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.

James Leveque

Definitely wish I would of started this business sooner. I started in Financial Services about 4 years ago. I was working in the Boston Public School System and was for a way to make extra income. Honestly I wish I would’ve taken it a lot more serious once I got in this industry. I played around with it, worrying about what people would think of me or if they would support my new venture. The fear of worrying about what others think of you is a real thing, once I was able to get past all that head trash that’s when I started making things happen. I would not change anything about my experience. Everything happens at the right time & that was my journey. Read more>>

 Sha Bowers

Many times I wonder what it would’ve been like if I’d started sooner. I started my business in college. I was actually working my dream job at the time. Before starting my business I knew doing makeup was something I was good at, but eventually I became in love with learning, the transition and the moments. Looking back I wish I had started my business a lot sooner. Read more>>

Katrina Berg

Absolutely earlier! My first degree is in Education — Early Childhood Education. I learned a ton about teaching styles and methods — I’m so grateful. It has helped me be a better human & mother as I’ve tutored, taught in public school, charter, and within my home. However, LOL, I wish I’d made “creating” my priority instead of graduating from two different Universities. (I started regularly painting and selling my work at age 28, after graduating twice, marrying, and having my first child.) If anything, I could have just taken classes that interested me instead of focusing on the needed classes for my diplomas. While receiving tools from the classes that interested me, I could have also been going to artist workshops, showing my artwork at markets and local shows, taking commissions, and most importantly: refining my process and style. Read more>>

DJ Mini

If I could go back I would have started earlier! Because once I had started there was already a teen DJ who was throwing parties so I had to quickly prove myself and gain the trust of others especially with me being a female DJ! If I started sooner I may have been able to be where the other DJ is at but I’m glad I started when I did because the opportunities I’m getting I never saw myself having if I didn’t launch when I did. So I like where I am right now and it’s only up from here!! Read more>>

Shannon Hernandez

I’ve been a consultant for the past decade, and that definitely began at the right point in time for me. But I do wish that I had shifted my mindset from “independent consultant” to “consultancy” earlier in my journey for a few reasons. Read more>>

 Jonathan Coleman

I believe I started my business at the right time, however I wished I learned all these valuable lessons that helped me to improve my business earlier. I’ve always been in the field of public relations on and off throughout my life, first starting as an errand boy for a local talent agency that had it’s own PR department, and throughout my 20s I had several jobs outside of my PR, such as working for call centers and companies like Convergys (OnStar) and iQor, I was working on my PR business on the side while working a regular 9 to 5 until I was able to fully transition over a run my business full time. So I guess in a way I wish I was able to start sooner, but really if I could turn back the hands of time I would have done a lot of things differently as far as how I operate my business, etc. Read more>>

Will Richardson

This is my third attempt at starting a business. I tell people that this is a re-startup to a re-startup, to a startup. Read more>>

Jacklynn Lomeli

If I could go back in time, I most definitely would’ve taken the leap sooner. Fear always held me back, I’d think, what if I don’t make it, what if I didn’t make enough, what if my business didn’t continue to grow, but rather just die. The fear of proceeding in life to pursue what I loved the most, especially to be able to work for myself & make my own schedule. In the end, everything happened the way that it did to get to where I am at, but fear & insecurity definitely stopped the process. Now me, would tell old me, let it RIP! There’s only one way to find out. Read more>>

Taylor McCormack

I wish I had started my business way sooner! Marketing and PR had always interested me, but I didn’t know of anyone personally that was working within that realm so it honestly seemed unattainable. When I first started my business, I was 23, working on a finance team and was just about to finish up my BS in Accounting. The whole time I went through school for accounting, and even while working my job in finance I felt so unfulfilled, that’s when I decided I needed to take a leap of faith and at least try to do what I was actually interested in. Looking back now, if I had started sooner I wouldn’t been so miserable for so long feeling like I was working towards absolutely nothing because nothing else I was doing was bringing me joy. Read more>>

Donyea Tollie

The right answer to this is no, I wish I hadn’t of started my business earlier. My journey comes with first accepting that everything happens for a reason and my journey doesn’t look like anyone else’s except mine. Read more>>

Nate Bont

Life presents itself at its own pace. However, I wish I’d have started earlier on this path. When I finished high-school the push was to attend college which was not the right thing for me. Who knows if I’d be more successful as a business by now but I’d have been happier, regarding work. It’s hard to look back and wish for something different as we can’t know what else it might have changed. Read more>>

