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.

Elena Miller

I sometimes wish that I had started my business sooner. I originally went to school for Broadcast Meteorology, but soon realized I didn’t love being in front of a camera, which makes it difficult to be a weather woman! So I went onto the new’s side of things for a few years. Read more>>

Mikayla Bronkema

If I could go back, I think I would have started my business sooner if I could have! But, many parts of life have played out to beautifully that I’m not sure I would change much of it! I started photography back in high school, sometime in 2014. Read more>>

Lupe Voss

Looking back, each of the businesses i started and co-started, were synchronized at the right moment. They actually happened because of the previous business. When I reflect, I see how the opportunities for the next happened because of where I was at in that moment. Read more>>

Yobe Qiu

If I could go back in time with the knowledge I know now, I would’ve definitely started my business years sooner. I first started byYQ Multicultural Books and Toys in July of 2020, right at the start of the pandemic. At some of the most critical points of the development of my business I was stuck in lockdown, and it was very difficult to grow. Read more>>

Chelsea Terry

I vividly recall the season of my life when I took the leap and decided to go all-in on my photography business. For years leading up to that point, I had been toying with the idea of photography as a career. However, life at the time was throwing curveballs my way; I didn’t have a clear vision of where I would be in the next year, let alone five years – hardly a solid foundation to start a business, I’d tell myself. Read more>>

Loucinda McGary

I wrote my first novel when I was 27 years old, but I didn’t start to seriously pursue publication for another 24 years. I continued to write and take writing classes and writing workshops, but I did all that in and around ‘real’ jobs that provided me with a steady income and benefits. Read more>>

Schaelynne DeHaan

I think my photography journey started at the perfect time. When I was 20 I decided to move to Australia for a year where my love for traveling started. When I came home, I googled jobs that allowed me to travel and of course one of the first things that popped up was a flight attendant. Read more>>

Toniqua Green

We embarked on this adventure back in 2022,during The Pandemic. My business partner and I were having frequent legacy conversations and tossing around ideas that would help on our journey. Read more>>

Tenice Holman

In October 2023, Organized To The T marked its 7th anniversary. Initially focusing on professional organizing, I later incorporated design and more recently virtual support services in 2022. When asked whether I would have started my business earlier or later if given the chance to go back, I’d say neither. Read more>>