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.

Francisco Amaya

Absolutely before. I wished I never had to wait to rediscover my passion. A poignant tale of an immigrant wanting to be a photographer but thwarted by the complexities of their status. In the heart of the American Dream, there exist a narrative about the DACA recipient. We were kids taken across borders following their parents. We don’t know our native country and feel unwanted in this one. Read more>>

Mia Marrero

While I truly believe I started tattooing at the best time, something I wish I would have done sooner would be to give myself understanding and grace concerning my dream sooner. Even though I was so intrigued by the tattooing industry, I was so held back by things like “what would other people think?” or “how would this relate back to your college degree?” I would always think back to who I “should have” been or what was a typical path for someone my age. Read more>>

Helen Woltering

For a long time I wish I had started my business sooner. While studying at the University of the Arts in London, I had conceived a business idea during my time in the fields of fashion and media production. Despite my passion for these areas, I sensed an essential element missing, leading to a sense of emptiness and an identity crisis at the time. My pivotal encounter with coaching occurred during a seminar in central London. Read more>>

Jahleel Gordon

If I could go back in time, I wish I would have started my business earlier. Simply because where I am in life right now with being a new mom and finally getting started in my career, I would’ve had more time to pour into it deeper. But in contrary to how I feel, I’m glad I didn’t because the knowledge I have now has allowed me to execute much better. I know much more now than I did then. Before I just had an interest in skincare, now I eat, live, and breathe skincare. Read more>>

Alex Etter

I love this question! I truly came into business at just the right time. I graduated with a degree in criminal justice and social work in December of 2016, moved towns and quickly figured out that what I went to school for and what I was meant to do with my life, were not even in the same ballpark. I spent many years after, from 2017-2020 working healthcare and working on myself, figuring out what was next. Read more>>

Cristi Bundukamara

Reflecting on the journey that led to the creation of my business, I genuinely feel that the timing was exactly right. I started by business three years following the heartbreaking loss of my first biological son, who bravely battled a rare neurological condition. Over a decade, I devoted myself to his care, an experience that was both profoundly challenging and transformative. Read more>>

Amelia Castellanos

They say hindsight is always 20/20 – well, after the wild ride that was 2023 I must say, I think “they” are onto something. For over a decade I ran a digital agency based in DTLA that specialized in digital marketing + eCommerce. We were a one-stop shop with the ability to run your eCommerce business from A-Z, including content creation. It was an exciting time filled with constant challenges and pivots. Read more>>

Raven Gates

A part of me reflects on the desire to have started my entrepreneurial journey earlier, when I could share the joy of baking with my grandmother before her health challenges. Unfortunately, she can no longer join me in the kitchen today but is still my hardest critic. However, I was navigating the aftermath of being a survivor of sexual assault, grappling with a new diagnosis of chronic pain and chronic fatigue, and facing the verdict that my health ruled law school out of my future. Read more>>

Rori Mitchell

If I could go back I would have started my. Business sooner than I did. I started my travel business and just a few months later we were in a pandemic that shut down almost all travel. I had my very first group cruise plan which was cancelled due to Covid. I think if I had started sooner I would have been able to get more clients and have more time to master the travel industry. Read more>>

Miles Brown

I truly wish I could have started my business much sooner. I wish I just knew what I wanted to do sooner. My grandma would always tell me “Miles you need to use your voice” and I never knew how I would do that. I was working but didn’t know that my passion to teach and to speak could be my business. I had been speaking in church and with my fathers business for years before I knew how to take those skills and turn it into a paycheck. Read more>>

Natasha Davis

Honestly, I wouldn’t have started my business any sooner or any later. Journey Accepted Life Coaching was established in July of 2023 and it was at just the right time. There was a strong inclination that it was time to leave my job and step out on a journey of entrepeneurship. Prior to starting my business, I had been working in Property Management for 3.5 years. Read more>>

Kenneth Ortiz

Sometimes I find myself wishing that I moved forward with becoming a professional photographer earlier in life. Although I believe that I stepped into the photography community at a good time in my life, I often wonder what kind of progress and person I would’ve been had I taken myself more seriously. I started exploring the opportunity of being a professional photographer in 2019. Read more>>

Natasha Trinidad

Sometimes I do wish I started my career a lot sooner. I’ve always known what I’ve wanted to do, but I still went to college and got my degree — which I do not regret either. I feel like everything happens for a reason and I’m doing everything on my time, but some days I do wish I had that head start in my career. Read more>>