Mutant Glue

If I would have started this career sooner, I feel as though I would have gotten more accomplished and more opportunities. Essentially they would help me in the long run, but I’m happy with what I have received this far. Read more>>

Elin Tegels

I feel as though my “career” and my creativity ended up merging together at the perfect time. I always had the creativity in me, and when it came down to picking a career I chose to do it in fashion. So no, I do not wish I had started it any sooner or later. I do wish I had allowed myself the freedom to express myself outside of my 9-5 sooner. But like anyone just starting a career out of college you’re often hyper-focused and can get burnt out and not want to do anything for yourself. Allowing a few years for a break after college to get back into sewing for myself was perfect! Read more>>

Vibebrations

That is an awesome question. We have discussed this several times and we used to want it to happen earlier. You know, like how Michael and Janet started early. However, we realized that everything happens for a reason and when it is supposed to because it has all led up to moments like this. Read more>>

Vivienne Isebor

Sometimes I get lost in my thoughts and ruminate about whether or not I have wasted my years and should have focused on my creative craft. I compare myself, meticulously remembering people I shared stages with and how amazing they are doing in their journey. I am so proud and happy for them, and then that shifts into a disappointment in myself. At college when you choose your degree options it feels like a pretty unsupported decision for such a huge life decision. I remember mulling between Psychology and Music, and having what felt like a revelation: I can still do music while studying Psychology and get an accredited degree, but I can’t do Music and do Psychology. Read more>>

Dhalton Horsman

I sometimes wish i had started singing sooner in my career; which was about 2018,, Back in high school the choir teacher was always trying to get me to join, always saying “c’mon man, its in there, let it out” i did not know what “it” was but i do now. Read more>>

Svetlana Vasina

Starting my creative career early has been a huge advantage for me. I’ve been drawing for as long as I can remember, and my talent was recognized at age 5 when my mother enrolled me in an art class. Growing up in a small village in Russia without any artists in the family, that early exposure to art sparked my passion for it. Read more>>

 Franco Zizza

I wish I did start music at an earlier age. Music wasn’t on my radar as a younger person. I gradually fell into playing and writing songs due to being surrounded by musicians. I didn’t properly join/form a band until I was 22 years old. Most musicians are in this field starting at a young age which I feel gives an advantage to understanding the creative and business side. Also developing your skill as a musician on your instrument at a younger age gives you more time to become more than an average player. Obviously, it all comes down to passion and how much you put into it. I always feel like I am playing catch up within the world itself but luckily paving your own niche and not being in the machinery of the mainstream music world has its blessings too. Working hard and putting in the time definitely improves any chance of achievement .From the start it has been an uphill battle of learning the instrument, songwriting and the business side. But the sun always rises the next day and you can continue your path the way you envisioned especially in the days of today society. The progress shows and it’s a slow and steady race that I am willing to see the end of. Read more>>

Bayda Asbridge

Being an Arab women raised in the Middle East, I didn’t have a lot of say on what or where to study or what career to pursue in the 80s. I wanted to study art, but my father wanted me to study English literature because he could see more doors opening for me if I did. Financially children are tied down to their families too, so I had to follow my family’s advice. I finished my BA in English lit, Masters in TESLOL and started my PH.D. in Linguistics, which i never finished. I loved my field of study and I excelled but I was very miserable. Read more>>

Huong Vo

ABSOLUTELY sooner! Looking back, it was one of the biggest mistakes of my life that I still regret to this day. Two weeks after I graduated college, I quit the job I had throughout college because of the toxic environment. Little did I know that I would still be experiencing the lingering effects of the 2007 recession in 2010! I spent 12-hour days looking and applying for jobs to no avail…a total of over 200 jobs with only a handful of interviews and no offers. Read more>>

Lainie Garcia

I wish I would have started sooner. I have always been a creative person in my younger years. I believe after high school, about to start college, is when I realized I was meant to do something creative in my life. I was told that college would be the best route and that way you could always have a stable job in life especially in the medical field. So, I decided to go to my local community college and try the traditional college degree way. I quickly figured out college wasn’t my path but I did end up figuring out that my passion for makeup started. Read more>>

