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.

Douglas Dangerfield

At times I wish I had started my business as a Real Estate Agent sooner than now. However, when I think of it, I am Grateful for having the drive and determination to have started it late May 2024 than when I had originally thought of it in 2002. I feel that I appreciate everything that I’m Learning now that I would 20 years ago. I value what I know, what I’m taught and continue to learn and grow. I feel that if I had been doing it since 2002 that I would have become complacent and bored. Whereas now everything I learn from people is new and exciting. I do not take anything for granted and I am working hard to be the best agent I know I can become. Read more>>

Kaysha Rajani

I often reflect on the time when I started my business and question whether the timing was right. Initially, I would quickly say that I wished I had started it when I was younger, so I could have enjoyed the benefits of business ownership sooner, such as having a flexible schedule and being my own boss. However, I now realize that I would not have been prepared to launch a business without my prior experience and knowledge in marketing and communications. Skills such as meeting deadlines, managing customer expectations, and creative problem-solving have all transferred from my previous roles in project management to my gifting business. I am grateful for the over fifteen years I spent developing a strong work ethic and being part of a team before taking the leap to work for myself. Read more>>

Corey Winn

Personally, I wish I had started my business sooner, but growing up being entrepreneur wasn’t a “safe” choice. I was expected to finish high school, go to college, get a degree (or two in my case), and get a job with good benefits, a pension or 401k and then start thinking about a family. My parents wanted to make sure I was financially independent and could take care of myself with all of the boxes checked. So, I checked all of the boxes. I went to college, then to graduate school, graduated with a Doctor of Physical Therapy degree, I worked full-time plus hours, I got married, I had a baby, and then my priorities shifted. I remember taking her to daycare at 6 months old so excited that I’d seen her crawl for the first time. I told her teacher who looked at me and shattered my heart saying “oh she did that yesterday”. I was missing so many milestones and it broke my heart to go to work full time or more hours everyday as a physical therapist and leave her with someone else to watch her grow up. I’d love to say that I jumped into the world of being an entrepreneur then, but I was too scared. I continued with the safe option. Read more>>

Randii Ianeke

At times, I do wish that I would have started my business sooner, however, it wasn’t feasible at the time. I started my business in September of 2016, after receiving my Bachelor’s degree a few months prior. I attended Louisiana State University (geaux tigers!) on a full-ride scholarship for gymnastics, and once my senior year came to a close, so did a 20 year long competitive gymnastics career. So while I wish there was more time for me to hone in my creative writing skills and alternative healing practice, it wouldn’t have been realistic with my schedule. Read more>>

Kelsey Hawkinberry

If I could go back in time and start my business sooner I don’t think I would! I think the timing was just right for me personally. In my early 20s I was all over the place. I didn’t know what I wanted to do or where I wanted to be. And I definitely wasn’t ready to commit to something as big as starting my own business. I would start things and quit within months because I didn’t like it. I’ve always had the mindset that life is something to experience, so I knew I didn’t want to waste my time pursuing things that didn’t align with me. It took me until my mid 20s to realize photography was something worth pursing. Read more>>

Keonna Rutley

I believe I started Infinite Glow Candle Co. at a perfect time. I thought about starting a business a few times over the past 20 years but I could not come up with an idea that I could fully commit to. For years I wanted to do something with food because I worked in restaurants and that’s what I knew. But I lost my passion with cooking because of working in restaurants for so many years Read more>>

Janice Perez

Art has always been a part of my life, from as far back as I can remember. When I was young, I loved cutting construction paper into shapes, coloring, and experimenting with anything creative I could get my hands on. Over time, that love for creating grew into something much bigger, and I started making my own art pieces. When I think about whether I wish I had started my creative career sooner or later, I honestly feel like everything happened at the right time. While I’ve always loved art, it wasn’t until more recently that I found my specific passion—combining my love for JDM cars with my creativity. If I had started earlier, I might not have had the same focus or vision. If I’d waited, I might have missed the joy of building Roadstar Roadsters and connecting with people who share the same passions. Read more>>

Abinandhan Srivatsav

This whole conversation started a while ago when I decided to change my career from being an Engineer to moving to the world of Visual Effects. Coming from an Asian household, I was naturally expected to be either an engineer or a doctor. The idea of anything else was not good enough, because I was told it was a poor man’s job. I went to school for my bachelor in engineering against my will and I was neither good at it nor was I interested in it. I didn’t have the greatest of grades, and I used to spend most of my days playing video games. At one point, I played it professionally. After graduating I joined a big e-commerce company for a job. Being neurodivergent, I was able to pick up the patterns at the job and become good at it. But, I was still not enjoying it. Something wasn’t quite fitting for me, not yet. Eventually, I reached a burnout, and at the same time, I went through a very critical health situation with my dad where he had to be hospitalized for 8 months. I came back to work, and I started hating it. I wasn’t enjoying it, and used to wake up wondering why am I doing this to myself. Read more>>

