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.

Gloria Green

At the core of my career is a deep love for both art and science. I have two “careers” On weekdays, I am a pediatric clinical dietitian, looking after children with cancer in the in-patient unit at SickKids hospital (Toronto, Canada) for 28 years. I devote my weekends and evenings (and just about every moment I can) to my work as an abstract artist — managing both the creative and business side of my art. I create abstract art paintings, I have been doing so for 18 years. Read more>>

Bobby Ray Connell

I’m at the age of 55 years old this coming January. The last 4 years of my life has been a non stop roller coaster in this career that i have chosen. Singer/ Songwriter/entertainer/ Performer. There is not enough hours in the day to do everything that needs to be done. It’s almost crazy to start a career not knowing if it will pay off or not, While other people my age are starting to talk about retirement I’m Just getting started. They say it takes 10 years to make it in this city, I don’t have 10 years, that will put me at 65, Read more>> 

LaParis Hawkins

One thing I know for sure is that everything happens in perfect timing. I started Tailored Pieces in April 2020 at the height of the global pandemic. I was furloughed from my luxury retail job on Madison Avenue in New York City. I was redecorating my apartment and decided to make pillows out of head wrap material. I posted the pillows on my Instagram stories and finished decorating. Read more>>

Danielle Barbee

I wish I had started my business earlier like when I finished college. However, I knew nothing about entrepreneurship or even what I was most passionate about even though I had been tutoring for a couple years by the time I finished undergrad. After teaching for 5.5 years, I switched careers and began working for the missile defense agency as a cost analyst. I enjoyed my new position, but I missed working with students. After tutoring through a third party company, I decided to branch off and start my own company. Read more>>

Sarah Lake.

I first entertained the notion of starting my business after feeling reluctance to return to teaching as my children started school. (I had resigned after becoming burned out and- as much as I loved my students- dreaded the thought of returning.) But it was the spark and passion I felt creating really compelling photos of children that made decide that it was ALL I wanted to do from now on. Read more>>

Ashley Longoria

I believe everything happens for a reason and at the right time. I had been working a corporate job in Houston but also wanted to start my own business. I’ve always loved flowers and being creative. I wanted to create something that combined both of my passions. I taught myself how to make bouquets and centerpieces by following online tutorials. I started creating wedding florals in 2017 and did both for about 3 years. Read more>>

Vetrica Taylor

My career was started at the perfect time. Before I became a business owner, I was an Executive Chef at Regional One. I learned so many aspects on running a business from the financial side. A lot of the things I learned were not taught in culinary school. From creating a spreadsheet to control food costs, scheduling employees to control labor costs and much more. Read more>>

Morgan Bender

If I could go back in time, I would have established my LLC in 2011. I began my journey with film photography in the darkroom in 2009, and by 2010 I was booking clients as a side hustle pretty consistently. Life as a freshman in college in 2011 was crazy busy, I was working three jobs and going to school full time. Fear was what held me back, I had no clue what I was doing, and I was too shy to reach out for advice. Read more>>

Karriema Calhoun

Absolutely. I wish I started my business much sooner. In my head, I always believed I needed to have this perfect business plan and execution strategy for my business to be successful. Instead of trying to be perfect, I needed to simply start and commit to growing and improving, because the truth is…that’s how being a business owner works. You try and try again, learning and growing from your mistakes. Read more>>

Julia Baker

Fingers crossed that I don’t put a hex on us, our business at the age of eight months has been so much more wonderful and fulfilling than we could have ever expected. Later I give the backstory on why we formed our business, but I can share why we love our business. This year, one of my partners welcomed her first child. With the structure we have created she has been able to prioritize her family. I could elaborate, but to prioritize your family says it all. Read more>>

Morgan Brown.

I 100% wish I had started my business sooner. I started calling myself and my work a business when I was still in college studying photography, however, nothing was really “real” in a sense. I had a name and I was starting to get clients, but nothing was really official in terms of legality. It took a decent amount of time for me to learn what it really meant to have a legit business and get all of the paperwork filed. If I had started my business earlier and really gotten to that nitty gritty portion of having a business earlier, Read more>>

Ayo Kuyinu

My dad was a physician who worked for 40 years but owned his own medical practice. Aside from being a great doctor, my dad knew very early on that he wanted to be his own boss. He learned this lesson quickly after several bumps working for others. He knew it was time to control his own destiny when it wasn’t working when he was controlling others’ destinies. Read more>>

Kisha Stanback.

