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.

Schae Beaudoin

I started my PR firm Deadbolt (https://www.deadbolt.live/) a little over a year ago – late spring 2023. Truthfully, it was born out of a desire to disrupt my routine and establish myself further in the industry. Anyone who’s been through the job application process in the last couple of years knows how energy-consuming it is. Read more>>

Little Rock Home Repair

Sooner for sure. Little Rock has been hard work but has brought so much freedom to control my time, finances, quality, and reputation. There is really nothing like working for yourself. But I think it did take the pandemic to shake up my well-worn routine and open my eyes to the idea of change so I’m not sure it would have actually happened sooner. Read more>>

Hernan Guadalupe

I firmly believe that things happen when they are meant to happen, but if I could pull a Marty McFly and travel back to the past, I would have started Rollstar Jiu Jitsu Academy sooner. This thought has nothing to do with regret or correcting any wrongs. Instead, I say this is because of the countless success stories I have experienced since opening Rollstar’s doors in the Spring of 2022. Read more>>

Elizabeth & Aaron Vovk

For years, we both worked corporate jobs while gradually building our photography business. We believed we needed to reach a certain number of sessions or a specific income level before we could leave our corporate jobs and focus solely on photography. Read more>>

Cassidy Applebach

I graduated cosmetology school at 18 knowing I wanted to be a salon owner. I didn’t quite know what that looked like, but I wanted to work for myself. I wanted the freedom of making my own schedule and working as much or as little as I wanted. I was a young stylist with very few clients so the idea of having overhead was daunting! Read more>>

Katie Valtchev

I started my business in 2021 after quitting my corporate job during the pandemic. Much like the rest of the world, I was in a contemplative place reflecting on what’s important to me and how I could live in better alignment with my values. I was ultimately deciding how I wanted to spend my time and who was going to be in charge of the way I spend my time. Read more>>

Olivia, goes by Liv McGann

If I could go back in time, I would not change a thing about my journey to finding myself as a photographer. From a young age, I’ve had a knowing that I would be an artist in some capacity. I would tell my grandma that I want to be a photographer for National Geographic when I grow up and would go to art camps instead of daycare. Read more>>

Rose Freedman

I started my business in March of 2023, which sounds recent, but it was in the works for years. I met my husband back in 2013 who was a videographer for a non-profit organization, and we got married in 2015. I’ve always been in love with the idea of working in the wedding industry, but was too intimidated to start my own business. Read more>>

Teni “Ten” Lacy

I started TopTEN Cookies Clt back in September 2023, two years after packing up my life back in New York City and moving to a new state that I was not familiar with at all. I moved to Charlotte, NC towards the end of 2021 with my fiancé and our 3 children, and I’ve been a stay-at-home mom ever since. Read more>>