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. 

Daisy Helm

I started Drinks on Daisy after developing a passion for mixology and realizing how much I enjoyed creating memorable experiences through cocktails. At the time, I was in a phase of life where I was looking for something that combined my creativity, love for hospitality, and desire to build something of my own. Read More>>

Tricia Woviotis

There are a few times that I look back and wish I had started interior design sooner. I had jumped from career to career looking to find what I was passionate about. I liked most things and found that I was pretty good at most of it, but the desire just wasn’t there. Read More>>

Mark Love

It was 2016 when I ‘officially’ started my business, selling my mystery novels at book festivals and craft shows. I’ve been interested in writing stories for many years, long before then. In college I took a couple of creative writing classes, then studied journalism for a bit. Read More>>

Angela Umali

If I could go as far back as my elementary years… I would cultivate my love of photography. It wasn’t til later in life that I invested in the time and energy to learn this craft. Read More>>

Gina Schreck

Sooner. Without a doubt — and I’ll tell you why it’s more complicated than it sounds. The first time the idea hit me was back in 2010. I pictured a workspace that felt like a community instead of a cubicle farm — somewhere people actually wanted to be. Read More>>

Janie Haskins

When I was growing up, I often thought about being a professional artist. But instead I became a journalist and then a lawyer. During those years I’d browse listings for art classes and then find excuses not to sign up. Read More>>

Britani Crosby

Part of me wishes I started sooner but then I don’t think I’d have as much knowledge and experience as I do now. I started grooming animals back in 2016 after my husband found an add looking for help at a grooming shop, I was already working as a veterinary technician, since graduating college in 2014. Read More>>

Jaimz Dillman

Being a show producer kind of happened accidentally. I was a part of a local theater’s Fringe show and it was so successful we wanted to do it again. The theater moved on to do a different production so a friend and I picked up where we left off and began a 10-year run of a troupe we never meant to have. Read More>>

Tim Packman

I attended college right after graduating from high school in 1982. After three semesters, it became clear that college was not the thing for me at this time. I joined the Navy and it really helped shape me as a person and helped me get my stuff together. Read More>>

JUAN COON

I started as an emcee in a rap group. One day, our DJ couldn’t make it to a gig, so I filled in. I was only 13 or 14 years old at the time, and I found the experience incredibly enjoyable. Even though I was part of a group, I felt a strong sense of focus on my role, and I loved that! Read More>>

Tyler Bachmann

If I went back in time, I wish I could have started my creative journey sooner. I started my YouTube and Influencer journey early 2023. I have always wanted to create automotive content and had just purchased a Mustang, I saw it as an opportunity to start. Read More>>

Kaydence McQueen

I love this topic because I was always overly eager to make a career for myself and become something even when I was as young as 9 years old. I always strived for stardom and I was definitely an over achiever. Read More>>

Ra7ael

I had this instructor once—someone who had worked with major artists—who listened to my first single before its release because I wanted honest opinions and know if it was the right choice. They interrupted it even before getting to the actual chorus and started saying that I wasn’t ready to come out because the lyrics were senseless. Read More>>

Diana Linn Ennis

My ‘creative’ career happened as it should have. I have always been a ‘fan’ of music makers and curious about how and why they generate art. I was a liner note geek and de facto music nerd my schoolmates turned to for pop music information and recommendations. Read More>>

Micheale Washington

Here’s a response in your authentic voice: If I could go back, I would have started my creative career sooner. Music has always been part of who I am, but for much of my adult life I focused on building a corporate career in Talent Acquisition. Read More>>

Gabrielle Bennett

If I could go back in time, I honestly wouldn’t start much sooner. Mack Potato Studio was born during a season of life when I needed creativity the most. By day, I was building a career in sales and marketing leadership, and by night I was navigating motherhood, family life and loss, and all the beautiful chaos that comes with it. Read More>>

John Davis

I am 39 years old and I’m in a band based out of Knoxville, TN called Gramphix (gram-fix). You can find more information about Gramphix at our website, Gramphix.com. Sorry for the cheap plug. If I had my choice, I would have started/joined a band in my late teens/early 20s. Read More>>