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.

Niobe Alexandra

If I could go back in time, I would not change the timing of when I started Studio Kynd. I began the business whilst I was working as a nurse during the pandemic— it was a role I truly loved, but one that came with long commutes, emotional weight, and limited freedom. It was a time of deep reflection, and I feel like that is something that the pandemic brought for us all; time to reflect. My boyfriend (a graphic designer) was working from home during this time, and seeing him working on really exciting projects sparked something within me. I started experimenting with design during my time off and shared my work on Instagram. My first client reached out for help with a logo, and that was the beginning of everything. A month later, I had five projects, and I was making more money than I did at the hospital, so I made the bold decision not to return to the hospital. Instead, I poured everything into Studio Kynd. Shortly after, I embraced a nomadic lifestyle, taking my business to Spain, moving to Brighton and then on a one-way ticket to Mexico for a couple of months. Read more>>

Jennifer Canul

Honestly I first started my business back in like 2019-2020 but under a different name and I think it went way better back than than sometimes does now. I had so many clients then but I also was still starting still learning nails and what worked for me so it was definitely a lot of trial and error back then. With my business now yes it hasn’t even been a year and it has it slow days but I feel so much more confident doing nails now and I feel so much more comfortable running a business. Read more>>

Shradha Vora

If I could go back in time, I absolutely wish I had started my business sooner. Let me share the backstory. I moved from Texas to India just before COVID hit, planning to stay temporarily. Then the pandemic struck, and like many others, I found myself in an unexpected situation—stuck in India. As time passed, I made the decision to stay here permanently. I didn’t want to go back to the routine of looking for a job. Before this, I worked in school and clinic settings, gaining valuable experience in supporting children with developmental needs. But being in India, I realized something crucial—the urgent need for therapy services. Here, therapy is often a taboo subject. Conversations about having a child on the spectrum or seeking therapy are shrouded in secrecy, and parents often struggle in isolation, unsure where to turn for help. Read more>>

Heather Allen

If I could go back in time, I absolutely wish I had started my business sooner! I love what I do, and I often think about how much further along I could be if I had just taken the leap earlier. I officially launched my business in late 2019, but my journey in the creative industry started long before that. I attended cosmetology school, worked in salons, and eventually became a makeup artist. My work naturally led me into the wedding industry, and I was constantly inspired by the energy, beauty, and storytelling that weddings embody. Read more>>

Dana Ford

The Salty Cat Co has had many interations over the years, starting mainly as a handmade jewelry business on Etsy. That was just before I became a first time mom and time and energy were abundant. But life happens and as I focused on raising my daughter, my handmade business fell to the wayside. As my daughter grew older, and my professional career was established, I found myself thinking about my next steps and goals. And what kept coming up for me was the idea to transition from traditional employment to owning my own business. So in January 2024, I resurrected The Salty Cat Co with the idea to create and sell at vendor markets. I reflected on what I could make that would sell, how I could use tools and skills I already had, and where I could sell. I jumped in with both feet and haven’t looked back since. Read more>>

Michelle Mullins

I started Funky Ace at a point where I began to feel like I had a creative void to fill. I had a job in healthcare while doing pharmaceutical consulting on the side and had just begun searching for my next creative outlet. I always loved tennis growing up, so in a way, tennis, was also an escape from work. It was a way to de-stress, stay active, and maintain a positive mindset. And that’s exactly how I viewed starting my business: a way to break out of the routine and do something else that brought me joy. I also had an athlete mindset—the drive, the competition, and a little bit of stubbornness to try something challenging. Read more>>

Hamdullah Hamdard

If I could go back, I wouldn’t change the timing of when I started my business. Every decision we make in life is influenced by where we are emotionally, mentally, and financially, and for me, starting when I did was the result of both necessity and ambition aligning. Starting sooner might have been tempting, but I don’t think I would have had the clarity or vision I possess now. There’s a maturity that comes with life experience, and in my case, it helped me understand the power of storytelling and how to approach clients from diverse backgrounds. My experiences before launching my business allowed me to view challenges not as setbacks, but as opportunities for growth. Read more>>

Mindy Whetsel

I started my business in February of 2023. At the time, I was a stay at home mom who was kind of losing who she was. My kids are everything to me, but I wanted another purposeful job. I have always loved photography, but I really dove into it around 2013 after moving to a new state. I fell in love with it pretty fast, took classes, and started really learning how to use my camera. My first subjects were landscapes and my cats (who were my kids, at the time). Over time, I became better and had always dreamed of starting a business, but never quite felt like I was good enough or that it would actually go anywhere. Read more>>

