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.

Kamila Gornia

I started my business 10 years ago. Before that I had other side hustles that I was doing on the side in addition to working in a 9 to 5 job or being in college. I think everything worked out the way it was supposed to. The first few years of my business I was still learning a lot, I wasn’t very good at sales and I needed to learn all the “businessy” skills that I was missing from my previous side hustles. Honestly you could have so much life and career experience and it’s still probably not going to be enough for you to feel fully ready to jump into entrepreneurship. You don’t really know what to expect as a business owner until you’re actually owning a business. Read more>>

Andrea Zacarias

Looking back, I was deeply immersed in studying to become a nurse. I had two part-time jobs, one of them being a nanny. Despite all my efforts towards college, I found myself feeling stressed and unfulfilled. Most of my days were consumed by pursuing a path that didn’t align with my true passions. If you had asked me three years ago, I would have wished to fast-forward to a time when I was following my dreams. I often wondered how different my journey might have been if I had devoted all my energy towards my business and where life would have taken me; However, my perspective has shifted. Read more>>

Katia Facio

I began my photography journey end of 2021. It honestly feels like it was just yesterday though. There is still so much that I am still learning. As a photographer when I first started, like many, it started out as a hobby. Which slowly turned into a business. It’s still small and with lots of room to grow. I most certainly wish I had started a lot sooner than I did. If I had, I know that most of my goals as a photographer would have been reached by now. Or so I think. Read more>>

Ta’nyzha Linzer

If I could go back in time, I definitely wish I had started my crochet business sooner. I began crocheting when I was 10 years old, taught by my grandmother. At that point in my life, I was just starting to explore hobbies and interests, and crocheting quickly became my favorite. My grandmother’s guidance made the learning process special and enjoyable, and I’ve carried that love for crocheting with me ever since. Read more>>

Henry Vildosola

I didn’t start writing raps until I was about to turn 25, so I started pretty late compared to most people who do this. Growing up, I had heard (and internalized) this belief that people are either left-brain, logical, scientific people or right-brain, artsy, creative people. And I was really into science and I wasn’t very good at drawing so I just figured I was more the former than the latter. Sports became my main focus around age 12, and I ended up majoring in astrophysics in college and running track and field. Ironically, it was sports that led me to music. Read more>>

Ena Castillo

The way I ended up working as a creative is interesting. During my teenage years I used to be part of a folkloric ballet and we would travel across my home country performing dance shows, that ended when I started college as I had to leave my city and live in a college town where I was pursuing my undergraduate degree. During those years I ended up doing my work-study hours at the university’s marketing department and somehow, they gave me a camera to take photographs of their events, they also motivated me to start an online blog and start writing as part of some marketing campaign they were running. I remember that out of all my classes, I only cared about literature and philosophy, although I was rather good in accounting. By the time I finished my undergraduate degree I was fascinated by the creative field, mind you, I graduated from business school. Read more>>

Heather Bayles

I kicked off my career at just five years old, and I have to say, I have no regrets about that because that’s when I truly fell in love with Theatre! Looking back, though, if I could turn back time, I would choose not to take such a long break. I stepped away for twenty years, and that’s the one thing I’d change. Even if it meant just doing one play a year or trying to find an agent in Ohio—something I had no idea was even a possibility back then! Read more>>

Hannah Anema

I am currently in the throws of transitioning to a full-time artist. I would rephrase the question, “if you had the option, would you start your creative career sooner or later?” I made my art business official 3 years ago and I feel like things are really taking off this year. I have thought to myself, many times, what it would be like if I finally decided to become a full-time artist. Currently I run my art business on top of a full-time job working for the Minnesota Department of Natural Resources as a fisheries specialist. I have a very unique job working on one of Minnesotas largest rivers, the Minnesota River. Read more>>

Frau Sakra

I came to art late, but I don’t regret for a moment what I did before transitioning to art. I had a 15-year career in publishing in New York City. As a book editor, I learned to do picture research and immersed myself in the subject matter of the books I was working on. Those experiences have carried over into my art practice and are invaluable to me now. I had a child, whom I had a wonderful time raising with my husband, artist and set designer Daniel Saks. Our now-grown kid, Kira Saks, is about to enter their senior year at Rhode Island School of Design and is already selling their own art and zines. The saying “You can do it all, just not all at once” sums up my life pretty well. Read more>>

Auriel Jones

As a child I was heavily involved in the performing arts. Saturday mornings were total chaos. My mom would chauffeur my sister and me around to dance class, piano lessons, and acting class. Her goal was to keep us busy on the weekends but the arts became something that was so engrained in me. My first love was tap dancing. I really excelled in class and it was something that brought me so much joy. I’ll be honest, as I got older my interests changed and my mom wasn’t the type to make us stick with something if we were no longer invested in it. Read more>>

Kody Desmond

If I could go back in time, I wish I would have started my creative later. I started my social media journey when I was 16 years old by posting random dances and lip syncing videos on Tik Tok. At this time, I was growing my viewship and fanbase very quickly but quickly came to terms that I didn’t have a specific niche. Starting at the age of 18, I started to discover what I wanted my viewers to take away from my social media accounts. I am a huge advocate for mental health, especially within the LGBTQ+ community, and providing a safe space for people to fully express who they are. Read more>>

Naser D. Shahrivar

I started painting at the age of seven, I just wish that I had taken classes early on because the struggle was real. I had to learn all of it the hard way, trial and error. I wish I had listened to my ninth grade teacher when he said “Be good at one thing!” But, back then my idol was Leonardo da Vinci who was a painter, draftsman, engineer, scientist, theorist, sculptor, and architect. With this in mind I had a difficult time in being good at just one thing. Read more>>

Ekaterina Fredricks

If I could go back, I think it would’ve been great to start my photography career sooner. I started taking it seriously when I moved to the US in 2020, which was a huge change in my life. I was figuring out a new country, culture, and everything else, and photography became my way of navigating all that. Read more>>

Veronica Labretta

I started studying artistic disciplines when I was only 6 years old, so it all started as a game. But I felt free, when I was in the theater and had to perform in front of many people, when you act, dance or sing, when you do something that gives emotions to an audience for those moments you feel like you are in another world. There is only your character, a new life, you stop being the person you are every day, and it’s beautiful when you can make someone move. In my artistic career I have studied musicals, screenwriting, dubbing, acting and the question I get asked most often is… Read more>>