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.

Claire Howard

I started my business when I was in my early 30’s and I had two young kids and I knew that I wanted more. I now have 4 kids who are my entire world. The most challenging thing for me as a business owner has been juggling my personal life and work life. It is hard to find a healthy work/life balance on most days. I struggle to be the wife that I want to be and the mom that I wanted to be all while also running my business the way that I want to. If I had started my business in my 20’s I would have been able to focus much more on by business without juggling and navigating motherhood. But I also am a firm believer in God’s timing and I think He knew what was best for me all along. Read more>>

Vanessa

I launched my small business in April of 2020, and looking back, it honestly felt like the perfect moment to start something new. With COVID in full swing and everyone stuck at home, I saw it as an opportunity to bring a little joy into people’s lives. Whether it was helping families connect or offering something special for those enjoying quiet moments alone, I wanted to brighten their days in any way I could. Read more>>

Tory Zamakhovskaya

Looking back, I sometimes wonder what would have happened if I had started my business sooner. But ultimately, I believe I started at the right time for me. I launched Khoade during a pivotal moment in my life—I was working a corporate job, feeling the pull to create something of my own, and experiencing a personal wake-up call when my mom was diagnosed with cancer. That moment solidified my desire to have more freedom and control over my life, and it gave me the push I needed to finally take the leap. Read more>>

Kanika

I often wish I had started building my brand, Kanika’s Kitchen, and establishing my presence on social media much earlier. If I had, more people would have known about me, trusted my work, and felt confident buying from me. Looking back, I wish I had found the courage to put myself and my offerings out there for the world to see. One of my dreams is to launch a cookbook, and if I had begun growing my audience earlier, I could have been at a point where I was ready to launch and share it by now. It’s a lesson in taking the leap and believing in myself. Read more>>

Chloe Bott

If I could go back in time, I wouldn’t change a thing about when I started my business. I was not the person I am today, nor was I ready to take on the responsibility of owning my own company. Every business I worked for along the way shaped me into who I am now. Each experience, every challenge, and all the lessons I learned refined not only my skills but also my understanding of what it means to be a leader—not just a boss. Read more>>

Jill Johnson

As they say, “timing is everything.” I am a business owner of less than a year, but have always felt that I would land here. There has only been a few times in my many decades as a working professional that I wasn’t very clear about what was coming next. As I am typing, I can still recall every single relationship (both good and bad) that has gotten me to where I am today. Every single email, led to a conversation and every conversation, led to a meeting. Those touch points for almost 30 years are now clients and relationships that I consider magic. I have never taken them for granted and many of them are still important and relevant to my consulting business. I think there are moments that you know when to jump. Read more>>