The uncertainty of entrepreneurship causes many entrepreneurs to put off starting their business. For others, losing a job or other economic hardships push them starting their businesses earlier than expected. In our conversations with thousands of entrepreneurs we’ve seen so much variety in when, how and why people started their business and so we wanted to share a wide variety of views and reflections on the question of whether these folks wished they had started sooner or waited longer before starting their businesses.

Ashli & Shannon Mccoy & Clark

If we could go back in time, honestly, we wouldn’t change a thing about when we started this business. Let us tell you why. We launched this brand during a time when life was serving all the “figure it out or fall behind” vibes. Everything felt uncertain, and we were trying to find our footing—both career-wise and personally. We didn’t have it all figured out (not even close), but what we did have was a clear vision and the drive to create something meaningful. Starting sooner? Maybe we’d have gotten a jumpstart, but would we have been truly ready? Mentally, emotionally, or even skill-wise? Probably not. Starting later? Let’s be real, we might’ve overthought ourselves out of the whole idea entirely. The truth is, timing is everything, and while it wasn’t perfect, it was exactly what we needed. Every mistake we made, every win we celebrated—those moments built the foundation for this brand. Starting earlier might’ve changed our trajectory, but not necessarily for the better. Starting later? We might’ve missed the window of opportunity that brought us here. So no regrets. We started exactly when we were meant to, and that’s what makes our journey so powerful. Read more>>

Sara Hanson

Yes! I almost started my business a few years prior (2019) after years of work in property management with cleaners I wasn’t satisfied with. I regularly touched up after them, and found myself becoming a pretty great cleaner! I had far less supportive people in my life at that time, and I didn’t have faith in myself. When I met my husband, he encouraged me through every hurdle and helped bring Busy Bees Cleaning LLC to life! Read more>>

Brandon Slade

I started Untapped Learning while teaching middle school. Many parents were nervous about the transition to high school and worried their students wouldn’t receive the same level of care, coaching, and accountability I provided in my classroom. When they asked me to coach their students, I realized the need for more support during this critical stage. If I could go back, I would’ve started Untapped years earlier. I had the idea and knew it would work based on research, but I lacked confidence and kept waiting for permission. I’ve since learned that if I feel strongly about an idea and the research supports it, it’s worth trying. Starting sooner might have allowed me to help more students earlier, but the timing ultimately gave me the experience and clarity needed to build something sustainable and impactful. Read more>>

Jennifer Salvetti-kulla

I launched JSK Fine Art Appraisals in 2020, during a pivotal moment in my life and career. At the time, I was managing the gallery at Art & Frames, which gave me incredible insight into the art world and firsthand experience working with collectors. I had been with the gallery for a few years, and while I loved the work, I started noticing a gap in the market for professional fine art appraisal services in San Diego. I knew I had the expertise and passion to fill that gap, and starting my own business felt like the natural next step. Looking back, I think the timing was perfect for me. If I had started sooner, I wouldn’t have had the same level of confidence or the depth of experience that came from working in the gallery and completing my formal appraisal training. Those years gave me the foundation I needed to establish my credibility and understand what clients really value in an appraiser. Starting later might have given me more time to refine my systems or build a broader network, but I also think I would have missed out on the lessons and growth that come from diving in and figuring things out as you go. Read more>>

Stephanie Mckeon

It’s such an interesting question, and honestly, my answer reflects the journey I’ve been on. I started my coaching business almost immediately after earning my certification. At the time, I was in a whirlwind of life changes—I was very pregnant with my first child when I began my certification program, gave birth during it, and navigated the newborn stage while finishing my training. It was an incredibly challenging time, juggling sleepless nights, new motherhood, and certification coursework, but it was also deeply rewarding. I leaned heavily on the support of my fellow coaches and mentors during that period, and I’ll always be grateful for their encouragement. When I officially launched my coaching business, I wanted to help everyone with everything. On one hand, it felt exciting—I thought I could be a resource for anyone who needed me. But it also felt overwhelming. I was a new mom, working full-time, and coaching part-time, all while trying to manage my own ADHD symptoms. I was constantly on overload, burning myself out trying to juggle so many roles. Read more>>

Al-karim Moloo

If I could go back in time, I don’t think I would have started my business sooner—I believe the timing was just right. My partner and I founded our accounting firm over 12 years ago. Before that, I was working at an international accounting firm. I really enjoyed the work, but I also felt limited. I wanted more independence, control over my future, and, most importantly, the opportunity to build something of my own. When I decided to take the leap into entrepreneurship, I turned to a mentor I had been working with. We had a series of in-depth conversations about business philosophy, risk, and the realities of starting a firm. After reflecting on these discussions, we agreed that it was the right time to move forward and start our own practice. By that point, I had gained the experience, skills, and resources I needed to make it work. Read more>>

Rockell Jackson

I honestly think my business started at the perfect time, everything unfolded how it was supposed to. At the time I was still applying for jobs in every industry seeing what I liked best and then I got in trouble with the law. Getting in trouble changed my entire life and hindered a lot of careers and jobs that I could apply to. I was convicted in 2014 and started my business in 2015 when I was 20 years old. I received unsupervised probation and no jail time. My current job was a contract so it was soon to come to an end. I was applying for any job available and was having issues getting an interview due to my new record, but with the Eastern Shore being such a small place it was never easy to get a job even without a record.  Read more>>