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.

Kendra Gayle Lee

It’s an interesting question because, on some level, I’ve always been immersed in stories. I loved reading from the time I was a tiny kid. I focused on literature in grad school. And, because I love people, I’m always watching for and listening to how their stories unfold. But the way I deal with stories now–as a bookseller–happened at the perfect time in my life. Serendipitously. Read more>>

Kelly & Chris Fernandez

We purchased our first Volkswagen bus in 2018 and were hoping to have it restored and ready to go in a year, but the bus was in pretty rough shape and looked straight out of the 70s. The restoration took much longer than expected and after two long years, turning our beaten-up beauty into a stunning, bohemian photo booth bus, we were finally ready to launch. However, around this time, we were in the middle of a global pandemic where nearly all events came to a screeching halt. I used to wish that we were able to start our business sooner but looking back now, I wouldn’t change a thing. Read more>>

Sonja Anthony

If I could go back in time, I actually would have started my hair business sooner because the market was thriving for a few years beforehand. The idea was formulated in 2016 for me to start this hair business since i already had prior knowledge of commercial hair from working with other big name companies. After research and preparation, I filed for the LLC in 2017, and then I went into retail in 2018. At the time, I was in the claims and insurance field for almost a decade. So, for a while, this was something that I was doing on the side while I was still in my career…. not thinking that this would become my future career. Read more>>

SVN TVVN

I feel like anytime is the right time to change and start something new, it’s never a wrong time to do things because you’re just going to learn from everything you do. Saying that, I rarely look behind me and reminisce about what could’ve been what should’ve been. We started our brand “ UNKXNOWN EXISTENCE” when I was a senior in high school. That raw energy of young folks trying to do something different is something that only photos and memories can capture. I would Cherish those times even if it would happen 10 years from now or earlier on. Read more>>

Alex Pistorio

I do wish I would have started my business earlier! I started this as a part time hobby while still working my full time job. I think in the back of my mind I always envisioned and dreamed of doing this work full time but knew at that time in life it was more of just a hobby and side passion for me. When Covid happened, I transitioned into staying at home with my daughter, and decided to pursue blogging and creating full time. Read more>>

Denise CreatiVisuals

I’ve always said the one change I would make in my career is starting sooner! As the years pass, we always notice business owners starting at younger ages and becoming successful faster than tenured business owners. I believe this would also have been the case for myself, had I found my passion sooner. I was always committed to having a stable income and job growing up. From the age of 15 to 31, I have never been unemployed. If you are in a Caribbean upbringing of any capacity, you are trained from young to work hard and maintain a good career. Read more>>

Shamere Lee

If I could go back in time I definitely would have done a few things different as I’m sure so many people would say the same. Im a firm believer that everything happens the way it suppose to for a reason but with that being said I would have started my business earlier. I was a single mom of two daughters & working two jobs wasn’t gonna cut it. Read more>>

Ardell Wright

To answer the initial question, yes. I think about how it would be if I started when I get this idea at 15 verses my mid to late 20s. I also wish I had someone to guide me in the direction of using my creative imagination. I officially started around age 25 or 26, I was just fired from a corporate job making decent money and I was a little traumatized about being let go even though I was performing at a high level. Read more>>

Nicole Dukes

If I could go back in time I wish I could have started my business sooner. Initially, Pretti-n-Plush Boutique was started in July 2020 during the pandemic whereas I was uncertain about the future. I worked full-time as a human resources professional for the local government yet the pandemic changed how we conducted our business operations. These changes challenged me to reconsider the idea of entrepreneurship. I always desired to have my own business in the fashion and beauty industry to display my creativity and help women embrace their flaws and confidently create and live a beautiful life they love. Read more>>

Aleah Torres

I have had a passion for photography ever since I can remember. My grandmother ignited my passion by constantly capturing all of our best moments at family functions. When she passed away, we were so blessed to have all those memories she captured printed for generations to come. At the age of 18, my father gifted me my first canon camera for Christmas. I can honestly say, I had no idea how to use it. Over the years, I practice on nature, animals, and eventually people. Read more>>

Elona Krasavtseva

I became a performer when I was already 33 years old. Prior to that I had a regular job for about 7 years and i ran a business in the area of events management and Investor Relations. The sarcasm of the situation is that it all was happening in Russia. When I was a young graduate my country Russia at that point chose a democratic way of development and I was involved with an American company helping my country building free market economy. By the time I turned 30, it all has changed, and the Investor Relations industry was not needed any more. Read more>>

