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.

Nikki Tomlin

When looking back I wish I would have started my business sooner! I was one of the only people in my college program that said they wanted to work for someone else. I didn’t like what I was hearing about having to run a business and then I started working for other people and found out quickly, it wasn’t for me. I started a business in the little ways in waves. I would get the bones set up like a bank account and book keeping along with some socials to promote my work and then I would let it go because I continued to work for other people. Read more>>

Sandra Beatrice

This has to be one of my favorite questions in life and I am sure many people contemplate this more than once. A few years back I learned a little mind trick to help me not lose myself in this question, which I can’t wait to share with you! But first, would I have loved to have had the courage to start this amazing journey sooner? Absolutely! However, I do know who I once was, and that person is a lot different from who I have grown to be. Although, I am not sure what would have actually happened, I can honestly say that I do not think I would have made it very far in this industry had I started this journey sooner. Read more>>

Payton Pruitt

I’m the Singer/Guitarist for a band called Carver Commodore. We started back in 2017 with two members, and have slowly found our core members over the years, the most recent being our bassist, David, in 2021. More than anything, I wish we could’ve all met when we were 20 and started making music together back then. By the time we all found each other, we were all in our late 20s for the most part. Read more>>

Latasha Stephenson

Personally, I didn’t realize my purpose in life until after college, so I actually think about this often. To be transparent, I’ve always wondered how different my life would be if I knew that I wanted to act, as a kid. Would it have ruined me or my childhood? Would I be a household name by now? What would I have acted in? What kind of impact would I have made? However, the more I think about it, the more I realize that it wouldn’t have worked. Read more>>

Noredia Akwara

If I could go back in time, I would have started my brand sooner. While I was in college, I had another brand that shifted a few times and it took me a bit of time to decide what I truly wanted to see and curate for my customers. After a few years, I took a step back from that brand. While looking to re-start in a different direction and my creative senses still going, I formally launched she knows the deal. There are times when I wish I had a certain insight or timeline that would have made things easier, but at the end of the day everything happens how it should. Read more>>

Armani Robbins

If I could go back in time, I really wish I would’ve waited to start my business. I opened up Mani Maker Services in August 2022 after I had quit my last job and decided to become this entrepreneur. In reality, I was not even close to ready to being capable of opening my business – I didn’t have any money to get materials & supplies, no real guidance to help during the process, I was literally just a gal and a dream. Although it was a struggle to get things started up, it was still rewarding that I was even able to accomplish the start up of my first business. Read more>> 

Quani Bates

If I had a Time Machine, I would have an immense amount of wisdom to gift my younger self. Many agree that hindsight is often 20/20, and this was surely the case for me. I would tell my younger self, start where you stand! In other words, begin with what you have. I think people often hesitate to break the norm due to funding. However, misunderstand the creative ways to start a business. Now, when I look back on things I always wish that I had started this journey sooner. Read more>>

Heather Edridge

My current business is my second chapter. I previously ran a Home Staging Company for 20 years. As I got older it was just getting more and more wearing on my body. So the time came where I just had to make a change for my health and well being. I had no idea what to do next….but I always had this thought in the back of my mind, “Being a travel agent would be the coolest job ever!” I would say to my self, “I wish I had done that.” Read more>>

Willy Kwak

If I had the opportunity to restart my business, one of the first things I would have done would be to start sooner. I’m naturally a perfectionist so I’ve always felt that I needed more information before I started in order to minimize risk. What I didn’t realize until after having been in business for a few years is that getting 70-80% of the way to being ready is typically all that’s needed to launch it and you can always iterate along the way. Read more>>

Brian Loeffler

I began photography when I was 16 years of age as it was my dad who taught me the craft. I bought my first camera, a Canon AE-1, when I was 19 while I was at Ohio State, and no subject was off limits as I enjoyed photographing just about anything. I had the unique opportunity to work at the Columbus Zoo’s golf course, the Safari Grill, during the summers of 1991 and 1992. While there, I made a lot of friends at the zoo who allowed me to photograph the animals. I saw everyone’s reaction to the photos I took, but my goal was to get my Bachelor’s Degree in Business. Read more>>

Katrina Moldova

Starting a business is always a risk, but it’s one that can come with great rewards. While it’s easy to look back and wish we had started sooner, it’s important to remember that everything happens for a reason. Perhaps waiting until 40s was the best choice for me, I allowed myself to gain the necessary experience and knowledge to succeed in my chosen field. As the owner of a gallery and being an artist I have a unique set of challenges to navigate. Read more>>

Nancylee Bielawski

Sometimes, I do wish that I had started my creative business earlier. But at the same time, I feel that the way things actually unfolded was a gift. Today, I am both an artist and an equine veterinarian, though that road has not been linear. I had always been artistic in high school and undergrad. Even though my teachers had suggested I follow an artistic path, I could not quell this desire to be involved with horses in what I perceived then, as a “bigger” way. Since I loved science as much as art, I initially chose to follow a path to veterinary school. Read more>>

