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.

Leif Heron

Absolutely—I wish I had started sooner. I officially took over Heron Events in April 2023, purchasing the business from its previous owner who was retiring. At the time, I was working full-time as an IT project manager and feeling increasingly unfulfilled by the corporate grind. I craved more autonomy, creativity, and the satisfaction of building something of my own. Stepping into the world of event production felt like the perfect intersection of technical precision and artistic expression.  Read more>>

Jasmine Bledsoe

If I could go back in time, I wouldn’t necessarily change when I started Joviality Designs, but I do wish I had stayed more consistent. I launched my business in 2017 during one of the most emotionally difficult seasons of my life. I was grieving multiple losses and trying to find my way through the weight of that pain. Creating beautiful things gave me something to hold onto—something joyful in the middle of sorrow. Read more>>

Solange Abreu

I actually started my business while I was still in college. I was fortunate to have a great support system, I had great faculty and a business professor helped me build my first business plan and understand the fundamentals. Even before that, I had been in the event industry since high school, planning community events and even my own prom! I always knew what I wanted to name my business, and the passion and commitment were already there. That part came naturally. Read more>>

Charles Boucher

I believe I couldn’t have started my business any sooner than I did and I definitely wouldn’t have wanted to start it any later.

I started my first business in October of 2023. Although it only lasted just over a year, that business was the springboard that got me to where I am today.

Prior to going out on my own, I was managing a luxury vacation rental company in the Mission Beach / La Jolla area. I had been with that company for nearly six years. During that time, I learned so much. I didn’t necessarily have the credentials or experience for the role I was given, but I had a boss who believed in me and gave me the opportunity to prove my worth. Through hard work and dedication, I rose to a level I once thought was my end goal. Read more>> 

Declan Clifford

I didn’t start acting until 29 and sometimes I wonder what life would be like if I started straight out of school. I always wanted to be an actor but following my dream was terrifying to me and I know so many people feel that way. I didn’t officially start taking acting classes until 29. I had a career as a lawyer for 6 years before I enrolled in my first acting class. But ultimately I feel now that all those twists and turns on my path to becoming an actor made me the person I am today. I lived a lot of life and that fuels your inner artistic world, and you can bring a lot of experience to your characters. Read more>>

Emily Landham Mahoney

I often wish I had started writing and drawing earlier. Hilariously, I did! I started in elementary school writing short stories and drawing graphite portraits. I even started a small business and had a few folks hire me to do portraits of their children. (Funny sidenote, since I was doing portraits in pencil, I called my business Shades of Gray. This was way before the book!) Read more>>

Lil’ Debbi

I started making music officially in 2029, and dropped my first song on my 20th birthday. From then all the way to 2022 I wasn’t really taking my music serious. After I gave birth to my daughter is when I really locked in and began to be more consistent. Looking back on those years not doing anything to now, sometimes I do wish I was working on my music. However looking where I’m at now, I have no regrets. I think back then I wasn’t mentally ready, and I wasn’t sure of myself. I now have full confidence in my music and have mentally and emotionally prepared myself to take on whatever comes with pursuing a music career. Read more>>

Zachary Weiss

I’ve been interested in the arts as long as I can remember, making films on home video with friends growing up, drawing and writing, but music has always held so much magic for me. I got my first guitar when I was 11 or 12 and as soon as I could play a chord without the strings buzzing (much) i began writing songs. I remember playing my first song for my parents and feeling so proud of creating something out of nothing. Read more>>

Kris Rosenblum

From early childhood, I drew in bursts—little visual love letters to the world. In high school, I dove deeper. My dad, bless his instincts, found me private lessons while we lived in an artist community. It felt like a beginning. A doorway cracking open. But then came adulthood—and the weight of survival. Read more>>

Muye Yu

I started learning piano at the age of three, and by the time I had enough control over my fingers—around four years old—I was already experimenting with simple melodies and harmonies using both hands. My more structured, life-oriented creative journey began at 18 when I entered college and majored in music production. Read more>>

Malachi Beasley

Neither. Before I used to beat myself up about how late I came into the craft. I felt inadequate as an artist because I had been in the military for 6 years and I was afraid that I wasn’t “vulnerable enough”. This haunted me through undergrad all the way through grad school. I think the logic in my head was ” Every one will think I don’t care or dislike me because of something I had to do”. Some of it rang true but most of it was just an idea in my head and when I finally moved through my own insecurities I stopped beating myself up and decided to be the artist I dreamed of. Read more>>

Natalie Collins-Smith

I actually started out on a completely different path—I earned a master’s degree in clinical psychology, thinking I would become a marriage and family therapist. I spent several years working on my practicum hours, but after having my first baby, I made the decision to step away from that career and be a stay-at-home mom. A couple of years later, I had my second child. With a husband who’s an airline pilot and away often, I knew that trying to juggle raising two small children and launching a business at the same time would stretch me too thin. Read more>>