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.

Deb Kelley

I had been working on my company for three years before I decided to turn it into my full-time career in 2008. It was something that I did in the evenings after I got home from my full-time marketing job for fun. When my “9-5 job” moved to a new location and several people were laid off, I was one of them. I had a long talk with my husband. My business was increasing rapidly through word of mouth, and I just had a feeling that it would take off if I could dedicate myself to growing it full-time. I was terrified and excited. I was losing a significant salary for the unknown, but it was one of those things – I didn’t want to look back and have regrets about never trying to go out on my own. Read more>>

Kimberly Vann

If I could go back in time, I actually don’t think I would have changed the start date for becoming a business owner. The reason I say this is, I’ve grown so much in these last 5 years of salon ownership that I don’t think I would have appreciated the lessons if I had started when I wanted to.  Read more>>

Edward Kearney

It was the spring of 2018, and I was fresh out of my first full time corporate gig, with wide eyes and a “can’t lose” spirit that fueled my desire to finally make something of my own. Having always dreamt of this moment, the moment in which I would create something of my own, I know that excitement and many nights of fantasizing of this moment only fueled my fervor for starting. Read more>>

Christina L Turner

For me, it is both. I possibly would not have started my business if I hadn’t been a single parent trying to keep a roof over our heads and food on the table. If it had not been for the experience of working within the New York State Assembly for Assemblyman Author O, Eve there world not have been a Alsace of New York Events and Design. Read more>>

Tamara Merrill

I’m not sure that ‘Do I wish I had started writing sooner?’ is the right question. I started writing very early. According to family legend, I wrote my first book at age three on a folded piece of paper, using a few scribbles and a wobbly capital A (the only letter I knew at the time.). I then told my grandmother that it said, “Once upon a time, a queen lived in the tree. The End’ Read more>>

Kika Claude

I wish I had started sooner! For the backstory, I thought I wanted to be an attorney since my teenage years. Everything I did was geared towards attending and graduating law school. I sped through college, taking as many classes as I could just to graduate in 3 years and attend law school. I was the youngest person in my class! Read more>>

Tasha D

If I could go back in time, I would’ve definitely started sooner. Although, I was already in the beauty industry working for MAC in my early 20s, I was boo’d up and was “playing” the wifey role and missed out on some amazing opportunities trying to hold it down. Read more>>

Breyonne Parker

If I could go back I would’ve started the same time, because I needed the maturity I have now. I worked as a freelance designer for other companies but never my own. I got to a point where the amount of hassle wasn’t adding up to what I deserved and I took a break. I actually started B.Nefertiti Accessories as just a design company in 2014. Read more>>

Lo’Reece Chisholm

To be honest, I am one hundred percent okay with the time frame that I decided to get started in my business. I don’t feel as if I should have started sooner, or later; I started exactly when God wanted me to. The reason I say this is because, owning a skincare and aromatherapy business was never in my plans, thoughts, or dreams; my plan was to become a veterinarian. Read more>>

Lexis Carter

I honestly can say that I’m glad that I started later, I always had the urge to start something of my own but ultimately the reason why is because I had my kids in my mid 20’s. My daughter was born in April of 2016′ and it was time for me to lock in as a new parent to make sure I did my best to provide. Within three years I had my son in February of 2019, and I switched careers from the retail industry to the medical industry. Read more>>

Sirena Andras

I wish I’d had the guts to start my own agency sooner. It took me 12 years at my former employer to realize that I was holding my creative identity back by working for a company whose values didn’t align with mine. Read more>>

T. Sasha Phillip

I definitely wish I had the confidence to start sooner. I was always the creative individual I am today, but the confidence took time. I started creating when I was about 10 years old. I would use those “how to” drawing books from the library to practice. I fell in love with the visuals from the Disney animation of Hercules. The five goddesses were so beautiful to me. I used to hang my completed drawings on the hallway walls of the house; it was my gallery. Read more>>

Kate Payne

My only wish (not a regret) is I wish I had started my photography and artistic journey and been more serious about it much earlier in life. It would have given me more time to chase the light.

Charles Brantley

This is an interesting question because it’s not that I ever wanted to do anything different than have my own business. In other words, I have always wanted that. The interesting dynamic is that it has been difficult to establish as economic climate can fluctuate over the years. Read more>>

Sara Jade

I believe whole-heartedly that all of my experiences shaped me into the artist I am today. Although part of me wishes I had possessed the confidence and self-belief sooner to “just go for it”, I would not change my past experiences. My story is deeply weaved into the music I create and I would not trade that for the world. Read more>>

Bethnie Rose

In a way – yes. I don’t prefer the idea of living in regret, however, are there things I wish I would have done sooner? Definitely. I think not understanding yourself as an artist, and even a human being, plays the biggest part in what you become. I always wrote songs or poetry from as young as 7 years old – but did I understand WHY I was doing it? Not really. Even in my late teen, young adult years, Read more>>

Alexandra Forby

I sometimes feel like an outlier when it comes to this question as so many tend to put off their dreams and start their creative journeys later than they want. I, however, tend to look back and think I rushed into it too soon, though that may have to do more with the business side of being an artist than the creative side. Going to an art and design school for college may make it seem like I was always on this path, but at the time art was what I was known for at school and that made it feel like just the logical next step. Read more>>

Victoria Simmone

Often times I find myself getting lost in my thoughts, wondering where I would be in my journey by now had I been more dedicated from the beginning. However, the lessons I’ve learned and knowledge that I have gained along the way has been beyond rewarding. I always knew I wanted to be a creator of some sort. I was blessed with many talents, but the problem was I didn’t know how to take advantage of those said talents. So for a while they kinda laid dormant. Read more>>

Daphne Greene

I think most artists wish they could have started their career sooner at one time or another… I know I felt pressure not having played in bands untill halfway through college, and not starting my own band till a year after graduation, not to mention persevering through several major speed bumps like projects breaking up, sustaining a major injury where I couldn’t walk for six months, or going through a global pandemic which put my usual musical career on hold for a over a year. Read more>>

Tiffani Nicholle

Growing up I was always a writer. I would write poetry, and short stories all the time, but I didn’t start writing music until I was 23 years old. In the past, I’d often look at younger creatives and wish that I’d had an earlier start, but I’ve since grown to know and understand that everything happens as it should. In my younger years, I was working through a lot of childhood trauma, so I honestly couldn’t see past my own circumstances which held me back creatively. The older I got, the more I leaned into writing as an outlet to share my story and as a vehicle of healing. Read more>>

Olwen Dowling

I have had two careers. Both in the arts. I feel lucky that I worked in theatre for 20 years and then returned to my art. All that I learned has helped enrich my visual arts. I had a degree in Visual Arts and Biology. Both aspects of learning have also contributed to my understanding of the world as an artist Read more>>

Kenny Koughs

I definitely wish I would’ve started sooner. I can proudly say I’m not the same person I was growing up. I understand this because I didn’t believe in myself and I didn’t really try for much of anything because I allowed myself to be around the wrong people. People who I ultimately allowed to keep me from being happy. Read more>>