Jen Deeb

I started Brand U Solutions close to 9 years ago when I first moved to the Emerald Coast from Long Island, NY. Since then, it’s grown at a very stead pace, allowing me to continue to grow the business as I grew my family. After many years of being asked about photography, if I offer it and if not, who to recommend; I figured it was time to make the investment into the equipment for that to be possible. As someone who always loved photography as a hobby, now having this service to offer to my small business clients was something I was super excited about. Read more>>

Emily Burgio

My dad bought me my very first camera when I was sixteen – I asked for a camera instead of a car! I would take photos of everyone and everything. Starting a business was something I thought only special, qualified people did. I never felt I fit in that category, especially at a young age, so I just did it for fun. Two years later, my life turned upside down when I lost my both my sister and my dad. My dad was my best friend and my biggest supporter. I tucked away the camera, and tucked away the dream. Read more>>

Anne Jean Pierre

If I could go back, I definitely wish I started sooner. As early as 6 years old, I wanted to be a designer, I used to change my room around a lot and my parents living room and redo things. After graduating high-school, my goal was to study architecture, unfortunately with the crash, I was discouraged to pursue anything related to housing and I let others opinion and fear get the best of me. The desire to really go for it started a few months. Read more>>

Chanelle James

If I could go back in time, I definitely would have started my business sooner. I always knew that I wanted to write and had the idea of becoming an author. However, I originally was going to write short stories that related to life situations. It turned into poetry because I found that when I wrote my feelings I felt better. Being a business owner at that point was not at the forefront of my career, because my career is being an educator. Currently, I still teach and run my business. Read more>>

Alexandra Bobbitt

If I could go back I would definitely start my business sooner and done so much differently at the beginning but I have learned a lot from each mistake or hesitation that has taught me so much. Firstly, if I could go back I would have started drawing again much sooner, or even never stopped to begin with. The process of drawing and creating for me is so soothing I regret ever stopping in the first place. Someone had taunted me for it in college and I let my insecurities get the better of me. I stopped on the spot. It wasn’t till I found that exact drawing, half finished, years later that I picked up my pencil once again. Read more>>

Birdie Thompson

If I could go back in time, I do wish I would have started working in photography sooner. Just before I began, I was working in television production as a production assistant. Once the was canceled… but then picked back up… and was being moved to Atlanta, I decided to take photography more seriously. For me, starting sooner would have looked like me going the route of photo assisting. I like to think that I would have found a great photographer to assist for and learn from until I felt I was ready to go out on my own. Read more>>

Andrew Lander

It would have been spiritually fulfilling to have started acting sooner. However, financially I started at the perfect time. Many creatives have trouble running the business side of things. By the time I had started my creative path I had already started a digital marketing business and shut it down. I learned so much from my mistakes that it helped me avoid making the same mistakes when I decided to become a voice actor. Read more>>

Lacresia Chestnut

I always say I should have started with Lavish and Thrifty back in 2015 when I got let go from my job in December right before Christmas. I lived alone and was responsible for paying for my mortgage, student loans etc. It was because of my spending habits that I was able to not only survive but thrive during the 4 months that I was unemployed. My good spending habits helped me to save a decent amount of money to have just for situations like losing my job. Read more>>

Steve Griggs

My desire to be a full-time visual artist started very early in life. It is what I most wanted to do, but I didn’t know how to make it work. I believed the trope about ‘starving artists’ and didn’t think I could make a viable living from my art. I chose an alternative career path in design, which I thought would, at least, feed my creative desires. I maintained that career while my partner, Sue, and I raised children, bought a house, and did all the things associated with adulthood. Read more>>

Maximo Menendez

More than my creative career, I wish I had started my passion earlier. I pursued my career pretty early since I was in high school. However, I started learning more about the world and how one survives much later on. I find getting a job and settling down more difficult nowadays than it was for my parents. I graduated from Full Sail University in 2019 when I had 20 years old. My professors always hyped me up and liked my work and way of doing things. They always told me I would find a job quickly since I was great in many areas. In the end, it was much more difficult than I expected. Read more>>

Carolyn Wong

If I could go back in time, I wish that I had started my creative career as soon as possible. I wish I could tell my younger self that I would never regret pursuing my passion, and that I would regret it if I didn’t try to see how far I could go. My journey with art started in my childhood and carried on until high school. After that, I decided to pursue a less risky direction and spent my university education studying the sciences, very quickly realized I had no interest in that, and then became a caregiver to young children. Read more>>

Halimah Smith

I’ve thought about this so much after taking my art seriously and sharing it with the world. I started creating consistently during quarantine because why not? I along with everyone else had all the time in the world so it just made sense. I dealt with stress and anxiety during the lockdown and creating art daily was one of the only things that brought me peace, hence the name of my brand. Once I did start and see how much people loved my work, I wished I started much sooner. Read more>>

Meghan Kraemer

I started my career at nineteen and even though it was a huge commitment. I do not regret my journey to be where I am today. I feel like I had to grow up early at that age specially becoming a mom which has taught me a lot. I feel like either if you start sooner or later it all works out in the end as long as you put the effort into it. Read more>>

