Almost every entrepreneur has had to decide whether to take the leap now or wait– perhaps they wanted to acquire more capital, experience or connections. Given how common this predicament is, we asked some successful business owners to reflect back on whether they wish they had started sooner or waited for a better time.

Taelyr Wilson

If I could go back and start sooner or later I really wouldn’t want to change anything. I think everything I had been doing and the knowledge I acquired prior to prepared me as much as it could up to the point so I do think it happened at the right time. I believe everything happens when it’s supposed to, and although there were and still are challenges I really wouldn’t change anything. Read more>> 

Erica Soto

If I could go back in time, I wish I would have started my business sooner. Waiting was a decision that fear decided. When I started my business, it was under the encouragement of a good friend and mentor who held my hand and told me exactly what to do to get started. Before then, I was at a low period in my life. Read more>>

MeiMei Fox

I’ve absolutely loved my career, which has been purpose-driven nearly from the start. After graduating Phi Beta Kappa with Honors and Distinction with a BA and MS in psychology from Stanford University, I wasn’t sure what to do with my life. So I gratefully accepted a position as a Business Analyst with the prestigious management consulting firm McKinsey & Co. Read more>>

Sejal Thakkar

I spent the majority of my legal career career practicing as an employment law attorney, specializing in defense. From 2003 to 2015, I navigated the complex landscape of employment law, representing various clients in legal matters. While this path allowed me to develop a deep understanding of legal strategies and nuances, I realized it wasn’t the perfect fit for me. I’ve always been more inclined towards conflict resolution and fostering positive workplace environments. Read more>>

Hannah Wentworth

For me starting my business was a slow and steady experience. I have been pursuing photography as a career since I was 15 years old. When I say slow I’m not exaggerating! When I was younger, I did not have the business knowledge or experience of what it truly meant to own and work hard on something like this. Read more>>

Claudia Rollin

If I could go back in time, I do not wish I had started Harlow & Dahlia Events earlier simply because I wouldn’t have had the right set of skills to undertake the many, many complex dealings that come with owning a business. I started the business in my early 30’s while I was a director of Marketing services and had accumulated a long range set of professional experiences under my belt. I had also woken with a large set of different personalities which will come in key later on for the business. Read more>>

Angela Thompson

I feel incredibly lucky that I started my business at the perfect time for me. I just had our oldest child and stepped away from corporate America when I began consulting with a former colleague on a very limited basis. Over the years, as my children grew, my business expanded as well. Read more>>

Mya Johnson

I believe that timing is everything. I feel if I had started my business any earlier than I did I may not have had the knowledge then as I do now and even when I first started. There is always a learning curve in everything you do but timing also has to be right. I would not change anything about what I have learned or my experience in general. Read more>>

Royce J

Looking at things from a birds eye view, I believe this question can go either way. Of course I wish I would have started my business sooner for the simple fact of the learning curve and being much closer to being/feeling established in my field. On the other hand, starting my business later could also have had its advantages as well. Read more>>

Steve Stewart

Timing is much more important than people think. Looking back on my experiences, I find that the successes usually occurred when all the elements came together at the right time. When I started managing the band that was to become Stone Temple Pilots, music was at a pivotal point. Read more>>

Kristina Pearson

Call me crazy, but no. Although I’ve always known I would become an entrepreneur, I needed to honor my core values and listen to intuition. It was only after navigating simultaneous life changing experiences that I firmly believed I was ready to navigate the demands and pressure of being a business owner. I had developed greater confidence in who I was as an individual, along with unwavering trust in myself and talents as a designer. As a result, Haus of Lola was born. Read more>>

Yazmin Coleman

I currently own two businesses. One is a partnership with a successful business owner in the community and that business has grown steadily in the last year, The idea stemmed from a work trip conversation and with her business expertise the idea came to life and in the last year we have been able to create a non-profit entity and get credentialed with various insurance companies. We were able to hire our first contracted therapist in September. Read more>>

Debbie Sallee

Twenty years ago… if I would have started my own business being a Wedding and Event DJ how different my life would have been. I spent years in the corporate world in many different fields, always the dream of making it to the top of the ladder. I actually achieved the goal and it was rewarding, but didn’t seem to fill my cup. Read more>>

Leshay Reed

If I could go back in time, I would not have started my business any sooner. I started my business as a side hustle while working full-time in higher education. Although I knew I loved social media, I didn’t understand how to make it my career and at the time, I was not ready to be a business owner. Read more>>