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.

Ray Brito

When I first went out on my own, we just had a baby and it was the very height of Covid. I wasn’t allowed to go to any of my wife’s doctor appointments throughout her entire pregnancy, no one was allowed to visit our daughter in the hospital when she was born, all of the schools were closed and our kids were all doing virtual school, almost everything was closed besides some grocery stores, everyone was wearing masks and disinfecting their groceries, businesses were failing left and right, and everyone’s life was turned upside down. It was the craziest time I’ve ever lived through. If I could go back in time, the only thing I’d change is when I chose to make the move. I would have started the business years earlier. Read more>>

Susan Popovich

I think I started my business at the right time for me. I was forty six years old when I decided to open Southern Treats. I would imagine everyone is different. A lot of people expect young people to have it all figured out by the time they graduate high school or college. I think every job and chapter in my life helped me get to the place I am now. I was in the medical field for twenty years. There were a lot of ups and downs. It was very hard and I learned a lot of valuable lessons. I needed that job. I thought I needed the 9-5 stability and benefits. What I learned is there is no stability in any job. I learned that at a young age when my father lost his job after thirty years, because the company went bankrupt. That loss changed him and me. I saw there is no real stability in life, It really didn’t hit home until my mother passed away though. She worked her entire life and was so happy to retire and start living her dreams, but she was diagnosed with Parkinson’s Disease and died six years later. That lesson taught me not to put things off until the right time. Today is the right time to live your dreams. You have to take a leap of faith and that’s what I did.  Read more>>

David Lederman

Having started my first business at the age of 18, I would say start a business doing something you love as soon as you can. That doesn’t mean the first one is going to hit. My first business was NOT a success. Oh no, it took another 10 years before i was living off my own business. I started about 12 different businesses while i worked at an e-commerce shampoo company before one became successful. I started GEMS BUSINESS SOLUTIONS, my marketing Agency in 2019 after having helped other businesses become a success. I feel I could have taken a bigger jump sooner but i found that the experience i gained working in different industries and trying to open different businesses allowed me to have a very broad understand of how businesses work, in a general view, and finding all the overlapping key points that make a difference for success in business, no matter the industry you are on. If i could coach my younger self, i would have experimented more and learned as much as i could about people, systems and budgeting. “The sooner you start, the sooner you will know what doesn’t work. That’s how you find what works.” David Lederman Read more>>

Jacqueline Calderon

Sometimes I think about how things would have turned out if I had started things right after high school instead of after graduating college. I think that I would have been less doubtful of failing and willing to take more risks. However from a financial standpoint I would not have had the capital to begin anything with. The same can be said if I waited to be older and more financially stable, I would have probably not want to begin a business anymore. Ultimately, I don’t regret when I started. There were struggles, of course, but each one taught me valuable lessons. However I feel that I was in the sweet spot of being both cautious but willing to take the plunge. Every challenge helped me grow both personally and professionally. Would I have succeeded sooner if I’d started later or earlier? Perhaps. But I think the timing was exactly right for me, and that’s what made the journey uniquely mine. Read more>>

Stephen Quinn

I started my business back in 2020. I was just getting started in my photography career. Life wise I was just graduating from NYIP. If I could have started sooner I would have went to school sooner and started my business at the same time. Read more>>

Jeff Hare

Growing up poor in Ohio, it was pretty certain that path the most kids would take. We’d make it through high school, maybe even a 2 year trade school education after that, enter the workforce, start a family and live the same life our parents did. Maybe a little better off, maybe not,…but there weren’t many options available. Without that optimism of a bright future, I never really had the direction or even interest in pursuing something big. I always dreamed about it, but kids like me didn’t have the guidance or opportunities other’s had, so I like to say I just let my life lead me. After high school, some friends wanted to move out of town (about 4 hours away) so I did. I was miserably lonely and homesick at first, and didn’t have a job or any money, but I made it work. I slowly got my footing there and stayed for 5 years when the idea to move back to my hometown came up, so I did it. Not for a reason, but because my life led me. Read more>>

Plea

was that I kept thinking I had to be “better” before releasing myself as an independent artist into the world. When I saw people cry to my music, it created an imposter syndrome in me that took me years to work through. I thought good artists came from big cities or people with money, not from a young girl from little, border-town, Imperial Valley, California. I couldn’t believe my music touched hearts the way music has the power to magically do. Read more>>

Melanie Echeverry

If I could go back in time, I would have loved to start my makeup career earlier—before becoming a mom. I officially began at 21, but my passion for makeup had always been a part of me. Growing up in Venezuela, I dreamed of studying this art, but financial, family, and country-related challenges delayed that journey. Makeup has always been my comfort and my way of connecting with others through beauty. Starting earlier might have fast-tracked my path to success. That said, graduating as a makeup artist while raising a newborn taught me resilience, love, and the strength to navigate challenges with grace. Read more>>

Andrina Zhang

I believe most people who are enjoying their current creative career won’t refuse to start the journey earlier, I’m one of them too. However, I’d love to share a little more about my experience and convey some peace I’ve been looking for myself if anyone else needs that as well. I always feel happy for my friends if they can find something they enjoy at younger ages. Most musicians I met started their music journey when they were little and were already very professional when I met them. I didn’t consider myself a musician until lately. I do have the idea that — it’d be great if I could start music tech / production earlier — lingers in my mind sometimes. Music Tech is the 4th subject that I’ve been trying to specialize in since the beginning of high school, and I almost can’t avoid thinking if I picked the subject “right” at the very beginning. But after trying to clear my thoughts and attribute things correctly, I did spend a lot of time exploring other things and making sure they were not for me. I may be somewhere else in another universe with other building blocks in my high school years. 16 yo me and 18 yo me both had fun, so all is fine after all. Read more>>

