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.

Maya Newlin & Jasmine Krause

Although KAMO Studio was formally founded in April of 2024, both of us had dreams of starting an interior design business prior to meeting one another in 2022. It did take several months after meeting and coming together before we finally pulled the trigger.

Cofounder Maya says, “It was a dream each of us had individually, then intertwined when we were aligned and both felt it was the right time. There will never be a perfect moment to start the journey of entrepreneurship. You’ll always wish you had more experience, more connections, or more stability. Taking the leap and just starting is the first step toward gaining those things.” Read more>>

Nellie Wells

If I could go back in time, personally I wouldn’t change anything. I think my business started during a perfect season of life for my little family. Before we moved, I didn’t have the space for an in home bakery. We had moved less than a month before I decided to start my cottage bakery, on March 22, 2024. Now that I am coming up on my one year Anniversary with my small business, I am full of gratitude and I can’t wait to see what the future holds. Read more>>

B.w. Jackson

I would make a distinction between the creative work and the technical work. I have just about always had an urge to write, and an urge to improve my writing — a natural inclination to become absorbed in tinkering with phrases and sentences. But I wish I had been more intentional in my efforts earlier. I didn’t begin to approach creative writing with a serious mindset until after college, when I no longer had regular writing assignments, and I realized I needed to be writing all the time to stay sane. The stable jobs I had in my twenties (as opposed to the various unstable jobs) were all heavy on writing and editing. That was enough, up to a point. Eventually, I needed to be devoting my writing energy to my own creative vision. I pivoted into jobs that required less writing so that, as much as possible, I could selfishly guard my writing for myself. Read more>>

Renée Ortiz

Oh, the what if’s… I often ponder, what might have happened if I had stayed at Otis and went all in for a career in art at a young age. It was exciting to be admitted into what was then called Otis Art Institute of Parson’s School of Design. I worked hard at creating a portfolio to earn a spot. I started immediately the summer after graduating high school. Even though I came from an highly sheltered Catholic school background, jumping in made sense. I became our class representative and fought for a first year’s gallery show. But navigating life there was difficult. I got scared into making ‘normal’ life choices and transferring to a more traditional college (LMU) to get my teaching degree instead. Maybe I thought that keeping art as a hobby would be enough. Read more>>

Christina Brennan

I started playing music at a young age, with the guitar being my first instrument. In terms of learning, I couldn’t have started any earlier, and when it comes to pursuing a career in music—a field that’s notoriously tough to break into—the earlier the better.
Music has always been my true passion; there was never really anything else I considered doing. After graduating from high school, I earned my bachelor’s degree in songwriting from Berklee College of Music in 2018. Like many grads, I found myself facing the big question: “What now?” and “How do I turn everything I’ve learned into a successful career?” Read more>>

Lynette Hulse

Looking back I wish self doubt hadn’t been an issue. Starting my business later would have meant missing out on valuable experiences and growth opportunities. Conversely, starting sooner could have allowed me to learn from mistakes earlier and build a stronger foundation. In hindsight, I wish I had started sooner, trusting in my abilities and seizing opportunities without hesitation. Believing in myself is the key to building success. Read more>>

Kristin Brown

This is a hard one because I do feel like the timing of starting my business was right. I started my business in the fall of 2023, if I could go back I do wish I would’ve started in the summer of 2023. I started training with my mentor in March of that same year and I just wanted to be really ready before I started offering my services to paying clients. I did so many practice photo sessions to make sure I had my lighting and process just how I wanted, but I do feel I could’ve started my business sooner and offering sessions to clients sooner. During this whole process of starting my business I was pregnant with my 4th baby and took some time off in the spring of 2024 when he was born. It would’ve been nice to have been able to start sooner before I took off for maternity leave, but in the end it’s all worked out! Read more>>

Natalie Jeans

Yes! I do wish I had started my photography business sooner. I have been a photographer for 7 years, but only full-time for about 2 years. I began simply as a mom looking to capture pleasing images of my son because I was dissatisfied with how his school images would turn out. I would have spent more time refining and perfecting my craft back then instead of treating it like a “hobby”. Had I transitioned from Corporate America 7 years ago to photography full-time, I would have saved myself a lot of work-related stress and been able to explore my creative side freely and unapologetically. I have always loved and appreciated the arts and with photography, I can bring stories and moments to life. For me, photography is fun, yet challenging in a good way. Read more>>

Bryce Fluker

I wish I had started sooner—coaching would have been a great way to engage more with the athletic and competitive communities I was already part of, but from a different perspective. Fitness and competition have always been a part of my life. I grew up in a household where my parents and sister competed in road races, my parents organized competitive running events, and my father coached high school cross-country for 13 years. He was also a scholarship hurdler at Southern Methodist University before receiving his draft notice. Read more>>

Scott Leopold

If I could go back in time, I absolutely wish I had pursued my creative career sooner. One of my greatest regrets is not immersing myself in a life of creative expression earlier on. Growing up in poverty with an unstable home life and learning disabilities, drawing and daydreaming became my escape. I was naturally talented at art and excelled in it, but the need for financial stability pushed me toward business. Read more>>

Cristiano Costa

If I could go back in time, would I have started my creative career sooner or later? It’s a question I’ve often pondered, especially given the winding path that led me to where I am today. Looking back, I believe I started at exactly the right time—though it wasn’t the easiest road.

