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.

Lauren Lewchuk

It’s easy to say that I wish I had started much sooner in my creative career than I actually did… basically I wish that I believed it was possible and that I didn’t let people convince me that being an artist wasn’t reasonable. Letting people convince me that I needed to have a “real job” and do art on the side is what made me wait so long. I barely even believed that being an artist was possible when I was in college… I ended up majoring in graphic design because it was perhaps the “closest” thing to being an artist. I think a lot of people have gone down that road as a sort of compromise. Read more>>

Jesse Haswell

I guess I need to go back to the beginning to when I first picked up a camera. After my mother passed away in 2004 I began living with my dad and then step-mother in Paonia, CO. That following spring we had a series of rain storms that left the foliage vibrantly green and the earth rich brown. On one particular day the storms let up leaving crystal clear blue skies and a small halo of clouds around Mt. Lamborn. I was fortunate enough at the time to live in a house that faced directly towards Mt. Lamborn so upon seeing such a magnificent scene I knew I had to capture it. Read more>>

Aimee Fuller

I started my business 12 years ago in January of 2010. I was a stay at home Mom that had experience in photography and was more of a hobbyist photographer. I would take pictures of my own babies and over time friends and family would see my work displayed in my home or shared on social media, and ask me to take their baby’s pictures as well. I really enjoyed working with babies and capturing that small moment in time before they grew. Read more>>

Natalie Kreidler

I started a “creative career” during my first year in college, pursuing fine art alongside my school work because I had realized that was what really made my life feel rich and that’s what I wanted to be doing with it. I started to take commissions and do art directing for musicians pretty quickly after I decided to pursue art seriously. I don’t think I started at a bad time and I’m thankful now for all of the experience I’ve had- but I’m definitely realizing I could have taken it slower and not worked myself so unnecessarily hard with school and art at the same time. Read more>>

Chanel Ebanks-Texada

Absolutely! I definitely wish I started to pursue my career in makeup sooner. The reason I did not was because of influence. I knew I wanted to be a makeup artist when I was 18 back in 2013 . The adults in my life shut down the idea of me going to cosmetology school vs college because they didn’t view being a makeup artist as a ‘real job”. I was once told “you are too smart for that”. Being that I wasn’t able to support myself and relied on others, I didn’t really have much of a choice to do what I wanted. Read more>>

Hector Bernal

Part of me sometimes wishes I could have started my creative career sooner. But I am beginning to see that I started just in time. If I would have stated sooner, I would have not been able to experience the creative awakening during those years where I was trying to figure it all out. I had just graduated into a recession in 2009 and I had no clue how to make furniture other than I knew I wanted to make furniture. I was too worried trying to find a job and start my career in design. No stable employment, all the time in the world, and with enough youth and adrenaline for life my creativity escalated! Read more>>

Lauren Virdure

If I could go back in time, I would certainly have started my career sooner! Don’t get me wrong – I am a firm believer that things happen when they are meant to happen. However, I would have liked to take steps to prepare for the career path that I desired. I started dancing at 11 years old, took a break in high school for cheerleading, and resumed dance training in college. Read more>>

Claire Vohman

I knew I wanted to be an artist since about 6. I always wanted to do the posters in school, and I thought I really was good. Looking back, I was good at ideas and composition, but still to this day my drawing skills are lacking. I never had the confidence to pursue it until I was 35. I started in 1998. I did study graphic design before that, and did that for a while, but having full control of my creativity is what I wanted. Read more>>

Chrissie Forlie

I would have pursued this career much sooner! I originally tried to pursue modeling back when I was in High School, but Beauty standards were very different back then. Being a size 6 at 16 trying to break into the modeling industry was definitely a struggle. In a society where there is so much pressure and expectation on a woman’s appearance, it often spiraled into insecurities and the Body Dysmorphia would start to creep in. Read more>>

Amanda Lovett

There have been times I wish I had started sooner, and perhaps focused more in a specific area, but the reality is, had I done so, I wouldn’t have near the life experience from which to pull. Every blessing I’ve been given, every trial and tribulation I’ve lived through, every journey I have taken has greatly contributed to how I develop my work. For example, after having spent 20 plus years working in the field of graphic design, primarily focusing in the area of layout and design, Read more>>

David McLaughlin

If I could go back in time, I would like to have started my business sooner! I started Sati Soda October of 2019, but I’ve known I wanted to start a ready-to-drink company for 15 years… I just didn’t know what kind of drink it would be. Several of my friends own kombucha, yerba mate, and chai companies so I just didn’t have a sense of certainty as far as developing something different from the norm that was functional and would benefit people. Read more>>

Wendy Crist

My husband Tim and I have always been “makers”, or creatives. We have been a couple for just about 30 years now and we’ve not always had the money to be able to buy what might be our taste so we would just figure out a way to make something similar. For decades we just created in order to fulfill our own needs and wants. While I suppose making a living as an artist or as a creative sounded fun it didn’t seem like something that would pay the bills. Read more>>

Londen Underwood

If I could go back in time, I wish I would have started my business later. When I first started my business in 2012, it was a fashion styling business for men. I fell into the field but did not know anything about running a business but was in a situation where I was no longer employed and needed a backup plan. Entrepreneurship was not a part of family conversation, so to have my own business was foreign. Although I was good at styling customers, I was not passionate about it. Read more>>

Annie Jones

I always loved dreaming and making those dreams come true From writing short stories of villains and heroes and far away adventures to making costumes for Halloween or just painting alongside my uncle in the afternoons, or making up lyrics to songs I would play on the piano at 5 years old, Since I was little I was always creating, I was always most alive when I was creating. Read more>>