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.

Anastasia Ellis

I wished I had started earlier or took more serious sooner. I’ve been writing songs since I was 4 years old, singing in choir and theatre since elementary/middle school, and started learning about music production in high school using Maschine. I always knew I wanted to be a singer but I never knew how to get started and after my mother passed when I was 11, I didn’t have the same encouragement to go after my dreams, let alone just be myself. Read more>>

Alisha Bacon

I started my business as a Smoky Mountain elopement planner in 2019. At the time I was a professional photographer, photographing mainly tourists in the Smoky Mountains on vacation. The idea actually started with a simple conversation with my husband in a Mexican Restaurant in my hometown of Knoxville TN: The “What if” conversation. We quickly dismissed the original idea due to some hurdles in our state’s laws on who can be an officiant for an elopement or wedding. We thought it would be too hard, be too much to start up and moved on. Read more>>

Ciara Dutcher

I started my photography business when I was in college, I had no clients other than family and hadn’t really made a name for myself just yet. When I started my photography was pretty basic compared to other professionals at the time and I got discouraged that I wouldn’t be up to par and I couldn’t get clients like other photographers did. But I didn’t quit, I kept learning from not only the internet but other photographers in my area. I got new equipment and actually invested in not only myself but my business. Read more>>

Tatiana Nchotu

At times, if I could go back in time, I wish I would have started Braids That Speak sooner. I had always been a braider throughout middle, high school and even college and after. It was just something I did because I truly enjoyed serving black women and I always did a great job. At the end of 2018, I decided to leave my 6-figure IT job because I wanted to work with black women full time. In 2019, I took everything seriously and decided to go at it full-time and I built my clientele from my home salon. Read more>>

Jacob Pinkston

Started the business beginning of June 2021. I at that time was working a full-time job and didn’t know what to do with my life but wanted to do something different but also for myself. I was scared of taking a risk to work for myself because at the same time my wife and I just had our daughter. I played it safe and worked during the day and at night worked even more to start building this business. If I would’ve started later then I don’t know if I even would’ve went thru with all this but in a way I did wish I started the business earlier just to get things moving. Read more>>

Abigail Theroux

In the winter of 2021 I made the decision to officially quit my Job at the salon I was working for and open my own business. At that time in my life I had been struggling off and on working through the pandemic. I was weighing the pros and cons of working for myself and wondering what that would look like in today’s current economic climate. Ultimately the decision was easy as I wasn’t happy with the salon I was working for and knew, that no matter what the outcome, I would be much happier on my own. As a long time professional hairdresser it has always been difficult for me to determine when would be the right time to branch out independently. Read more>>

Brieria Willis

The answer to this question is both yes & no. I started my business when I was 23 years old and I’m currently 27. I had just finished college a few months prior & was looking for marketing positions while working in the banking industry. I was very discouraged during this time period due to being told I couldn’t work in the marketing department at my then job because they were looking for external candidates & i was suffering from post grad depression. All the job interviews I went to were not aligned with what I wanted to do in life so I kept turning down job offers because I knew I was destined for better. Read more>>

Kyara Betts

If I could go back in time, I would have started my business right after college. However, when I graduated high school, I was hell-bent on going to x-ray school and needed to acquire an associate degree before I applied for programs. By 2015, I was graduating and looking for a program, but instead, I was hired by the Internal Revenue Service. So, I began working until being accepted into the X-ray program. By 2017, I got accepted into the Einstein X-ray Program. I don’t think the staff understood that I had to work to put myself through college, and without a scholarship, I would not be able to afford it. Read more>>

Katherine Lake

How do you decide when to start a business? Is there a “perfect” time – a time when it is clear to take a risk and do something completely different? During my first 30 working years, I was an employee of various organizations. Large and small, public, private, and governmental – I saw it all! On and off, I’d play around with the idea of how great it would be to run my own business. I loved the idea of being able to design and do things the way I believed they should be done. Control, at last! Read more>>

Melissa Wenhold

The concept for Earth Girl started years ago when I hosted a spa party as a baby shower for my best friend. At that time organic and “green” products were not a thing… it was next to impossible to find organic, clean spa and body products. I ended up making all of the products for the spa party, and it was such a success that I created Earth Girl. Life got in the way, however, and I didn’t truly focus on launching Earth Girl until 2017. The good news is that the market was much more open and interested in organic spa and body products, but there is quite a bit of market saturation is this space now. Read more>>

Maria Martir

Maria Innata arose at the perfect moment that it had to start. Despite the idea of this project was in my head for a long time ago, I wouldn’t change the moment of its beginning. In 2020 the whole world experienced an event that everyone got surprised by: The pandemic. This made the world stop. Those times were difficult for everyone, but I think we can save many good things from all the chaos like pausing and taking a breath. I hadn’t been able to start my business because I hadn’t had the time to do it, and when the pandemic arrived, Read more>>

