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.

Kayla Harris

Omg, yes!! I wish I would’ve started way sooner. I started in 2019 while I was working as a Men’s Sales Associate at Belk of Florence. Growing up I never thought I would’ve made baking into a business. I think if I started sooner rather than later then I would’ve been further along and I would’ve had a bakery by now. If i started sooner I would’ve had way more time to practice and perfect my craft. I most likely would’ve went to culinary school after I graduated high school instead of jumping right into the workforce. Read more>>

Tasena Renner

A do-over isn’t given, but I’m sure glad I gave myself a second chance to participate full-time in my passion. I knew by age 14 I wanted to draw people for money, and I did visit a university with plans to go, but I didn’t go. I, instead, went to a technical college at age twenty-two and got an Associates in Health Science. I had plans then too for transferring to a university and getting my BFA, but I again I let finances overrule my heart and desires. Read more>>

Bre Cain

Honestly, I don’t wish I’d started my business sooner because I wouldn’t be the woman I am today without going through everything that brought me here. Becoming a mom changed me in ways I never expected—it made me tougher, gave me perspective, and showed me what really matters in life. I started my business when my kids were still young, and while it would’ve been amazing to have more time and fewer distractions, I know I wouldn’t have had the grit or the guts to do what I’ve done without motherhood shaping me. There’s something about balancing nap times, tantrums, and business calls that builds a kind of resilience you can’t fake. Read more>>

Miranda Heitmann

When I graduated high school, I went to college and played volleyball and pursued a degree in Psychology. When I graduated, I used that degree to work in foster care and child protective services for nearly ten years. I worked in various departments during my time in drug and alcohol testing, managing a group, foster care specialist, licensing specialist, and training. Read more>>

Janis Greenwood

Starting my own business has always been a lifelong dream. Looking back, I sometimes wish I had launched Foundation by Design sooner, but I’m grateful for the journey that brought me to where I am today. Starting later allowed me to grow and gain valuable experiences in my previous roles, but taking the leap 11 months ago has been one of the best decisions of my life. I wouldn’t change a thing! Over the past year, I’ve had the privilege of meeting incredible individuals in the wedding and event industry, many of whom are entrepreneurs themselves. It’s been such a blessing to bring joy and beauty to people’s lives through flowers, whether for life’s big milestones or its quieter moments. Read more>>

Altoria Brown

I started my business WinkLilly Beauty my sophomore year in college in 2017. It was the hardest year for me academically and challenging personally with family and friends back home. I felt challenged in all angles of life and the one thing that brought me relief was doing my makeup, styling my hair and masking what I was dealing with internally. I started my business wanting to supply others with products to help them feel and look beautiful no matter what they were experiencing internally. I can’t really imagine if I had started it sooner because until I experienced what I did, I hadn’t thought deep into the power of beauty products. Read more>>

Sarah Schrenker

If I could go back in time, I wish that I would have started my business sooner, and if I am being honest, the thing that was holding me back the most, was myself. I never truly believed that I would be capable of being a successful photographer, let alone running my own business. Photography was more of a hobby for me, a creative outlet that I used to capture the smallest of moments, to big life changes. I started picking up my camera and learning more about the art of photography when covid hit the world. Read more>>

Marterra Cromwell

If I could go back in time I would have started my business sooner. I spent a year doubting myself and being scared to start. I found reasons not to start at that time and kept waiting for the perfect time. I wanted an opportunity to come along instead of creating one for myself. Then I took a year finally taking the steps necessary to start my business. Although I love the journey I know I would have been further along in my business if I believed in myself and trusted God from the beginning. Read more>>

Taylor Davis

I feel very fortunate to have started my business at just the right time. I had been working in the entertainment industry on the representation side, and while I loved the work, I didn’t feel I was able to express my creativity as much as I would have liked. Reflecting on the feeling that I started my business at the right time I feel like I learned to trust my instincts, The concept of my candle line came to me like a flash, and I listened to my gut. That was the path I was meant to take in that moment of my life.  Read more>>

Jazmine Limon

I do sometimes wish I’d started my career as an artist sooner. I’ve been creating art forever but doing it as my actual career is pretty recent. If I’d started sooner my following might be bigger, my style and ability would be more developed. However, when I think deeper, I realize that my style might not at all be what it is now had I not begun after the birth of my daughter. With her birth came my biggest inspiration. I’d always been searching for what it was I wanted my art to look like, revolve around. I knew I wanted it to be spooky, and kinda cute, and baby skeletons kinda just made sense. Childlike in theme but creepy in nature. So, although I would be farther along if I’d started sooner, my art also might not be what it is. Though I’m always trying to make the next piece better than the last, especially in terms of ability, I’m very happy with what I’m painting in theme. Read more>>

Gregory Alvarado

This is something that I talk about often when people ask me the same. I am absolutely confident when I say, I started my company when it was meant to happen. Now, this doesn’t mean the path was pretty and planned out, because that is completely the opposite. But when I think about it, I had been prepping for this for years. However, what I’ve learned and when I learned key components, everything happened at the right time, and I am still figuring things out. Read more>>

Amy Godin

If I could go back in time, I absolutely wish I would have taken the leap into running my photography business full-time MUCH sooner! I started my business (back in 2009) when I was a student at Algonquin College studying Photography. My first wedding client was looking for a college student to capture their big day, they wanted to stay on a tight budget and mentioned that they liked the idea of having photos to help a student build their portfolio—an opportunity I couldn’t resist. That experience was so wholesome and made me realize that weddings were where my heart was. However, after graduating Photography, I furthered my education and took Business Management and Entrepreneurship at Algonquin. I kept photography as a side hustle while always just taking what felt like the “safe” route chasing jobs that provided a steady paycheque. Read more>>

Jasmine Mota

If I could go back in time I definitely would have started my business sooner. My God Given talent was doing hair, I had been doing hair since the age of 12. However I was ambitious about going to school and getting a degree in Law. I married young and eventually had my son and my dreams and wants for myself changed. I began working in Law enforcement while going through a divorce; needing to provide for myself and my son. While working in a career job I was treated poorly because I didn’t have childcare nor a support system for my son. They didn’t care about me or my well being. Read more>>

Paige Drysdale

I could go back and start my business sooner, I absolutely would—though only if I had the mindset I have today. The lessons I’ve learned and the growth I’ve experienced have really shaped the direction I want my business to take. With the knowledge I have now, I can already see ways I could’ve made things smoother and maybe even accelerated my success, but that’s the all apart of the journey. Read more>>