After my divorce, I made a bold decision: to return to university and pursue my second degree, determined to become a Portuguese teacher. It was a challenging period, balancing studies with work, pushing against all odds to carve out a new future for myself. But amidst the chaos, something unexpected happened—I found the strength to write a book. Read more>>

Henny

I have always been a late bloomer. I started school a year early, so I was a year younger than all my classmates. While that might not seem like a huge deal, this has been one of the defining experiences of my life. I always felt that I was playing maturity catch-up, constantly trying to prove that I belong among my peers. These formative years created a lot of self-doubt in my life, which inevitably led to shying away from my natural interests as a shot in the dark attempt at being accepted. I was a naturally curious (and anxious) kid, always looking to escape to the dream I had in my mind since I would deny myself access to these possibilities in my reality. Read more>>

Vince Schmit

As a creative, I wish I threw myself way more into the arts and medias that I enjoy at a much younger age. I always seemed to get inspired and dabble here and there in different formats, whether it be a Podcast/Sports & Culture website in 2010 with a friend or editing videos for myself for random social media purposes and then starting another podcast in 2020 with someone who was telling me, “enough talk and just do what you want”. So, I had this creative namesake of “Wasted20s”, believing I did waste my 20’s not doing and living up to my potential as a creative but I was then in my late 30’s and now early’ish 40’s and not wanting to have to rebrand as Wasted30s, 40s or beyond. Plus, having one of my children already being a teenager, I probably don’t have many years left being seen as “cool” enough to have such a title for the branding name attached to my work. So, would I like to have started earlier? Absolutely. Read more>>

Suzanne Adkins

I spent my childhood and adolescence creating art. That was put on hold in college. Most of my young adulthood was then spent studying and training for my Optometry career. I did a few art shows during that time, but only did a handful of projects. I always thought I would have time for art and my creative work after graduation. Time seemed to get shorter every year. As my Optometry career progressed and I started a family, I realized I wouldn’t have this ample block of time I thought would be available. Thing just got busier. I also started feeling unfulfilled in Optometry. The more skilled and experienced I got, the boredom set in. I felt like I was on repeat daily. I decided to make time where I could and restart my art projects. I recently restarted my art projects a few years ago. That meant painting or drawing when the baby slept. I usually stay up late at night to get larger chunks of time to devote to projects. Read more>>

Elizabeth Williams

If I had the choice to start my modeling career sooner or later, I would have definitely started sooner. My interest in modeling first sparked when I was in eighth grade, but I didn’t seriously pursue it until I was 16. That’s when I enrolled at Bella Modeling School in Dallas, Texas, to learn from professionals in the industry. At the time, I was still in high school, so a few times a week, I would head to the modeling school after classes for my lessons. Looking back, I realize that if I had started earlier, I would have gained more experience and, more importantly, taken it more seriously as a potential career rather than just a hobby. When I first began, I didn’t truly believe that modeling could be a viable path for me, I saw it as something fun but never something I could actually turn into a profession. Read more>>

Mike Murray

Much sooner! I had no idea I had musical compositional skills in my teens. I was in a local funk band during high school as a drummer. Growing up in the NYC suburbs during the 1970s was filled with distractions. The experience was short-lived as I ended up dropping out. In hindsight, I should have stayed put or sought opportunities to hone my percussion skills in different bands instead of eventually confining myself to the high school marching band’s drum section, although that was a great experience too! Read more>>

Kelly S Smart

I have been an Artist for my entire life. However, I just started vending about 15 years ago when I was 40 and only on a regular basis about 5 years ago, I have worked an office job since 2002 and that left me only a little time to pursue artistic endeavors. Summer of last year the company I was employed with closed down and that began a new chapter of my life. Although I wish I could have done more with my Art earlier on; I am now getting the opportunity I have always wanted. It’s kind of scary to depend on my Artistic pursuits to bring in enough income for me but it’s also exciting to look at the possibilities. The future seems to be wide open and full of promise. I look forward to continuing this new journey to see where it takes me. Read more>>

Ellex Swavoni

I’ve been making work and studying the same things since I was a child. Sculpture and music were the two art forms that informed the way I approached everything. I was always interested in the way things were made, why they were made and the people who made them. I never denied myself the process of making. I always found a way to acquire tools or information that would at least get me closer to manifesting the objects I was imagining. I would use the internet and television to learn as much as I could about how things worked and correlated those ideas to structure my approach to making. However, I did deny myself the community that would come from sharing the things I was making and thinking about. If I could go back into time (though I don’t have any regrets) I would’ve been more urgent about sharing. Read more>>

Jasmine Clements

If I had to reflect on my journey, I think starting sooner could have been amazing because I could’ve gotten the chance to make mistakes and learn earlier. There’s so much value in trial and error, and I think diving in at a younger age could have helped me refine my craft quicker. But also, there’s something to be said about starting at the right moment in your life, when you’re ready for the commitment and growth.

