Almost every entrepreneur has had to decide whether to take the leap now or wait– perhaps they wanted to acquire more capital, experience or connections. Given how common this predicament is, we asked some successful business owners to reflect back on whether they wish they had started sooner or waited for a better time.

Tiffany Smith

Starting a business is always a huge venture and risk. You always think you are ready to make that leap, but I fear you learn so much hands on once you start that you don’t realize how much you don’t know until you don’t know. If I could go back and start sooner or later I would choose later. Read More>>

Laura Masteller

As a nurse, there are so many things that you can do with your career. I never thought that owning a medspa would be one of them! I was not a “girly-girl” growing up and I still am not, but I absolutely love aesthetics. I love helping people feel better about the skin they are in. Read More>>

Carolyn Heefner

If I could go back in time I would have started my social media marketing business back in 2013 right out of college. I wish I had started my business way sooner than I did. I don’t know if I didn’t think I could do it or if it was a confidence issue or what. Read More>>

Liyah Jammeh

If I could go back in time, I think I’d still start my business, DVN ALN, exactly when I did — in 2022. It was during the height of COVID, a time when the world was standing still, and people were forced to slow down and really think about their health and well-being. For me, that was a turning point. Read More>>

Vic and Sasha Barrera

Oh, we would most certainly start it much earlier! Although, it’s rarely so simple. It certainly wasn’t easy to decide that in the early stages. Read More>>

Emily ‘Bird’ Lambert

I didn’t take my design work full-time until the summer of 2025, almost a decade after I first started dipping my toe into the creative world professionally.At the time, my wife and I had just moved to a new state with our two young kids for my corporate job. I was commuting two hours a day, three days a week. Read More>>

Nikkie Mullet

I wish I had started my business much sooner. I met my husband in 2011, who was caring for his sick grandmother at the time. There were no other options for his family to alter her care situation so it made sense for me to relocate from New York where I was born and raised, to Ohio where he is from. Read More>>

Kara Payne

Definitely sooner. I remember sitting at lunch in my hometown of Saint Petersburg, Florida, with some longtime friends when we were discussing the fact that I was a 20-something Pastor’s wife. This has to be in like 2018 or 2019. Read More>>

Gustavo Bernal

When I started in the film production business, I always focused on the execution, the creative process, and the safety of the workplace. This focus was present throughout most of my career. However, I discovered that I love to pivot by nature. I don’t like to do just one thing, but multiple things, and thrive as a professional. Read More>>

Stacy Chen-Yi

I sometimes wish I had started sooner, instead of spending years in graduate school pursuing a degree in public health that had little to do with my true passion. Read More>>

Gena Lashay

My journey hasn’t been traditional, but it’s mine—and I own it completely. I believe there was purpose in my process, and I wouldn’t change a single thing. I am right where I’m meant to be. God’s timing is perfect! My acting career began in grade school and continued through high school, where I was an active member of the drama club. Read More>>

Roxanne Luciano

I always wish that I would have started my career sooner. If I was mentally prepared that would have been something I would have taken on immediately. However, I simply wasn’t ready and I did not want to enter the music/entertainment industry without having some type of mental clarity to be able to focus and give it my all. Read More>>

Fvllaz

If I could go back in time, I wouldn’t say I wish I started my creative career sooner or later I think I started at the exact time I was supposed to. I began seriously pursuing my art and music around a period in my life when I was searching for meaning and direction. Read More>>

Martin Renteria

I started this career path at the age of 27, there had been a lot of people throughout my day jobs that told me, “you should be an actor or stand up comedian because this job isn’t the right fit for you, you have to do something with what you have.” I would just nod, smile and say “yeah maybe one day.” Read More>>

URIEL BRG

I released my first full song when I was 21, but it wasn’t because I lacked interest or passion—it was mainly because I didn’t have the right connections, access to instruments, or knowledge of music theory. Sometimes I wonder what it would have been like if I had started my music career in 2015—perhaps I’d be much more established by now. Read More>>