Angel Prince

If I could go back in time I’d change nothing. I have to believe that everything works out exactly how it’s supposed to. Every experience, every job, every loss and every win are all pieces of the puzzle. The puzzle that has created my business. The business that I began when I was only about 13 or 14 years old right in my room at the mothers house. Read more>>

Yilmaris Rivera

Flannel Panels started back in 2019, during a difficult time such as the pandemic. I had just lost my job and with a career background of fashion and my MBA, I decided to get creative and start my business. We started selling flannels at local farmers markets in the Orlando area, and began venturing out towards festivals, pop up shops, and comic cons. Josh and I have always wondered, had we started years ago where would we be today. Our business has grown and succeeded so much in the past few months that if we would have started earlier we would already have opened up our own local store front and have built a team of employees. Read more>>

Michael Ballerini

No, I don’t wish I would have started earlier, I came in at 26 and in my opinion that is super early. I look at it as I started when I was supposed to. If I started earlier I may have failed because I was not mentally ready to handle large amounts of capital in my early years. If I started later it would not have been a bad thing though as I would still have had the same drive and determination I had at 26. Read more>>

Sarah Tran

I officially registered the LLC for my graphic design & marketing studio, Cloud 6 Studios, in December of 2018 — but I do wish I had started the business earlier. In truth, I had been freelancing since I was 16 years old (though I did it in secret). I grew up studying Fine Arts and I always knew I wanted to be in a creative field, but I also wanted to start a business. I don’t have a problem against working for someone else. In fact, Read more>>

Tamara Al-Haddad

I feel like I started just at the right time in my life. Upcycling and refinishing old furniture has been a passion of mine for many years, and turning this passion into a business has been my dream. It wasn’t until I was diagnosed with cancer in 2019 that I decided the time had come. I am so blessed and thankful that I have been cancer free for the past two years, but an experience like that will change how you see life; it will change your priorities. Read more>>

Kyle Lee

I wish I would have started sooner as Fashion and Creativity has always been one of my passions. I started my brand in 2018 when I was in college, I finally decided to take the risk and get into the process of starting my business. After I started my business over the years I ventured into other areas of creativity such as Modeling, Photography, Creative Direction, etc. The only thing I would change about my Experience is starting sooner, I think I started at a great time but I feel as though starting sooner would have given me more of a head-start at my craft giving me more experience under my belt. Read more>>

Sheila Lopez

I started modeling in 2014 and I was 27 at the time. It wasn’t until my late 20s that I gained confidence to be able to do something like modeling. I was always the person that tried their best to avoid taking pictures and dressed in overly baggy clothing as a way to hide. I was apologizing for my size and never felt beautiful enough to take pictures. I started modeling after a friend made introduced me to local photographer in Austin, TX. Read more>>

Xavier Cooper

I absolutely wish I could’ve started my creative career sooner. Growing up I always had a creative mind. My imagination was very wild and vivid. I experimented with a few creative things but I never went all the way with anything. I rapped. I made beats. I wrote poems. I use to draw but I wasn’t so good at drawing. Honestly speaking, it took me a long time to find out that creating content and being creative was something that was apart of me naturally. I didn’t truly find that out until last year. Read more>>

Dani Sade.

If I could go back in time I honestly wouldn’t change anything. I feel like everything happens for a reason and on the perfect timing. Divine timing is everything and I feel like I was placed exactly where I needed to be. I am only 25 years old and I honestly feel like I’ve accomplished so much within my career in which little time since I’ve graduated high school back in 2016. If there was anything that I could change looking back It would definitely be my consistency. in the past I wasn’t as consistent as I should’ve been with my career. Read more>>

Jason Kane

It’s hard not to sometimes think about the “what If’s” how I could of done this or that sooner or taken a different approach to my musical journey completely. But it probably would’ve been no fun at all and completely soul sucking. So at the end of the day when I think about it, everything happened right on time in its own funky way. The good, bad and ugly. This whole musically circus took over my life at a young age, around 12 or 13 is when I got the bug and when I first set foot on a stage. Read more>>

Yelena and Justin Williams

We started the See The World Eat The Food blog in 2020 after a year and a half of dating right in the middle of the pandemic. It would have made sense to start sooner since we were already seasoned travelers and both loved writing about local restaurants, as well as restaurants we dined in during our travels. It didn’t help that we began the blog during the pandemic when travel was much harder and many restaurants had to completely change how they approached their business model. Read more>>