Grant Goldsworthy

I’ve made art since I was little boy, and always had the confidence in my own taste to make art that I liked. I came into art as a musician – I love to sing. I started playing in garage bands at the age of 13, and have been making music since. I picked up a camera along the way to take pictures of my band’s album covers, friend’s album covers, live shows, etc. My work shooting portraits of musicians quickly escalated to shooting models, and other creatives. Read more>>

Maya Dukaric

I wish I had gotten into content creation and influencing years ago when it first started! I was almost scared to post online! In high school, I started to post on YouTube and create a YouTube channel! My first video did so well and got over 5000 views. But coming with views also came with some hate comments. I remember walking into Highschool the next day and everyone was commenting and making fun of my videos… Read more>>

Meghan Chambers

I have participated in some level of creativity throughout my life – growing up remotely in Alaska, practicing art served both as an important connection to exploring the natural world around me, and for needed escapism during the long and dark winter months. I cannot say I grew up knowing I’d be a professional artist, but I did know I’d be creative for years to come. Read more>>

Chelsea Simone

I do sometimes wonder what would be different if I had pursued a professional career immediately after high school instead of earning my BFA. I think I was much more confident and less inhibited right out of high school. When I went away to college, I was in classes with dancers that were more flexible than me, thinner than me, had better technique than me, etc. This made me self-conscious and I was sort of forced to sit with that. Read more>>

Baltazar Barron Jr

I Became a Marine 1973 i was sent to Okinawa from Okinawa to Vietnam,for Evacuation of the people. i did my 3 year tour, at 29years old 1991, working construction i had an accident at work, i couldn’t work for 6 months, i was always creative so i wanted to try out painting, my first painting was a copy of Thomas kinkade, summer home. it came out beautiful that started my Art adventure, i have 400+ pieces of Art, i have been featured on Inland Empire Magazine. Read more>>

Tim Breaux

I think I started my creative career at the right time. It was when I was in my early 40s. I studied linguistics through college and graduate school and pursued an academic career as a linguist until a life-changing experience happened. I was diagnosed with breast cancer when I was 40, just after I started teaching full-time at a university. All the treatments went well, and I have been cancer-free. Read more>>

Kayo Bogdan

I think I started my creative career at the right time. It was when I was in my early 40s. I studied linguistics through college and graduate school and pursued an academic career as a linguist until a life-changing experience happened. I was diagnosed with breast cancer when I was 40, just after I started teaching full-time at a university. Read more>>

Rob Nelson

I wish my creative career had started sooner. Like most people, everyday life and its challenges came first. Having a regular job, a family, financial responsibility, and the need to make a living, pushed my creative aspirations and goals aside. I finally decided to take the plunge and pursue a career in scriptwriting, with the mindset that whether I succeeded or failed, it was better to try than not try at all. Read more>>

Sara Fair

I always wanted an art career sooner but needed to have it later since I didn’t have the discipline or understanding of what it meant to run a business. Like many people, my art career has taken many turns and a backseat while raising a family (with her supportive husband) to juggling a career full time outside the arts. “Before 2010, I was able to paint full time but did not understand anything about business.” Read more>>

Tzu-Ying Chan

I believe every experience holds significant value. The journey of exploration, continual learning, and personal growth across different phases in life has profoundly contributed to my understanding of self. Even if I could start anew, I would make the decision based on the circumstances and experience of previous stages. Each phase of my journey served as a valuable learning process. Read more>>

Robert Abernathy

This is a great question. I pursued a career in music briefly while going to college at Jacksonville State University. But once I graduated, I immediately dove into my career as a teacher. I loved teaching and coaching and it dominated so much of my time that music and performing was not on my radar anymore. 15 years into my career as a teacher, I started playing shows more and more frequently as well as began to work more diligently on my craft as a songwriter. Read more>>

KeShun Baber

In retrospect, I find myself contemplating whether I would have preferred to commence my creative career earlier or later. Navigating my teens with limited resources and lacking a business mindset, I now appreciate the advantages that come with age. Over time, I’ve gained access to opportunities that were once beyond reach, and my journey reflects the benefits of maturity and going with the flow strategically. Read more>>

JD Walker

Definitely sooner, but I know it all has to be in God’s timing. Read more>>

Simone Scholes

I began my career at Art College but was very quickly pulled onto a different track of the corporate world of fashion. Over the years I always painted occasionally in my free time painting family and friends in watercolor and pastel, even winning an award at a local art association gallery show for a portrait of my son, but I lacked the vision of how I could incorporate this into a full time career. Read more>>

