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.

Erin Fitzgerald

I’ve known I wanted to write since I was ten years old but wasn’t sure how I’d get from Point A to Point B. Studying journalism in college seemed like the answer, but instead I landed in the world of finance for a long stretch.

In what I call a “positive midlife crisis,” I hit forty and questioned everything I was doing with my life. It was plainly “Now or never,” because if I didn’t start somewhere, I wouldn’t at all. Yes, I wish I’d started earlier but I don’t think my brain was ready. I’d spent years writing snippets of stories, half-finished manuscripts with no resolution and no hope. It took my brain time to figure out whether there was a story worth telling and whether I could “close the loop.” So while I wish I’d started earlier, I also think it came full circle when I was ready. Read more>>

Robert Mcgraw

I started in October of 2023 when I was between jobs. That was my 3rd start. Returning to corporate and the conflict with the demands of life kept competing for my time. That would happen again in late 4Q23. I took another “corporate job” as a Director of Talent Management, finally adding recruiting to my scope. This time I kept the business going though. Though it was on life support, I was starting to understand the benefits of owning a business. The end of that 3rd bad experience, confirmed for me that I would be happier if I built my own business. Luckily, we are financially in a place where there is a runway to get it started. Read more>>

Randy Pulayya

Thinking back on the launch of West Indies Peppa Sauce, it was the right timing in our lives and in our careers. We started the ideation phase in the summer of 2023 and registered our business in the fall. Shauna’s background is in marketing for fintech companies, and mine is in sales and account management for logistics technology. In the spring of 2024, while still working full-time and raising two young children, we launched our business. Shortly after, I was laid off. The perfect storm hit a few months later when Shauna was also laid off! Read more>>

Zack Fite

If I could go back in time, I wish I had started my business sooner and not been afraid to fail. The biggest lessons come from experience, and in any industry especially a new one success comes from being willing to take risks, learn from failures, and keep pushing forward. Every setback is just another step toward growth, and the sooner you start, the sooner you gain the knowledge, skills, and resilience needed to succeed. Waiting only delays the inevitable challenges, and facing them head-on earlier would have meant faster progress, more opportunities, and a stronger foundation for long term success. Read more>>

Carrie Everitt

I sometimes wish I had started my business sooner, but I have no regrets about prioritizing my family. I taught high school art for 13 years and then decided to stay at home with my children for the last 11. While raising my kids, I took on a few commissioned pieces and taught private art classes, never really considering other avenues like merchandising my work. Read more>>

Alicia Starks

If I could go back in time, I still do not wish to have started my business sooner. I started my business in September of 2021, during the pandemic. At that time I worked full-time from home due to the Pandemic’s Quarantine. I worked as an Sr. Account Executive, for a Logistics company. My love for food and charcuterie was always there, but the pandemic quarantine gave me an extra push to really tap into my love for food and food styling. I went back and forth in my mind, trying to figure what is next for me, business venture wise?! Quarantined in the house and not having access to our everyday resources and essentials was a major eye opener for me. Read more>>