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.

Patricia Ferreira

I wish I had started my business sooner. I think back to all the time spent unfulfilled and supporting someone else’s goals and wonder why it took me so long to choose me. I started my current coaching business in 2015 After almost 33 years in corporate America. Before this time, I had dipped my toe into entrepreneurship and always chose the job over myself. Leaving the safety of a salary, health insurance, and other employment benefits felt irresponsible and selfish. Read more>>

Adela Dan

As a photographer, do I wish I would have started my business sooner? Yes, absolutely! If I could go back in time I should have listened to my gut instinct and been more confident to start photography earlier in life. It was always my number one passion since I was doing modeling in my younger years. Then life happened and I was stuck working a 8-5 job then I started a family and well I just never thought having my own business would really come true. Read more>>

Matthew Miner

Some therapists have the potential to create their business as soon as they get out of massage school and they are completely okay starting that way. I feel that for most, they end up looking for experience and employment first. For me, I wasn’t ready and am very thankful for the work experience I received working at a couple of spas and finding a home with chiros, physical therapists, and other (much more) experienced massage therapists. They showed me everything to build enough confidence in my craft to pull the trigger and venture out in my own. I owe a gratitude to everyone during that 8 year span. Read more>>

Kevolyn White

If I could sprinkle some fairy dust and go back in time, I would love to have start on this road a few years earlier. I love what I do! I have always baked and tried new recipes…I have always been the family baker and go to for goodies… and that is where it all started and came to life. In California, unfortunately, we were unable until a few years back to cook/bake out of our homes legally as a business. I had heard about the changes that were happening, but was a bit afraid of the paperwork involved and walking away from a decent 9-5 job. Read more>>

Brandi Jenkins

I definitely wish that I would have started my business sooner because if it had been up and running during the start of the pandemic that definitely a would have been an opportunity to help students with disabilities and their parents as far as making academic gains during a huge transition period or maintaining progress that was made prior to the pandemic. It also could have helped more parents and teachers at a time when students didn’t have access to certain materials in the classroom that help them understand information presented to them. Read more>>

Lydia Coutlee

I think I started my business at just the right time. I always knew I wanted to have my own business, I just didn’t know the when or what about it. I started sewing baprons in 2015, when I was pregnant with my 3rd and last baby. I had very kind neighbors who were willing to teach me how to use my sewing machine and help me make a pattern. They got me started and I kept it going. Read more>>

Yandry Mastromihalis

If I could go back in time in time I would have started my business way sooner. I’ve had a range of jobs between non-profits, education and corporate. But I never fit in well.. I was always too outspoken, had too many “new ideas” and could not play by the “office politics. I always felt like my skills were underutilized and that I had so much untapped potential. I was so frustrated with bureaucracy and felt like there was a better more efficient way of doing things. I noticed and how most employers were afraid of firing bad employees and would rather turn a blind eye. Read more>>

Elizabeth Rogers

When I was a soon-to-be college graduate, one industry in particular, grabbed my attention- travel. I considered life as a flight attendant or even working with a travel agency, until I learned the salary was rather low. A friend told me about the lucrative income in radio sales, not to mention the tremendous amounts of perks and fun. For eight years, I worked as a radio sales rep at a rock station, but as I began a family, the late hours and demanding schedule tired me. After radio, I co-owned, then owned an advertising agency up until 2018. Read more>>

Barbara Bullard

Considering the thought of looking back in time and wishing to have started my business sooner or later is not a consideration for me because whether I’m focused on the present or past does not change my purpose. The choices I make may morph, but the foundation remains the same. I am a storyteller. Whether it’s through marketing, public relations, or film and video production, the core of my existence is to support the stories of the marginalized. It has been my quest from childhood, sitting in front of the television alone contemplating how the story I’m viewing can be made better or to be clear, feel more authentic. Read more>>

Asia Suber

If I could go back in time I would have definitely started my business sooner. I started my business the year I graduated from college. It was a time in my life where I was discouraged. I was sending job application after application trying to get my foot in the television world and getting rejected due to my lack of experience. I think growing up and going through high school we are taught to go to college, but we are not shown what we should do if that big career job doesn’t pan out how we thought just because we have a degree. Read more>>

Angelia Bills

I started Eagle Productions LLC in 2020 after working in the marketing field for 25 years. While beginning in the year of the great pandemic had been a challenge it was also a blessing because my business was launched in a time when businesses were in dire need of marketing solutions to reach their consumers. One of the reasons that I left my career position, was because I felt that I had hit the glass ceiling as marketing vice president and my income had become stagnant. I had only two choices: Read more>>

Giselle Gallardo & Nick Machado

We launched our small business in June of 2020, right in the middle of the pandemic. At the time, we were worried that this idea wouldn’t go anywhere but we were excited to dedicate our spare time (thanks to the pandemic) to building something from the ground up. Although launching during such an unprecedented time did come with some challenges, we didn’t notice that the timing was actually perfect. Looking back to when we first started our business we now realize that our boards were a little escape from reality for many. Read more>>

Lisa Morris

I’ve always had a vision and a desire to be a creative behind the lens…from the time I was a young girl. Whether it be hiding outside to get the perfect wildlife picture or capturing those candid moments at youth camp, my camera was always with me. I finally took a chance in 2014. I was at the point where both of our kids were driving, I had more time on my hands, and I was ready. I’ll never forget how excited I was after my first senior shoot. Read more>>

Dr. Stephanie Wall

If I had started my business sooner, I would have had more time to build strong relationships with customers and clients. These relationships are essential for any business, and I would have been able to get a head start on developing them had I started my business sooner. In addition, starting my business sooner would have given me more time to learn the ropes of running a business. Read more>>

Ally Barrera

I started my business in the midst of Covid. In late 2019, I had recently moved back from Miami where I had two of my biggest job opportunities working for some amazing chefs and gaining so much experience. I had started a pastry chef position at a local bakery in Houston and was working there for about 6 months when Covid hit. Read more>>

Shameka Burrell

Yes, I am at the point of relaunching my company. I first started my company right before Covid and was building clientele, and due to lack of confidence I went back to work. Even though it was Covid, I wish I would have started my company full time two years ago. I started my company to first education small business owner and minority on the importance of keeping good financial record. I also wanted to families how to budget no matter what financial status. When I started this journey, I realize that a lot of individuals did not file taxes and added taxes to our services Read more>>

Naomi Hertsgaard

I came to home organizing, a career that doesn’t require a degree, after receiving both a BA and a Masters Degree. I spent years working in healthcare in a career I knew wasn’t right for me. Regret is a strong word and I’m not sure I would say I regret my degrees or my previous career but I do wish I would have honed in on home organizing earlier than I did. Had I known I would start this business I would have pursued different degrees and sought out mentors in the field. Hindsight is 20/20. In reality, I don’t see how I could have started the business earlier than I did. Read more>>

Aun’Jenelle Weaver

I do wish I would have started earlier. When I first started 21 and The Moon I was working a corporate job. I wasn’t feeling fulfilled career wise and knew that I wanted to start a jewelry line. I had been making pieces on the side and would give them to friends and family, but kept putting off on actually launching the brand. I couldn’t decide on a name or logo so I just kept pushing the brand to the side. Looking back I wish I would have just started it sooner. Read more>>