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.

Olivia LaBarre

Part of me wishes that I had started my animal communication and Reiki business sooner than I did because I love what I do. But another, wiser, part of me knows that I started it exactly when I needed to. Looking back, I can see how each step I took led me to where I am now. Read More>>

Briana Dumont

If I could go back, I honestly wouldn’t change when I started my business. My journey into Briwitched Blessings really began long before it officially existed. I started reading tarot when I was around 12, and over the years I kept hearing the same thing from people-that my readings were accurate, that they felt seen, that it helped guide them. Read More>>

Susana Ipanaque Huacacolque

Honestly? I believe both of my businesses were born exactly when they were meant to be — not a moment too soon, not a moment too late. There is something quietly beautiful about that, even when the journey has been anything but quiet. La Peruanita came to life in one of those pivotal seasons — the kind that reshapes you from the inside out. Read More>>

Kym Schnittker

Out West Chic Boutique was born at a really meaningful transition point in my life—just as my oldest child was heading off to college. At that time, I still had three kids at home, ages 17, 15, and 5, so while I wasn’t done raising children, I could feel that season beginning to shift. Read More>>

Adreon Patterson

Looking back at my entrepreneur journey, I wish I had started earlier. After dipping my toe into independent contracting, I finally leaped in 2020 (COVID era) to turn gig work into a profitable side hustle. Read More>>

Stephanie Ton

I don’t wish I started sooner or later. I think I started exactly when I needed to. There’s a level of life experience, confidence, and perspective that I bring to my business now that I wouldn’t have had earlier. Read More>> 

vandor hill

Honestly, I think I started exactly when I was supposed to. Whack Donuts came out of a really heavy period in my life. Between 2017 and 2020, I lost multiple close family members and mentors,my grandmother, my mom, my aunt, a mentor from high school, and my best friend’s dad. I was navigating grief while still trying to show up for work, community, and myself. Read More>>

Mariana Orellana

I actually started pretty early, back in high school. At the time, photography was just something I loved doing. I didn’t think of it as a career yet, just something I was naturally drawn to and excited about. I was young, curious, and honestly a little in over my head, but I kept saying yes to opportunities and figuring things out as I went. Read More>>

Lisa Cheek

I wish I had started writing sooner, but I didn’t have the confidence. Plus, I had a demanding job as a film editor for twenty-five years which provided little time for anything else. Even though I’d never had a writing class, I wrote radio commercials and television promos for years. But writing a thirty seconds ad is not the same thing as writing a book. Read More>>

Emily Betros

I think my work with clay unfolded exactly how it was suppose to. I don’t think I was ready to trust being in this kind of career until recently. For the first few decades of my life, creativity and play were experiences that felt out of reach for me. They seem frivolous, even irresponsible to engage in. Read More>>