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.

Neida Garcia

Reflecting on my journey, I often find myself thinking, “I wish I had started my creative business sooner for sure.” In 2015, while working as a transplant nurse at Tampa General Hospital, I opened Reflection of Memories on Etsy. Initially, it was just an outlet for my creativity—a way to unwind and perhaps bring a little joy to someone with my handmade jewelry. At that time, I wasn’t aiming to build a real business. It was more about finding balance in my life and expressing myself through art. However, as the months passed and orders began to increase, I realized that this venture was more than just a hobby. It became clear that I had stumbled upon something I was deeply passionate about—not merely the act of creating jewelry but the unique opportunity to be woven into people’s stories in small yet meaningful ways. Read more>>

Jessica Keesee

If I could go back into time, I would’ve started in 2018 when I wanted to. I didn’t believe in myself enough to do it and Mother’s Day of 2020 during Covid, I decided to bet on myself. I wish I would have had the courage to start when I originally wanted to not when it finally felt safe to me. Read more>>

Stetson Patton

If I could go back, I 100% wish I had started my business sooner. Social media came out during my senior year of college, and from the beginning, I was completely obsessed with learning everything I could about the platforms. At the time, though, a “social media agency” wasn’t even a job or a thought. I was ahead of the curve—making over $100 an hour on the side helping people set up Facebook profiles (business pages didn’t exist yet) and linking their accounts to their websites. I knew social media was going to be huge, long before it became what it is today. Read more>>

Jeremy Reeves

I was ready when I was ready. I believe we started our business in the right time, August 2019. 8 months before the world shut down! What a wonderful lesson in perseverance. The first eight months were humming along and the years since have been the real growth personally and professionally. Starting earlier would have had its own challenges and I wasn’t spiritually mature enough. Starting later, I wouldn’t have had the opportunity to experience struggle as deeply. It truly was divine timing. Read more>>

Tavasha Ancrum

I truly wish I had started my business way sooner. I started it in 2020 but I was already taking clients way before incorporating it. However I took my business seriously pretty late I’d say. I also took a couple breaks in between due to personal reasons which I feel kind of set me back a little. Read more>>

Zelda Morning Star

If I could go back in time and had the option to start my business sooner, I honestly don’t think I would’ve. Though I am so incredibly grateful to be finally following my passions and dreams in life by currently owning my own tattoo studio, I genuinely believe it needed to happen in divine timing. It’s funny how skills from different jobs that I have developed over the years have now shown value with owning my own business. I truly feel like I have been cultivating myself to be ready to pursue this path for most if not all of my life thus far. I think I needed to heal from a lot of painful experiences in my younger years before ever feeling ready to do anything like I am now. I had to really learn how to love myself before I ever felt even worthy of putting my artwork on any kind of display for others to see. Read more>>

Cat Cox

Sometimes I wish I would have started my business sooner. Baking is a very physical job. It requires a lot of energy and lifting. Production baking is not what most people imagine – decorating cutesy cupcakes. It is physically demanding. We are often working in a very hot environment, standing on our feet for 10 hours a day, slinging 50 lb bags of flour. I’ll be 42 soon, and sometimes I wonder about how long I can do this work. Ultimately, though I don’t think I knew enough when I was younger about the business to maybe pull it off at the caliber I can now. Read more>>

Le Poodle

This plagued me earlier in my career and, ironically, hindered me from starting at first because I began music at an age that would be considered “late” in the game around 25 years old. It is laughable now because at 25 you are such a baby. However, the only examples we had in the industry were prodigy children (we now know more about how toxic the industry was/is and what unfortunate experiences these young stars went through). I’ve technically always been musical since I was very young even if I had a different interest every week. I was still involved at one point in dance, music lessons, going through my dad’s music collection, making playlists and burning CDs for my crushes, and obsessively downloading music once Limewire hit the streets. Read more>>

Mike Mchugh

Sooner. I began writing music at 11 years old and obsessively focused on learning guitar and playing until high school, where I still still played music but never thought i could make a living as an artist so I focussed on scholastics and sports until graduating college. After college I began writing again after my cousin gave me a Bob Dylan album (the Best of Bob Dylan). Since then I have been creating music, playing in bands and producing. If I focussed those eight years of high school and college I would have been more advanced musically because there are more opportunities to learn during that time. Team sports especially took up too much time and energy away from music. Read more>>

Jessie Lillis

My immediate family has always been very involved in my hometown’s local theatre scene, so I’ve always lovingly joked that I was doomed to this life. My first time on stage I was, I think, about three, and I sort of just never stopped after that. Despite having a deep love for theatre (and, fortunately, the unyielding support of my parents for whatever career path I chose), I inexplicably kept trying to leave the industry. When I went to college, I had no intention of participating in theatre, but somehow ended on stage every semester and left with a theatre minor. After graduation, I again said I was done with the creative field and got what I thought was a sensible job in corporate HR at a large company in Washington, DC. During my several year stint there, I found success but a huge lack of fulfillment. Someone at that company talked a lot about the idea of having your “career ladder” up against the wrong building. You can climb all the way to the top of it, but if you’re at the wrong building, it might not matter in terms of your ultimate happiness and fulfillment. Read more>>