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.

Gene Folkes

Although, I do not look back often, If I had to go back in time, I would have definitely started my business sooner. I grew up in an era where opportunities for black and brown people were intentionally nonexistent or limited in this country and I could not reconcile my desire to be a business owner one day. I recall having vivid dreams about owning a business, leaving a positive signature on my contributions to my industry, and building upon the legacy started by those innovators of color that have gone unrecognized for so long. Read more>>

Jarrod Mason

I am a firm believer in the idea that everything happens for a reason and on its predetermined timeline. Since I was a kid growing up on a small ranch in rural Colorado, I was exposed to lots of let’s say tinkering. There was always something that needed to be fixed or maintained and often my mind would race with new inventions or new ways to do things. So from a young age, I had that entrepreneurial spirit within me, it was just a matter of time before I settled on an idea to pursue and went after it. Read more>>

Jenny Germano

I often think about this question a lot, especially seeing young adults starting businesses in their 20’s. I founded ICS Consulting at the perfect time, at age 42. Honestly, I would have not been ready any sooner. I am enjoying the journey I have embarked upon and everything I have learned about myself and business along the way. I would not change a thing, including the ups and the downs – that is what made me a better person. I continually work on improving who I am as a business owner, career professional and I am always looking for growth opportunities. Read more>>

Josh Hanna

If I could advise my younger self, I would tell him that you’re going to spend nearly 16 long, frustrating years working at a career in banking…only to leave with no real, useful skills for being successful in life. If I could go back to do it all over again, I would’ve started my photography career in my early twenties when I knew I was interested in it and not waited until I was in my mid-30’s to take the leap into full time. But being young and afraid of taking an unknown risk prevented me from taking that step of faith when I should have. Read more>>

Tishana Richards

I feel like I started my business right on time as timing is everything, but if I could choose I wish I started earlier. There was a time when I had started another business idea that eventually led to the one I have today. It took a series of events and connecting the dots to finally get my current business started. It was like a lightbulb moment. I essentially started my journey into entrepreneurship in 2009. It was right after I graduated college and the economy wasn’t much different than it is today. Finding work was very difficult so I had to get creative with the ways to survive and soon pay off those looming student loans. Read more>>

Lisa (LC) Campbell

To be utterly real, I never thought I would become a salon owner, there was no “Big Dream” of opening a salon. When I started my career 10 years ago I wasn’t even sure where I was going with it but of course I had the fantasies but I had no clue that this is what was meant for me. Don’t get me wrong, I’ve always known I was destined for something great, something big, something incredibly bigger outside of what I may have limited myself to. Read more>>

Tatiana Boone

If you could go back in time do you wish you had started your business sooner or later? Give us the backstory Even though I believe I would be further along in my profession if I could have started sooner.  The lessons, hardships, and meltdowns have all made it worthwhile for me to start when I did. when did you start your business, where were you at life-wise/career-wise. Read more>>

Patrick (3Patch) Oliver

If I could go back and tell myself ANYTHING about my art, painting, and business it’d be to start developing a way to make money off your passion so you can become self sustaining, thus giving you more time to do what you love – creating art. All without sacrificing the work as a whole of course. But, if I had started making art prints and clothing of my work 6 years ago when I was 18… I’d be in a way more comfortable position now and probably another tax bracket. But, that’s okay, I’m still happy with where my business is at currently and all I can do is move forward. Read more>>

Mallory

I often think about where I would have been had I started taking my music seriously earlier. I’ve been singing since I was four, and writing and recording since I was in high school, but I was using my gift for the advancement and entertainment of others. I only recorded features and sang in choirs and ensembles. Part of me wishes I would have been as aggressive then as I am now so that I could have learned the game earlier and been further in my career now. Read more>>

MICHELLE GAGLIANO

I love this question, because it is so complex. Many times, I do wish I had started my career earlier, but at that time women were not encouraged to be be full time artist and mothers. It was an either/or choice, and I wanted both. The advice early on from my male professors was that only serious female artists did not have children. So, I chose the married with children route. I loved being at home with the children, as it was a wonderful creative time for myself and the kids. We had a great time. Fast forward a few years and I found myself a single mother needing to support my family. Read more>>

Cameron Johnson

This one is a I wish I would have started sooner, but at the same time I wouldn’t change anything. I wish that I would have known sooner that this could be an option. I have always made jewelry – I can remember making earrings with puff paint on posterboard that I cut into different shapes, wire bracelets made from telephone wire (my dad worked for a telephone company, and he had them in his work van), beaded necklaces, wire wrapping sharks teeth, etc. Read more>>

Brad Russell

I was 18 years old, standing in the foyer of my dad’s house where I was living at the time. The question he asked was, “what are you going to do with your life?” My answer came from the heart, “I just wanna play music!” His answer was what shaped the next 15 years of my life. “You can’t make money doing that,” he told me. Had I chosen to be a rebel at that point in my life things would have been different. I don’t want to say I wouldn’t have my wife and kids had I moved forward with my dream of playing music for a living, because my wife and I are soulmates, and would’ve ended up together anyway, but it would’ve been on a different timeline. I decided to turn away from music for the next 10-15 years and focus on building a career and family, my greatest accomplishment. Read more>>

Lexi Stambaugh

Personally I feel like I started my business at the perfect time. I first started blogging about my recipes in 2017. It took me several years to get used to the technology, analytics, and grow a small following. I feel like those two years were necessary for long term success. In 2019 I met a group of local bloggers who were in the same boat as me; Feet wet in the blogging industry but looking to grow even more. Some of the more experienced bloggers took me under their wings and taught me crucial information about social media influencing. I feel that if I had started sooner or later, I wouldn’t have met the incredible people who helped shape me into the food and travel blogger that I am today. Read more>>

Tanzania Brown

Looking at who I am today, I often do wish that I would have began my modeling career sooner. Don’t get me wrong, I’m happy I’m where I am today regardless but I wish that the confidence I have today was a part of me back in the day. I wish younger Tanzania had the courage to brush off the naysayers and doubters, and went hard for myself like I do today. I’d say I’ve made my younger self proud though, regardless. I’ve stepped out of my comfort zone. Ive put the opinions of those who felt I was not worthy of modeling because I was too big, or not pretty enough to the side. Read more>>