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.

Candace Stribling

If I had started my jewelry design business sooner, I would have been able to establish a foothold in the industry and grow my business to its full potential. With five years of experience, I could have learned and adapted to market trends faster and more efficiently. Not only that but with the proper planning, I could have explored new avenues for marketing and selling my pieces. Read more>>

Kimberly Crawford

I have often said, I wish I had gone to college for graphic design, knowing what I know now. However, looking back, I can see how my adventures in life have lead me to the place I am today. All my jobs and life experiences made me the artist that I am today. Read more>>

Reyna Papotto

Do I wish I started my creative career sooner or later? To be honest, for the longest time I had a different answer to this question every day. As a twenty-three year old, I am finally at peace with saying I wouldn’t have changed a thing within my creative career timeline. I’ve rushed for things to happen in my creative career, the outcome was never satisfying. Read more>>

Aubrey Kim

I’ve been drawing since I was young, but I got my first drawing education in my mid-20s. But I didn’t think it was too late. I’m still learning art like a freshman and I think I learned how to paint at the right time. Don’t be afraid to start doing what you like at any time. Read more>>

Allie McIntosh

A lot of people ask me whether or not I regret starting my creative career as early as I did. And honestly, I have to admit that sometimes, I do. I began my creative path on a professional level when I was fourteen years old, and became very busy at the age of fifteen. I had to leave a school I loved, as well as cherished friends to pursue my dream of being a singer-songwriter, because I had important opportunities in Los Angeles that I couldn’t pass up. Read more>>

Dusty Leigh Huston

I do! I have been singing and performing since I was a child, at various events, weddings, ceremonies, etc. but I didn’t start performing professionally until 2011. I started later in life, due to being a military wife and a mother. There wasn’t a lot of time for pursuing a full-time music career until much later. Read more>>

Nick Kuchar

Hindsight is always 20/20! I was blessed to become a full time artist in 2011 after years of waiting tables (and before that toiling in the design industry). Looking back you always wish you found your niche earlier in life. However, a lot of times it is all those things you learn along the way you can put in your toolkit that lead you to success. Read more>>

Cristina Inciarte

I firmly believe that in life, everything happens in its own timing, and looking back with regret serves little purpose. However, I must admit that it’s natural to reflect on how things could have unfolded differently. Hindsight is indeed 20/20. When I consider my creative career, I’ve often found myself thinking, ‘If only I had started earlier!’ But I’ve come to realize that it’s never too early to embark on this journey. Even small, gradual steps taken as a young creative contribute to defining one’s style, creative vision, and overall story. Read more>>

Suzanne King

I definitely wish that I would have started on my art career sooner in my life. Starting a small business in my late 30’s had it’s challenges for sure! I definitely battled with self doubt and depression in my 20’s, which would have been the prime time to begin, I think. Still, I always seem to hear “better late than never”. I’m very grateful that I’ve had the opportunity to grow my business, no matter what comes of it in the future. Read more>>

Jennifer Messina

Yes! throughout my childhood and early 20s, I had to learn self confidence. That did not come overnight. It took a lot of failure and rock bottoms to get to a point of “not caring what anyone thought” and loving myself to its fullest. For me, I ended up in an outpatient rehab program to learn self love and boundaries. Though not everyone needs as extreme as a rockbottom, the lessons I learned jump started me to successful and motivating career where Im flourishing Read more>>

Mary-Craig McKnight

Starting in the hair industry has been one of the biggest blessing in my life. I definitely wish I would’ve started this career sooner. It has helped me grow in life so many ways. I’ve learned so many techniques and met great people along the way. Read more>>

Dontez Craig

Oh yes, very much sooner. I really did wish that I started back in my teens where my creativity was still at all around high with the unlimited drive to create. It also makes me miss the very active imagination I used to have back as a kid. No limitations, no rules, just create without a second thought in mind. Read more>>

Dr. Zackarina Jenny-hoe

Yes and no. I think in my heart of hearts, I wish I had allowed myself to explore drag earlier in my life because it’s so right for me and it truly makes me feel energized. When I was younger, gay and in the closet, Rupaul’s Drag Race was what I watched by myself feeling my first real connection with the Queer community. I loved all of the performers’ confidence and liberation and thought to myself “Wow, one day I wish I could be like them.” Read more>>

