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.

Hannah Hastings

I started my business in 2017. I had just graduated college and gotten married. I found myself in a very tough place as I was living with chronic unexplained pain (which was later diagnosed as endometriosis). Read more>>

Rose Winter

I started as a content creator in Christmas 2022 and wish I had started earlier! Especially during the pandemic when people were craving content and connections. In saying that, I am a firm believer that it’s never too late to start. Read more>>

Kendra Montogmery

If I were to go back in time, I do wish I had started my business sooner than I had. Pitch Black Entertainment LLC was started in 2020 and established in 2021. It was just the brink of the pandemic, my oldest kids were just about to graduate high school and I was making major lifestyle changes and other unexpected changes arose, and I knew I needed to do something as I was a full-time student and stay at home mother. Read more>>

Hope Mueller

In my mid-forties I was on the board of a large non-for-profit organization focused on developing female leaders in the healthcare industry. I started my board seat at the same time as an incoming president of the chapter who was approximately ten years my senior. Read more>>