Lynn Alker

My art journey and subsequent career started at the best time in my life. At the age of 60 I began taking traditional painting classes and after a year I pursued abstract art. As an avid collector of abstracts this was a natural gravitation for me. Within a few years I was actively entering juried exhibitions and had gallery representation. Being a self taught artist requires me to be disciplined and maintain a rigorous work ethic. I don’t believe I could have accomplished the work I’ve done, as a younger women, raising a family and juggling other responsibilities. Read more>>

Handstand

I got a very late start to music, despite being raised in a very musical family. Sometimes I think that’s because of my naturally rebellious tendencies, other times I think it’s because of the sheltered environment I was in. I didn’t get the opportunity to go to shows and see people that looked like me succeeding in music, so I didn’t even know it was possible. I put my creative energy into gymnastics, cheerleading and teaching anyone that would let me how to do flips. Read more>>

Marny

Looking back on my journey in photography, I do wonder how things could have been different if I had started earlier. Although it was a hobby of mine in high school, I didn’t consider it a viable career path. It wasn’t until I switched career paths a few years later that I felt like I could pursue photography seriously. Starting a creative career while also working a full-time job was both exciting and challenging. I think starting earlier would have given me more time to fine tune my skills and establish myself, but I don’t think I would have started off with as much confidence on the business side of things. Read more>>

J Hall

I have dabbled in creative work most of my adult life but didn’t take the time to focus on specific projects and see them through until I started my podcast a couple of years ago. A lot of the delay had to do with the things I was doing in terms of career and education – I went from professional ministry (with crazy hours) to graduate school (where I worked up to three jobs at a time to make ends meet) to working in higher education (which again has crazy hours). We also have four kids, so the spare moments were spent hanging out with them and being “Dad”. Read more>>

Magdalene Nsek

I actually am glad that I realized during the COVID-19 pandemic I wanted to be in the makeup world. Being in lockdown gave me time to figure out who I really was at my core so my brand would be authentic. A lot of MUAs feel like they have to compete with beauty influencers on Instagram and that can make someone insecure if they’re not careful. I’ll admit that I almost fell in that trap but continuing to grow and learn helps. Read more>>

George

I feel slightly torn on this question. Simply because of the joy, opportunities and friends my creative journey has brought me, I will probably always wish that I had started down this path sooner. On the other hand, I firmly believe that everything in this moment was built from every moment and decision I’ve lived through before now and I couldn’t have possibly ended up where I am now surrounded by the people I am had it not been for everything that’s come before. Read more>>

Mark Goodner

Real Estate has always been an obsession for me. I started reading books on the subject in my early teens and was initially licensed just after graduation from high school. Real Estate put me through college but a “bust” in the late 80s pushed me into the corporate world. Life happened, though I had my fingers in real estate through buying, renovating and selling our personal homes, I was never able to become fully immersed. Another way I stayed involved was with my wife’s start up company, C Good Staging. After 15 years she has a thriving home staging business. Read more>>

Jennifer Matthews

If I could go back in time, I would have started my business much sooner. I started my business in July 2022, after I had graduated from Walden University with a Ph.D. in Criminal Justice with a specialization in Law Enforcement Administration and a dissertation centered around body-worn cameras, making me an expert in the field. However, prior to graduation, I had over 6 years of experience and training in body-worn cameras. I had connections in the industry as well. I could haasve started my company and begun getting my feelers out and gaining name recognition so that once I graduated my degree would have enhanced my business. Read more>>

Damondray Christle

I’m actually glad at the time I started I was just a teenager. Better sooner than later right? When I first started I didn’t know too much about acting but, I knew I could do it. I felt you just needed to be natural. I was in school plays and was doing alot of stuff at my church at the time. Starting later would of had me a late bloomer but, again I’m glad I started when I started because it gave me a desire to learn and want to do more acting it became a passion. Read more>>

Caleigh Scozzari

I wish I started my job sooner because organization has always been needed to help others mental health and keep them from being overwhelmed. I started my business in 2021. Going from a stay at home mom to a business owner has been the best learning experience for me and I enjoy every minute I spend organizing and helping others. I’m very blessed. Read more>>

Nikol Straws

It’s such an interesting question, and at almost 50 I have plenty of time to look back over my life and ponder on the what if’s. I do wish I had found and delved into the world of DJ’ng sooner. I have always loved music – I come from a very strong musical family with ties to churches, venues and celebrities. There was ALWAYS music in our house growing up, and I was exposed to so many genres at a young age – Jazz, R&B, Tropical, Blues, Country, Classical – it was all there. I sang in choirs and played instruments and wrote lyrics – tying all that together into a DJ career in my younger days would have been so much fun! Read more>>

Jennifer Pincelli

I started my business the year I turned 31. I went straight into the workforce right through High School and after, taking classes in Graphic Communications and working in that field for a few years. Still, I ended up switching jobs frequently, never finding what really suited me, from banking to childcare to office management. I enjoy spreadsheets and some office work, but I never felt anything was my calling. I was working as an office manager when I was laid off. Read more>>