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.

Jenniffer Willis Tatyana Sinn

We started Well Reserved in 2017, just before having kids, and we experienced a lot of momentum in that first year. It felt like the perfect time—exciting, full of energy, and driven by our passion to create a wellness experience that connected people in meaningful ways. But as we grew our families and careers, it became tougher to prioritize the business. What started as a side hustle had to take a backseat to the demands of life, and for a few years, we couldn’t fully give it the attention it deserved. It wasn’t until 2024 that we decided to prioritize Well Reserved and put everything we had into making it a full-time venture. Looking back, starting earlier had its advantages—we were driven and ready to make a change. But if we’d pushed harder when we were balancing new families and careers, we might not have been able to give the business the full focus it needed to grow and succeed. Read more>>

Amy Moore

If I could go back in time to start my business sooner or later, I wouldn’t do either to be completely honest. In October 2023, I was listening to a sermon series called Bold Moves from Twin Rivers in St. Louis. The messages were powerful, but the third one is what really spoke to me. This sermon along with Bob Goff’s book, Dream Big, were the two reasons I stepped out in faith to start my business. I never really thought about being a small business owner other than seeing some adorable brick and mortars over the years and thinking of all the things I’d have inside if I ever opened my own. My dream has always been to write a book, devotional or self help but faith-based for sure. I started writing very young and continued into adulthood, working for a local newspaper and eventually as a freelance writer, which I still do today for a marketing firm out of St. Louis, Intergetik. I started a blog at least ten years ago, then took my creativity to a more hands on approach, making jewelry and decorative bottles that I displayed at a local coffee shop in the town I used to live in. Read more>>

Christina Ball

I can’t help but feel excited about how my career journey could have started sooner! I truly believe it would have brought me so much more fulfillment. As a young dreamer, I always wanted to be an artist, but I got caught up in the belief that artists don’t make a living, which held me back. Despite my passion for the arts, I explored a variety of other careers, but my heart was never in it! One of my fondest childhood memories is finding my mom’s old drawings—her incredible talent completely captivated me. I wanted to be just like her! However, she felt that pursuing a career in art wasn’t practical, having to support our family. Still, the arts have always been my refuge, my way of expressing everything when I felt lost. Read more>>

Maria Loram

If I could go back in time, starting a creative career wouldn’t have been possible. I never actually dreamt of becoming an artist. I’ve been drawing since I was a toddler, but I never thought of it as a career because I couldn’t fully express myself through painting or drawing. It took time—and the life I lived—to discover the medium that felt right for me. If I hadn’t experienced everything I did before finding ceramics, I wouldn’t have had the depth to express anything meaningful. I needed to learn, to take in the world, before I could give something back. Now that I’ve found my passion, I often feel like there’s not enough time to explore everything I want to in ceramics and art, but I’m actually grateful I didn’t discover it earlier. I’ve had the chance to dive into so many interests—travel, study, and master different hobbies—before fully committing myself to art. Now, I devote all my time and energy to ceramics, and I’m so happy with where I am. I wouldn’t change a thing. Read more>>

Joshua Manculich

What a great question! It begs the question; what is a creative career? I see potential for re-framing the question, as a lot of our backstories dip and dive into creativity, even when art might not be the focal point. My work as a therapist and an artistic director has led me to believe that ALL humans are innately creative and inquistive. Sadly, sitting eight hours a day beneath the pressure of modern expectations dampens that innate drive to create. I was lucky to have a childhood in which I played in the dirt, without excessive access to electronics, and I had the ability to spend time to foster my imagination. So to answer the question, I wish I would have started seeing myself as a creative person earlier in my life! Read more>>

Isis Destiny

Growing up I loved everything about performance art. From guitar, viola, to singing. Dance to cheer. There was a point when I began booking gigs for myself at 13, at local farmers markets and pop ups. I was showing up to the local open mic at New World deli every Monday to sing the songs I had learned that week. I fell off for a few years because I had a lot going on in my home life, but when I came back to music I began working on an EP. I was around 17 at the time when I was first stepping foot in a recording booth working with producers at Mosaic Art Studio to record an acoustic demo EP, yet life got in the way again. Read more>>

Julie Ward

I’ve always had a creative side, but professionally, I pursued a career in public relations and marketing. I worked for agencies for the beginning of my career, then transitioned in-house. Like many people, I learned a lot about myself during the forced pause of the COVID-19 pandemic. I was having an especially rough day being away from family and scared of the unknowns of COVID-19. I loved how children began creating rainbows to display in their windows, so I dusted off a pack of sidewalk chalk and made a rainbow on the sidewalk. I was surprised by how therapeutic the process was, silencing my thoughts and concentrating on creating. I started to leave inspirational messages, receiving gratitude from neighbors passing as I worked. My chalk art became a bright spot for others, and for the first time, my creativity provided me with purpose. The affirmation made me want to keep going. Read more>>