Looking back, I wouldn’t change when I started, because I think every step, even the challenging ones, led me to where I am now. Read more>>

Ashley Miller

Professional dancers usually have to know when they’re extremely young and if they want to pursue a professional path. Many pre-professional programs and summer intensives end at 18 or even sooner. My parents did not put me in any extracurriculars until I watched a documentary, “Living a Ballet Dream” about New York City Ballet and School of American Ballet dancers. I fell in love and begged to start classes. I was eleven years old, which is considered late for a dancer to start in order to make it as a professional, I grew up in a small town with few options for dance studios. We were not well-off and even at my studio with an income-based sliding fee scale, I could only take a couple of classes a week, and they were very recreational. Read more>>

Jc Wayne

I was creating art, poetry and stories at a very young age, and while I was interested in and good at most subjects in school, art and music appreciation/choir classes were my favorites. Both of my parents were highly creative (they met at a Studio Art class as students at Brown University), and my childhood home was often filled with creators, but neither of my parents seriously pursued their artistic talents since they were of an age of conventional family expectations and roles. I did attend an arts high school in Providence, Rhode Island and went on to study Art History (and International Relations) at Brown as well. Unfortunately, my art teacher in high school gave me a particularly severe critique that essentially convinced me at age 15 that I had insufficient artistic talent to pursue art further and that I would never make it as an artist. Read more>>

Deatrice Snuggs-mccloud

I definitely wish that I had decided to pursue my career in the beauty industry right after I graduated high school. Unfortunately, I allowed people to talk me out it only to end up in cosmetology school 17 years later. Of course, I can’t help but think about where I would be now if I had started my journey then but nonetheless, I am extremely grateful that things happened the way that they did. Read more>>

Sarah Thomas

If I could go back in time, I would have fully jumped into being a professional MUA as my main source of income. As a single mom for so long I think I was scared of the risk rather than seeing the reward. Even with my career getting to do makeup and some events here and there it really wasn’t until the last few years that I really just took a leap of faith. I think had I had enough confidence in myself to take that leap sooner that my growth would be much bigger than it is right now. I think I would have been able to help other women who were in the same or similar situation. Read more>>

Marion Fague-bass

I was raised in an artistic environment. My mother was a musician and music educator, like her mother before her. My father was an actor and an educator. I grew up studying ballet, piano, violin, and was always involved in chorus, choir and theater. I tried my hand at painting and other visual arts, but as far back as I can remember I wanted to be an actor, and that’s where I focused my energies growing up. Read more>>

Trevor Joseph

I started making music over 17 years ago however, it wasn’t until about 5 years ago when I truly decided to begin making it a career for myself. When I look back, there are times when I think to myself, I should be a lot farther than I am today. Although, I’ve come a long way, that type of thinking motivates me to move forward. When I feel like I’m behind, there ain’t no time to waste by staying still, I have to take the next step without hesitation. I’m proud of where I am, and I’m proud I’m still going. I’ve seen a lot of people give up, but just because it doesn’t happen all at once doesn’t mean it’s not happening. I like my journey, and I like my story. I think if I would’ve reached higher levels of success sooner than now, I might’ve not been mentally prepared for it. Read more>>

Emily Coldiron

I started my creative career after burning out from both corporate and non-profit work. I felt like many of the career milestones that were supposed to bring me joy were actually meaningless once I achieved them. The reality is that I had suppressed a lot of my creative energy and I found it difficult to thrive in an environment with a lot of constraints. Once I left my last role, I knew that it was time for a change. However, it was hard to find the confidence to pursue drawing and painting as an entrepreneur. I had to work up a lot of courage to start posting/sharing my artwork. Once I started to do that regularly, the commissions and clients started coming through. I would’ve loved to start sooner but it took years of work to dismantle my self-limiting beliefs. If you have a vision, the best thing to do is try and just give yourself a chance. Read more>>

Kevin Avery

This is a great question and I actually think about this quite often. I 100% wish I would have started my fine art photography business when I was much younger! Being a professional photographer, I can genuinely say that this is the first time in my career that I honestly love what I do for a living. I tinkered around for years with so many different odd jobs and “careers” and I never could find anything that really clicked. I grew up thinking that in order to live here in Southern California I would have to have a “normal” job that made a certain amount of money and I chased that idea for way too long. I wish I could say I had this big brave moment when I finally took the leap into the life of being an artist. However, I was kind of shoved into it by the global pandemic. Read more>>