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.

Ondre Gipson

If I could go back in time, I wholeheartedly wish I had started my business sooner. True Hustler World Wide and its mission of entrepreneurship and education through True Hustler University are more than just business ventures for me—they literally saved my life. I launched True Hustler World Wide during a pivotal moment in my life. Read more>>

Kristi Scott

I would have started my business sooner. I had dreamed of going out on my own for years – really since childhood I felt like starting a business. I did some freelance work in my late 20s but never felt like I could settle on a niche. So I kept going to jobs and industries I could fall back on. I was in the nonprofit space for over a decade but then in 2020 I got some opportunities to go into a new industry – tech sales to nonprofit customers. Read more>>

Matt Derda

If there was a machine that would let me go back in time to start my business years ago, I wouldn’t even hesitate to use it. In my case, I would actually tell myself to keep my business going on the side no matter what. I started a company when I was in college. It was a professional improvisational theater company, which performed and taught corporate workshops and team-building. After college, I moved to Chicago to study improvisational theater at Second City and the Improv Olympic (iO). Read more>>

Felicia Adderley

This is a good question! I am a physiotherapist and I opened my own practice in the Bahamas in 2016. I went on a bit of a journey with my career trying to decide what area to specialize in and settled on lymphedema. The pandemic hit in 2020 and of course lockdown and tons of strict regulations and accompanying expenses came with it. Read more>>

Caren Cooper

ok backstory– I started a side hustle way back in 2015 while I was still working in corporate. In 2020 I was freelancing and the project I was working on was dying a slow death. I was not sure I wanted to look for a job again having experienced ageism and difficult time finding the freelance position. My Contract end date was 3/31/2020. We all know what happened 2 weeks prior. So really the pandemic gave me permission to become an entrepreneur full time. Read more>>

Danielle McLaughlin

I opened my business in 2020, the same year of the pandemic, not too long after I was furloughed from my corporate job of 11 years. While I ended up being recalled to work and remained there for another 3 years, It was still a creative outlet for me. I never intended to open my business around that time. Pouring candles was something I had done since a young age with my Mom, a former candle maker. Read more>>

Reyna Esquivel

During the 2020 COVID quarantine, I like everyone else took up a hobby. Mine happened to be nails. I started out with a $10 acrylic kit from CVS and did my first set of nails on myself that took about 12 hours and as soon as I touched something, they all fell off, after that, learning the techniques was a challenge for me that I wanted to become proficient in. Read more>>

Lori Robbins

I do sometimes wish I’d begun the path to publication sooner, but central to my identity as a writer is that I’m a serial late-bloomer. This pattern began when I was a teenager and decided to ignore conventional wisdom that dictated dancers had to begin training at a very young age. The result was a ten-year career onstage that defied the odds. Success as a dancer, of course, meant that I didn’t attend college until long after my peers got their degrees and began their grown-up lives. Read more>>