IVY BAILIE

I could be more exact by saying that I didn’t realize that I could have a “career” as an artist. I am not formally educated or trained as an artist. Creating and drawing and painting are activities that I have enjoyed since childhood, but they had always been just that, activities to be done in spare time or when I wanted to give a handmade gift. Here’s the timeline. I audited one course in college called “Painting For Pleasure” in which the students were required to spend a bit of time in each of the mediums of oil painting, acrylic painting and watercolor painting, and then choose one of those mediums to complete the semester. Read more>>

Melissa Adao

My name is Melissa Adao, and the dance community knows me as Bgirl Mel. I am a 44 year old competitive Bgirl, and my breaking journey started 7 years ago, which is an uncommon factor in the breaking scene. Starting this dance at a later age brings both physical and mental joys and challenges which I have been transparent in sharing on my social media. By doing so, I’ve been sharing a message to the world that “you’re never too old, and it’s never too late to pursue your dreams”. Read more>>

Christina Conway

I wish I had pursued my creative career sooner. In my younger years I spent far too much time being concerned with fears of criticism and watching others create. Throw your self doubt out the window and do it anyway. Read more>>

Abby Chu

I think this is a question that almost everyone has thought about at some point in their lifetime, regardless if they are an entrepreneur or not. History has a way of presenting itself and I think for myself, I could have had a very opportune time to start my business. Covid during 2020 impacted all of us and at the time, I wasn’t employed as a regular benefit earning employee at a hospital, but rather, employed as a student intern that was required for my coursework. Read more>>

DJ Carr

Neither, I believe that things happen when they’re suppose to, and not always when we want them to. Getting my first camera in 2011 was important for my development as an artist and an individual. I was in my first year of college, adulthood had just started.. I was in a position to really take a deeper look into what was happening in the spaces I was choosing to be in. Read more>>

Lea Pascal

No. 20 year old me had no idea that she was an artist. I came to screenwriting in my 30s, attended UCLA’s MFA Screenwriting program in my mid-thirties, and just finished my first decently funded short film at 39. I also just had my first baby at 39. I truly do not think I could have done any of these things any earlier and been any good at them. Read more>>

Felicia Madison

Being that I started my career in my 50’s of course I wish I had started it earlier. I never really knew what I wanted to do growing up, or I did but my parents just were not supportive (broadway dancer). After college I floundered and went from job to job to job looking for fulfillment. Before I was able to find my passion I found myself married and pregnant. Motherhood became my full time job for 30 years. Read more>>

David Kang

Reflecting on my journey as a musician, I’m often tempted with the notion that perhaps I didn’t start taking my career seriously as early as I had hoped. The past eight years of my college education have proven invaluable. I’ve been surrounded by incredible teachers and colleagues who are passionate about their craft and strive for excellence. Yet, my educational path has been driven by insecurities and a persistent desire to catch up with peers whom I deeply admire. Read more>>

Elijah Patchen

I think that when it comes to this question, I often had thoughts over the last couple of years that went something like “if only i had started earlier, I would be so much better/more successful/happier” or whatever. However, these thoughts often resulted from me comparing myself to someone else. The comparison game is a zero-sum game that leaves you feeling empty and resentful. Everyone is on their own journey. Read more>>

Anthony Cally

I’ve tackled this question in my head quite a bit. Possibly from a lack of imagination ( or a fear of the constant variables that would make up an alternative future), but i do feel like i picked this up at the right time. I moved to Los Angeles right after college graduation without any job prospects or any idea what I would do once I got out here. Read more>>

Chandler Vatavuk

This is an interesting question, just for the aspect of it being a dichotomy of age. I started my career of acting at a younger age in college, 20+ years ago, but I stopped it, and I am now re-birthing it in my 40s. So my answer would be, should I have continued it instead of putting it on hold for 20 decades? That is the question. Read more>>

Gunner Lindbloom

Yes I absolutely wish I would have discovered my writing gift as a young man. If I had, I probably wouldn’t be here right now. I would be on some remote trout stream on Labrador, quietly living out my days with my wife. But such was not God’s plan.I always knew I have the gift or creativity. It used it in my criminal life before prison, for various scams and hustles. I used it on girls. Read more>>

Joanna Beckett

No. Had my creative process begun earlier or later, my approach to it would have evolved differently. It wouldn’t necessarily be better or worse. The energy of my work would have mirrored a version of myself from another juncture. You would see different paintings. Read more>>