If I could back in time I would have started my business sooner. In the past couple of years I have had the opportunity and pleasure to see so many people launch successful businesses with FREE resources and passion. That’s all it takes, passion and finding resources, and of course time. When I initially opened my business I did all my research online and networked with other business owners. I am not saying it’s easy at all but I definitely believe that with time and resources I could have started my business when I was in college. Read more>>

Emma Seiz

If I could go back in time, I would not have started any sooner or later! The path was paved for me given the circumstances of the world at the time. My business and art journey started during the pandemic. I was a college student, at the time, in my senior year, struggling to job search while finishing my BS degree. Read more>>

Ashley Griffice

110% I would have started it sooner. I started Be Kind Birmingham in October of 2021. I had been working at the family printing business since 2011 and although I love working there, I just wanted more. Had a crazy idea to buy a school bus and convert it to a mobile store for the homeless and low income families in Birmingham, Alabama…and so that’s what I did. Read more>>

Stephanie Rosette

When I think back about my business and when I started it, I would’ve loved to start it sooner! I started my business at the end of 2017, I was pregnant with my son Mordecai. I had just been fired from a hospital job because of my pregnancy and restrictions and I was devastated. The camera has always been in my life, so I picked up the camera my dad gave me and decided to start my business! Read more>>

Erica Ross

If I could go back in time, I would have started my photography business sooner. However, for a significant amount of my life, I never even imagined photography being something I’d pursue professionally since it was always just a favorite hobby of mine. I started taking photos for fun when Myspace was still the most popular social media platform. Read more>>

Yoli Castillo

I chose this topic to discuss because I feel it really spoke volumes to me in my own head. People have always asked me or made the comment of “Don’t you wish you started this sooner” and my reply is always no. I say this because, you yourself know when the right time will be. When I was in cosmetology school I always gave myself realistic goals to do something. Read more>>

Shanita Adkisson

I Started my Business March of 2022 , the reason I Chose to Start my Business is because I love beauty & Lashes so to be able to Change a woman’s look with just a small enhancement Is something major., As far my Career threw out the years I’ve been in the Hospital field Working in Surgery help to break down the rooms after Cases, help to set up for the next case in Surgery as well doing patient transport. If I could’ve started my Business years ago I feel that would’ve helped me to be more successful , Read more>>

Amanda Danielle Garza

I took the leap and started my first business Amanda Danielle Brows + Beauty as a side gig in October 2019.
I had been working in the cosmetics industry for over 10 years and was fortunate enough to work with some of the biggest beauty brands in the industry but still wasn’t fulfilled. Most of my days were spent driving across Texas going just to spend a few hours in store and drive back. Read more>>

Kanika Blair

I used to wish I started sooner. But now my thoughts are that I’m at the perfect place in my life and career. Everything has aligned and has happened as it should. When I first started creating art, I wasn’t where I wanted to be in my life. Art was my escape, where I can create my own world, thoughts and feelings. Art has helped me mentally, spiritually and physically. If I would’ve started sooner, I don’t think I would have the same mindset and inner peace that I have now. Which in turn has made my mind clear enough to create and be the best artist I can be for myself and for others who enjoy it. Read more>>

Sol Rodriguez

One of the questions I get asked a lot is when I “learned” to draw and it’s always a hard one to answer simply because there is no straight answer. As a child I always gravitated towards the creative projects at school, I excelled in art class, I would spend hours watching cartoons and trying to draw what I saw. Drawing has always been my happy place so there has never been a time where I wasn’t making art and I truly think I was an artist before I even understood what that meant. Despite that, I was always hesitant to share my work and for a long time it felt that art wasn’t something that would ever be more than a hobby. Read more>>

Roger Kornegay

I was working as a social media manager and content creator for yelp. When the panic hit and we all went into quarantine, I was laid off from my position leaving me as a creative with no outlet. With heavy desire to assist the businesses in our community, my wife and I decided that we wanted to do something that would help local businesses keep the doors open while we watched many close because of the pandemic. Read more>>

Makayla Samountry

The best time to start will always be yesterday. I think once you realize something is successful, you will always wish you had started sooner, and the biggest advice I always give other creatives asking about starting a social media platform, wondering if it’s “worth it” or if they will even be successful is that you will always wish you started sooner! Sometimes the hardest part is simply starting — because it’s intimidating, it’s daunting. But we all start at 0, and the genesis is truly the most important part. Setting up a solid foundation is crucial, so don’t be afraid to take your time. Read more>>

Deion Kieley.

This is a difficult question because I truly believe that our experiences shape our creative flow in a way.  When I was just out of high school I truly had the belief that I was impossible to be a “successful” musician but in reality my point of view was very naive at that point in my life. Starting sooner meaning going all in at that point would not have worked because in that time who I was then and who I am now are drastically different due to my life experiences. Read more>>

Taylor Brown

Although I wish I had entered commercial modeling/acting earlier, everything I’ve done so far from blogging, videography, and photography has gained me some type of monetary value and platform. I remember A New York based modeling and talent agency wanting to sign me my freshman year of college. Back then, I was interested, but I wasn’t able to grasp what it was all that was about. My flexibility also did not allow me to deal with unforeseen travels and dropping out of school so I chose going the University route. Read more>>

Michelle Sokol.

