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.

Chef K.y.

For years, I always had a dream of opening a restaurant or starting a catering company. I would find myself constantly coming up with new names and concepts for these future businesses, but that small voice in the back of my mind would keep steering me away from my dreams with the question, “What if it doesn’t work out?”. In October of 2019, I was working as Head Chef at an assisted living facility, when we received word it was being bought out. The company that came in made it clear that it would be making dramatic changes, most specifically to our food budget. For Chefs, food is art. Every plate is a canvas. Taking that away, is essentially taking away what makes us special. So I left that job, and began Lyft driving fulltime until I could find a new place of employment. All the while, Covid 19 was beginning to wreak havoc across the world. Due to Covid, my regular income with Lyft had become nonexistent and my chances of finding a job became bleak. Read more>>

Carina Chavez

In short, no. I think starting my business when I did was the right move. A girls trip to Glenwood Springs in January 2021 would start the movement towards my business, unexpectedly. My friend had brought her camera and she let me use it a few times and after that, I was sold. I knew I needed to start somewhere so I saved up and got my Canon Rebel t7. I was working at a job in an office that wasn’t bad at all. I was making a good income, had a couple work friends, and had my weekends to myself. But I also wasn’t happy. I also knew I wanted to have a family within the next few years and wanted to be there for my kids the way my mom was there for me and my sister. She was a single mom who raised her two daughters by herself while working and starting on her own business. I guess you could say entrepreneurism is in my genes. Read more>>

Donna Low

I often find myself wishing I had discovered this industry earlier, as it could have been a pivotal moment for my entire family. With daughters and grandchildren who are central to my life, starting sooner would have provided us with the financial stability and resources to navigate life’s challenges more easily. However, it’s important to remember that it’s never too early or too late to get started. All you need to do is reach out. The information we provide isn’t something you would have learned in school, and I am incredibly excited to teach people that you don’t have to struggle throughout your life. Read more>>

Vayda Martinez

If I’m being honest, I do wish I had made my business official sooner. It took me almost four years to take that step, and during that time, I kept thinking about the potential opportunities I was missing out on. While it wasn’t always easy, I knew I needed to work up the courage and prepare myself before jumping in. I spent a lot of time doing research—learning what it really takes to run a business, figuring out the do’s and don’ts, and getting my feet under me. Looking back, it feels like I could have moved faster, but I also know that everything happens at its own pace, and I was building up the right foundation before taking the leap. Read more>>

America Franken

I started my business, ATX Sweet Serendipity, in April 2024 at just 16 years old. Looking back, I sometimes wish I had started a year earlier. If I had launched at 15, I would have had an extra year to refine my skills, develop better marketing strategies, and grow my customer base. It could have been an opportunity to perfect my treats and create a more polished business presence online. Read more>>

Rob Oriti

We started Him&His Design during a pivotal moment in both of our lives and careers. It was in 2020, and I was at a crossroads—my creative energy was bursting, but Covid had also halted any and all business that we were involved with. Starting the business felt like the natural next step. We had both stopped working because of the pandemic and it was our “now or never” moment. While it was a leap into the unknown, we were determined to create something that felt authentically us. Read more>>

Cecily North-rudow

I often joke with my husband that if I could time travel I would go back in time and start my business sooner. I started my business at 34 after going through college and getting my first master’s degree. But life changed pretty abruptly at 34 and I wanted to find my passion and needed something that I loved and could do from anywhere. Ten years later, I only wish that I had started sooner. If I had even known it was an option at 18, I would have signed up and gone through travel agent school (yes that was a thing at one point) and really dived into the business back then. It would have been a constant and a support for all of the ups and downs that life has thrown at me in the past 26 years of my professional career. My host agency has truly become a family to me and I would have loved to have started with them on the ground floor and grown my business while they grew theirs as well. It also would have been fascinating to be part of the internet jump, when brick and mortar travel agencies started closing due to the internet but continue to make the jump to an at home business. It would have taught me more resilience, how to adjust to changes and to learn new technologies and adapt quickly. Read more>>