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.

April Martinez

Heck yes is the short answer. I have been in social service for 22 years and while it was very meaningful and I was passionate about the work I love running my own schedule. When I started my business Covid had just locked down the country and a lot of people were facing mental health and were overwhelmed. My business was started as a way to support families during this difficult time. Cleaning is therapeutic for me and I love to see my clients’ faces when their homes are touched by Joyous Gems. Read more>>

Dr.Jessica Mosley

I actually wish that I would’ve taken the leap of faith and became an entrepreneur sooner than later. There’s so many benefits to being an entrepreneur. I love that I get to impact and change lives! I’ve always been entrepreneurial minded. From having a lemonade stand, to outselling everyone when it came to my girls about that I was a part of, to starting a publishing company/media branding company, to now owning medical training schools, and also starting a nonprofit for Battered women, children, and those re-entering society. Read more>>

Jasmine Nickerson

I started my skincare business and journey in 2018 after having my first son. Being a mompreneur has been a fun and exhausting experience! I was just starting to work at a call center when I started the journey with our business and my son had a break out and I wanted to make something at home for it; before I knew it I wanted to make a whole line! I believe that had I started sooner before having kids that I could have the open schedule and availability to really flourish through this business and pass to my kids! Read more>>

D’Yani St.Cyr

No. In 2003, I graduated with a bachelors degree in marketing. After graduating I worked a number of corporate jobs and had my daughter in 2005. 2013 I started my brand Grin’d&Bearit while working 13 hour shifts. I would work on the business on my lunch breaks, off days, and when I got off work. It was very difficult working and starting a business, but the business motivated me to want better. I used money from working to establish my business. I’m glad I did not start sooner than I did because I needed the experience working in corporate environments to understand how business is structured and managed. Also building a business takes a lot of hours, time, and commitment. I have learned the key to operating a business is patience. The world of business is constantly changing, with various highs and lows. Maturity has enabled me to withstand challenges while growing a notable brand. Read more>>

Konica Cherry

I think I started my business at the perfect time. I don’t think I would’ve started my business any sooner or later than I did if I had the opportunity to go back and start over. I was 22 years old when I first started my business and I am 26 now. I was very young and I am still young now, however, It gave me the time I needed to fail. I feel like success means nothing without those low moments. When you experience the downsides to being an entrepreneur when it is time to celebrate those wins you appreciate them so much more because it’s like “Dang, I just went broke stocking up on inventory” but then that restocking leads to increased sales and increased sales leads to more exposure and then next thing you know I’ve secured another store location. Read more>>

Shawn Fitzwater

This thought pops into my mind on occasion. I always knew that I had artistic skill from an early age but never really pursued art as a business or even steady hobby. I would just draw when I was bored. I only took one “art class” in high school, technical drawing, which I think I chose last minute just to fill an elective then failed the class because i didn’t feel like drawing nuts and bolts all day and instead would sketch up my dream home or cartoon characters instead. I dropped out my senior year, got my ged, and started working with a friend full-time as a land surveyor at 18 years old. I went on to work this job for nearly the next 20 years. Read more>>

Jackie Macias

If I could go back in time I think I would have started earlier, but I also believe that everything this far in life has happened when it’s supposed to. I have always had a deep passion for art and photography. If I would have been more confident in myself and started earlier, I could have enjoyed my hobby for longer. At this moment I get to enjoy photography with my husband and we run the business together so I couldn’t ask for it any other way. The business was always designed to be a side job in addition to my career in order to have an outlet that gives me joy and is also at my own pace. Read more>>

Natasha Taylor

I don’t necessarily wished I would have started sooner, I wish I would have been more intentional and put the business first in my Hair Business. When I started my hair business I was still living in Baltimore,MD, which is where I am from. I was working in corporate and hated it, I started selling hair because I was already doing hair on the side(mainly extensions) so it made sense. At the time I didn’t think I was going to end up doing hair professionally so I was focused on my hair business but I still wasn’t doing that “right”. Read more>>

Eli Lawliet

My business, The Gender Doula, is both a business and a calling. I received the idea from the business in 2018, while I was in my second year of my Ph.D. at Berkeley. At the time, I was applying to law school. My plan was to get a JD/Ph.D. and work in the academic realm. So imagine my surprise when the idea of being a gender doula came to me! While I waited for my acceptance letter from law school, I spent a lot of time connecting with my body and deepening my spiritual practice. Read more>>

Michael Williams

I’ve been tattooing now for 23 years, and I’m glad to have spent so many years with such wonderful artists learning all that I have. I’m glad to have taken all of those great experiences, and used them to create my shop Lucky Leopard. Although I’m glad to have put in the time, and I’m glad I’ve finally made that step, I do wish I had done it sooner. Saying that, I’m honestly just excited to be here in my present, and wouldn’t change a thing. Read more>>