Damaris Villalva

I don’t wish I had started my business earlier or later—I truly believe I started at the right time. However, launching Raiz Marketing at just 25 years old came with a heavy dose of imposter syndrome that I still grapple with today. Starting so young, with only a few years of professional experience, made me question whether I had what it took to succeed. Would clients trust me? Would my voice carry weight in rooms filled with seasoned professionals? These doubts were amplified as I compared myself to others who started their businesses later in life, with decades of experience to draw upon. It felt like I was constantly trying to prove myself—both to others and to myself—and that pressure was overwhelming at times. Imposter syndrome wasn’t just a fleeting thought; it was a persistent cloud that made me second-guess my decisions and question if I truly belonged. Read more>>

O’thainia Johannes

If I could go back in time, I definitely wish I had started my business sooner. I launched my business during the COVID-19 pandemic, after being laid off from my job. That experience was a wake-up call for me. It made me realize that I didn’t want to rely on someone else for financial stability or risk experiencing a lack of cash flow due to circumstances beyond my control. Starting my business sooner would have given me the opportunity to fully embrace entrepreneurship earlier. Instead of having to return to the workforce once COVID restrictions were lifted, I could have focused all my energy on building and scaling my business. It would have been a chance to establish myself in the market, and create the financial and personal freedom I’ve always envisioned. Read more>>

Cliff Powell

This is a tough one. Creativity has always been a constant in my life, even during my career in construction, architecture, and real estate development, where problem-solving and design demanded imaginative thinking. However, when it comes to painting, I do wish I had discovered and pursued this talent earlier. That said, there’s a paradox here: if I had started back then, would I be as passionate about it now? Painting became a form of escape and catharsis from corporate life, and perhaps that timing was exactly what I needed to ignite my passion. So, while it’s tempting to wonder about an earlier start, I believe the journey unfolded as it should. Read more>>

Mickael Jacquemin

be in life, whether in our careers or personal lives. For me, I’ve always felt behind, and that feeling started very early. I remember when I started music at the conservatory at age 11, I felt so old in the music theory classes because I was the oldest, and the youngest was only six. I vividly recall wondering why I hadn’t started earlier, already feeling like I had to race against time to catch up. That feeling stayed with me, especially in high school, where I lost two years due to a lack of interest in my studies and a much greater passion for starting metal bands. When I finally got to art school, once again, I was one of the oldest students, and I found myself wondering what I had done wrong in the past to end up there. Read more>>

Tandi Murphy-hall

I would have definitely started way sooner!!! I’ve always been a singer- When I was younger, I sang in various church choirs, traveling choirs, school choirs & would even make & sell little tickets in the apartments that I lived at when I was in elementary school- For people to bring lawn chairs & watch me perform from my stairwell and/or balcony!!! But I didn’t have enough self confidence & love when I was younger to follow my dreams of being in a band… It wasn’t until I was in my 20’s that I got enough courage to try being in a band & then it took another decade before I had ANY confidence in what I was doing! Read more>>

Andrew Wade

I wish I could have started this journey a lot sooner. I’ve always had that interest in me, I remember at 14 wanting to get into an acting class but we couldn’t afford it so I kind of just put in on the back burner and thought.. one day I will be able to take that class. That day was almost 15 years later at 27 years old but better late than never right? Now I’m taking classes, landing roles and putting my all into it and hoping this can lead to so much more. Read more>>

Courtney Lund

Looking back, I wish I would have started creating in my younger years. It wasn’t until I was in my thirties that I started to experiment with woodworking. I had this idea to make a hanging rack for my room out of salvaged materials we already had. Old barn wood and some salvaged doorknobs made up my vision. My husband, who I usually turn to in order to help me create something, was busy with his own projects at the time and I didn’t want to wait for him to have availability to help me with my own. I thought, you know what, I can figure this out. It’s not complicated, I can make this. I’ve always been handy enough with tools, being exposed to them growing up on a horse farm, so I took the challenge. In doing so, I quickly uncovered a love and a passion I didn’t know was hiding. By taking on that small challenge, my creative self was born. Read more>>

Heather Blood

I wish I had started in the cradle! I truly love what I do, but I feel like I’m always playing catch up. There’s never enough time in the day for me to finish all of the projects and ideas I have. Having multiple jobs and interests certainly doesn’t help, as my time is always split between performing and social media. In regards to performing, I wish I had started earlier just so that I would be further along in my skill set (a better dancer, singer, improviser). For social media, if I had started earlier I would probably have a bigger audience. I do think my experience with everything would be drastically different had I started earlier, but I am quite happy with where my life is now. Read more>>

Leena Kazak

This is such a great question, and my answer is a little long-winded, but here it goes! The idea for my novel first came to me about nine years ago—I even wrote the first three chapters! But, as life often does, things got hectic. I met my now-husband, and between dating, wedding planning, marriage, and becoming parents, I lost sight of it. My focus was on my corporate job, which I genuinely loved, and building our new life together. Fast forward eight years, and I hadn’t written another word, though my characters were never far from my mind. One day, I decided to pick the story back up, and this time, I finished it. It took me about a year, and I ended up completely rewriting those original three chapters, but the heart of the story stayed the same. Read more>>