Martinaene Johnson

At first, I wished that I had figured out what I was really passionate about in my early twenties, then maybe I’d be much further along in life. But I feel that everything happens according to divine timing. What also helped me figure out I that I was a creative or wanted to expand on being a creator was remembering the things I loved to do as a child up to my teenage years. I loved writing, reading, puzzles drawing and being a performing artists in the middle of my living room or bathroom mirror with my imaginary mic in my hand. At one point there was an attempt to be a fashion designer or teach my imaginary second grade classroom. How fun, right? I went through all the stages of what I could possibly do not realizing all that I was doing went hand in hand and I was already on the right path as a creator. I finally broke out of my stage fright a bit and began my teenage years as a model. I’m walking in my purpose now as an educator, but still following my passion as model, writer and puzzle maker. I’m still exercising my skills in making more crafts and maybe you’ll get to see me on what will be your favorite movie one day. Read more>>

 Jon Theis

For me I started super early but I would always back out when things got real and would chase some other creative pursuit thinking the answer was outside of myself when really it was internal. So it was more developing staying power and working through my issues which in turn allowed me to truly create as my authentic self than anything else. I also got caught in success and goals and all the other things one can create in their head to get in the way of creating good art. Read more>>

Jewelee Wilson

I wish I would’ve taken things more serious in the beginning. Music has always been my go to outlet for everything. I knew I was skilled in it , I just wish I would’ve had more knowledge about how to handle things when I first started out. Read more>>

Desirae Woltz

I most definitely wished I started it sooner. I started training in the 10th grade. Since I did cheer and track for most of my schooling life, I had rhythm, but I was stiffer than a door knob. It’s a common thing for people who dance to start in elementary school or even younger. Read more>>

Dehe’Miah

Yes, I wish I would’ve started a lot sooner than what I have, because I would be a lot further than what I am right now in my opinion. I had turned away from it when my brother was murdered 7 years ago. He was my biggest support system when it came to music and singing and performing. Once I lost him I felt there was no longer a need for music. Read more>>

Monte Henderson

I recall falling in love with music at the age of six. I didn’t realize that I could actually sing until I was eight years old. I was walking home from school sining “Sentimental Thoughts” by Alexander O’Neal, don’t as me how I knew that song, and a lady sitting in her front yard heard me and said “Wow you have a great. voice”. of course, I was feeling myself a little bit after that. needless to say, there was always a melody of some sort in my head and i would often times get in trouble in school for humming while working. At home I had keyboards and a drum set that I would play around with as toys, I sang in the school and church choir, and I could spend hours in my room, listening to music and dissecting musical elements. Music was all over me, but I was too shy to show off my talents. Read more>>

Ruchita Newrekar

I was a good academic student in high school. So when it was finally the time to choose my major for under-graduate studies, I went for something scientifically intensive like engineering in chemical technology in spite of being aware of the creative side. I failed to consider what I was thoroughly passionate about then and went for a more obvious and safe option. Four years later, after I graduated, I realized that I am not truly happy being an engineer even though I am adequately good at it and decided to pursue the idea of having a career as a professional jewelry designer. I have been terribly happy ever since, but often find myself wishing I had recognized and worked on my creative aspirations sooner. Read more>>

 William Weygint

I had always been drawing as a kid as a means to pass the time on weekends or procrastinate with school work. It was an imaginative escape from the misery of post-standardized testing, public school-work. I never considered drawing “art” or self-identified as an artist; my parents were artists and I was inflicted with the bratty aversion to exhibiting any likeness to my them. I began taking visual art seriously however when my High School band members split up and went separate ways. The lack of control in this setting drove me (in my mid-twenties) to pursuing a different creative path and I began taking painting and drawing classes at a near-by Community College. When looking at the careers that some of my piers have had with a steeped background of art high schools (not simply art class in high school) and going directly from undergrad to MFA and than into residencies I regret my lack of creative direction in youth and do wish that I had a more creative path in my earlier years. This experience however has inspired me to grasp the moment and appreciate the numerous resources and inspirational network that I do have access to. I also feel that having a varied background gives me a lot of experience in settings that most artists haven’t been around. I therefore have an unusual worldview, skillset and array of stories to draw from when constructing a work of art. Read more>>

M.K. Harris

My journey to starting this fabulous business was a rollercoaster of excitement and growth! Looking back, I knew starting sooner wouldn’t have been the right call. I needed time to find my true focus, discipline, and that inner spark that sets the world on fire. Read more>>