Anne House

If I could go back in time – wow! What a prospect! I’m a big fan of time-travel stories – books, movies, etc and I can’t imagine really changing much because of what I would have lost out on. I would have liked to try sooner than 50 but I would have lost out on my kids and such. I’ve been singing for a very long time, since I was about 5. Always in chorale groups though. Since I was young, I’ve wanted to be a singer. Dreams of being on the stage were common. But I’ve always been a ……fluffy girl so those dreams were pretty remote – then wasn’t the time. I grew up, had a family, took workshops and classes. Once my kids were grown, though – all bets were off! I could start doing things for myself. With the advent of artists like Megan Blue, Sarah Potenza, Katie Kadan and Jennarie I thought “well, maybe I can”. Then came Lizzo and Keala Settle I was finally convinced that at the ripe age of 50 I could……… And now I do! Read more>>

Imani

This has been a question that used to pop into my head a lot when I started my content journey. And with where I’m at in my journey I feel like i joined right when I was meant to. Some people like waiting until the right time to do things such has having the right equipment or knowing more about their craft. But with anything you learn as you go. You should never feel pressured into doing something and you shouldn’t hold yourself back from taking a risk or doing something new. When I first started back in 2020 I never thought I would be in the place that I am now surrounded by the amount of support that I am continuously given. Read more>>

Chesca Lilly

There’s a degree to which it just gets down to defining “career”. I’ve been hobby-drawing since before I can remember; even my previous off-the-cuff dates for when my brain switched on and I consider myself to have “become an artist” (fourth grade, drawing every Warrior cat from their book descriptions along with their family trees), but I keep finding work from earlier and earlier despite thinking it’s all been lost by now. Read more>>

Molly Kiernan

When I first started performing comedy, I was twenty-five years old. Trying out an improv class was part of what pulled me out of a bad period of depression (along with therapy of course), and it changed my entire life. I soon started working as an assistant in television, essentially re-starting my career, and spending years getting coffees, picking up dry-cleaning, sometimes working for great people and other times being treated pretty poorly — you know, the works. This is also when I started learning how to write and perform, and it took me a really long time to learn how to do comedy well. Read more>>

Kennedy Michelle

If I could go back in time, I would have definitely started earlier. Even simple things like doing musical theatre or voice lessons, I have only really “started my career” last year. I’ve sung since I was little but just around the house, never outside for performances, extra-curricular activities, or voice lessons. I took piano lessons from around 6 years old to 12 years old and although it has helped to an extent, voice lessons would have been more beneficial to me first and then learning piano later. I rarely use piano now, just to write songs, and even when I am writing songs, I mainly use guitar. Read more>>

Esan Sommersell

If I could go back in time, I most definitely would have started my artistic career sooner. Growing up, I developed a thick callous of doubt, largely influenced by my loved ones. Even my own mother would ask me questions that were meant to be practical—like how I would survive financially as an artist—but they left me confused and second-guessing my path. If I had been able to quiet that noise earlier, I think I could have focused more on the pure joy and therapeutic release that art brings me. It was never about money for me; it was always about expression and connection. Read more>>

Melissa Skirboll

It’s such an interesting question: on the one hand yes, absolutely, I wish I had started sooner. But, on the other hand, I believe, philosophically, that everything happens when and how it should. Had I followed my heart as a teen I would have applied to acting programs and pursued a B.F.A in Theater. There are opportunities that you miss out on when you don’t have that intensive four year training: relationships with other students that you carry with you into your professional life, networking and introductions that can take years to find on your own, and just a grounding into the world that can be difficult to achieve later in life. Read more>>

Miranda Atkinson

My creative dance career has almost always been a part of my life, though I have vacillated between it being my primary professional focus and a hobby. I’ve always loved dance and art, and I vehemently believe in the power of creative expression, but as I’ve grown older, my passion has shifted from seeking those experience for myself to finding ways to create those experiences for others. Nurturing people, and their own pursuit of fulfillment and meaning gives me purpose–it’s the role I see myself playing in my community and the world. Throughout my career, I’ve done that while teaching dance, counseling students in higher education, and through mentoring, but my belief in the importance of people helping and believing in each other has been a common thread. Read more>>

Kymiah Isby

My first fashion show ever was the LA Fashion Week in March of 2023. I recognize this as the start of my modeling career. I applied for The Model Experience in December of 2022. I saw an advertisement encouraging models to apply, and although I had no knowledge of modeling, I felt led to make the first step and to apply. I was accepted soon after which meant that I needed to work on myself and my walk. Of course the big day came and I had so much nervousness and also excitement. When I entered, I met so many great people and creatives. It felt like home. Everything felt right, like this was the correct place to be. If I could go back, I definitely would have started even sooner but I’m glad that I started when I did because I don’t think that my journey would have been the same. I feel like if i started sooner, I would have been way more seasoned and successful but I am still working and I know that it will mean a lot more to me with the journey I am on. Read more>>

