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.

Chelsea Willett

It’s hard to say if I wish I had started it sooner because the journey was rich of meetings, beginnings and endings that all informed my work and life. I originally launched solo and full time in 2018 but had been working as an artist since 2002 and as a graphic designer since 2013. I quit my job and hoped to make it hustling art shows and popups and supplementing with graphic design. The momentum was great at first and I did so many art shows and popups for 2 years that I definitely burned out. It was also expensive financially and energetically and not all of them had a great return. I ended up leaning in graphic design much more and allowing my art life to breathe and join the popups that I fancied. Read more>>

Karlynn Only-sydnor

If I could go back in time, I do wish I had started my business sooner. Personal training or coaching wasn’t my first career choice, I originally studied to be a computer engineer. I had a passion for fixing things and solving problems. I also loved math. I would coach and train clients on the side for extra income but I never thought of it my main career. In the eyes of my family and friends it wasn’t a sustainable career choice. However, I did know that ultimately I wanted to be able to help people live healthier lives; It was something I had dreamed of doing since I was a kid. As I was going further and further into my education as an engineer, I began to feel that this was not the right path for me. I couldn’t see myself fulfilling my passion in the direction I was headed and I wasn’t sure how I was going to get there. So I switched gears completely and began to pursue a degree in business. Once I started studying business, things started to make sense and I could see how I could do what I loved for a career. I still didn’t jump right in to forming my personal training business. I got a job with my local government and worked there for almost 10 years before I was able to do personal training full time. In those 10 years I got married, had four kids and finished school. Read more>>

Rashaad Slowley

If I could go back in time, I wouldn’t change the moment I started my business. I truly believe everything unfolded for me according to God’s timing. Interestingly, I never dreamt of owning a fitness business or becoming a health and wellness coach. Six years ago, I was working behind the Genius Bar at the Apple Store. I trained a lot of local athletes on the side, despite not having any formal certification at the time. Thanks to my athletic background, I had a solid understanding of how to train and how the body should move. Eventually, I decided to go part-time at Apple and enrolled in the American Academy of Personal Training. It was a full-time, four-month program that really taught me the ins and outs of personal training. After graduating, I was hired at Equinox and within just two months, I had a full-time schedule. From there, I continued building my career—working with brands, maintaining a full client list, and earning several certifications. Read more>>

Victoria Rosas

If I could go back in time, I would start my journey right alongside the opening of Roses Esthetics in the heart of the Poconos in 2023. My path began when I became a licensed esthetician in 2019, embarking on the entrepreneurial journey I always envisioned, driven by the desire to be my own boss and the understanding that true growth requires starting from the bottom, learning every aspect, and working my way up. Roses Esthetics is a reflection of my journey to embrace inner beauty and self-confidence, and the name holds personal significance, inspired by my last name, Rosas, which means “rose” in English. Originally from Queens, New York, I grew up with a birthmark that was a source of pain and insecurity, and at five and six, I underwent surgery to remove it due to cancer risks. My early dreams revolved around law and criminal justice, but a pivotal call from my mother led me to beauty school—a path that connected me to my grandmother’s legacy as a 1970s cosmetologist and ultimately shifted my focus to self-love and skincare. Each lesson and every experience has shaped my journey, from learning under established spa owners in the Poconos to building Roses Esthetics into a space where others can feel beautiful and empowered. To aspiring estheticians, follow your heart, and let your unique story fuel your journey; the beauty industry is full of growth and fulfillment, and while the road to self-employment is challenging, it is profoundly rewarding. Read more>>

Michael Brown

I really got serious with my business about 2 years ago (BROWNBOICOLLECTIVE) my mind and support system is much more better. I wish I could’ve started sooner but just with the energy and support I have now. I was surrounded by too many crabs in a barrel to ever elevate with my career. Read more>>

Lanre Ako

From the moment I picked up a camera as a kid, pursuing creativity in filmmaking and photography felt natural, but it wasn’t always easy. My parents encouraged me to do something different, to express myself, from a very young age. By age eight, I even had a little website where I’d post videos I’d filmed on our family camcorder. Nobody really watched them, but I fell in love with the process of filming and editing just for the fun of it. But bringing a camera around, especially after moving to a new city and school, didn’t exactly make me popular. I remember getting picked on, kids asking, “Why are you filming? That’s so weird. No one’s going to watch that.” It was seen as “cringe” to do anything out of the ordinary. That attitude followed me all through middle and high school. I kept making vlogs, videos with friends, and trying to build an online following, but I learned to do it quietly. The teasing made me feel like I had to hide my passion, so for a long time, it was just my “weird little hobby.” By college, I’d almost given up on it entirely. I couldn’t see how I’d ever make a career out of creative work, especially when people around me would joke about anyone trying to make videos. Read more>>

Shijia Luo

“If you get on the wrong train, immediately you realize it, get off at the next nearest station. The longer it takes you to get off, the more expensive the return trip will be.” This quote resonates deeply with my journey of finding my way to a creative career. Like many, I spent my early years focused on what seemed like a “proper” career path, one that aligned with conventional expectations. I began my career in business, yet felt a lingering sense of dissatisfaction — an unshakable feeling that “my element” was missing. As a child, I could spend hours drawing, completely lost in the process. My creative instincts were strong, but they were tucked away as I grew older, overshadowed by other expectations. Signs and quiet urges would occasionally nudge me toward art, but I didn’t answer them, leaving that kid who loved to draw uninspired and disconnected from her dreams of becoming an artist. Read more>>

Therron Dumas

I most definitely wish I would have started sooner. I started at 38, I’m 51 now, and I’ve done 64 movies, if I would have started younger… Beyond the fact that I would have done more of course, I would have been able to do different types of film, especially the action genre. Read more>>

