The uncertainty of entrepreneurship causes many entrepreneurs to put off starting their business. For others, losing a job or other economic hardships push them starting their businesses earlier than expected. In our conversations with thousands of entrepreneurs we’ve seen so much variety in when, how and why people started their business and so we wanted to share a wide variety of views and reflections on the question of whether these folks wished they had started sooner or waited longer before starting their businesses.

Emma Golden Miller

I feel I branched out on my own at the exact right time. I wouldn’t have done it any sooner or any later — it happened exactly when it was supposed to. Let me explain. Read more>>

Andrew Guasch

Reflecting on my entrepreneurial journey, I see each phase of my career as a crucial building block towards where I am today with Authentic Dynamics. My time as a server from 2011 to 2016 was foundational, teaching me invaluable lessons about human connections, empathy, and the art of service. I learned how kindness, humor, and making people feel special not only enhances their experience but also encourages loyalty and trust. Read more>>

Ieashe Deal

If I could go back in time I would have started my business sooner. My mother has always been the guru of creations in my eyes, but it did not start with her. Growing up my mother was always working on something it did not matter what it was. Read more>>

Brittany Powell

My journey into the world of cosmetology began unexpectedly in 2015, marked by personal loss and a shift in perspective. Despite my initial career path as an English teacher, life’s challenges led me to embrace my passion for hairstyling, a skill I had nurtured since middle school. Read more>>

Jordan Sylvain

I would have liked to start my business sooner, but COVID could have been a hinderance and ended up being the catalyst. I love being my own boss and wish I would have started sooner, but I am glad I didn’t have the uncertainty during the mandated closures. Read more>>

Gloria Holloway

My experience being an artist has been more of a journey. I’ve learned so many things from signing contracts to actually creating. I honestly wish I had started sooner but I’m enjoying every step and wouldn’t change a thing. Read more>>

Ashley Walters

I always knew I wanted to live a creative life, but I never knew how to properly express it. Growing up, I would tell people that I wanted to be an optometrist, then a journalist because at the time, I believed it sounded more respectable than saying “I want to be on stage creating art. Read more>>

Sarah Lobotsky

I started my career as a creative. I worked as a graphic designer for print advertising for a decade before the 2008 recession. That’s when I decided to go to school to become a teacher. Now, 15 years later, I am so grateful that I can lean into the arts, while also loving my work in the classroom. As an avid art collector, I have been inspired to pick up the brush again. Read more>>

Madison Banks

Sometimes I wonder if I should have started sooner myself. I didn’t go to college until I was 21. I felt leagues behind everyone else, especially since I hadn’t really touched digital mediums before. I was always a traditional artist. Read more>>

Karen Merkin

When I was contemplating what I would study in college, I was choosing between teaching elementary school or commercial art/ illustration. My parents’ advice was to become a teacher, because they believed I wouldn’t be able to earn a living as an artist. If I could choose again, I would have definitely studied art in some capacity and started my art career while I was in college. (Although my classrooms did have the most creative bulletin boards.) Read more>>

Stacy Wong

I think it was the perfect time to start my creative career. I had always dabbled in making art while working fulltime at a corporate job but 10 years ago, life circumstances and an opportunity to jump start my creative endeavors was calling me. Working creatively gave me greater flexibility to support my family and their needs. It allowed me to work from home, be more present in the moment, and attend my boys’ high school extracurricular activities without feeling guilty. Read more>>

Evan King

As a freelance ballet dancer, the question of whether to begin ballet earlier or later always intrigues me. While many would consider it a straightforward decision to start sooner, my perspective differs – not necessarily. Commencing ballet at a later stage does present its own set of challenges, such as grappling with flexibility limitations or requiring more focused conditioning. Despite the political and cultural context I navigated during my youth while trying to discover my true passions, pursuing ballet as a career never seemed viable. Read more>>

Preeti Varma

I have no regrets about when I started my creative career. Each stage of my life offered unique insights that informed and enriched my life and creative work. Starting a creative career later in life, after accumulating years of life experiences, has given me a distinct perspective. So, while starting sooner may have had its advantage, I cannot deny the value my past work experience offers in supporting my artistic endeavors and art practice. The time is always right when you are ready to pursue your passion. Read more>>

Mark Mou

I wished I had started my creative career in animation much earlier. I would say my undergrad experience with film production as well as Pandemic really change my views on the film and animation as mediums. Read more>>

Kelly Bartnik

It was socially ingrained in me for a very long time that being an artist doesn’t make any money. It was always the expectation and the assumption that I would need a ‘normal’ job in order to support my creative “habit.” And for years, I did exactly that and most of my peers were doing the same thing. Read more>>

Grace McGinnis

It can be tempting to look back on my life, specifically my 20s, and wish that I had made different decisions regarding my creative journey. When I started taking my first college art courses, I had all of the enthusiasm, and none of the maturity or endurance to complete a formal art degree. During that time, I was struggling pretty heavily with depression, anxiety, and alcohol abuse, and I ended up withdrawing from more classes than I completed. Read more>>

Nevin Shoker

I definitely wish I would’ve started it sooner. Even though I started creating and making music at the age of 14, I didn’t move to LA to fully pursue my passions until I was 23. If I had moved to LA when I was 18 and went to college out here then I feel like I would’ve leveled up a lot faster. Mainly due to the creative environment that exists out here. My hometown of Modesto, CA is a quiet place mainly for families. Read more>>

Mingeon Jang

If I had engaged in music at a younger age, I believe I would have cultivated a much deeper understanding of it. More importantly, this profound understanding could have allowed for a broader and more diverse range of expressions in my musical journey. The emotions and imagination of a younger age possess a truly remarkable power. Read more>>