Taylor Green

If I could go back, I would’ve definitely started my creative career sooner. I started blogging after a school assignment in 2016; however, I didn’t start really thinking about making more out of it, and expanding to YouTube until 2018. Even during 2018, I still never kept a tight schedule on things until recently. I feel like if I was able to truly focus on my long-term goals and take things more seriously back then, I would’ve been a lot further in my YouTube/content creation journey. Read more>>

Frankie Raye

Sometimes I wish I could go back 15 years and tell myself to just go for it. Now. Yesterday, in fact. When I graduated high school in 2007, I was motivated, excited, and confident that I would become a musician. I thought I’d enroll in a music academy, major in songwriting, and that it would just happen. However, I was told over and over that I was making a mistake by not following a traditional college career path. So I enrolled in a state college, and didn’t pick up a guitar or write a song for another seven years. Read more>>

Chris Warren

I didn’t start podcasting until 2020. I was 34 years old. In regards to music, I started playing guitar and writing songs when I was 14 but I didn’t record anything professionally until about 5 years ago. I was on the older side of the spectrum when I started pursuing my creative endeavors. When I was teenager, makeshift recording studios weren’t what they are today and were not readily available. In the early 2000’s you had to actually go to a studio to record and pay for studio time. Read more>>

Jane Theodore

I have had a creative career, in various iterations, for most of my adult life. My training is in graphic design and I have worked in that sector for many years. I have also made fine art, including a series of hand-painted serigraphs, which are in private and corporate collections internationally. I also started an e-comm fine art stationery business, from which I learned a great deal about retail. But I exclusively focused my attention on painting in 2013, and absolutely, I wish I had started sooner. I still have so much to learn! Read more>>

Doretha James

If I could go back in time, part of me wished I would have started sooner to be further along in my creative career. But I understand now that things happen the way they are supposed to happen. You have your own one unique journey. If I would have advanced prematurely, I wouldn’t have the tools to catch myself before getting to high on a hill.I started my creative career a couple of years after my youngest child was born, after I realized personally I had nothing going for just me. I realized, in order to keep giving to my family, I had to do some self-care. Read more>>

Michael James Cisarik

With many aspects in life, we always wish we had started or discovered something sooner. And I feel the exact same way with creating art. Sadly, sometimes you don’t know what you are capable of until you stumble upon it! Discovering art as an outlet during the COVID-19 pandemic was a blessing to say the least and I would never expect it would amount to what it is today. That being said, I am hopeful that it is also just the beginning. Read more>>

K. Sahagian (of Speak Easy)

Both I and Eric (guitar and vocals) left our day jobs early 2021 after being more or less furloughed because of the pandemic. This seemed like the perfect opportunity to take a chance doing only music for a living. Brendon (bass and vocals) left his a little while after that. Looking back, I definitely wish we had all taken music as a career more seriously sooner. The value of the time that could’ve been dedicated to working on our music (or music business) would’ve seriously outweighed the value of whatever money we were making prior. Time is invaluable and also every day we get a little uglier, which is totally unmarketable. Read more>>

Aaron Carter

Of course! I feel as though everyone wishes they started earlier than they did, but I am a big believer of everything happens for a reason. I didn’t take creative director, designing and content creation seriously until after Covid. Obviously covid is still a thing, but I’m referring to after everyone hopped on the train of social media and their creative endeavors. I started creative direction during peak covid and it all stemmed from me just having a lack of passion for my current hobbies. I knew that I wanted to do something in the fashion industry, but I didn’t know where I saw myself since I wasn’t interested in design at first. Read more>>

Kerlyn Joseph

I started my creative career back in late 2010. My platform of choice at the time was YouTube. Back then, I didn’t realize the potential that the platform possessed. I posted videos here and there. Over time, I picked up the frequency of my videos, and later I even started a ‘Thrift With Me’ series. What I have learned over the years is that time is so critical as a creator. In other words, you have to put the time into your craft and then “do the time”. Over night success is possible, but rare. Read more>>

Brooke Boltz

Yes, I wish I had started my firm sooner. The firm grows each year, so if I had started sooner, it would have had more years to grow by this point in my career. That said, I value my prior experience because it taught me the legal and managerial skills I now employ in my current practice. I was mentored by an exceptional trial lawyer at my prior firm and I could not have had that experience at my own firm. Read more>>

Nickell Linda

Photography has been an interest for a long time but I started taking this craft more seriously in 2017. After a trip with some very experienced photographers to Great Smoky Mountains National Park, I came to a realization that photography was an creative outlet and with practice I could improve my skill set. Finding the time to practice composition, creating images, and developing my style were challenging but having mentors were the key elements of my progress. Seven years later, my work is more refined and purposeful, had I started earlier I would have taken more classes to learn how to use my camera and the fundamentals. But instead I had to learn on the fly while creating images I’m proud to put my name on. Read more>>