Eric Kebschull

Starting my business when I did was actually perfect timing; I am one of those people that believe everything happens for a reason, so I have a hard time believing that starting my business sooner or later would have made sense for me. The simple fact is that a perfect storm of events happened in order for me to start my own business as a coach. Prior to starting my business, I was working in the insurance industry setting auto accident injury cases. At one point I actually enjoyed this line of work; it was challenging, intellectually stimulating, and at times fun. Over time, however, the job became mundane, bureaucratic, boring, and even soulless. The industry felt like a constant battle of winners versus losers, with no sense of compromise or shared purpose in what we do for a living. In other words, it was just another job for a paycheck. Read more>>

Shayna Toledo

If I could go back in time, I would 100% start my business sooner. When I first had the thought about going into business for myself it was literally the scariest thing I’ve done career wise but in the end it was the best decision for me. I, unfortunately, let the fear of failure keep me front branching out sooner and that will always be a regret for me in my career. Read more>>

Egypt Davis

If I could go back in time I don’t wish I would’ve started it sooner or later. I think I started it right on time. I was a Stay at home mom of 3 girls, an 8yr old, 1yrs old, and a 2month old. Not expecting my business to take off the way it did, I was forced to juggle my children and my business at the same time. I think that was to help prepare me in the future. I know God had bigger plans for me. Read more>>

Tami Reed

I kinda fell into being an influencer/blogger didn’t want to do it when I first started Talking with Tami. I thought I was going to be a tv personality so the blogging aspect came later on! Everyone was joining social media platforms but I was stubborn and didn’t want to do that. Now I kick myself because I could have been further alone in my career. I was just focused more on television and other things. I would have hired a team of experts to help me with all facets of media etc but as well all know that takes time and money. I just started Talking with Tami pretty much grassroots and the brand grew on it’s on. Read more>>

Ashley Vargas-Butler

When I think back, to when I started Doula Strong I do wish I would’ve jumped into it sooner with both feet. But in the same breath I would not have changed a thing. The timing in my life seemed perfect, the decisions that I am currently making to move us forward would not have worked if it were years ago. My business started like a seed about 10 years ago. I was pregnant with my first, and did all the things; I researched, I educated myself, and I chose a provider that I thought would help me have the birth I wanted. What I was met with was dismissal, I felt like they weren’t listening when I spoke, everything was chalked up to this being my first time birthing. Sadly, the dismissing continued right into labor. Read more>>

MARCO GONZALEZ

Had I known earlier in my PR career that going solo was the way to go, I would have definitely done this a lot sooner. I actually started my own business as a result of a career transition that left me unemployed in 2021. It was one of those things, as they usually are, that came from left field and I was completely blindsided by the unexpected events that ensued after leaving a very comfy corporate job in the Hispanic media space. After rigorously interviewing for months and getting to be the first runner-up for various executive corporate communications positions, I decided it was time to move on and follow my colleague’s and friends’ advice of starting my own practice and going off on my own. Read more>>

Sofia Daguano

Looking back, if I could turn the clock, I’d seize the chance to dive into my passion for the fashion world much earlier. It’s incredible how many young talents nowadays discover their creative fervor – be it in photography, art, or fashion – during their high school years. Witnessing these prodigies craft their paths from the get-go is inspiring. This is why we have so many young creatives very well known in the market today, winning awards and shooting with the biggest celebrities and brands. Reflecting on my journey, the seeds of fascination for fashion were planted early on by my family’s deep-rooted involvement in Brazil’s fashion scene. The allure of this world drew me in, and even though I always knew it was my calling, I chose a slightly divergent path by pursuing advertising in college. Read more>>

Barbara Cooney

“Embracing Entrepreneurship: My Journey to Success with Sosospiffy Staging and Design Life has an incredible way of leading us down unexpected paths, and my journey is a testament to that. As a former broadcast journalist, my career path was exciting and fulfilling, but it was my later venture that truly defined my success. At the age of 52, I took a leap of faith and founded Sosospiffy Staging and Design, marking the beginning of an extraordinary chapter in my life. Read more>>

Zoey Bullock

I started my business right after I had my first child, and I really wish I had the courage to start much sooner. Starting a family gave me the big push I needed to move away from working a traditional office career as I really wanted to be at home more. Looking back at my experiences as a business owner, I’ve learned it is okay to pivot and shift into new areas of business, it isn’t always the first idea that will stick forever. I’m very happy with the time that I started and have gone through many evolutions of how I approach balancing business with my life at home. Read more>>

Natasha Feghali

I know that I wish I had started sooner in business and that I was more financially free now. Since the market has changed we have seen major hiccups in our business and this leads me to believe we should have started sooner. Read more>>