Elyse Johnson

If I could go back in time, I wish I had started my art career sooner. I started teaching art in the school system right out of college, but I didn’t really expand my art career until almost 8 years after graduating. One critique I have of my college, is that although they made me a wonderful artist and teacher, they didn’t require any marketing or business classes. Thus, I lacked the confidence and the know how to push my art into the art world. I was fortunate that my husband’s degree was in business and entrepreneurship and through his guidance I was able to learn how to sell my artwork. Read more>>

Carlos Solis

I have always had artistic inclinations. I started very young at the age of 3. Fortunately for me, I have a family who always supported me and stimulated my creativity and interest in the arts. However, as you grow, you understand the reality of your situation. I grew up in Venezuela, South America. In a city called Maracaibo. My dreams of becoming a professional artist ended at the age of 15-16. Too many distractions came along. Ones were justified others weren’t. I guess a combinations of political turmoil, a declining economy and youth distractions “forced” me to put aside my dreams to become an artist. Read more>>

Funky Punky

From time to time, I catch myself wishing that I would’ve began my career as a Dj/Producer sooner than I did. I feel like I would be closer to checking off items on my career bucket list. However, when I do have those thoughts I have to remind myself that my journey is just that, MY journey. I have accomplished A LOT for someone that has only been doing this for two and a half years. If I would’ve started djing and/or producing earlier I wouldn’t have the three degrees I have now and I wouldn’t carry those life experiences with me to use as inspiration. Read more>>

Rhys Meatyard

I am not a person that typically dwells on what could have been – I tend to believe that all of our previous decisions and experiences mold us into the shape our present takes – but as an artist in my 40s with just over 3 full years consistently showing my work, its something I get asked a lot. I think as humans we tend to believe that our lives have a set course and that once we embark upon it and commit ourselves to following through, it becomes ever harder to see how we could change things. To be honest, that is a big reason why I am so open about my life, because I want to live as an example of finding your way later on in life. Read more>>

Martez TezThaGreat Mosley

I definitely would have started sooner. I didn’t take it as seriously as I should because I didn’t know I could make it Into a career. After I began selling poetry to the older classmen in Highschool, I knew writing was going to be an outlet for me. I never imagined I would get paid for it. I also wouldn’t have let some people’s opinions sway me from doing music earlier in life. I would’ve started learning more about the industry and business and moved to Atlanta sooner as well.. Read more>>

Jesse Trotter

I started cosplaying in 2014 with my now ex-girlfriend. I had learned a lot of my crafting skills from LARPing and after watching a show called Heroes of Cosplay on the SyFy Network I gain interest. I actually bought my first cosplay but it didn’t fit so i slowly altered it and that was my first steps into cosplay itself. Over the years I have grown in both skills and as a artist but sadly as I get older it gets hard for me to make costumes. I wish I had started sooner so that I could have done more with my career as an artist. Read more>>

Kara Rainer

In a word, Yes, I do wish I had started sooner in the acting industry. But, I also now believe, that everything that is for you, comes to you at the right time. So it’s hard to look back and say, “boy if I had only started earlier”, or “if I had just been a little braver”. No, I think I had to learn a lot of things along the way and then finally one day I knew I was ready. I knew I loved entertaining by the time I was 3 0r 4 years old, and I was probably 20 years old when I finally admitted to myself that I wanted to be an actress, but I was too embarrassed to tell anyone and I thought people would think it was a hopeless path. Read more>>

Kimberly Santiago

My family has always guided me towards their image of stability. Stability in a typical Puerto Rican household is college and a corporate career. I have loved music since I was old enough to utter my first syllable. I was never encouraged to follow my passion so I often find myself wondering what would have happened had my musical capabilities been nurtured earlier. I love my life and I am extremely grateful for every lesson learned. I do believe I would’ve been way further in music career had I started sooner. Read more>>

Mariah Mitchell

I wish I would have started taking art more serious earlier on. I always new I loved to draw but I didn’t start expanding my interest until I was 24 years old. I’ve been drawing all my life just for fun. When the pandemic hit in March of 2020 I started painting and taking commissions. I wish I would have started sooner. I think starting sooner would have been good for me because art had opened so many doors for me. I have gotten to meet so many amazing people and experience so many awesome things with my art career. It’s always better late than never so I’m grateful regardless. Read more>>

Maureen Famiano

I’m a big believer in timing. I loved what I was doing as a journalist working in morning show television as an executive producer. I never really gave an entrepreneurial spirit much thought. It came up only because guests to my shows would ask me to be their consultants over and over after I would help them with their messaging during their tv appearance. After so many said the same thing I thought perhaps that’s something I could/should try. Read more>>

Beth Schwartz

I loved my career as a physician. Being a visual thinker, pathology was the ideal specialty (think microscope, not forensic crime drama!). Not only was I able to provide needed medical care, support my children and be a foot soldier for feminism, I was able to feed my brain. But in the shadows, on the weekends, I was making art. As I lurched towards retirement, my creativity was blowing up. I was soon to be the proud possessor of closets full of interesting creations, seen and enjoyed by very few. Read more>>

