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.

Shelby Smith

I’ve always had an entrepreneurial mindset, drive and hustle. I didn’t always apply it in to the right areas of my life in the past. I carried ideas with me for businesses and still do to this day for years as an adolescent and young adult, meanwhile I dabbled in trades, school, adventures and generally speaking a party everyday lifestyle. Always telling myself that I was successful if I could work hard and party hard. As I got older and time passed, I felt like the party wasn’t fulfilling me and neither was the grind of working 2 jobs and reporting to work for someone else. Read more>>

Francesca Cavallin Mead

I don’t wish I had started my business sooner or later. I believe I started it at exactly the right time for where I was in life and mentally. That said, the path wasn’t linear. Read more>>

Tiffani Lear

If I could go back, I’d start sooner—not to avoid mistakes, but to make them earlier.Starting young gave me time to fail, restart, and learn lessons I wish I’d known sooner. It’s like that scene in Ted Lasso where he’s underestimated at darts. He quotes Walt Whitman: “Be curious, not judgmental.” People judged me—the blonde, the girl, the “kid”—but curiosity was my superpower. I asked questions until I annoyed people, but I also uncovered answers no one else had. Read more>>

Izzy Miller

As a young person, it might sound strange for me to say that I wish I had started my career earlier. However, I think that if I started earlier I would be a lot further along today. Many successful teen actresses and actors started working in the entertainment industry when they were babies. They gained opportunities and collected contacts before they could talk. I have spent the last three years discovering what I like to do and finding the path that I want to take. Read more>>

Sangeetha

I’ve thought about it, but no—I don’t wish I’d started my creative career any sooner. I spent nearly two decades as an electrical engineer before becoming a full-time painter. And honestly, I’m grateful for that. That career gave me financial independence, stability, and a bunch of skills I now rely on. It also built my tenacity and gave me the confidence to take risks—without the kind of stress I might’ve felt at 21. Starting again at 40, with childlike passion and adult resilience, feels like a privilege—and yes, still a risk. But it’s a risk I can take on my own terms. I get to follow my spark with intention, not pressure. Read more>>

Aureo Luis Meireles

When I started performing like an dragqueen I was In Salt Lake City in 2013. I was 45 years old, I think if I had started sooner I would’ve more chance that today have more success. And having more opportunities. Read more>>

Perry B. Anthony

I have had a rough life. I always say because I went to foster care I missed stages of my life and it wasn’t until I was 27 that I feel I had entered my college years. I wore a script of a homeless hitchhiker and decided to live my characters life tweet my adventures and stream my journeys in hopes to get my feature funded. I wish I would have started earlier in life. When I was 8 I started writing a book on the computer. My mom saw a bad word and told me to delete it. I tried to explain I was aiming to reach a bigger audience. She made me delete it. Read more>>

Nicolás Urricelqui

Everyone’s journey is unique, and that uniqueness is what makes us stand out as artists. Where I come from, with all its obstacles and limitations, is exactly what shaped my personality and identity as a musician. It gave me the voice I now use to express myself creatively. So, let me introduce myself and share a little more about how that journey unfolded. Read more>>

Keara Jewel

This is a tough question. I used to always think about the “what ifs”? What if i had started younger or when the idea first hit me? But i came to realize that everything happens at the right moment and i have so much knowledge and wisdom now that i can fully comprehend this career path. I started modeling this year and i have already been casted into winston salem fashion show and i have modeled for the Carolina Fashion Awards. My acting journey began last year when i was cast into a Carrie musical and i got the role of Erin in the webseries Struggle’s Of A Pretty Girl. I am glad i started at the time i did because i have learned to discipline myself. Read more>>

Malia Dishon

I look at phases of life as stepping stones, and each one has something valuable to offer. So while I wish I started songwriting sooner, it unlocked in me at the time it needed to. When I was working in social media and marketing, that’s what I needed to focus on at the time. And I learned a lot that is now helpful to me as an artist. Read more>>

La’Chyia Petty

Honestly I wish I would have started earlier. Growing up I knew I was a good writer and I knew I loved being creative. I started out with writing short stories and poetry but after while it wasn’t as fulfilling for me. I feel like if was introduced to singing earlier I could’ve been more developed vocally. I’m in between whether w should have started earlier or now because if didn’t experience life the way I did I wouldn’t be able to write and express my self vocally on an emotional level. Read more>>

Scott Calmeise

I definitely believe I should have started sooner. When I was a child I wanted to be an actor, more of a martial arts actor after watching many martial arts movies with Bruce Lee, Jackie Chan, Jean Claude Van Damme, etc. However at the age, I was already doubting myself that I’ll never be successful into acting so I turned my attention to sports. Acting was not of any interest in me until college when I attended Bellarmine University. It was at Bellarmine where my passion into acting started to creep back in. I took a technical theater class my freshman year. And in my senior year, I took an Intro to Acting class. A couple years after I graduated from college, I was able to be in a Netflix film as a background extra. Read more>>

Tom Rizzuto

Honestly, I do wish I started sooner. Only because part of me misses having the time and energy to do the things I did when I was younger. To be clear though, my work back then was mostly terrible. In fact, I’m very grateful that I started writing and doing music before everything was archived forever online. I look back on things I did that I was so proud of and I am mortified that ever I let anybody read or listen to them. Read more>>

Sally Nichols

A group of court-certified interpreters started the Minnesota Translators and Interpreters Cooperative (MNTIC) after years of struggle with the Minnesota Judicial Branch administration over diminishing value of our remuneration. In this context, we dreamt about what we wanted our work to do in the world. We wanted to have interpreters’ professional skills be properly remunerated, yes, but we also wanted to see language justice in our community, we wanted to make quality interpretation and translation services available to all, we wanted to educate clients about how to use interpretation and translation services effectively, and we wanted to mentor up-and-coming new interpreters. Read more>>