Amy Doslich

daughters had a pink bunny that she carried around with her everywhere, and I thought it would be the best thing if I could make her a book that had her and her favorite bunny in it. I’ve always liked drawing, so I watched some YouTube videos, and I bought an iPad, and I told my husband I was going to try to make a children’s book. I had no idea what I was getting myself into at the time, but it unlocked a creative side of me that I hadn’t used in a long time, and I truly enjoyed exploring that side of me again. But I do wish I had started this whole journey earlier. I would have had a lot more time to devote to the process without managing two small kids along with a full time job. That being said, I would have been missing the driving force as to why I was really doing it because my kids wouldn’t have been born yet. So it’s almost as if it happened exactly when it needed to happen. Read more>>

Autumn Eliza Sheffy

I began my career with ballet classes when I was five years old. I LOVED dancing, and to this day, it is one of the things that bring me the most joy. I finally convinced my mom to sign me up when, on top of a mountain, she said if I skied down she would take me the next day for classes. I zoomed down the hill. I may not be the type of dancer who winds up in musicals like “Cats,” or “A Chorus Line,” nor can I “kick my face” as they say, but dance is one of those things that fuels me. I never really wanted to sing; my Mom was the one who realized I COULD sing and helped me perform onstage. My first singing performance was at a local festival in my town singing “Me and My Teddy” with the lyrics taped on a teddy bear’s stomach in case I forgot them. I got the bug after that. Read more>>

Jenni Prange Boran

I’ve wanted to be a writer since I could hold a pencil, and I am a writer today. Getting from point A to point B, however, was not a straight path. I was admittedly unfocused, trying out other forms of art here and there, muddying the writer career track waters. So, yes, I have had moments of wishing I’d been more focused earlier on, but that’s my ego doing its dirty work. Read more>>

Luis Cruz

When I think about a question like this I always think to myself what would my like look like if I started sooner. The question that wonder a pond my head are “would I be where I am today with my career? and or would I be even better then I am today?”. I started my passion and career for color guard my sophomore year of high school back in 2019 , I attended Cherokee high school located in Canton, Georgia. Through beginning stage of me starting this journey I was in foster care so which ment life was a lot different for me then everyone that I went to school with. Read more>>

Christopher Sherry

If I could start over, what a wonderful thought. The thought makes me envious of those who start life with a ‘built-in’ ambition. They know, maybe even before they can talk, that they want to be a fireman. Then there are those who figure it out sometime before they graduate from high school or even college. Then, again, there are those of US who sort of fall into ‘something’. There were several careers I pursued before falling into art as a profession, (even now that is a hard phrase to say, professional artist). Read more>>

Forrest Elliott

Often I find myself reflecting on this question when I am working in my studio. After graduating with my Bachelor of Fine Arts degree a little over a decade ago, I pursued various roles within creative industries but didn’t prioritize my personal creative practice. For eight years, I focused on building brands and managing operations for companies within the arts & entertainment industry, as well as, residential real estate. Read more>>

Kirkland Green

I think the natural answer to this question is ”yes”. Who doesn’t want to be doing the thing they love the second they start loving it, right? That’s what I thought initially. I was so upset by the fact that I was writing music, but not recording. I was singing in my room when I wanted to be singing at Jazz Fest. It was extremely difficult to understand that being an artist would take time. I grew up in a small rural town in central Louisiana. I believe it’s still classified as a village. Read more>>

Carrie Smith Libman

I always knew I wanted to be an artist and felt academia was the best way to pursue my work while making a living. I quickly moved from one checkbox to the next: BFA, MFA, teaching experience, adjunct position. I realized I moved so quickly through all the known academic steps I had never not been in school. I didn’t know what my work looked like outside of a semester by semester critique construct or access to woodshop. I took a hard turn and left academia. I was seeking experience to be a better artist and teacher and wanted to put down roots. I moved back to my hometown of Pittsburgh and pursued what turned into a corporate path while maintaining small acts of a studio practice. Read more>>

Reese Schroeder

Looking back, I certainly wish I had pursued art as a career in lieu of architecture. The rigors of the architectural profession did provide creative outlet in ways likely not possible in other fields, and the daily practice led to inspired ideas for my art along the way. However, the ever increasing responsibilities of working in, and growing an architectural practice limited my freedom to explore those relational design thoughts I continued to hold. Practicing in eight states, each with their own requirements along with ever changing building codes, zoning, materials, assemblies and legal issues kept me very busy on top of managing staff. Read more>>