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.

Alexis Nettles

I used to toy with the idea of what it would be like if I started creating content sooner, but now that I’m older, I realize I wouldn’t change a thing. I’m very grateful to have matured a bit more as a person before allowing the internet to play such a huge role of my life. That’s not to say it’s bad to start young (there are some incredibly talented, young creators out there!), it’s just to say that there is a lot that comes with being perceived on the internet, and I’m personally glad I wasn’t doing what I’m doing now in my teenage years. Read more>>

Caitlin Bentley

I don’t think I would have been ready if I had started my business sooner! When I started Feral Notions, I was reeling from postpartum depression, the onset of chronic illness, and serious burnout from my job as an animal shelter veterinarian. Oddly enough, what I went through made me braver — I had faced some really scary times, so trying to sell sparkly quilting rulers on the internet didn’t seem like too much of a risk! Putting myself out there with my business seemed daunting before, but after that dark period, it was small potatoes. Read more>>

Caitlin Turner

I launched The Pour Tour after spending several years in my former career, where I gained invaluable experience scaling businesses, building teams and always making sure that our customers had an amazing experience. During that time, I developed a passion for creating memorable experiences through unique events, particularly those centered around cocktails and social gatherings. The idea for The Pour Tour came to me as I noticed a gap in the market for high-quality, tailored mobile bar services. Read more>>

Katrina Hess

Learning new things as an adult always feels like I’m starting too late. I remind myself that 5 years from now I’ll be glad I started 5 years ago. Around 2010 I knew I wanted to transition from my graphic design career to designing and making clothing so I launched a custom outerwear business. Sales were going well but one of my other projects unexpectedly took off and deserved full-time attention. I put the outerwear business on hold knowing I would come back to it one day. Read more>>

Lyn Larson

Starting a business in my mid 50’s has been both exciting and scary. I had worked for someone else in the balloon industry for 10 years. Late last year she decided to make some changes and eliminated my position. It came as a shock since I was her only full-time employee and we had expanded the business to 2 shops. I felt I was an essential part of her growth and success, so it was difficult for me to move on. But I didn’t have a choice. It was time for me to do something else. But what should I do?!? Read more>>

Moriah Kennard

I don’t believe I would have started my business any sooner or later. I started at exactly the right time, having gained invaluable knowledge from my previous jobs that shaped me into the business owner I am today. Teaching taught me how to build something from scratch and to trust in my own skills for success. Serving helped me master multitasking and perform well under pressure. Had I launched my business earlier, I wouldn’t have developed the interpersonal skills or self-motivation I possess now. I’m grateful that it took the time it did to start my business focus in on what type of clothing brings me joy. Those experiences ultimately led me back to my true passion in fashion and sustainable clothing. Read more>>

Sara Azadi

If I could go back in time, I wouldn’t change a thing about when I started Tushbaby. I launched the business when I was 40, and by that time, I had spent nearly two decades in advertising. This was crucial because I had learned how to build, grow, and launch brands that truly resonated with consumers. Starting earlier would have been possible, but I wouldn’t have had the same level of insight and maturity. My experience gave me the perspective and confidence to create a brand with longevity and elasticity. Read more>>

Shawna Solomon

Later, knowing what I know now. As many have, I became a a entrepreneur out of need. Knowing what I know now, starting later, to be properly prepared would have been best. I didn’t have the proper systems and processes in place until the business was stuck and I was ready to scale. My husband had gotten sick and it was up to me, to make a way. I couldn’t do both, be at the hospital and at the store. Nothing was in place, outside of me. I was everything, the lifeline of my business, Had to shift the business online only, operating out a Facebook group and shipping from his hospital room. Read more>>