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.

Stephanie Swilley

Having started with art in my 30s – married with kids, I often wonder what it would have been like if I had found this passion in my youth. The closest I’ve had to formal training were my public school art classes in elementary and middle school (I was in band, so there was no room for art class in high school). Read more>>

Lauren Gibson

I have been sewing since I was a little girl, altering my hand-me-downs to make them unique and my own. I owned a boutique for 4 years and a lot of my customers were musicians who wanted something extra or unique for stage or shows. So I started adding flare and creating here and there custom pieces for known artists. I decided to create my own unique piece 3 years ago for our local music awards to bring attention to my boutique. Read more>>

Kenisha Mcgee

I started doing my own hair at 11 , so at that age I knew I was going to be a great stylist. Looking back the only thing I would change is that I never would have stopped working on it . Over the years I tried to convince myself to do other things when knowing in my heart this is where my power comes out the most by being creative with my hands. Read more>>

Zavior

I wish I would have focused on my gifts sooner but, I dont think I would’ve wanted to start earlier due to the amount of people who were taken advantage of at my age. Id probably be further than I currently am but i wouldn’t really change anything Besides me focusing on instruments. Read more>>

Morgan Moody

Absolutely! I wish I took my social media serious when I was in college from 2012-2017, I would’ve been beyond bigger than where I am today. But I thank God and the Universe, because timing is everything. Read more>>

Jenny Kimmel

I think that we are all artists in our own right, everyone is capable of creating beauty in a day, uplifting another, having a unique perspective, using their voice. It took me a long time to call myself an artist, it was a scary term for me, an embodied term, and I spent my youth learning to be courageous enough to claim it. My “regular job” as a Montessori gardening teacher was anything but “regular”, but I did earn a steady paycheck and was of the world in normal working hours, toiling with the rest of humanity. Read more>>

Adria Chavers

I’ve always considered myself an artist. Always. But I never considered making a business out of it. A.C.Creativity was birthed out of the pandemic. Our family lost someone very close and very suddenly. It was through that experience that I said to myself that I was going to do something with this passion and these skills. I wasn’t going to let another day go by – we never know when our last day will be. Read more>>

Smittybones

From a very young age, creativity has always been a part of who I am. As a child growing up in the late 80’s/early 90’s, I found myself captivated by Disney movies. With a piece of tracing paper and a VHS player, I would pause the screen and meticulously trace every detail of my favorite characters, sparking a deep love for portraiture that still exists within me today. Read more>>

Michael White

I’ve always wanted to sing but never found the confidence until way later into my 20’s. I was doing karaoke a lot and a lot of people were asking me if I had my own music and I kept saying no. They told I should, and at the time my partner at the time told me to make my own music. Read more>>

Dr Slay

Around the time when I was preparing to graduate from high school I wanted to attend school for music production. I shared this desire with some older family members and was ultimately swayed to venture onto a different path. They believed that making music wasn’t a “real” job and wouldn’t be lucrative. So with that bubble popped I decided to major in business since having my own company was the only other career move that felt right to me. Read more>>

Reba Kolbeck

Even as a girl young I always knew that I would own by own specialty shop/business. My first job, starting at age 14, was working at a seasonal ice cream shoppe where I grew up. I worked there for 9 years! All through high school and college. When the owners decided it was time for them to move on to something else, they offered me the business. At that time, I was 21 years old, and it scared me to death wondering if I would be able to handle it on my own. Read more>>

Eric Adler

I started an apprenticeship under a master tailor named Manuel, who only made one-of-a-kind couture pieces. When I began my journey in the fashion industry I had a dream to start a brand and go into wholesale/retail sales at brick-and-mortar stores. As my experience grew in the custom/bespoke clothing niche of the fashion industry, my dream shifted to wanting to design/create/manufacture custom and small-batch clothing for my clients. Read more>>

