted to be present, to create something meaningful, and still make a difference in people’s lives. That’s when I gave myself permission to start. Read more>>

Christine Cowles

My husband, Mauricio, and I launched a home staging business in 2017 while still working full-time, and it took a few years of steady growth before we felt confident enough to transition fully into being self-employed. Prior to that, most of my career was spent in the non-profit sector, where I gained valuable experience and built strong professional relationships. Read more>>