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.

Haley McClain Hill

If I could do back in time, I wish I started my business sooner! My grandmother served 20 years in the Air Force, my mom worked at NASA, and my dad worked in software sales – I did not grow up around entrepreneurs but I always loved being creative and expressing myself through dance. Read more>>

Jenavi Kasper

I have struggled to make peace with the timing of my business because while I feel I could be so much “further along,” I also would not have the necessary life experiences to do the work to the degree I do it now. And I find that is an issue that many entrepreneurs struggle with — no matter how fast your business is growing, it always feels like you can and should be doing more, which is the blessing and the curse of having a perfectionist mindset, which is most business owners I know and the women who I have as clients. Read more>>

Kait Haynes

I wish I could go back in time and do the things that scared me sooner. I’ve always been a creative person, I’ve always enjoyed drawing, taking photos and videos, editing images, and putting together displays and shows. I took 3 years of video productions class in high school and absolutely fell even more in love with the art of photography and videography. Read more>>

Ashley Messer

I have always been passionate about visual arts, collaboration, horses and entrepreneurship. I started barrel racing when I got my first horse, Misty, at the age of 15. I started to get more involved in horse training and giving my own riding lessons before I started down the path of obtaining a four year degree. Read more>>

Nicole Castagneto

I don’t believe in questions if I should have waited or if I should have started sooner. This belief can be limiting and allow doubt. I believe in the now I will show up with all the vigor and fire I have. I will always wish I could know more, have more resources and wish be in the right location, but with that belief I won’t think outside the box. Read more>>

Gabbi Music

I’m a person who needs goals in my life, something that I work towards to. I’ve overcome many obstacles in life, because I have ability to think outside of the box and I have determination to search for the solution, until I succeed. Few years ago I drifted to a situation, and I didn’t know how to go on. I felt that I was trapped not only in my professional but also in my personal life. I had accomplished professionally pretty much everything I wanted. Read more>>

Ashley Dreager

I think about how my business would have been different all the time had I started prior to 2020. There is a significant learning curve in starting a digital business from all the tech, systems, and processes to network and audience building. Sometimes I think I could have grown faster and accomplished more had I entered the freelance space in 2018 or 2019, but that could have also come with other challenges. Read more>>

Lauren Ashley

If allowed to go back in time, I would choose to start my business sooner. Despite the challenges and uncertainties that come with entrepreneurship, the feeling of betting on oneself and pursuing one’s passion is incredibly rewarding. Certainly, there have been tough days and experiences that have made me question my decision to leave my corporate job for entrepreneurship. Read more>>

Dr. Garrett

Yes, I absolutely would have started my business sooner. Mid-way through my masters in music in theory and composition doors began opening that lead to incredible teaching opportunities. Within a two years I was teaching at three colleges/universities, yet driving up to 50 miles between them. Read more>>

Chad Marshman

Solaris began as a homebrew outfit with a deep focus on experimentation and creativity. Everything was fair game back then. Each 25 gallon batch of beer was split 5-ways into 5 gallon carboys. Each carboy would be its own little test in a larger study. Sometimes we would try 5 different yeast strains, sometimes 5 different hop varietals, sometimes water profiles, you name it. Nothing was off the table. Read more>>

Kimberly Christopher

Well, honestly, I had a “just go for it” attitude when I started my business, so if I had to go back in time, I would still start my business exactly when I did. I launched Roxy Cosmetics in 2018 after receiving several product-related inquiries during makeup application sessions. I had been doing makeup on myself, friends, and family for years, and there was always someone questioning whether I sold the products I used. Read more>>

Latasha Boddy

I always knew that the beauty industry held a special place in my heart. I attended cosmetology school in 2006 in Hattiesburg, MS. Unfortunately, life happened and I didn’t finish the program. Fast forward 16 years later, I wanted to accomplish the goal I set out many years ago and I enrolled in an esthetics program and became a licensed esthetician. Read more>>