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.

Courtney Zuber

Honestly, I think I started Simplee Cone at the right time. If I had started sooner, I might not have had the experience or clarity I do now. And if I had waited, I probably would have talked myself out of it! Every step of my journey working in the floral industry, learning what clients need, and figuring out the gaps in the market led me to create Simplee Cone. So, while there’s always that ‘what if’ thought, I feel like the timing was exactly what it needed to be! Read more>>

Tiarah Linnear

I definitely would have started my business sooner. I began researching the coffee industry long before I officially committed in 2024. At the time, I was working in an orthopedic clinic, but I knew I wanted more. I was raised to believe that success meant going to school, getting a stable job, and working my way up. But deep down, I always felt undervalued. I wanted to create something of my own—something that would represent my people, honor my family, and build generational wealth. Read more>>

Anya Cherrice

I’ve always drawn. Always painted. As a child, art felt like a second language—one I spoke fluently but never dared to claim. I carried it with me through high school, where I dreamed of applying to art school, longing to dedicate my life to creativity. But when the time came, I told everyone I chose journalism because I wanted to change the world. The truth? I was afraid. Afraid of what people would think, afraid I wouldn’t make money, afraid I wouldn’t be taken seriously. Read more>>

Joanna Milo

Although I’ve now been a “career artist” for over 15 years, I do wish I had started, with a clear vision, much sooner. Like many artists, after college I did the “sensible, responsible” thing and got a “proper” job at an advertising agency, in order to earn a steady paycheck while I worked on figuring out what I really wanted to do with my life. Although I relished the idea of seeing my artwork on the walls of galleries and collectors, I didn’t know how to go about making this happen, and I didn’t have the confidence or support to pursue this dream, so I did what I thought was the next-best thing, and worked in the art and graphics department of the ad agency, segueing between design and project management. Read more>>

Gabriella Buckingham

My life has been a slow journey to becoming the artist I’ve always known I am. I knew this was my path from a very young age; just not what form it would take. I loved ballet and acting too but gave both of those up by the time I was fifteen. The world of art and creativity is something I was always aware of. My father collects paintings so I was lucky enough to experience a world full of pictures when growing up in various homes in East Anglia. We moved a lot. At school, art was the subject I excelled at. I remember winning the art prize there one year and at the local village fete! Strangely, apart from constantly drawing through lessons I don’t remember doing any art at home, other than sketchbook homework and my parents didn’t keep anything I made when I was a child. Read more>>

Edward Gibbons-brown

This question hits close to home because even though I’ve been in theatre since I was 14—acting, directing, writing, working as a stagehand or running the sound and light boards, studying it in college, and even starting my own community theatre company in Upstate New York—I didn’t move to NYC to really get serious about it until my mid-30s. Meanwhile, I watched so many of my peers make the move in their 20s. And then, often, I watched them move back home to build different lives. Read more>>

Anna Gaseitsiwe

If I could go back in time, I wouldn’t change when I started my creative career—I believe I entered it at exactly the right moment. My journey has been anything but linear, and that’s what makes it so valuable.

I initially started in art school, drawn to creative expression, but I eventually pivoted to criminology, where I built a career overseeing anti-money laundering investigations. At first glance, these fields seem worlds apart – and they are! However, my time in the field of financial crime investigations sharpened my critical thinking, gave me a unique lens on risk and ethics, and ultimately gave me the stability to return to my creative roots with more confidence and a broader perspective. Read more>>

Lo Eugenio

I’m still only a couple years into my dance career, but sometimes after going on social media I fall into the trap of comparing myself and wishing I had start sooner so that I would have as many opportunities as other dancers. But then I remember everything happens for a reason and I have to appreciate the journey as much as the destination. Read more>>

Michael Bussewitz-quarm

I do wonder what would have been if I had started my career before age 45. Many things had to fall into place for me to take the leap however. Although I have always wanted a career as a composer and conductor, reality was such that a teenager who grows up in the 70s and 80s, in poverty and with a chronic illness, had limited options in our society, where health care is not a universal right. Read more>>

Glenn Hughes

I graduated from college with a degree in fine arts and immediately started working as a graphic designer. I eventually worked my way up to being the Art Director and stayed at that job for about four years. I became very unfulfilled so I started to look for a change and ended up in a completely different field, taking a job in criminal justice. I stayed at that job for 30 years and retired. The job was okay at first but as time went on, I knew I had to find a way to recharge my creative talents and find a way to relieve the stress of my daily job. I had completely given up drawing or creating art at all. My wife kept encouraging me to start drawing again. Read more>>

Aaron Castillo-white

Graduating into the height of the Great Recession, and without a safety net, I focused first and foremost on securing my finances. The opening years of my career were wasted on overwork and hustling in too many side jobs and gigs to count, with a single-minded focus on paying off my loans. As a result, my creative life and emotional well-being suffered. Read more>>

Kate Morstad

I have always been a creative, but I never dreamed I could use my artistry to create a career. Especially this late in life.

