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.

Pinhwa Su

I wish I had started my business sooner, but I also truly believe everything happened exactly when it was supposed to. I officially went all in as a full-time content creator and social media manager in April 2025, after being laid off earlier that year from a supply-chain logistics career I had been in for nearly eight years. Read More>>

Haley Amos

Looking back, it’s always tempting to say I wish I had started sooner — mostly because hindsight makes it easy to imagine getting established faster or reaching success earlier. But honestly, I think I started my business at exactly the right time for me. Read More>>

Bri Zamora

If I could go back on time i wish i would had started my business sooner. Read More>>

Miranda Kelton

Looking back, I truly believe I started my business at exactly the right time for me. I’ve always been creative, but I was searching for a career that would grow with me and not feel stagnant or repetitive over time. Photography ended up being the perfect fit because it allows for so many different creative outlets. On any given shoot, I’m not just taking photos. Read More>>

William Briggs

That question is strange for me because I have vacillated my whole life between creative and technical. Overall my heart wishes I had taken a chance, made the leap, and started way sooner, but my head says only now do I have the life experience so that I have stories worth telling. Read More>>

Shannon Kennedy

I began dancing around the age of four at a studio that emphasized creating well-rounded dancers. I trained in a variety of styles such as contemporary, ballet, tap, jazz, modern, and more. I quickly fell in love with ballet, and it became my primary focus until I was introduced to gymnastics. Read More>>

David Oliver

The Midnight Muralist The door slams, Ollie has packed the vehicle to the ceiling of ladders, paints, drop clothes and a billion other things to get the job done. He leaves his family in the safety of the bed, with his wife. As the car starts and peels out into the night, you can hear an old Allman Brothers classic on the radio. Read More>>

Erika Alonso

I started painting full-time in my early 30s, but I always wanted to be an artist. Instead of going to art school I went to college for marketing and spent my 20s working in marketing & communications. However, during that time I learned so many important skills like website design and development, SEO, social media marketing, etc. Read More>>

Brittney Coke

I don’t regret when I started my creative career—I truly believe I began at the exact right time for me. Classify Beauty originally started as a personal blog in 2017, created by me (@iambrittneycc), during a season when I was balancing career growth, personal development, and discovering how I wanted to show up creatively. Read More>>

Austin Whitney

Of course hind-sight is always 20/20. So, if I could go back in time I wish I would have started sooner. I mean, I’ve played guitar for over 17 years so music has always been a very influential part of my life. However, the creative aspect of writing my own music is something I wish I would have stuck with sooner. Read More>>

Nicole York

I’ve been a creative for as long as I can remember. As a kid, art class was always my favorite. In high school, I explored more mediums like pottery and photography. And in college, I took drawing classes every semester until I settled on my major. Read More>>

Amarilis Rosario-Tillema

I have lived many lives. I have been a creative soul since my early childhood. I imagined, created, danced, and dreamed of all the things I wanted to be a part of. I struggled within the confines of a traditional family that maintained more practical views of what being a woman meant. Read More>>

Maggie Hudson

I don’t wish I’d started sooner or later—I genuinely believe the timing was exactly right. Everything I did before this prepared me for where I am now. Years as a personal trainer and group fitness instructor gave me a deep understanding of movement, strength, injury prevention, discipline, and how to train consistently over time. Read More>>

A.D. Slaton

I started Stillriver in March 2025, after spending 13+ years building news and sports streaming platforms. But if I’m being honest, I wasn’t fully committed. I took a role a few months later because I wasn’t sure I had what it takes to run my own thing. Read More>>