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.

Madaline Feine

If I could go back in time, I wouldn’t change the timing of when I started my business—I truly believe I started it at the right moment in my life. I launched my photography business in 2022. At that point, I had just stepped into motherhood and was navigating huge life transitions. I was craving something that was mine—something creative, fulfilling, and flexible—and photography gave me exactly that. Read more>>

Dhaisy Vue

I say this to all of my students and peers… if I could go back in time, the only thing I would have done differently is start sooner. Not just getting my license early but also taking it more seriously to begin with. I was 20 years old when I got my esthetician license but because I was just a lost soul at that point, I wasn’t expecting much from this career. I felt like building a career in this industry was too good to be true. As I started seeing my own personal and professional growth, it motivated me to be the business woman I am today. Read more>>

Nicole Valenzuela

Sometimes I wonder where I’d be if I had started my business earlier. In theory, I might be farther ahead. But in reality, I couldn’t have built this business without living — and learning from — everything that came before it. Read more>>

Camron Robles

As with most life decisions, I sometimes wish I’d made the move sooner. I found that I was hesitant when faced with change, I think most people can relate to the that feeling, “better to be comfortable what you know rather than uncomfortable with the unknown.” Change, even good change, is scary! Read more>>

Kristin Isfeld

I grew up fishing oysters from the Lynnhaven river and Chesapeake Bay with my dad. I love oysters. I would eat alot of them before we even got home. It was almost a problem. But my dad was happy that I was so interested. Flash forward, I moved back to Virginia Beach as an adult and became involved with the Lynnhaven River Now organization. They are a non-profit that has restored the Lynnhaven River to its former glory as a thriving ecosystem and estuary to the Chesapeake Bay. It had been devasted by overfishing and land runoff polluting the water. Planting out oyster beds helped filter the water and re-establish the natural balance. Now there are farming, fishing and recreational activities all over and the river is thriving. Read more>>

Eduardo Sierra

It was recently that I started to work on user research projects. Understanding how users experience products and prototypes piqued my curiosity about design.

I went on to create icons, UI interfaces and module mockups on Figma. However, UI design has its guidelines and I wanted to have autonomy to explore my creativity. Read more>>

Frank Belmont

I wish I had started Bormont Entertainment much sooner. For years, I was deep in corporate America, working with some of the biggest beauty brands in the world. I was hesitant to walk away from all the perks that come with that life—great pay, stock options, company cars, top-tier benefits. It’s hard to leave that kind of security behind. Read more>>

Jacqueline Thornton

I love this question because I can really relate to it on a personal level. I started my interior design business at what felt like the perfect time—one of those rare moments when everything aligned just right. I was in a job that wasn’t fulfilling me, and it had started to take a toll. Then, unexpectedly, I was laid off. It was incredibly scary—I had never been laid off before—and to make things even more uncertain, my husband had just finished anesthesia school, so we were both in a phase of starting over. It was overwhelming, to say the least. Read more>>