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.

Carla Welechuk Kowski

That’s a great question, you know they always say hindsight is 20/20 and so often we look back and have regrets. I started Alea Beauty in 2018 after a cross country move to Columbus, Ohio from Seattle, WA. I was 42, had gone through a nasty divorce, just saw my youngest off to college and at the beginning of a new relationship. Read More>>

Vanessa Munoz

If I could go back In time I would definitely wished I done this sooner. We started working on Mírame Hair Salon May 2021… we officially opened August 2021. I still had my full time hairstylist job and was juggling between the demo, and remodel. Read More>>

Raffaele DiLallo

My business, Ohio Tropics, started with a website back in 2017. I wish I had started it earlier because I would have benefited from the ‘golden days’ of blogging but as they say, today is the next best time to start anything. The online world has changed rapidly since then, and it’s part of the business and adaptation is really important. Read More>>

Ramone Dixon

People often ask if I should have gone full-time in the wedding industry sooner. Looking back, I don’t think doing it earlier—or waiting longer—would have put me in a better position than where I am today. Before becoming a full-time Weddings and Events Entertainer, I worked as a chef in Houston and was a member of Unite Here. Read More>>

Ashley & R. Carnie Littlefield

Honestly, R. Carnie and I both believe in the timing of everything so to put it simply, we believe we started Maker’s Market Tennessee (previously Maker’s Market Texas) at just the right time. What we currently have as a business model actually started back in our hometown of Austin. Read More>>

Karen Stuth

I’ve often been asked if I wish I had started my publishing company sooner. The answer is neither yes nor no. I believe Satiama was founded exactly when it was supposed to be, but I do wish I had another 30 years to expand it into its full vast potential. Read More>>

Nancy Peham

I officially started Helping Hands Personal services in November 2001. I had worked in the corporate environment for about 14 years and was unhappy with the career choice I had made. Even though I considered my income to be good I wasn’t happy going to my job every day. Read More>>

Diane Russo

I have always worked in the corporate world under Vice Presidents of major corporations. I never dreamed that I would become a professional artist at the age of 57. I wish I would have discovered my artistic talent earlier in life so that my parents could have experienced my art. Read More>>

Jonah Reid

If I could go back in time, I would have started my creative career sooner. I began writing around age seven and started taking music seriously at sixteen, but at the time I did not fully understand the business side of entertainment or the value of consistently documenting my work. Read More>>

Ashley Velez

I wish I would have started sooner in my career. As a kid you would think anything is possible and it would have been beneficial to gain more experience. I started a couple of years ago auditioning and was not immediately selected at the time. Read More>>

Tanya Venter

At an early age I know that I had a creative advantage and knew that I can make beautiful things. I just didn’t lean into that creativity and believed I didn’t have it unfortunately. Thought I needed a reason or homework to create work and I didn’t have the creativity to create something for myself. Read More>>

Tito J Medina

If I could go back, I would’ve started sooner not because I wasn’t talented enough back then, but because I spent too much time doubting whether my creativity could actually become something real. When I first started creating, I was in a phase of life where survival came before passion. Read More>>

Heather Heath

I definitely wish I could have started my career earlier, and more organized at the start! When I started Sugared Edge I didn’t think it would go very far, I had a toddler, I enjoyed baking, I enjoyed art, I didn’t realize how far I would fall- just completely head over heels in Love with this career. Read More>>

Kendal Rhone

I do wish I would’ve started earlier, but at the same time I think everything happened the way it was supposed to. If I had started sooner, I think my journey and perspective would’ve been completely different. I appreciate every experience that led me to this point because it all shaped me into the artist and person I am today. Read More>>

Megan Dardis

In an ideal world you follow a certain trajectory right, graduate high school, go to college and earn a degree and set off into this glorious career path. Well, my path didn’t follow that straight line. About two months after I graduated high school I gave birth to my first child. The college applications I had filled out, never sent in. Read More>>

Claire Cepukas

I’ve always felt a strong pull toward creating which is what led me to pursue a Bachelor of Fine Arts. I spent my university summers tree planting and immediately fell in love with life in the woods. After graduating, rather than develop myself as an artist, I moved out west to continue frolicking outdoors and to build a life more rooted in forestry. Read More>>