I was raised to be practical, so I went to college, got a degree, and got a respectable job in the financial industry.

But I’ve always been creating on the side, whether it be art for friends, custom cakes, playing piano, teaching dance…whatever I could do to keep the creative juices flowing. Read more>>

Leticia Soul

I’ve been a creative all of my life. As a child I loved to sing and dance. I always performed in choir, and I studied performing arts through dance since a young age. I felt safe in choir because I was able to sing out, but I wasn’t the center of attention. I used to be extremely uncomfortable whenever the attention was on me because I didn’t have confidence in myself or my appearance. I had friends, but I was also teased quite often as a child. I highly underestimated the power of me. As I became older, I got a little more comfortable with being myself out oud. I won a pageant at my college after performing a song and it shifted my perception of what I was capable of. It wasn’t until 2014 after I graduated from college and moved back home that I decided to take my artistry seriously. Read more>>

Ari Phillips

I think that I’m happy with when I started releasing music. I started writing songs when I was 14 so about 7 or 8 years ago would be my initial start. As such a self conscious kid that constantly worried about what people thought I really think it would’ve eaten me alive to come out with music. In comparison to today I have my own internal doubts or insecurities, but I’ve just learned to accept that the best I can do is be myself because there’s only one me. Additionally with my social anxiety I think I wouldn’t have been able to handle all the attention that I get now. Read more>>

Sally Leyba

I had always wanted to have an antique store/tea room/quilt shop. I was married for 21 years and unfortunately, he was not very good with money. I never felt like I had the money confidence to start my own business. So I worked many years as a paralegal, administrator for hospital, CEO and graphic designer. I started a side business with a Booth at my local antique shop but Covid put an end to that business. So I pivoted and started posting things on Instagram, which then led to live sales on Instagram. This is the best time of my life and I’m in my retirement years so I really wish I had started earlier. That’s my advice to everyone. Start your dream earlier. Read more>>

Javen Moore

Honestly, I feel like my business started at the perfect time, however I wholeheartedly believe had I stayed confident & consistent with promoting myself & my makeup artistry, I would definitely be much further right now. I would have been more organized & more discipline on my goals. Being so young, anything can blind you & throw you from your vision & I wish I would have had the ambition that I have now because I feel unstoppable & I know for a fact that God has me every step of the way. Read more>>

Sheraton Liv

I do wish I had started my jewelry business earlier. When I was younger, I was eager to explore entrepreneurship on my own and didn’t want to follow in my family’s footsteps.

The first company I launched was almost an instant success. In fact, I became one of the leading companies in the industry at the time. While that may sound ideal to many, achieving overnight success as a young adult was tough to navigate. I quickly realized that success built over time and through perseverance is far more valuable, as it gives you the chance to understand how you’ve arrived at where you are. With my early success, I lacked that deep understanding of the business landscape and competition. Other companies learned from our successes and improved upon our ideas. Read more>>

Chante’l Armstrong

If I could go back in time, I wouldn’t change the timing of when I started Armstrong To The Rescue. I believe everything happened when it was supposed to. I officially launched the business in February 2024, but the vision for it had been in my heart long before that.

At the time, I was deeply immersed in my career in training and development, specifically in the healthcare and therapy sector. I was already leading teams, implementing training programs, and developing onboarding structures, so the foundation for what I do now with Armstrong To The Rescue was already being laid. Read more>>

Erika Seonjoo Lee

Looking back, I wouldn’t have started my creative career any sooner or later – the timing was just right. Before this venture, I had 3-4 different careers in related fields, but my current path was completely different. I had worked my way through various positions – from intern to operations director – and then made the decision to start fresh as a front-line cashier in my new chosen field. Read more>>

Ruti Wajnberg

If I could go back in time, would I have started my creative career sooner? It’s a question I’ve thought about before, especially on the days when running my upholstery business, Find The Thread, feels like a dream I should have pursued long ago. But looking back, I believe I started at exactly the right time. Read more>>

