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.

Lizette Sinhart

Real Estate is my second career. Previous to working in real estate I worked in the Beauty/ Fashion space as a sales executive. I was itching to change careers for a while, but I let fear & money hold me back. I came home from work one day absolutley miserable because I had a 2 year that I was dropping off at daycare at 6:30 am and picking him up at 6:30 pm. Having my first child helped me make the jump. Transitioning into a new career in your late 30s is not easy especially a career that is essentially is a small business but is 100% commission based. Read more>>

Natalie Barry

I feel like I started my business at the perfect time in my life. I started working as a freelance makeup artist in 2016 and received my Esthetician license in 2018. Not long after, I rented a private suite in a salon and Natalie Elizabeth Beauty was born! At that time, I was still working my part-time job at a skincare and waxing center while doing hair and makeup for weddings on the weekends. I knew that I had a deep desire to be completely self-employed as a solo esthetician and makeup artist, Read more>>

Caitlin Penny

Before starting Copper Theory, I was working at a print shop and doing graphic design at a consulting office where I gained my experience and started networking. I always knew I wanted to be my own boss, so by the time I was a junior in high school I decided I wanted to be a designer. After that I moved out and started college at the age of 17 and received my BFA in Fine Arts & Graphic Design on my 21st birthday! Read more>>

Jasmin Williams

Due to the fact I am not where I want to be, I doubt myself at times lol I’m human but in all honesty NO I would never redo what I have started. I have no regrets, sure I have taken a few loses and hard lessons I am still learning about the business, however I am proud to say I started something I love! Read more>>

JayLynn McDaniel

I love this question so much and I ponder about it often- I definitely wish that I had the skill set, the purpose and the idea to start a business while I was in my early 20’s rather than my mid to late 20’s. If I had started CandlesbyJay earlier, I think I would’ve made better choices personally and I would have had a head start on setting and building a solid foundation in my life. But at the same time, CandlesbyJay was born at a time in my journey where it just made sense. I believe everything happens for a reason and everything happens when it’s supposed too. Read more>>

Rebecca Sheer

I was in my late 30’s when I decided to go rogue and start my own store front. I was an Assistant General Manager at a great hotel company. I had the skills, knowledge and experience to continue my hospitality career an move up in several areas. I truly loved working at hotels, but I had just reached a point in my life where I wanted something that was all mine. Baking had gotten me thru some hardships in life and still I couldn’t let go of the procurement side of business that I really enjoyed. Read more>>

Steph Cano

I absolutely wish I had started sooner. I had a passion for photography and art at a young age. When I was around 15 I began shooting film photography, and I wish I would have continued straight out of high school, but I did not believe I could make a living doing it. I was still shooting on my off time, mainly for friends, family, and a few clients I made off of craigslist. As much as I wanted to quit my job and pursue my passion full-time, I kept having self doubt. Some people close to me would tell me that photography is overrated, a hobby, and not a real job. Read more>>

Robert Queen

Wow, what a question! To answer this is a unique form of my life I think I would say I should have started off a later sooner beaming toward that I stayed in retail for nearly 15 years but prior years to me even considering a business was a struggle to begin with. I did not start out with money or a degree in business I just started doing graphics from a broken laptop and a crack screen. Yes I could see and at times where I couldn’t I just used my phone for higher definition of graphics and still do often. Read more>>

Michael Lambard

If I could go back in time I wish I would have continued to paint from when I was a teenager. My love for art grew in the early 90’s as a Street Artist. Being able to work with so many different local artists was such a rewarding time. When I was 15 I became a father and realized I needed to make some money. Being a Barber for 10+ years allowed me the financial security to start again. I started drawing a lot more and eventually that led to me painting and doing it full time. I don’t wish I started sooner nor later but continued from when I was a younger kid instead of having the decade long drought. Read more>>

Andrei Stoica

Photography has been around me all my life in various ways. I was born in Romania while it was still behind the Iron Curtain and travelling outside of its borders was very difficult for many reasons. However, in the early 70s travel restrictions were not as bad as in the years that followed, so my parents managed to take a few trips to Western Europe. They filled up the trunk of their car with cans and jars because they couldn’t afford eating at restaurants, but they did enjoy those trips immensely and brought back thousands of color slide film photographs. Read more>>

Moriah Boone

I wish almost every day that I had started my creative career sooner. I am blessed to have the opportunities that I do now and absolutely nothing excites me more than delving into a multidimensional character or acting out an intense scene. I only wish that I had remained true to my younger self from the beginning and pushed for more exposure to the industry early on. Read more>>

Bonita Williams

If I could go back in time I would definitely say I wish I started my creative career sooner. When I say I started if I’m being honest I feel like I started when I was like six but of course at six you don’t even know what exists as far as making something into a career like maybe just watching cartoons knowing if you can draw and have a story line cartoons go on TV. But Id say I realized and have been consistent in creativity Since 2021. Read more>>

Ebony Brown

I absolutely wish that I would have started this business earlier. I formally began Potty Camp a little over 2 years ago and I had no idea the impact that it would have. Potty training is something that many many families struggle with and to be able to relieve that burden is priceless. I’ve developed a bond with many families all over the metroplex and it feels amazing to know that I’ve changed the dynamic of the household in just a few days. Read more>>

Joseph Johnston

Definetly sooner. At the end of the day, everything happens exactly when it is supposed to. With that said, businesses take time. I have plenty of friends who are younger then me or my age that have been in the game far longer that I am and are simply ‘ahead of me.’ Starting sooner would have simply gave me more time to develop allowing me to, theoretically, be farther ahead now then where I’m currently at. Read more>>