DOMONIQUE CARTER

I started Million Dollar Walk at the height of the pandemic. I felt as though that was a significant time for change. I also believe I started at the necessary timeframe, on God’s timing. Not only to set my eyes on new beginnings, but to allow me to make errors and correct them as I go. Read more>>

Benita Akadie

I absolutely wish I could have started my career in esthetics sooner. I had known since I was 2011 that I wanted to be an esthetician. It didn’t live up to my parent’s expectation so I dabbled in many other things. I sent so much time researching the subject of skincare and skin science that when I did finally decide to take the plunge, I had an arsenal of knowledge at my disposal already. Read more>>

Jules Schaefer

I grew up in a time when it was believed success could only be achieved with a college degree. This was repeated often during my high school years, at that time it may have been accurate. I delayed my dreams of a career in the beauty industry because of this ridiculous idea that I had to go to a traditional college. Read more>>

Margaret Dowling-Murphy

While part of me wishes I started pursuing art professionally years ago, I know the years I spent doing other things brought me to this point in my life. As a former communications professional, I learned writing and marketing skills that I use today. As a high school teacher, I learned how to execute various roles, juggle deadlines, and navigate different personalities in addition to making connections with many of the amazing people who are still in my life. Read more>>

Chamcee Blackwell

If I could go back in time, I would have started my business two or three years after I picked up the camera for the first time. I learned later in life that being passionate about what you do in life yields better work- better outcomes. I initially picked up the camera as an outlet because O didn’t know how else to express what I was going through in life at that time. Being 16, Read more>>

Kelly Croop

In the end, there is a never a “right time” to take the leap into entrepreneurship – sometimes you just have a find a “good time.” With that said, I am grateful I started my business when I did. Read more>>

Chris Robles

Back in 2019 I was living in South Central Los Angeles, CA and I felt like I wasn’t progressing as fast as I wanted to in my career. I had always thought about the idea of starting a business but I wasn’t entirely sure what it it was and I also wanted to move in my current organization. Read more>>

Rebecca DeMarce

After working for other salon concepts for 17 years I decided to open my own salon. I wish I would have done it so much sooner. The team environment we’ve created is amazing. I love the freedom I have to treat my employees to things they deserve. Read more>>

JABBAR WILLIAMS

No, I wouldn’t have wished to have started my logistics business sooner nor later. I’ve come to appreciate that timing in life is everything. My entire life leading up to the point of launching my logistics business has played a part into my success and impact I’ve been able to see within a 2-year time. Read more>>

Felicia Lucas

I am confident that I started my business at the apporiate time. Life is all about seasons and tapping into the correct season is important. My business was birthed as a result of me actually experiencing my own personal transformation of releasing 145 pounds. What makes my business successful is that I can fully identify with my clients who have struggled with their weight over the years and are at the point in their journey that they’re able to see an actual example of someone who was successful. Read more>>

Taylor Woodford

I started midsizemidprice in late 2021 amidst the hustle and bustle of wedding planning. I was inspired to start this page after being discouraged with my experience shopping for wedding dresses & other outfits for wedding-related activities. I found the majority of stores (both online & in-person) catered to people sizes Small-Large, and opportunities for other sizes was very limited. Read more>>

Dontae Muse

I wish I could have started my creative career sooner than I did but I now realize that I wouldn’t have been able to. There was still so much I needed to learn, even about myself. I started when I was ready. Read more>>

Janai Rodriguez

If I could back in time, I’d keep everything just as it is. The beginning of my creative journey started while I was in the deepest depression of my life. Therapy was helping, yet, I still felt I needed another “outlet”. I first discovered “acrylic pouring” back in 2017 or so. For those not familiar, its were you take paint, layer it in a cup, turn said cup over and create organic, free flowing shapes and patterns. I realized just how “free” I was feeling as I was creating a beautiful mess on the canvas. Read more>>

