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.

Kristine Harris

I have been an AFAA Personal Trainer and Group Exercise Instructor for over 18 years and got certified as a Comprehensive Pilates Practitioner in 2020. I started my own business, Kore Fitness Studio a year ago and I feel like it was the right time for me. I have been working in a physical therapy clinic as a Personal Trainer and Pilates Instructor and feel that the experience that I gained was invaluable. I was able to develop my strength for meeting people where they are at in their journey to wellness through exercise. I had the opportunity to create a studio that uniquely fits the needs of my clients and my business has been growing steadily this past year. I feel like it was the right place and time for me and I wouldn’t change anything. Read more>>

Janet Constantino

When I was a senior in high school, at 16, a beloved English teacher, Mr. Bloom, encouraged me to hone my observations into cohesive scenes, telling me I had the makings of a writer. His encouragement helped me to see a potential within myself that I hadn’t yet recognized, igniting a passion for writing that would ultimately–decades later–shape the creation of my novel, Becoming Mariella. Professionally, I became a licensed psychotherapist, and have been since 1983, although now I work very part-time. I wrote when I could, and longed for the “someday” when I could write everyday. When I finally went for an MFA in creative writing I learned more than I realized I didn’t know. In retrospect I wish I had pursued both the writing and psychotherapy alongside each other.  Read more>>

Tanja Aelbrecht

I started our business three years ago and I wish we had done it sooner! At the time of starting our website business (Chunky Squirrel), me and my partner were working together at our wedding photography business. While wedding photography initially started out being fun, we forgot one crucial aspect: to build the business around the life that we want and not the other way around. We’re both introverted people and we love to be location independent. Wedding photography requires you to be extraverted all day and you’re bound to places and dates years in advance. Now we can work from anywhere and only occasionally meet clients in video calls. Read more>>

Tiffany Watts

Growing up, food was always a passion for me—I used to dream about being a Taste Tester when I found out people could actually make a living eating! But my life path took some twists before I could turn that dream into reality. Right out of high school, I became a young mom and had to focus on supporting my daughter, so I worked in jobs I didn’t love during my college years and even afterward to keep up with what life demanded of me. When I was diagnosed with lupus In my early 20s, I had to make some serious lifestyle changes, including switching to a vegan diet to manage my health. Food took on a new meaning then, as I realized it was essential not just for enjoyment but for keeping me healthy and able to raise my daughter. Read more>>

Sam Wyllie

I would honestly start my (current) creative career at the exact same time! I think those previous professional experiences made me a better business owner and ultimately helped me get to where I am today. I can’t imagine trying to run a business right out of school with minimal experience in the professional world. I learned workplace etiquette, how to write an email, how to receive client feedback, how to deal with difficult people, and so much more. As miserable as it was during those years in corporate, I absolutely needed those experiences to properly run the business I have today. Read more>>

Debbie Carroll

I absolutely wish I’d started my creative career sooner as a painter. For many years, as far back as a college graduate, I’ve said one day I wanted to paint. I never really had much training as a painter, but somehow felt this was something I could do – one day! After graduating from college, I traveled to Europe on a trip arranged for students and recent grads by the University of Illinois. This was a life changing trip in many ways, I enjoyed seeing art I had studied in school, met other young people, and it gave me the impetus to move to Texas, where I worked in the travel industry for many years as a result of that experience. Read more>>

Scribbles Who

If I could go back in time, I think I would have started my creative career sooner, but with the understanding that each part of my journey has contributed significantly to who I am as an artist today. I began my career writing songs for others in South Florida, where I had the incredible opportunity to collaborate with artists like Trina and Flo Rida. However, I took a break from music for a few years, questioning my talent and whether I truly belonged in this industry. During that time, I was exploring different aspects of life and the music business, which gave me valuable insights into resilience and adaptability. Read more>>

A.b.y Songo

Me having the knowledge I have now and start making music when I was younger I would of been known globally at least or close to it because I had to prepare myself to get all the knowledge I could while making music. Read more>>

Haze Savage

I started making music when I was 13 years old and it wasn’t something I took seriously for the most part is was just for fun I used to walk around showing off the music I made I’ve had very bad feedback at first it almost made me wanna stop . Then one day I went to the park and continued showing people I knew there the songs I’ve made out of 30 people 1 person in his late 40 told me you’ll always have more critics than supporters and it really stuck with me . Later that day I went home and practiced until I felt it was good enough to show I noticed that when I would freestyle if the song was a hit my homies would really jump out of they’re seats so my main focus was rhythm, melody, harmonizing and lyrics but if I knew how to control my vocal range how I do now back then it would have been an easier start for me . Where was I at I was just the ghetto young bul from the block hanging with the 60’s catching reck and making money I wasn’t even aloud at some of the other kids my age house because of my lifestyle choice in and out of juvenile lock up. I probably would have been signed if I knew everything I know now then Read more>>

Rasheeda L. Johnson

I’ve had scholarships to art classes since around 7 years old at a major museum in my hometown of Pittsburgh, PA. As I kid, I didn’t realize that art was something I could choose as a career; all my young life I was told to “go to college and get a good job”. Fast forward to today where I am thriving as an independent Artist and Teaching Artist. When I first quit my full time job doing retail window displays in March if 2022, I was extremely nervous and not sure if it was the right choice. Once my business began building to where it is now, I sometimes wished I’d made the choice to quit working full time for others a decade ago. I had to realize that, not only do things happen when it’s the right time, I also really didn’t have the right attitude or level of commitment to and confidence in my craft to do what I am doing now. I’m grateful for God’s plan for me. Read more>>