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.

Steven Mccracon

If I could go back in time, I would have launched my business during the COVID-19 pandemic. That period saw a surge in small businesses and entrepreneurs striving to make ends meet as traditional employment opportunities dwindled. Pop-up shops and expos were exceptionally profitable and productive then. Read more>>

A’de & Erin Nicole & Ru’cell

As a young girl, I have fond memories of my mother and grandmother gifting me craft sets, including candle making kits. The joy on their faces when I made candles for them left a lasting impression. Little did I know that this hobby would evolve into a passion for bringing that same joy to my customers. Our brand AHH Aromatherapy Co brand, founded in 2022 specializes in luxury candles, wax melts, and candle care bundles. Read more>>

Katrina Jarvis

100 percent I wish I started soon. When I first graduated massage school, like everyone else, I sought out day spas to gain “experience.” I did not have the confidence as a therapist yet to go out on my own. I did this for years and even then had to work as a bartender / server to supplement my massage therapy income. Read more>>

Meg Mcintyre

Though it’s easy to wonder how our lives might be different if we had chosen another path or found our way a bit sooner, I feel pretty strongly that I was meant to start my business when I did. I left my full-time role as a newspaper journalist in 2020, several months into the pandemic, when I realized that the work just wasn’t sustainable for me anymore. At first, I thought that becoming a freelance writer was just going to be a stopgap until I found something else, but I quickly realized that being in charge of my own work was incredibly freeing and empowering. It gave me the space and flexibility to explore, and that’s what led to me becoming a fiction editor. Read more>>

Kaysha Galbreath

Sooner, I have had a passion for photography since I was a teenager. I used to take photos for family and friends a long time ago. Then I found out I was pregnant, so I decided to put my camera down to raise my children. I recently picked my camera back up last September because I needed to make extra money to be able to support my family. Ever since then it has grown in ways I couldn’t image. I have been to Texas to work with an event photographer to take pictures at the American Paint Horse Association World Championship. Read more>>

Johnny Dowd

I started my musical career when I was 40 so, yes, sooner. would have been better. If I had started sooner ,I wouldn’t have had the wealth of experience I had when I was 40, but I probably missed out on a lot of fun. When I was young, it was all sex,drugs and rocknroll. When I decided on music as a career, that all went away, and there was nothing left but hard work. When I started I was washing dishes for a living, and that wasn’t cool. I decided to become a musician after seeing the movie The Last Waltz. I thought, “I must have as much talent as those people”. So 25 years and 1000 or so songs later, here I am, humbled yet still eager. Read more>>

Jose Germosen

Honestly thinking about it, knowing what I know now I couldn’t have possibly started my career as a creative at an earlier time. While my creativity truly started from when I first gained consciousness, I had to live my life to learn what making it a career truly took. For context, I knew I wanted to start producing music in high school but my personality at the time couldn’t allow me to express my full creative self. I thought pretty low of myself, and while I did maintain a sense of confidence, a lot of it was false. It took a lot of soul searching and “digging” for me to realize my self worth. Read more>>

Emily Patterson

There are times that I wish I had started learning production sooner in life but I do believe that everything happens for a reason and at the right time. My creative career started in 2014 when I attended my first music festival and my friends introduced me to FL Studio. I switched over to Ableton shortly after and began to teach myself production by watching videos on Youtube. I had stumbled upon a group of artists on Soundcloud who went by ‘Courteous Family’. These artists were making music I had never heard before and I instantly knew that I wanted to make music like this. Read more>>

Aleksandra Scepanovic

Embarking on a journey into the world of arts at age 52 was not just a decision—it was the culmination of a life rich with experiences, including my time as a war reporter in the Balkans, that shaped my perspective. If I could go back in time, I wouldn’t change the timing of this pivot. My career as a war reporter, witnessing the profound impact of conflict on people and places, deeply influenced my understanding of human resilience and fragility. This perspective carried over into my work in real estate in New York City, where I learned to appreciate the stories embedded in spaces and the lives they contain. Read more>>

Christy Nelson

I graduated from Mississippi State University in 2007 with a painting degree. Since then, technology has staggeringly changed what it looks like to be a full-time artist. For my senior thesis work, I had to make slides—not PowerPoint slides—but actual mounted individual transparency slides used in old-school slide projectors. My university at that time presented two paths for an art career: 1. get a teaching certificate to teach K-12 art, or 2. go to graduate school and pursue a “fine art career” with the perk of being able to teach at the university level. I do not fault them for teaching these as the only options, because historically, particularly in my state (Mississippi) those were THE options. However, the game was actively changing for artists. Read more>>

Leah Morrison

I went to school for Illustration back in 2008, after switching from an education major. It took me a few years to finish and I got married somewhere in the middle. When I graduated, Zach (my husband) and I knew that we wanted to have kids and I really wanted to be home with them while they were little. It seemed that it would be harder to start a career, pause to have kids, then re-launch a career, so we jumped right into having kids, all with the hope that I could pick up jobs here and there to do while the kids napped. HA! Ideals. Things didn’t quite pan out that way. Read more>>

Brenique Reed

I started my content creation right on time. I do not wish I can change anything about my journey. I believe everyone has their time and when it’s your time there is nothing anyone can do about it. You just have to believe in yourself. Starting sooner would have been a disaster because I was still finding myself and the internet would have definitely made me quit because we know how people can get in those comments. Starting later, well I would have not started because I would have really gotten too comfortable at my job and continued to use fear as an excuse. Read more>>

Celi Hairston

No, I believe to have started my creative career right when I was supposed to. The experience I’ve gained during my journey in life, personally and professionally, has sharpened me and contributed to guiding my path in the forward direction. Prior to my creative career, I’ve developed a lot of tools that have helped me better manage all of the aspects that come with the creative journey. I feel if I had started sooner, I would’ve made a lot of impulsive decisions, underestimated the value of my time, I would’ve been extremely stressed and overwhelmed as a result of poor project management, and overall a lot less structured, to name a few. Read more>>

Lorenzo Shelton

I started my creative journey super late. At the time, I was deep into a more traditional career path, working a job that paid the bills but didn’t ignite that creative spark in me. Life was stable, but there was always that feeling that I was missing out on something more fulfilling. The idea of creating, whether it was through vlogging, taking pictures , or any other form of content, had always been in the back of my mind, but I hesitated, thinking it was impractical or that I didn’t have the right skills or even the time to devote to creating. Read more>>

John Gibbs

For me, I don’t think it’s a matter of wishing I would have started earlier or later. I wish I would have pursued my own creative work more consistently earlier. I enjoyed working in various creative industries starting in high school when I worked for a ceramic sculptor. I was helping him make his work and not doing enough of my own. When I graduated from college, I started working for an art foundry casting bronze sculptures. I was in the creative industry but again I was making other peoples work and not doing enough of my own. Read more>>

Fabrice Nambona

Beginning 2020 is when I first bought my Sony A7ii and took filming serious, at the time i was working a regular job at Walmart which was really depressing i just felt uncomfortable like i didn’t belong there, then the manager wanted to fire me, so she asked me “why would i give you a second chance” and i told her “No i don’t need a second chance” so I walked out the door, and that was my last day working a regular job. I wish I started my career way sooner, maybe in 2018 I would’ve been a lot more advanced then I am today, and definitely know a lot more about the business side of it and to say “No” to certain clients, because it only brought me trouble at the time. To conclude it all I’m glad I started when I did because I feel like 2020 was perfect, I was bored it was during Covid Read more>>