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.

Charles F. Millhouse

I didn’t ever think I could be a writer, at least not one that published his work. That’s what held me back the longest. Self doubt can hold you back and if I would have known I could have been a somewhat successful author when I was younger I would have paid more attention in English class lol. Read more>>

Kristen Van Horn

I think I always knew I wanted to own a business. In fact, it was on my “bucket list.” My husband and I met working at a frozen custard stand in St. Louis, so I always imagined that one day, we’d own our own frozen custard stand. Read more>>

Julie Greer

I’ve actually been asked this quite a bit. I didn’t start my business until I was in my mid 40’s. I graduated college with a social work degree, was a youth counselor for a few years, then a stay at home mom with my 3 kids and then a preschool teacher for several years before I took this leap. Read more>>

Kayla Carreon

I started my business at the end of a bad break up back in 2014. I had been drawing since I was in middle school and I had dabbled in crafts while looking for something to distract me from the horrible situation I was in. Read more>>

Catherine Arruda

With hindsight, it’s easy to say that I wish I had started my business sooner. I launched Aster Candle in 2016 at a time when I was feeling pretty low and unfulfilled creatively. Read more>>

Ryan Smith

I graduated college in 2020 with my Bachelors in Biology and I had intentions on pursuing the medical field. I worked as a certified nurse aid while I went through my bachelors degree to help with experience and to pay my way through my degree. Read more>>

QUIANNA BRADLEY

I officially started my business 10 years ago, following an eye-opening motorcycle accident. During the recovery period, I had the time to reflect and plan, which led to the inception of my private chef venture. Read more>>

Renee DuBose

Ironically, when I did decide to start my business, I was almost immediately forced to stop and wait until later. I’d grown up loving to bake and loving desserts, it was always my favorite part of the holidays. Read more>>

Emily Kutt

I have wanted to own my own wedding planning business for as long as I can remember. The journey to get here couldn’t have been more meant to be. Naturally, I am a planner when it comes to my own life and aspirations so I had a 5 year plan that I was determined to stick to. Read more>>

Paulette Guthrie

I started my construction business, Central Point Services & Construction, in 2008 because I was working in the mortgage business, and I wanted to set aside some of the money I was making. Read more>>

Latrice Cole

I am grateful for starting my business when I did as it provided valuable lessons that shape my business today. I launched my business in 2018 while I was still a corporate climber. Read more>>

Adam Giriunas

When I was 18 and a senior in high school, I found myself at a crossroads with no clear vision of my future career path. Despite having hobbies such as producing music, playing sports, and collecting shoes, I struggled to see how these interests could translate into a stable profession. Read more>>

Luran Hou

If I reflect on my entrepreneurial journey, it traces back to when I was in fourth grade, launching a black-and-white magazine due to the constraints of expensive color printing. Read more>>

Katarina Lawrence

I started pursuing this dream of mine to become a reputable tattoo artist a couple times in life. First once in my twenties, my son was three or four, I was chronically laid off yearly at the pottery studio I worked for. Read more>>

Tracy Bates

In 2018, the idea of starting my own business as a virtual assistant began to take shape. However, I found myself feeling stuck, trying to navigate the complexities of building a business while juggling a full-time managerial role in the service industry. Read more>>