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.

Harold Tremblay

Sooner. Started performing out in my late 30s. More discipline in my 20s would have put me out in public during the heyday of blues music. Read more>>

Grace Kelly Ehinger

Definitely NOT sooner. I am 19 right now, and although I’ll be 20 soon, the amount of raised eyebrows I have gotten from other adults when I mention owning a business has been more than I would like. Read more>>

Joan Dao

Honestly, I wish I started later but I’m grateful I started at all. I started this as a student project university with no real experience in fashion, engineering, technology. let alone how to start a business. Read more>>

Jessia Martin

If I could back in time I wish I would’ve started my business sooner. I wish I believed in myself enough to step out on faith. I started my business in 2019. Read more>>

Lauren Clouse

My career started when I was 17 years old. My parents are self-employed small business owners and never pushed me to do anything except invest in myself. Read more>>

Jen Barnes

If I could go back in time, I absolutely wish I had started by business sooner. I started Go Family Adventure during the pandemic when I had time to go through all of our family travel photos. Read more>>

Jessica Martinez Castillo

If I could go back in time I would have gone full time with my business. I decided to launch my business back in December 2017, but i was still juggling other part time jobs “just in case”. Read more>>

Jarvis Fisher

I would have definitely started my businesses way earlier in life. I have always been involved with music, even as early as 6 years old. I started playing drums in my church which first started my love for music.. Read more>>

Tiffany Enowski

I’ve had a big interest in taking photos and creating videos from a young age (around 11 or 12), that interest grew into me getting a job right when I graduated high school and the first thing I did was save up to buy a camera. Read more>>

Elon “NolE” Cambridge

This is a hard question for me to answer because God’s timing is always perfect, so maybe this is the way it should be. As I reflect on the path behind me and ponder the possibilities that lie ahead, I cannot help but wonder what could have been, what might have been, if time had granted me two more years to cultivate my musical talents. Read more>>

Karen Williams

Sometimes I wish I had started my business sooner. Though I know nothing happens before it’s appointed time, I often wonder if the only reason I hadn’t started before, was due to my self-doubt and fear. Read more>>

Elizabeth and Karren Antonyan

We officially launched our design and development venture in 2021, drawn in by an opportunity that was too good to pass up—a charming bungalow that had seen better days in Sunland, CA. Originally intended as a long-term investment, the moment we began renovations, it became evident that we had uncovered something far more significant—Doonik Design x Development was born! Read more>>

Shelly and Glynnis Smith

We have been in the hair industry over 25 years and recently co-founded our Natural Hair Care line of products. I wish we had started the Hair care product business soon because 15 years ago, people were starting the natural movement and was eager to try new things. Read more>>

Kimberly Mota

The inception of De La Luna intertwines with my personal journey of self-love and healing, making the question of whether I wish to have started my business sooner or later a reflection of my broader life narrative. Read more>>

Robyn Woodside

Looking back, I do wish I had started my business sooner. I have always loved planning parties, and had a few people tell me I should do it professionally. I am a full time teacher, wife, and mother. Read more>>

Daniel Mills

Voice acing was not something I originally pursued as a career. I was always so worried about someone saying “You’re not good enough” that I was too scared to even try. Read more>>

Laura F. Muszynski

I started making ice cream about 10 years ago in Mexico. I had another business completely unrelated to food. And my business neighbor manufactured ice cream machines and he spoke to me about how good of a profit it was. So I thought it was pretty interesting. Read more>>

Hannah Downton

From experience I think most people follow societal norms. Graduate, move, go to school and get a job. This is a great path for most people but for some of us we have different dreams and in turn we create our own path. Read more>>

Dr. Kenyatta Starks

I am neutral because there are pros and cons to both. However, I started at just the right time because I wouldn’t have had the experiences I’ve had to help me in this journey. Read more>>