The creative journey is not a straight-forward pathway and is not simply one skill-set to be honed and polished. It is important to embrace all the ways one can nourish their being and to give essential space for the mind to grasp creativity in every way it is possible; the opportunities are truly never-ending and always surrounding us. Life presents many learning lessons. Read more>>

Jill Basham

I began my art career later in life. I was in my early 40’s. Art was not a path I seriously considered when I was young. My major in college centered on Urban Planning, The idea of planning urban public areas in order to have a positive impact had definitely appealed to me, but my career path took me in the direction of Transportation Planning, which I found rather boring! I decided to quit my work when my husband and I had our first child. I wanted to stay home with her. Read more>>

Matt Mann.

I absolutely wish I would have started playing music and writing songs much earlier then I did. Although I wouldn’t change a thing about how I grew up, I focused more on sports in my youth than music. I had a drum set growing up but didn’t spend enough time playing because I was always busy after school with soccer, track, and wrestling practice. I didn’t actually start playing the guitar until I was in my early twenties. Read more>>

Amina Hood

it took me more than three decades, 36 years to be exact, to discover a career that really moved me. In the beginning, it frustrated me that I hadn’t started my millinery career earlier. But as I continued to develop my business, I realized that each prior job and journey, toil and trouble, brought a valuable lesson. And everything I’ve learned has been important to my success. Read more>>

Andrew Morris

Pretty quickly after I started playing guitar in middle school, I always wanted to be a musician. I played in a couple different bands through high school in Warsaw, Indiana and dreamed of moving to Chicago to play blues in nightclubs. But as I was graduating high school, I felt that maybe music wouldn’t be the most secure path. I felt if I got a college degree I could always fall back on it if music didn’t work out. So I worked pretty hard at school and really wanted to be an academic. Read more>>

Geoffrey Boyd.

In hindsight, I believe that we started Outdoors With Geoff Media at the perfect time. It was March 2020 and we were in the beginning of the pandemic lockdown and I had transitioned career wise to a space that let me do more with my passions. I knew that I had what it took when it came to showing people how to make great barbecue. I was not so sure on making great content for YouTube and Instagram. My first cooking videos were pretty cringe, but I invested in cameras, mics and lighting and most importantly, I learned how to edit, which bridged the gap between the time I needed to get new equipment and sell putting out quality content. Read more>>

Alicia Waller

I took my creative career full-time in early 2021, after spending 5 years in marketing. This was the perfect time for me to make a change – and not just because I couldn’t stop doodling in the margins of my work notebook and painting during my lunch breaks! I essentially had the “wake up” moment that many people had during COVID – wondering what can I contribute to the world, will I be satisfied with my life in 20 years if it stays on this path? Read more>>

K G$

I started my music career in the early months of 2020. I was just finishing up high school and was very interested in music production and more importantly the hip hop side of music production. I already had a pretty firm grasp on the guitar, and the little music theory I had to go with it so I just kinda took that and ran with it. I started “producing” beats and after a while, Read more>>

Robert Coppage III

I can wholeheartedly tell you that I trust God’s timing. My passion for acting and creating film has burned since my childhood. In elementary I went from doing plays at the school, to getting a paid to act with professionals in local KC theater. By the time I was in middle school I was already editing my own commercials and TV shows on my step dads camcorder. I used to love watching myself on our big screen in the living room. Read more>>

Wilshley Coleau

I’ve always enjoyed drawing and doing crafts throughout my teen years and early adulthood, but I never considered it a proper adult until I was deep into my college career. Every day I ponder the idea of ‘what if I had learned X, Y, and Z earlier instead of now.’ Which may have caused me to be a better and different artist today, BUT there is no way for me to be that person that I think about. I’ve learned that no matter how much I wish to be further in my career than I am at the moment, I can’t magically have that happen. Read more>>

Tiara Hines-Abraham

I became interested in the beauty industry at age 12, I knew early on that I wanted to become a hairstylist. Ever since my teenage years there has been no other dream job for me. Hairstyling was something that came natural to me. I wanted to go to a trade high school where I could participate in the cosmetology program and graduate with my State License. The plan was to go right to work in a salon upon graduation. With that in mind I chose the best vocational high school in Baltimore at the time “Edmondson Westside High”. Read more>>

Jennifer Vineyard

I defintely wish I would have started my business earlier. I wanted to start a business for a long time but I always had the nagging voice of my mother in the back of my head saying, “you know, most businesses fail within the first 6 months.” This was intimidating and my lack of confidence in myself kept me from entering into the small business world. However, I do think that I had to wait to find the business that was right for me and built upon my talents. I started my business out of necessity. Read more>>

Eiman Yousif

I have started my journey in arts in 2016 after a long career as an educator. Being a teacher has been a route full of passion and accomplishments as well as stress and self-neglect. I wanted to find a way to distress after a long week of teaching, planning, meetings etc..so I decided to join a fun class of painting where you just paint your heart out. Soon after I joined, Read more>>