Roochita Chachra

Oh, I definitely wish I had started sooner! I’ve always been in the design world. After earning my B.F.A. in Commercial Art, I worked as a graphic designer for years. I even did a UX design immersive course but realized that wasn’t for me. It wasn’t until 2021 that I discovered Surface pattern design and everything just clicked. It felt like stepping into a whole new world of creativity where I could fully express myself. Read more>>

Marcos Morales

I feel like my artistic career started at the right time. I began writing initial song ideas in late 2019, just a few months before lockdown. I was working in retail and decided to go into freelance work in audiovisual production instead. Had I began at that time, I would’ve been too busy to write and perform consistently. When I started the band, I just quit my job mixing for weddings and corporate events. I enjoyed being able to travel while making a sustainable living, but found it creatively unfulfilling and keeping me from pursuing my own endeavors. Things were starting to fall into place now as I had a renewed desire to play my music to bring the creative vision to life. Read more>>

Kevin Alcantar

I used to feel like I got a comparatively late start in my current career field. I didn’t set foot on a set as part of the crew until my late 20’s and I think if you had asked me then, I would have told you I wish I had started sooner.. On the first TV show I ever worked on, I had an instance where a 21 year old crew member made a comment insinuating that I was too old for the entry-level position I was in. Earlier that year, I had switched gears in my career going from working at a non-profit organization to diving head first into entertainment. One of the driving factors was a feeling that perhaps I was running out of time to follow my creative dreams. So hearing something that explicitly poked at that insecurity about my age was difficult. Our society places a lot of pressure on having your life figured out at a young age and I wasn’t immune to that mindset. We have 30 Under 30 lists that conveniently neglect to mention the class background of those listed. Read more>>

Rachel Larsen

I definitely wished I would have started my creative career earlier in life!

I went to school right after the 2008 recession, so I was very conservative and went into accounting because of the perceived job stability. But, I never clicked with accounting & was hoping I would like it more once I started working as an accountant. Unfortunately, that never happened – and I was always daydreaming of doing the creative work, instead of doing the accounting for other creatives. I was working as an accountant for 5 years before I switched to pursue calligraphy & art. Read more>>

Rob Vintage

While it sounds nice to go back in time and start sooner, I’m glad that I had my late start in the arts. I started in my late twenties. I had spent most of that time working in the military and life insurance industry after my service. I learned a lot about myself but I wasn’t in the best place mentally at that time though, being in a war changes you. Leaving the military it was a rough few years trying to figure out my niche and what I wanted to pursue long term, that’s how I found my tattoo career. Starting sooner would have meant less time fumbling around different jobs and questioning where I fit in this life and more time spent honing my art skills. I have been an artist all my life but I let my family convince me that it wasn’t a viable career choice. Read more>>

Sarah Larsen

I wasn’t where I needed to be to truly harness my potential until life allowed me to be. I recall quite vividly my high school art teacher’s frustration as I had all the talent, but was more concerned with shenanigans than I was taking art seriously. As a teenager discovering who I was in the middle of Nebraska, it would take enduring an 18 year hiatus from art, and the loss of my parents before I finally did. Read more>>

Jessica Williams-speakman

I’ve thought about the timing of my creative journey a lot. I currently balance my passion for creative work with a full-time role as Director of Operations at MedFluencers and the demands (and joys) of being a mom. The reality is that for me, there’s never been a perfect time to dive wholeheartedly into creative pursuits—life always seems to have a way of filling up the calendar. Read more>>

Alexandra Johnson

I’ve actually always been interested in media-related things. When I was young, I used to carry around a camera and capture moments that I thought were memorable. As I got older, I would make videos for fun, even occasionally posting them to YouTube and laughing with my friends about it. It wasn’t until the pandemic that I began to reflect on my relationship with social media. With so much time to myself, I had to ask myself who I was and what I really liked to do. I found that I loved being on social media and seeing other people’s pictures and videos…and that encouraged me to start posting my own things. Read more>>

Rachel Cuesta

Life has a way of working itself out. Do I wish I had started my creative journey earlier? Absolutely. In my early twenties, I had the opportunity to partner in a photography business with a friend, but family pressure to find a “real job” and my own insecurities kept me on the academic path. At that time, I was also grappling with childhood trauma and discovering my identity—I simply wasn’t ready. I needed to experience life, learn, and grow before I could fully embrace my photography career. Read more>>