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.

Shaun Rajah

If I could go back in time, I do wish I had started my business sooner. However, I firmly believe that it’s never too late to pursue your dreams and make things happen. Read more>>

Sarah Khan

That’s a loaded question. It was my career that gave me the insights and experiences that I lead with in my business now. However, it’s also my career that brought me to the verge of breakdown and missing pivotal firsts in the lives of my kids. Read more>>

Thaís Mendonça

I always wanted to work with communication. Anything that brings me a way to express myself and to connect to others. I think that’s why I graduated in Journalism. Read more>>

Susan & Sicily

Starting a business is a pivotal decision, and the timing can significantly impact the journey. Reflecting on our experience, we started our business at a time when we felt reasonably secure in our careers but hungry for more autonomy and creativity. Read more>>

Jess Goodkey

Looking back at the past few years,I’d have to say no! I genuinely believe everything happens for a reason, and usually at just the right time. Read more>>

Stephanie Elakhras

Looking back on my journey, the question of whether I wish I had started my business sooner or later is one that carries a weight of introspection and reflection. Read more>>

Lori Parnell

I started Black Culture Candles in 2021. It was during the pandemic. The Black Lives Matter movement was in full swing and Black Joy seemed hard to find. Read more>>

Lexi Portaro

My first reaction to this question would be “sooner.” My next reaction would be “definitely sooner.” But in between those two resides a host of complicated feelings. Read more>>

Nafeesa Abdul-Akbar

If I could go back in time, I would have started my business sooner. As a born entrepreneur, I often avoided taking the leap and going all in for my business, because it was something so different from what I had been taught. Read more>>

Amy Hall

My husband and I have always dreamed of owning our own business, but finding the right business, at the right moment, that would fit everything we imagined took a while. Read more>>

Alyssa Moss

I started creating videos when I was 10 years old. It was always my favorite thing to do. I spent my youth posting on YouTube, far before it was cool! (Ha!) Read more>>

Ryan Watts

While I began my current career effectively in my 20s as a side hustle, I really began focusing on it around 2018 in a full time manner. Read more>>

Kyle Lyman

I always thought i started late in art and music. I used to draw some stuff like dragons from fantasy novel covers when i was young and in the 6th grade i played trombone. Read more>>

Frederick Fajardo

I wish I knew about tattooing earlier in my life. My parents weren’t super conservative, but I wasn’t around a lot of people with tattoos. Read more>>

Aaron Conaway

I’ve made up stories to entertain people for as long as I can remember, but while I had previously submitted a finished manuscript, I didn’t make the leap to published author until opting to self-publish at the auspicious age (for sci-fi fans) of 42. Read more>>

ZuRui Chen

If someone had asked me this question three years ago I would answered “earlier”. On one side, I always knew that my goal was to be an independent designer, and my dream is to establish my own brand and have my creative freedom. Read more>>

Gary Bennett

The TLDR here is Yes…and No. At 50 years old, after working as an electrical engineer for 28 years, the last 14 years running my own successful engineering firm, I felt it was time for a change. Read more>>

Khari Karade

Looking back, I wish I would’ve focused solely on my music and making it as an artist, instead of ever going to college. Although I’ve made some of my favorite songs and beats while at Morgan State, I started fresh out of high school in 2019 with no real idea of what to do with myself. Read more>>

Igor Djenge

If I were blessed with this extraordinary ‘holy’ cow’ power to rewind time, I would certainly revisit my high school graduation and choose to pursue the career I’ve been longing for: Read more>>

Jodyy Tee

Sometimes I do wish I started sooner, only because I would have had more experience and mistakes made sooner than I do now. You live and you learn mistakes will be made no matter your timing I just feel at a younger age I prolly would have reached my goals a lil sooner. Read more>>

Lee Daniel

Sometimes I often think about if I had Started earlier, however I don’t regret my decision to start when I did. I grew up dancing since I was a very young, but not in a studio more of a street dancer. Read more>>

Charlie Vue

I started the music journey back when I was 16 years old. I stopped following my dreams and passion because of the small city I was in, had no one else doing music and/or helping to motivate me. Read more>>

Diego Correa Bravo

If I could do it all over again, I would have definitely done it differently. I would have started this career a lot sooner! I actually almost did. Read more>>