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.

Richard Campbell

I’ve spent my adult life exploring the world, while working serious jobs in technology and consulting. It was only when I turned 40 that I read a book by one of my Professors from college that my life changed. Read more>>

Andrew Malozemoff

6 years ago I started a fledgling audio services business as a freelancer. At that point I had worked as a lawyer for 5 years. Once upon a time I loved music. I loved it so much that I studied it in college. Read more>>

Weston Gonzalez

Although I started westhaus in January 2020, right before a global pandemic, I think I started it at the right time. I spent over a decade working in-house as an event executive at studios, networks and streamers which gave me the foundation I needed to not only understand the events industry but also the ever changing landscape of the film and television industry. Read more>>

Todd West

I wish I could of started this business sooner. I had always been an entrepreneur and desired to have my own business. I had a young family to provide for, so my dreams were set aside for a while. Read more>>

Nicole Letoile

If I could go back in time, I would have started my business sooner. I initially started LEtoile Educaiton, LLC in 2020 but then took a full-time job, which meant I couldn’t fully dedicate the time to grow the business. Read more>>

Liliam Dominguez

This is a tricky question because creativity is a bottomless well. You can’t use it up. However, I was trained as an artist from the age of 12 but was never instructed how to make a living from making art. Read more>>

Traci Easterday

Sometimes yes, because it can feel like everyone else already has it figured out, or that I missed my chance. But for the most part, not really…I don’t think I was ready for this specific career until this point my life. Read more>>

Indigo McCoy

I’m glad I started my career early I just wish I invested my money in the content so would’ve expanded me when I was older instead of just saying whatever Read more>>

Sofia Forero Matheus

I have no regrets in life. The things that are meant to be for me will happen whenever they need to, and I don’t force situations to happen. But, and yes, there is a but, currently, my biggest and only regret in life is that I didn’t start my career as a filmmaker sooner. Read more>>

Gabi Brown

Absolutely! I do wish I had begun sooner, but then again, I believe things do come about at their proper time. I suppose that belief extends itself to knowing I probably wasn’t ready before now, hadn’t gathered the necessary life experiences or perspectives that have served to enrich the season of creativity in which I’m in now and produce the work I do. Read more>>

Tom Conner

I had always loved and learned painting and drawing from an early age, but as college approached I ended up in an architecture progam as the “sensible” way to be creative. The idea of “starving artist” was just too scary. Read more>>

Diohn Leoni

I started making art for sale in 2020 and started exhibiting sculpture in shows and galleries in 2023 when I retired from practicing psychology. Read more>>

Carissa Renard

If I could go back and do it all over again I would definitely try and focus on one thing. When I was growing up I was trying to do it all; play in my high school concert band, play piano in the side, work on my drawing skills in art class, etc. Read more>>

Amy Laskye

When I was young, I spent much of my free time with a film camera and was a staff photographer for my high schools’ yearbook and newsletter. Read more>>

Gv Lilshooty

If I could go back I would’ve took my music career a lot more serious when I was around 9 years old. If I knew the music wave would be like it is now . It’s a lot more easier and more access . Read more>>

Dina Valenz

I kicked off my creative journey back in my mid-20s, but now here I am, at almost 40 with more confidence and creativity than ever before. Read more>>

Andrew Ramler

We bought our first property at the age of 22, and if I had to do it over, I would have started even earlier. The real estate industry is incredibly taxing and requires a significant amount of energy. Read more>>

Cindi Yaklich

Boy! I was scrolling through the topics, and this shouted at me. I have said that the only (or one of the main – haha) regrets I have in life is that I did not pursue art as a career. Read more>>