Meg Viken

Time is an interesting thing to think about. I started my professional career as a photographer just after completing my BFA at Minnesota State University – Moorhead, but I wouldn’t say that I was truly on my career path as a creative until many years later. I wouldn’t change my timeline, and I believe I am better for the hills and valleys that I’ve met on this journey. Read more>>

Katie Shesko

I definitely wish I would have started my career sooner. At some level, I always wanted to be a flute player, but given my life growing up, I knew on some level I would never be good enough to get into music school and land an orchestra job. Which growing up, was really the only option for being a professional musician. That or teaching, which wasn’t the path I really wanted. Read more>>

Keosha Fletcher

Honestly, yes. I think about this often because of my up bringing. From my elementary years into my freshman year of Highschool, there was a lot of chaos and “maltreatment” in the home for me and my siblings. We weren’t really allowed to join in on extracurricular activities. I mean we weren’t even allowed to learn how to cook, do our hair, or take after school tutoring classes because we were told that we were “too immature”. Read more>>

Alexis McDowell

If I could go back to Alexis from years ago, I would tell her to immerse herself in her art and not waste time on other things, I was a rule-follower and very eager to please those around me so I listened when told art could not be a career for me. Read more>>

THE OSHI

Honestly, sooner because how indulged i was able to be with my craft when i started out. I had the time and Freedom to do so. The only difference now is that im at a responsible stage where stabilizing life is just a bit more important at times than sitting up making beats for hours at a time, I just have wellness priorities but music is one of them. Read more>>

Dwayne Boone

If I could go back in time I would have wanted to start my career sooner. I started working as a full time artist in 2011. Before that, I was working as a janitor. I was happy to make the shift in my career path. It’s been good because I’m making more money now and I get to make people happy with what I do. It would be have been even better if I started earlier. Read more>>

J.R. Bradford

So, the truth is that I started out doing comedy in high school. Acting wasn’t the goal for me. I thought I’d be a late night, talk show host like Arsenio Hall. That was the initial goal. However, my Drama teacher(Jan Golden) referred me to Sheran Godspeed Keyton, who was directing a play called “Why Love,When It Hurts”. That experience exposed me to a bunch of Jubilee Theatre legends and I wanted to do what they did(professionally). Read more>>

Toni Manar

I definitely wish I had started sooner ! It’s like I wish I could do absolutely anything in the world to go back in time and just start taking dance classes when I had the chance because I would be SO good by now. I am already great and just stated training at 24…what if I started as a kid or teenager! At the same time, I’m happy I didn’t because my journey is so impactful that its not only helping me develop and learn but its helping others also. Read more>>

Steve Caputo

I’m at what some call “The Next Chapter” of a life that has been blessed with love and good health. Long ago I learned how fleeting our time is, and decided then that it was not to be squandered on regrets. The energy and passion I bring to my art now is the function of the road I’ve traveled, and I hope that my images reflect the joy and beauty I’ve encountered along the way. Read more>>

Sundae Phillips

If I could go back in time, I would wish that I started my business sooner. I’ve always been creative and dreamed of having my own fashion business since I was in middle school. I would paint alphabets on my jeans, characters, and anything just to match the shoes I was wearing. I cut up anything that was in sight and looked wearable! My favorite thing to do was to cut one pant leg into shorts and make the shirt the same. Read more>>

Alexandria Campos

I absolutely wish I would have started my business sooner. I took an interest in hairstyling in my early teenage years, and the interest continued to grow as I got older. When I was about 17 or 18 I became confused at what I wanted to do, because I was also interested in the medical field. The medical field seemed like the safer choice for my future self, so I ended up pursuing that in my early 20’s. Read more>>

Camille Brown

At first I did wish I would have started my business sooner; but now I realize I started my business at the right time. There were things I needed to learn about business; so I’m glad I started it later. I learned a lot of business & interpersonal skills being a corporate executive with Blackstone Investment Group and other companies managing their Senior Living portfolios in the sales, marketing and brand building dept. Read more>>