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.

Patti Bevilacqua

I started fearLESS with MS in 2022—but let me rewind the tape a bit.

I left teaching in 2000 and went on long-term disability in 2007. Between those years, I earned my PhD, thinking I’d land a job in higher ed. Spoiler alert: that didn’t happen. So I wandered. Aimlessly. I volunteered. I walked my dogs. I tried to figure out who I was without the career that once defined me. I was grieving the life I thought I’d have until retirement. Read more>>

Dwayne Allen

Looking back on everything now, starting a business was something I’ve wanted to do for such a long time. I would have started my business long before I did, but the reality is, timing is everything.

As an apparel designer, creatively speaking, I’ve been captivated by the idea of creating new things and brining many ideas to life. At the time, I was working in the multimedia space dealing with video production, shooting, and editing. Every day I went to work and all I could think about were my own ideas on how to create new apparel and content, creating new ideas and concepts for a brand that represents what I stand for in my life. Read more>>

Rose McKinney

During a public relations class in 1985 at Drake University, I boldly declared that I wanted to own my own agency by the time I was 30. Well… life had other plans — and honestly, better ones.
Marriage and kids shifted the timeline, but also gave me exactly the experience I needed. I spent my 20s freelancing while raising our first two children, gaining hands-on experience, a glimpse of business development, and a growing vision for what my own agency could one day be. At 30, I returned to full-time work thanks to a freelance project that turned into a leadership role at an ad agency, where I built a profitable PR division. Read more>>

Rona Siskind

I received my early training in drawing and painting as an adolescent at the Roslyn School of Painting, in Roslyn, New York. It was there that I not only developed a solid foundation in figurative art and cultivated a lasting appreciation for charcoal drawing and oil painting, but also realized that being an artist was an important part of my identity and what I loved most. By the time I was a senior in high school, I painted there four times a week and began to consider a future in art. As a result, I applied to art schools and universities with the intention of majoring in fine art. Read more>>

Kimberly McCaskey

I started a creative ‘career’ right out of college… just not my own, since everything I created belongs to someone else. I was probably more suited for a fine art degree, and out of practicality, I got a degree in graphic arts. I was told it was the only way I had a chance at paying the bills. True or not, I don’t regret the degree, because it’s undoubtedly shaped me as an artist and the kind of art that I do. I wouldn’t even be doing some of the core techniques I use. I also don’t regret the time I’ve spent working in studios and creative agencies, learning from exceptionally talented creatives. I dabbled in fashion early on, learning that creative process… all things I’ve learned, and I’m always experimenting with incorporating that knowledge into my process. Read more>>

Tanja Caterina Eltze

As far as I can remember back, I was interested in art and design and I was always creative. The love for art was fostered by my parents, who took me to museums at a young age. I was by far the youngest child in our family, so by the the time I was around, they were pretty much done with the kids’ stuff. But these early art and design museum visits lit a fire. So I drew and painted, I crafted dresses for my dolls, I came up with new letter-designs for my school notebooks and I did an internship with a graphic design studio to draw and design the posters for our school play. However, when it was time to go to college, I chose a school that would allow me to combine my other interest – business – with my love for design. For ten years, I was first a trainee in conjunction with college, and then working for the international fashion house HUGO BOSS AG at their headquarters in Germany. Read more>>