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.

Chris Figueroa
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I sometimes wonder what it would have looked like if I had started this sooner, but I’m a firm believer in the butterfly effect—every interaction, every conversation, and every experience has led me to this moment. The decisions I made to take on bigger roles with different companies weren’t just steps forward; they were opportunities to develop the skills I needed to scale this business successfully. Read more>>

Ting Ma

I started my journey as a full-time content creator after both my sons went to college. Holding a master’s degree but having spent nearly two decades as a stay-at-home mom, there were times I questioned my value in society. It’s easy to feel that way when you’re not receiving the traditional markers of success like promotions or paychecks. But over time, I realized that the most valuable thing I’ve ever done was being fully present during my sons’ formative years. The precious memories, the lessons taught and learned, the love poured into each day—that’s irreplaceable. Read more>>

Quintin Cammack

I had no idea that my love for design and technology in the early 2000s would one day lead me to my passion and purpose as a fashion designer. Back then, I was simply drawn to creativity—experimenting, building, and finding new ways to bring ideas to life. I didn’t yet understand that these seemingly separate interests were actually shaping the foundation of my future. Read more>>

Amber Morgan

Looking back, I can say that I’ve always been an artist. I discovered my passion for drawing at a young age and took every art class I could from elementary school through high school. I wanted a career doing something creative that would allow me to continue using those artistic skills in some way. I earned a degree in Graphic Design and eventually landed a job that turned out to be more focused on sales and marketing than on the creative role I had pictured. Read more>>

Jake Bird

I would have most definitely liked to of started out much sooner in life. I don’t feel I started out incredibly late, but with how unpredictable life can be, I feel as if I could be much further ahead than where I am at now. I have been off and on playing the piano and guitar throughout my life, but everything has only been self-taught. I think if I had an actual instructor or more self-discipline when I was young, I could be where I want to be or at least much closer today. I started investing and making full original music with what I had at around age 20, after finishing two years of college. I was still here and there for probably 1-2 years not knowing if I could do something with it, but I kept going and glad I did. Now that I am turning 27 here soon, I would say I have improved a large amount within the five years I have been creating with the time I am given, Read more>>

Aa Dasilva

Occasionally, I regret not pursuing a writing career sooner, but then I’m reminded that so many things I’ve experienced in life helped me pen the novel that I did, when I did. If I’d penned my debut novel sooner, say in my early twenties, perhaps I wouldn’t have pursued my degree in clinical laboratory science, and I wouldn’t have yet had the life experiences gained by being part of a military family—both of which played a huge role in the inspiration (and content) of my debut novel, Periphery. Read more>>

Soupless

I feel that the answer most would give to this question, and expect one to respond with, would be to begin sooner. Conversely, though, I feel as if there is no other way for this to have gone, or to continue to go, had I started sooner or later. I think of how it might’ve been had I started sooner, much more immature, and with a blurrier lens of the world, and I am frightened by the path I might’ve gone down, maybe doing things not for personal growth but for external approval. On the other hand, I see where some of the advantages of starting later could lie, but at the same time, my path and relationship with music led me exactly to what I’m doing now, so I can’t truly imagine the spot that I’d be starting later, and that also concerns me. Read more>>

Kate Rouchell

Living a life free of regrets is often impossible. Whether we call them “regrets” or “things we’d wished we’d done differently”, it’s always an exercise in fantasy to imagine what butterfly effect one small (or large!) decision would have made on our current life trajectory.

Ultimately, I have few regrets in life because I choose to believe that the life I’m living is the ultimate gift. I know, I know, that sounds gross and lofty, but ultimately I believe it to be true. Read more>>

Ross Geraci

Well I started music way back when I would say I wanted to, I would have liked to have started taking on film projects at an earlier time I can certainly say that. I started recording music at the end of high school, and built up my indie label at the time. I did direct several music videos, including executive producing some animated ones which was interesting. In terms of my main series “The Zodiac Files” I did not release the first episode until during the pandemic, but my channel Planet X Filmworks (subscribe) was already established at that point with some live shows, and movie reviews. Starting sooner would have helped me build up my true crime audience, and gain more momentum earlier. Read more>>

Wendy Elliott-vandivier

I wish I had started my professional creative career much sooner. I have always made art since I was a young child, making drawings, paintings, sculpture and conceptual art. I attended Tyler School of Art, Temple University where I earned my BFA in Sculpture and graduated Magna C*m Laude. After graduation, I worked briefly as an assistant art therapist. I didn’t think that I could make a living as an artist and decided to change my career goals. I then worked for 9 years for the Office for Civil Rights, U.S. Department of Education, and then for 30 years as a Human Resources Manager in private industry. During this time, I was very involved with disability rights advocacy and served on the boards of several national and local organizations. After being laid off at age 62, I decided that I needed a career change and wanted to focus entirely on my art and advocacy. Read more>>