Kiana Lane

I definitely wish I had started pursuing music sooner. I know we’re not supposed to have regrets but that’s one of my biggest ones. I’ve been singing since I was little, like 6 or 7, and I’ve always loved writing but I didn’t put both of those things together until a few years ago when I wrote my first song. It was about a boy, naturally. I had just left college where I went to study music and I had a friend at the time who produced his own beats so I decided it was just now or never. If I had started sooner I’d definitely be a lot better at my craft, that’s for sure & I would probably have a few instruments mastered. If I had started like, in high school maybe, I’d have a bigger catalog and probably be further along in my career, but that’s what this era of my life is about. Read more>>

Garrett Wedan

Oh wow this is quiet the question that I have honestly not thought of before. Backstory is the perfect place to start to truly think about this. I started my chainmaille journey in November 2018 and decided in December that I wanted to do it for more then just fun. At this point I felt extremely set in my IT career, I loved my job, I had been there for a little over four years and saw myself retiring there. My wife and I had been dating for about three years things were going well, and I felt like life was in a good spot. Read more>>

Question Marker

It doesn’t matter whether you start art early or late. I formed an artist crew called ‘Mikihasi,’ which is a group of artists based in San Francisco and Korea, coming together to collaborate and create. It’s a precious relationship where we inspire and motivate each other. In fact, I started art later than some of my Mikihasi colleagues. But I don’t think that’s a problem at all. I believe experience is a crucial element. Because I started later, I had the chance to gather diverse experiences, and those experiences have given me richer stories, which are more firmly reflected in my artwork. Read more>>

Diana Haro

I honestly wish I would have put myself out there at an earlier stage in my life. I always knew that art was one of my biggest passions but I always carried self-doubt. I feel that as an artist we do criticize ourselves a little too harshly with details that we forget to look at the bigger picture. We seek praise but forget that it’s more about the creative process and just feeling accomplished with that. I’ve always been the type of person to try different mediums and creative outlets and to follow whatever feels right at the time. I did at some point stop making art for an audience because I was in a situation where my art was not appreciated and put to the side, so it made me step back (I’m talking years). I finally came into the realization that other people or opinions shouldn’t be taken personally, just create. Read more>>

Neeven Albediwa

If I could go back, I would have started my creative journey as early as possible. From a young age, I had this innate love for creating—whether it was filming, designing clothes, music and networking events or just imagining these big, bold ideas that could inspire people. But back then, I let the doubts of others influence me. People told me there wasn’t a stable career in being a creative, and for a while, I believed them. Read more>>

Julie Drake

I started my creative pursuits later in life, it was right before my 39th birthday. I was definitely burned out with day to day life & the monotony that it brings. Every day was the same for the most part, i’d go to work, take care of the house/kids and sometimes i’d go to a second job. Every day was merely an exercise in survival and necessary functions. There was no fun, creativity, excitement, nothing just one responsibility to the next. A co worker was going to an open mic & told me i should perform with her. It was the most excited i’d been about anything in awhile but she had to back out & i was disappointed. The idea of going to the mic lingered & finally i thought why not? So i went one night by myself and I did well, the audience really liked me. Doing the mic brought some fun back into my life so i just kept going! Read more>>

Michael Pushkarskiy

Looking back, I believe I chose the right time for myself. My experience and maturity became my foundation, and a mindful approach to my career allowed me to focus on what truly matters to me. In the end, I value my journey and have no regrets about when it began. Read more>>

Fernanda Granados

This is a tough question but I know that If I had started educating myself sooner in music, I might have had more time to refine my talents and skills. However, I think the experiences I gained before fully committing to my music career shaped the way I approach my art. Moving to Las Vegas recently has reminded me how important timing is in any journey. And now that I really analyze the journey I’ve had, I’m grateful to start at 33 because I wouldn’t have a mature approach towards my career as I would’ve at 18. Read more>>

Empress Pre

If I could go back in time, I wouldn’t change the timing of when I started my creative journey. Everything unfolded exactly as needed, aligning with my personal growth and life experiences. I officially began my creative career during a pivotal moment when I felt a deep calling to use my voice and experiences to empower others. At the time, I was navigating significant personal challenges, including health struggles, and rediscovering my purpose. This fueled my passion for creating platforms like Letz TalkQ, where authenticity and healing could take center stage. Read more>>

 

 

 

 

 

 

 

 

 

Troy Ramcharran

I started Ramar Event Productions at a pivotal time in my life. I wanted a career that brought meaning and gratification. I was ready to embrace the challenges of entrepreneurship and new beginnings, driven by a deep desire for happiness and purpose. It was a big leap into the unknown, but I had my family’s prayers and unwavering support. They wanted the best for me after years as an IT professional. That and fueled by passion and a desire to make people happy with music, I set out to create unforgettable experiences in the event industry. Read more>>