Kaitlyn M

While hindsight can often make us question the timing of certain decisions, I believe that everything happens for a reason. In the case of my photography career, I believe that the timing was just right. Starting my creative career later allowed me to gather valuable life experiences, gain a deeper understanding of the world, and develop a unique perspective that I now bring to my art. These experiences continue to shape my artistic vision and provide me with an outlet for my emotions and create stories that I find meaningful. Read more>>

Josh Miller

Looking back on when I first embarked on my photography journey, I realize that I wish I had started sooner than I did. I actually created the social media account for my brand a whole year before I actually started using it. Prior to college, I would take pictures with friends, but during my freshman year, I didn’t use my camera at all. It just remained in my room. Read more>>

Miyo Yamauchi

I think that the timing of one’s creative journey is never wrong. It is always the perfect time for individuals to embark on their own path of creativity. Personally, I feel that the timing of my creative career has worked out exceptionally well for me. However, I also acknowledge that had I started earlier or later, my journey would have unfolded differently, yet equally meaningful. Read more>>

Mia Risberg

I went to university dreaming of being a traditional art student, however I was only able to be that for one year. Afterwards I began working to support myself and pay for my studies. I was grateful to get a job in publishing, where I learned book design, under the mentorship of Cathy Aison, who was the art director for Vintage Books at the time. Working full time and going to school in the evenings was not easy however and it took me many years before I was able to graduate and return to my art practice. Read more>>

Eric Jefferson

I wish I would have started DJing as soon as I became aware of this incredible art form. I only have 5 years of experience as a DJ. I feel like I have much more to learn but I’m enjoying the process. Read more>>

Cody Jay

I definitely wish I would’ve started earlier. I’ve always been the person that felt like, “why would people enjoy my content or my personality when there are so many other amazing creators out there?” When I finally realized that I was unique and had plenty to offer to people, that is when I started my new career and I’m so glad I finally did. I’m now living my dreams. Read more>>

Kristen Rhoda

Absolutely. I can’t believe I let fear get the best of me. Read more>>

Tiana Dean

I honestly do wish I had started the music career earlier! I was so ignorant to the fact that this was something that could be done on an independent level and I feel if I would have started earlier I could have gotten artist development at an earlier age. I would have been able to be trained and coach on a younger level and have that mindset that I can do anything instead of starting as an adult and being set in my ways! Read more>>

Maria Rivillo

As for whether I wish I had started sooner, the answer is definitely yes. The 3D printing industry is growing rapidly, and there is a lot of potential for this business. Of course, there are some challenges that come with starting a new business. But if you’re passionate about interior design and 3D printing, I’m confident that you can overcome any obstacles. Read more>>

Jen Hestad

I don’t necessarily wish I would have started earlier but devoted more time to my craft in the early years. Read more>>

Chassidy Walsted-Fakler

I wish I would have started much sooner. Read more>>

Bria Walker

I definitely wish I started my creative career sooner. I tried many different creations before landing on my natural talent. Read more>>

Lyyfe Williams

I feel that everything is perfect timing. If I would have started sooner I don’t think I’d be where I am now. Read more>>

Jenna Michele

Yes, I wish I started this when I lived at home and did not have as many bills. I think I would be much further along by now. I wish that I had been provided the knowledge that being artist was even an option. Growing up, (for me) being an artist as a job was some ridiculous fantasy. I had such little knowledge of just how many career options there are for creatives. I think had I been born later in life and grew up with smart phones it would have been more realistic to me but smart phones/YouTube did not exist until I was already out of school. Read more>>

Steve Walker

I’m very lucky to have found this passion at the right time soon after retiring from the corporate world. I kept busy creating artwork which was very therapeutic and kept me busy for hours. Being in lockdown during the pandemic I was able to finish a large amount of artwork which got me through those difficult times. This allowed me to share my artwork at solo art shows with communities across Long Island and showing people how I evolved as an artist. I also entered juried exhibitions and to my surprise won awards for a number of my pieces. Read more>>

Ashton Charlebois

Absolutely. I wish I had done this earlier way back in high school! Read more>>

Isaiah Rhoden

Yes of course. Everybody wishes they had a earlier start in the things they’re doing currently. Its not about the start but the finish though. Read more>>

Ricky Reidling

I wish I would have had the opportunity to start my career earlier. Though I did take some acting/modeling classes in Atlanta, there was not a lot of opportunity in the area back when I was a kid, or at least that I saw. I have no regrets as I am truly one that believes everything happens for a reason. Read more>>