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.

Kendra Swalls

I started my first business in 2012 when I was 6 months pregnant with my first daughter, teaching full time and going to school at night to get my Masters Degree. Looking back that probably wasn’t the BEST time to start a new business, but I tend to leap before I look. Since I primarily work with moms to help them launch and build their own business I hear the comment more often then not “I wish I had started this before I had kids”…and I used to think the same thing. Read more>>

Kelly Hackney

I always tell people that God blessed the broken road that led me to entrepreneurship. Timing is everything, I truly believe that I had to go through what I went through and get to such a squashed place in my career to be ready to go out on my own. It’s been a wild ride so far and I’m excited to see what the future holds! Read more>>

Lord Phly

At times the thought definitely crosses my mind, wishing I began a little sooner, yet when I actually think and reflect I see it’s more of focusing on the small details of the business that began to grow around me! As LordPhly is been all about impacting, inspiring and motivating people, not paying attention to the business of that and how much Value began to be accumulated around me, yet not having a focus toward it; Read more>>

jeffrey equality brooks

If I could go back in time I wish I would have started my career so much sooner! And I wish I would have pursued an education in the fine arts. I would not have wasted my time or a single dollar on a college campus, ever. I come from a well-below middle class upbringing. While my family recognized that I was artistically oriented, if not gifted, I struggled with school immensely. And I still have tremendous difficulty reading and typing things (such as this) due to synesthesia, dyslexia, ADHD, anxiety, etc on top of severe asthma and other health issues. Read more>>

Carlean McWright

I do not have remorse about starting my business in August of 2017. I was only 23years old when I made a pivotal decisions My expectations of entering the “real world” (to jumpstart my career) quickly turned into a harsh reality. Many interviews, but just as many rejection emails. It became exhausting to read, “Thank you for applying, but we have selected a more qualified candidate for the position.”. Read more>>

Katharine Postal

When I first started by business, I was working full time as a Social Media Manager at a local boutique in Charlotte, NC. I had a few other clients on the side, and I always knew I wanted to eventually venture out on my own. When COVID-19 hit and we were all laid off – I was kind of forced to finally go for it. Read more>>

TAKA$

I would have started a lot sooner. I’ve been writing, singing, and performing live since 2010 but I’d never thought I could take the next step as an artist until I saw others do it. I saw kids like Lil Uzi, XXXTentacion, and many other young artists pursue their crafts at such a young age and realized I never needed someone to say I was good enough to try. I just had to try. Read more>>

Joseph Liberti

I began my career as a performing artist at the age of 71 . I was self-employed providing coaching and training to corporations and executives at the time and the creative urge finally overcame my resistance, I had a passion for jazz music and been playing flute for my own entertainment, mostly by ear. I learned to read and write music, performed regularly with top musicians in Colorado , and wrote, and performed several shows. I regretted not starting music earlier. I often asked myself ” where and what would I be now if I had started at the age of 17. Read more>>

Ian Campbell

I wish that I had come back to music as a career sooner than I did. When I was in my 20s, I started working as a musician and moved to San Diego to pursue it further. When I got there, I got a job to help make ends meet and ended up getting back into the business world and ignored my music for quite some time. During that time, I stopped writing and performing, and could tell that there was something missing. Read more>>

Heidi Ferguson

I have always been immersed in vintage and antiquing. My parents were avid thrifter so I few up in that environment. The punk rock scene in Portland Oregon in the 80’s and 90’s was my jam. I was a latchkey kid, so I was always hopping around second hand stores. I started selling the pieces that I no longer wore when I was in my 20’s. I also made a lot of my own clothing because I couldn’t find anything that I fancied in regular stores. Read more>>

Juss Reggie

I wish I even knew about the opportunities being a creative would create. 2012 Vine was the introduction to social media creating, even though YouTube had been around Vine was easy and quick all you needed was your phone. I want to be to a youth what no one was to me I always had this sense of humor and skill of composing humorous situations . Read more>>

Christina Fitzsimmons

Ever since I was about 11 years old, I always wanted to be a YouTuber. I would run around with my camcorder recording specs of my life and upload it to YouTube for fun. I never took it seriously until 2020, when I couldn’t fight the feeling that I was meant to be on YouTube. So, I uploaded my first video on September 1, 2020 and never turned back. I ended up getting monetized in 17 days and first video sits at almost 900,000 views. It completely changed my life and I think that I actually started it at the right time. Any time sooner, I probably wouldn’t have chose to upload that first video that ultimately jump started my channel. Read more>>

John McGuire

In ways I see missed opportunities throughout my life mostly due to not knowing what the next step might be and before I started, I certainly didn’t know what the first step was. You read these novels or comic books, and I wanted to find a way into that club, but the bad and the good thing is that there is no set way… which means there is no road map to follow and no easy button to push. Read more>>

Don Nguyen

When I first got the inspiration to make knives, I wanted to jump into it full-time right away, no delays, simply just full abandon and absolute commitment. This was 2010 – I was two years into community college, with no idea what I wanted to do. I had bounced around between music, chiropractics, physics, etc, and none of those were for me. Everything I pursued up until that point was to please others – my parents, their friends, my classmates, my teachers. I was motivated purely by sheer willpower and naivety. Read more>>

Seema Lisa Pandya

I am a creative on a journey walking with one foot in the arts and the other in sustainability and green building. At this point in life, the goal is building towards the merger of these two paths. The beginning of my journey starts with the influence of my parents. My mother is an artist and my father is an engineer. Their influence on me represents a balance I see as my right and left brained activity as my artistic needs contains both the free form expression and critical planning and construction for spatial solutions. Read more>>

Mike Wittenstein

This question needs a third answer. Did you start your business at just the right time? At the time, I couldn’t tell. In retrospect, I couldn’t have started Storyminers at a better time.  It was 2002, right after Y2K and when the dot com boom became the dot com bust. Clients weren’t buying and companies weren’t hiring. Atlanta marketers at Delta and Coca-Cola we’re being laid off by the thousands. If you were in the business of helping others sell services, things looked gloomy. Fear and uncertainty prevailed. (Sounds a lot like 2022, doesn’t it?) Read more>>

DEVIN ROBINSON

Kinetic Design Lab, LLC (KdLab) was officially commissioned in 2015′. However, I have been doing independent small scale work under the company acronym since Hurricane Ike hit and devastated the Houston/Galveston Metropolitan area in 2008′. There is a term in the A/E/C industry (Architecture/Engineering/Construction) referred to as ‘moonlighting’ and since entry level Architectural Internships pay very low on the professional services scale, I had to seek alternative types of commissions when and where I could to supplement the cost of living. Read more>>

Rosalind Cottingham

If I could go back in time, I wouldn’t have it any other way. I grew up working full time and attending college at the same time. When I look back now I often think about how I did it all. After many years of hard work I was ready to pursue my passion which was cooking. I decided to start my business in the year 2000, while I was still doing both, working and going to school. Read more>>