Megan Kelley

The timing was just as it should have been. I started singing as a kid in various Texas opry houses, and I started dabbling in songwriting around the same time. But it was in 2016 that I guess I really started laying the foundation for a career in the music industry. That’s when I released music for the first time and started toplining for a buddy who would send me guitar tracks. I would say I really got serious about the craft of songwriting and about the industry in 2020, and it was another three years before I made the move to Nashville. At that point in my life, I had an established career as an educator and I was playing gigs on the side to fund trips to Nashville for writing retreats and conferences. Every time I would visit Nashville, it got harder to leave and go back to Texas. Once I finally made the move and saw the shift in the songwriting experience, there was a brief moment where I wished I made that move sooner. But if I’m really honest with myself, I would not have changed the timeline at all. By that point, I had a solid network of friends and co-writers in the Nashville songwriting community, I had the life experience that I needed to have a perspective and something to say in the writing room, and I’d developed enough sense of self to be able to withstand all the times the word no is encountered in a career in music.  Read more>>

Emily (mle) Dang

Yes, my mother forced me to learn piano at the young age of about 5 years old. I remember enjoying the lessons when I was learning the beginning basics in one-on-one classes with a Vietnamese Female instructor, however, I quit as soon as I advanced to the group classes with a Caucasian Male instructor. Reflecting on it now that I am pursuing my passion in the music industry, I do wish that I stuck with the piano lessons since I was young because I could have been a prodigy! Music still has been my lifelong passion, so I did end up asking my father to get me a keyboard for a Christmas gift and taught myself piano again in fifth grade, around the age of 10. Read more>>

Haley Rice

I’ve had such a weird trajectory as an artist, I’m not sure I could even pinpoint where to go if I needed to go back and change it. I started as a singer with dreams of opera and musical theatre, and began that artistic journey very young. I followed it all the way to New York and then… did not book anything. After a dark night of the soul, and some encouragement from a mentor, I began to write– and that opened up a whole new realm of possibilities. Which later lead me to find the courage to produce, and next to direct, then to teach writing workshops, and ultimately embrace the multi-hyphenate artist life that I have now. Read more>>

Axel Balmaceda

I think starting 11 years ago helped me understand more and value the world of tattooing in a different way. Today, I don’t see it just as money or simply a job. Rather it is something special, since one gives a part of oneself in what we do. Although everything was complicated, that part is what made me a good artist today. Maybe if I had started later My path would have been easier and the process of adapting to the new digital platforms would be much simpler. with this, I feel that my path would have been different or simply my perspective on art would not be the same. Read more>>

Amie Hibbler

If you had asked me that question maybe six months ago, I would have expressed a strong desire to have started my creative career much earlier. However, I’ve come to realize that everything happens in a specific timing and order for a reason. While I still believe that building my skill set sooner would have been beneficial, I also appreciate the journey I’ve taken to get here. Read more>>

Jay Derosier

Of course!!! However; I am thankful I waited to build my confidence and knowledge with this world. The confidence to not get myself to worked up on this content world denying my style of work. Plus the knowledge that I gain from see others fail in certain situations to help me from not making their same mistakes. I believe that my story sooner or later will be someone’s own study and what to improve on what I’ve accomplished. Read more>>

Bryanna Urbaez

This might be a long story but it’s the only way people will truly understand where I started. My creative career started back in 2016/2017 when planning out a gender reveal for my bestfriend. She was the first friend in our group to have a baby and I always loved having parties so I was so excited to make this special anyway I can. In that time balloons weren’t a huge thing, it was more about little details to make the party pop like themed treats , cake pops, signage, the nice linen, lettered tables, and draping. She actually hired an event planner to help with everything and we felt like she wasn’t doing what we wanted and we ended up doing a lot of the work for her. Read more>>

Samuel Phanor

Honestly, if I could go back in time, I wouldn’t change when I started my creative career—I think I started at the exact right time for me. I officially stepped into the creative world in 2016, after leaving my second tour in Iraq and navigating my way through careers in law enforcement and the military. Life-wise, I had already learned a lot about discipline, leadership, and service, and career-wise, I had gained the structure and resilience needed to take risks and adapt. Read more>>

Allison Helfen

I started creating YouTube videos before you could earn money on YouTube. I had a personal channel and I posted videos of our two golden retrievers to share with our friends and family. If only I had known back then (2000) the earning potential for dog videos. Read more>>

Cooper Knight

Simply put, I’ve been drawing for as long as I can remember and find creative arts therapeutic. The moment I figured out I could earn a living doing creative and performing arts, I was a freshman at Longmont’s Silver Creek High School. Starting sooner would have meant being able to sell art at my high school for a competitive price, while still keeping up my grades. Now, fair enough, my mind found it best to work on one thing at a time, but with a little dedication and practice, I might have been able to pull it off. That’s what would have changed about my experience. Looking back, I wish I had started a career in creative arts sooner because getting good grades and selling copies of my art would have given me that necessary head start. Read more>>