Emily Henegar

Absolutely not. Don’t get me wrong, I’m sure many of y’all reading this are older than the age of 11 so I’m not saying it’s the magic age to start a business and sucks for you if you missed your chance. I don’t even think that you need a decade to master the skill of decorating cookies, to grow up with your passion, or to study business. (read the parable of the late-coming workers in Matthew 20 if you don’t believe me!) What I gained from these 11+ years, and what I encourage you to learn from me, was the childlike perspective of following the threads of my passion with open, curious hands. Read more>>

Sorenna Stewart

I definitely wish that I started documenting my life much earlier. I had an interesting upbringing and have been through a lot at my age. I feel like if I was able to record and vlog my life then, my audience may be bigger because of the relatability. However, I’m grateful for the audience I currently have and I pride myself on being transparent. Read more>>

Daniela (Dan-yell) Griffin

March 2020 began a personal transformative time for me. I was a week shy of having a one year old when the constant movement of a young working professional mother slowed down drastically. At the time I was closing in on year three in the field of college access and success. I work for a non-profit organization in Mississippi which helps students plan, prepare, and find ways to pay for college. We define college as obtaining a certificate, 2-year, or 4-year degree post-secondary. Read more>>

Morgan Tisby

That’s a difficult question. When I was younger I had always dreamed of being a music artist. I knew I was talented at a very young age and I had it all mapped out in my head of how my future was going to go. I was often involved in anything around me that was related to singing and entertainment. I was apart of school talent shows, church choir, local talent shows, and more. I think I was around 11 or 12 when I started taking my singing talents seriously. At that age, me “being serious” ,consisted of me learning how to write songs with my first keyboard. Read more>>

Crystal Hurt

1,000 times YES. I REALLY WISH I would have started the cosplay career sooner but I am pretty content with where I am right now (I’m still growing). When I started cosplaying, I was at a job that I HATED. I wasn’t happy with it, I was burn out, I felt stuck, and I literally thought I would be at that job FOREVER. I feel that if I would have started this sooner, my content would be ALOT more consistent. Not that numbers matter BUT, I would have a bigger following, and I would have more opportunities to grow my brand a bit quicker. Granted, I am happy with a slow pace, but an earlier start would have helped with the push. Read more>>

DJ Niick At Nite

Yes, Certainly! In fact, I often find myself sort of upset at the old me for not starting sooner, I feel like I’d more mature & knowledgeable within DJ-ing/Music Industry. The actual year I officially became A DJ was February of 2018. Leading up to me actually acknowledging myself as a DJ I openly just loved music. I played around with different DJ softwares for years for my own self enjoyment until I was kind of push out into actually trying to DJ by a hometown friend. That push lead me to actually taking being a DJ seriously. Read more>>

Sara Lynn Green

As long as I can remember I have always had a big love for art. I still remember the days when I would draw the PowerPuff Girls and little stick figures for my aunts co workers. It was a great feeling seeing something I created hung up. I took AP Art classes in high school, submitted a portfolio but I already had this ideal in my head that “my art was not going to take me places”. Because of this ideal I made up in my head I did not major in Art while in college. It wasn’t until 2019 that I started to take my creative career serious. Read more>>

Ebonee Copeland

If I could go back in time I definitely wish I would have became an entrepreneur sooner. I started my business in 2019 with the plan of having an e-commerce business selling beauty products. Shortly after the pandemic happened and my e-commerce plans didn’t turn out the way I expected. I also wanted to get in to real estate because I believe it’s important to have several streams of income. I took my time and researched what aspect of real estate I wanted to pursue. Read more>>

D.A. Alston

I was born a creative but I sadly didn’t always take it seriously. My mom would constantly tell me I should do something with my art or my words. But sadly fear of inadequacy and doubt hindered me from taking that leap. It wasn’t until I was a ‘young’ 26 that I finally took myself seriously. I wrote and published my first book , got a website, and put my foot on the gas. I do wish I would have realized what I was doing was worth putting that effort in a bit earlier. Doubt has the power to be debilitating. Read more>>

Melody Jean Moulton

As far as taking the art I make seriously and working to exhibit it, I definitely wish I had started it sooner. I am a self-taught artist and unfortunately let the fact that I didn’t have formal schooling affect my confidence in myself and my work. Up until 8ish years ago, I didn’t create on a regular basis. It came in spurts and I never tried to exhibit anywhere. I slowly started putting more time into creating art and then eventually started going down rabbit holes on the internet and applying to exhibitions and galleries. There was a lot of “No” amidst the “Yes,” but those few acceptances were enough to keep me going. Read more>>