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.

Ashley Hathaway

I love this question. To give some perspective, I started working as a bank teller fresh out of high school in 2005 and quickly worked my way up to management. I maintained my management position for ten years before experiencing corporate burnout. I am sure some of you can relate. I knew there was more to life than sitting behind a computer screen and I knew my creative abilities exceeded my ability to run a bank. While I loved my clients and team, I knew it was time to make a change for the sake of my mental and physical well-being. I had nothing lined up. I was scared- but I knew if I didn’t take the leap when I did, I never would. took a few months off to reassess. I realized I didn’t want to work for someone other than myself and I wanted the freedom to make my own schedule so I could create a healthy work life balance. I came up with a business plan, picked up my camera and got to work immediately in my community. I hit the ground running and slowly started to build my business. It was hard and it still is. I am constantly second guessing myself, wondering if I made the right decision. Read more>>

Markee Carter

I wish I could have started my business venture sooner if I had the right tools and education to start my journey. When I graduated high school in 2006 my first business venture was to open a laundromat, but I didn’t have the tools and basics to execute my vision. So I work in the retail and security job fields, while attending college to obtain a degree and live the American dream. After college and working in my career field I just wasn’t satisfied mentally. I was working for the state of Tennessee and I applied for a promotion and I was overqualified for the position. I still applied to try and move up, but I wasn’t accepted for the position. At that moment, that’s when I put into motion of starting a clothing company and slowly worked on my craft and style. Then I taught myself business management and marketing by reading variety of different entrepreneurs articles and YouTube videos. Read more>>

Asia Carter

If I had a Time Machine absolutely I would have continued my journey rather than start sooner. Back in 2021 I made the impulsive decision to buy an online lash course and teach myself how to do lashes. Based on my research and the information I learned from the course, I went online and brought everything I needed to take clients. A massage table, tweezers, glue, trays, lash fan, tape, eye pads, etc. I made sure to work on my mannequin until I was comfortable enough to work on my friends. The mannequin was a struggle I could never finish a full eye in a day but it wasn’t baddd you know? So when I went to my friend’s house I was ready but boy…. Working on a human so much harder. After 5 hours my friend had 10 lashes between both eyes lol. I keep practicing on my other friends and whoever would let me practice on them. And I was getting better with my placement, styling, and even coverage but it was not getting easy at all. I ended up quitting and selling all my lash products because it was just too much and too overwhelming. Read more>>

Jennifer Nestor

I have always done creative work, even during my Marketing and Communications career, but I do wish I had went through the publishing process sooner and released my writing years ago instead of letting the fear of failure or criticism stop me. Read more>>

Dana/georgettes Granddaughter Powell Smith

Looking back, I wish I had started my creative career sooner. Growing up I had all of the creative resources available to me. I was surrounded by Art. I have always created, even back then. But I created in private. I painted because it was relaxing. I never dreamt of being a professional artist. It was just something I did for myself. I painted very little after starting a family. It wasn’t until the pandemic, the killings, the Marches, that I heard the voice. “You have to paint!” I was so angry and disappointed in the world. I didn’t know how to reconcile those feelings. I heard the voice again. “You have to paint”. I ignored the voice for around 2 weeks. Until one day the voice got so loud in my head “YOU HAVE TO PAINT! I got up from the couch. I went in to my garage. I took out paint brushes and canvas and started painting. (I always had art supplies even though I wasn’t using them) I have painted almost every day since. Read more>>

Em Eden

My creative journey began later in life when it comes to making music but I don’t wish it happened any differently. I had a fascination with writing/reading poetry as a little one, getting lost in words in my many treasured (mostly birthday gifted) notebooks. My older brother wrote music and played in band so there was always music in the house. My dad has always been direct, when we were little he made it clear that my brothers were born with natural musical talent and that my sister and I were better off trying other things. I know he felt he was looking out for us but I think it deterred me from diving into music in a creative way. That’s not to say music wasn’t a huge part of my life long before I started writing songs. It gave me a way to escape. A way to get lost and feel connected with the artists in a way I couldn’t with anyone around me. A way to feel things I couldn’t describe and realizing them as I listened.  Read more>>

Bryan Kreutz

Sooner! I acted in a stage play with heavy dialogue as a child (9-10 years old) in St. Louis Missouri. being friends with child actors. Shortly after that huge co-starring stage play performance, my parents and I didn’t pursue acting. Instead, I was heavily persuaded to get into broadcast journalism, sports play-by-play, and TV/radio news. More than decade after graduating college with a broadcast journalism/communications diploma in hand and bouncing around from radio gigs, one with a CBS radio affiliate in Illinois, I realized I missed performing. I soon starting to take acting seriously again, getting called by first name with casting directors in both Missouri and in California in my early 30s after signing with talent agents in both states. I noticed there’s something special that happens when working with child actors. Read more>>

Christopher Grant Ward

I do, but you can’t really do anything in life until you’re ready. It wasn’t until 2016 I left my career in product management and UX design to pursue my music, study art and now, working full-time as an artist creating sustainable handmade aesthetic furniture pieces. I don’t think I could have left before then, I just wouldn’t have had the courage. After college, I worked in technology as a product leader, developing web applications for large corporations and several startup companies, managing design, development and customer experience. My tech career reached a “zenith” as Global VP of Product for Shutterstock, I led an eCommerce marketplace that made over $2m a day and worked in 46 countries and 13 languages, overseeing software design and development for a team of nearly 80. I had an office in the Empire State Building. I was at the pinnacle of my career and all I’d worked at and I was more unhappy than ever. Read more>>

Joyce Joseph

Hahaha, I hope these answers sound natural and not confusing. My apologies in advance. I believe that everything in life happens with time. For example, if I wasn’t an artist now, I would still be an artist in the future cause it always comes back to me. I kind of like the concept of “past, present and future intertwining at the same time”. But to answer the question, I don’t feel like I should’ve started my creative career sooner, but I do wish I had more confidence in my creative abilities when I was younger. So there’s kind of two stories to this. One in relation to music, and one in relation to visual arts. For music, my parents placed me in piano courses at the age of 3, singing at the age of 6. The learning of it was very much like “Go to school, practice every week, do performances” rinse repeat. When I used to take lessons in Philadelphia, my teacher (shout out to Alice) would always reward me with movies or restaurant days; those moments made piano fun to do. After I moved to Montreal, I had 3 different teachers, and I started taking piano exams so it stopped being fun. I quit at the age of 14 or 15? Comparison of other people’s skills in relation to mine was a huge factor in my growth for both music and art.  Read more>>