Marie Parmer

I honestly can’t imagine starting this chapter of my career any sooner than I did. I worked in marketing and advertising as a graphic designer and then an art director for over 30 years – almost entirely for others – before taking the leap to go it on my own as an artist. There’s a lot of stability and predictability in working for someone else, and that was perfect for me for many decades. I also really enjoyed my work. I thrived as a “worker bee.” It was my element. In art school, I was always painting, drawing; creating. But after graduation, I didn’t pick up a paintbrush for about 20 years. I just didn’t feel the pull. Plus, I was working, and later had kids, so life was pretty busy. I was creative in other ways – in my design work, at home cooking, making things, taking photos, etc. – but not painting. Many years later, a friend I reconnected with from art school convinced me to take painting classes again. She was very persuasive (and flattering about my work) and that was all it took! Those classes sparked a love for painting I hadn’t felt before. Read more>>

Rachael Hanel

My first job was as a newspaper reporter and copy editor. I majored in journalism in college. My family always watched television news and my dad brought home newspapers each day, so at an early age I was captivated by the drama of real life. I liked to read and write, so by about age 12 I thought journalism would be a fun career. I had never considered any other kind of writing. I loved to read books, but actually writing a book was nothing that had ever crossed my mind. In college I learned a little bit about literary journalists like Gay Talese and Joan Didion. I was intrigued by that blend of reportage and first-person narration, but didn’t get a chance to practice it while I was working as a journalist. When I was pursuing a master’s degree in history, I took a creative nonfiction workshop. I wrote a personal essay about a memory I had growing up as a gravedigger’s daughter. I enjoyed this type of writing and I thought, there’s more where that came from. At that point, I thought maybe I had a memoir in me. Read more>>

London Heist

When I first got to college, I started on the business school track. A couple of years in, after spending all my free time building a painting portfolio to apply with, I made the radical switch to the painting program at Indiana University Bloomington and earned my Bachelor’s in Fine Arts. I don’t wish I had started out in the arts department, to be honest. My business courses proved fundamental in establishing myself as an artist and making sales later on. In the painting program, I had 24/7 access to a private studio and the freedom to create anything I wanted. The only real requirement was that I was making a LOT of work. My later start in the program gave me a deeper appreciation for what a privilege it was to be in a residency-like environment, and I’m so grateful to have had the chance to take my craft so seriously with the support of my professors and fellow artists. Read more>>

Lamar Carter

So I know you’re not supposed to start things off with so but lol. I would say that’s something I had to overcome. In the past for five years I overcame that feeling cause sometimes I wish I did start early because I always wanted to be in the realm of the arts. Rather be music modeling, drawing painting anything of that creative field is something that I dream of being in. I love creating, I love being inspired and motivated by other’s creativity. I love how beautiful life is. We draw so much inspiration from life. Our experiences rather good or bad it’s a necessity to breathe our ideas to tangible form. In my late teens early 20s I was so friend dependent that if my friends wasn’t with it, I wouldn’t do it. It took me a very long time to Stand on my own two, and just go out there and enjoy my space, my time, and go after my interest things. Go after everything I always wanted. Read more>>

Ali Alassadi

Honestly, I believe that everything happens for a reason and at the right time. But if I could go back, I would have a heart-to-heart with my younger self. I’d tell myself it’s okay to love art and to be artistic—there’s nothing to be ashamed of, even if people around me didn’t value or understand it. Growing up, I often tried to fit in and even denied my love for art because I felt like it wasn’t “important” or that it made me different. But over time, I came to realize that this love for creativity is exactly what makes me unique and sets me apart. During the 2020 pandemic, I finally returned to art as a way to cope. It was my safe refuge when life got dark. When people began showing interest in my work, even wanting to own what I created, it was a life-changing moment. Selling my first piece made me realize that my art had real value. From then on, I invested in myself, my creative abilities, and quality art materials, putting everything I earned back into my growth as an artist. So, looking back, I don’t wish I’d started sooner or later; I’m grateful for the journey as it’s unfolded. But I would tell my younger self to embrace what makes me different—because that’s the real gift. Read more>>

Nat Rosa

OH DEFINITELY! I think I would be such a different person if I had taken art seriously or if I had been told pursuing art professionally was an option as a kid. Sadly, like many of my friend and colleagues, I was raised on the idea that yes, art can be a super fun and cool thing to pursue but it wasn’t seen as a real “career” (whatever that means) and that I was going to be a starving artist because art would leave me broke. Well, they both so right and so wrong. Art can leave you broke if you don’t surround yourself with other artists, share tools and resources with each other, and don’t know how to practice art in a way that is both fulfilling and sustainable. Read more>>

Jasmin Gonzalez

If I could go back in time, I would have started my career sooner than later. Especially before I became a single mom. I started the beauty academy back in 2019 and as a single mom, it was a difficult time. I worked a 9-5 Full-Time job and going to school on nights was very tiring. I couldn’t do internships or do more makeup courses because of work and my daughter. I do sometimes wished I have started after high school in 2011 when I wasn’t thinking about having children and had a lot of free time. I believe if I would have started sooner, I would have also gone through cosmetology school as well and would have been doing both hair and makeup for TV/Film and Special Events. My experience would have been off the roof and I would have had a very different look on my resume. But, as I look back, I wouldn’t have had the experience I have today if I started when earlier. Yes, there were some downs during my career because many people wanted free makeup looks but overall, I lived and learned so much during those times. Now, as a freelance makeup artist, I was able to work with other artists and learn from them. I know if I would have done this in my early 20s, I would have been so naive and selfish. I’m just glad I’m not like that as a makeup artist because I know I wouldn’t have made it til this day with that mentality. Read more>>