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.

Tara Waddle

This is tricky to answer, because you can’t get where you are today without going through something. My current skillset is a result of my history and experience. Here’s what I can say: I’ve spent more than 15 years helping other small businesses build stronger operations, clean up their processes, and scale. A lot of those businesses went on to hit seven figures. I loved the work, but it took me a long time to realize something important: I wasn’t just “helping out” behind the scenes or playing a supporting role. I was driving real, measurable growth. Read more>>

Kim Nunez

If I could go back in time, I do wish I had started my business sooner—but honestly, I believe I started at the time that was right for me. I’ve been decorating cakes as a hobby for over 14 years, but it wasn’t until 2022 that I officially turned my passion into a part-time business. At the time, I had just turned 30 and was working full-time as a state employee in an office/call center environment. While the job offered stability, I wasn’t feeling fulfilled—and I knew deep down that cake decorating was where my heart truly was. Read more>>

Joe Muscarello

The short and easy answer is that I wished I would’ve gone in business for myself sooner. However honestly, I would say that the timing was perfect only because you need to be able to process and learn from your experiences. Read more>>

Shea Hill

Becoming a travel agent has changed my life in so many ways; I wish I had stumbled upon it sooner! When I first started, I had an at home bakery and was a slave to my kitchen. My Friday and Saturday nights were filled with cake, sugar, decorating, loads of dishes, and late nights. This took a toll on my family. We couldn’t make plans for the weekends and we always had to be home on Saturday mornings for order pick ups. Sometimes people would come late and ruin what plans I did have! Additionally, my kitchen was always a mess because there would always be some order I needed to work on. I was tired of it and I wanted a way out without giving up the money it brought in. Read more>>

Wanessa Couto

If I could go back in time, I would have started my business a little later. I launched it at just 16 years old, and while I’m proud of that, I now see the value in taking more time to fully prepare. I wish I had understood more about the many details that go into running a business before diving in. Read more>>

Phylicia Barker Nelson

If I could go back in time I would tell the younger Phylicia to remember her past, to not give in or up on herself; and to believe in the person she has built over the years. I started focusing on myself after I realized I was wasting my talents that I have known for years were there. If I had of started earlier in my teen years I would have been more stable now in my 30’s. Read more>>

Jazmyn Averette

I do not wish that I had started my business sooner or later actually. I started my business in December of 2020, which was the same month and year that my mom passed away. Although her passing was the most traumatic experience of my life, it created a drive and passion for my ability to stay motivated to express myself through fashion while relaying positive, inspirational and creative messages through high quality garments. During my mother’s passing, I was at work and in the middle of typing a final research paper for one of my college courses. One thing that my mother always expressed to me was that she wanted to watch me walk across the stage and obtain my degree. Read more>>