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.

Teresa Dinneen

I think about this often and 100% wish I had started my company sooner than I did. Before starting I wanted everything, from my website to social media to my back end systems to be perfect before starting. Which I now realize is far less important than the actual service I was providing. I knew what I was doing, but was scared to fully immerse myself into the business so made excuses that the ‘business side’ of things wasn’t ready. Read more>>

Robert Matricardi, Jr., CFP®, ChFC®

Yes, I went to school for business economics and finance, however, started installing sprinkler systems after I graduated. The reason was that I needed a job, so I took one. Also , I thought Finance meant “stock trading” and that was a tough business in the late 90’s. then there was the ski lift operator, the retail manager, and the bank teller positions before getting the career position. Read more>>

Courtney Siler

If I could go back in time, I for sure would have started my business sooner. I officially started as a fitness trainer in March 2020 and I have truly enjoyed what I do. At that time, I was still teaching at a high school but I knew my path in life was to do something else. I believe I would of been where I want to be for my business if I started sooner. What would have changed about my experience is I could of gain the knowledge about a fitness trainer and other related certificates earlier to grow my business. Read more>>

Shannon Trudel

About 5 years ago I working at a corporate job I didn’t love, dreaming of starting my own business for the freedom and flexibility I desired. Ever since I was a little girl I wanted to have my own boutique but I thought I had to work at a corporate job for a long time to get the experience needed to run my own business. My husband was the one who encouraged me to start it and I’m so glad he did. If I could go back in time I would tell my younger self to start my business sooner, to go for it! The truth is, the best time to start is now, there will be a lot of things to figure out but you will figure them out. Read more>>

Simone McNish

When I started my business in 2019, I was working full-time and hoped to create an outlet to be creative outside of my 9-5 job. I had dabbled in blogging and content creation and decided to try my hand at social media consulting. I had a 3 year old and loved the idea of leaning into entrepreneurship before I had another baby, Read more>>

Irina Adams

I graduated from college in 2017 with a BBA degree in Accounting and Business Economics from Michigan. Today, I can proudly say that I have pursued a different dream of running my Photography business full-time in Arizona. If given the choice to invest time and money into College or start my business right away, I wouldn’t change a thing. Read more>>

Alyssa Mages, BS, CVT

If I could go back in time…isn’t that something we all wish for at some point? Regarding EVT, even though we did our soft launch in October of 2019 and then an official launch 8 months later right at the peak of the global COVID-19 pandemic, I wouldn’t change the timing at all. Up until June 2020, I was working full-time as the education & development coordinator at a 40+ doctor, 200+ support team member specialty & emergency veterinary practice. Read more>>

JoJo Williams

If I could go back in time I absolutely would say I wish I had started my business sooner. I started my business during the most difficult time in our lives, the pandemic! I had worked for many spas over the last few years. The spa I spent the last 5 years at unfortunately had to close its doors due to the pandemic. This was the first time in my life I was unemployed. Under such scary and unknown times, I did some deep soul work and discovered a vision of the possibilities of having my own business. Read more>>

Nyla McGinnis

As a 17. year old business owner, I honestly wish I started my business sooner. I started my business at the age of 14 in the year of 2020. In 2019 about to enter high school, I was starting to feel pressure about what my life after high school should look like. I felt as if, everyone had their own ideas about what I should and should not be doing with my life, but in the end I didn’t know who’s advice to take or which direction to go, but I knew I wanted happiness in whatever it is that I do. I considered many career options: Hairdresser, teacher, creative director, but I found faults in EACH field. Read more>>

Shianne Wisdom

i believe when i started my business it was “right on time.” at the time I was a supervisor at a Japanese clothing store called Uniqlo, at first I loved the job but over time I felt like I had more to offer and it wasn’t being seen in the areas it should’ve been. towards the end of my being at this job the graphics & web design side of my business started to pick up, so i said why not & i quit. another driving force that caused me to quit was that EVERYDAY i was there i suffered from headaches, ever since i quit my headaches are at a minimum! Read more>>

Bianca Johnson

It was first licensed in 2021. I talk about this all the time. I always say I wish I had stayed on the course of sewing from when I first started, I kept stopping and starting. If I kept at it, I feel I’d be further than where I am. I was never at a bad place, I just don’t think I really took it serious as far as turning it into a business, it was more so a hobby for me. I started to realize how gifted I truly am and said it’d be great to go into business. Read more>>

Danielle Neal

I started performing, writing and recording music back in 2018 never knew I would be here telling this story. I was at a very stagnant part of my life and was looking for something fresh and passionate something I desire. I was job hopping career to career even tried college for many years but music & entertainment had the bigger impact on my life the first day I started it. I couldn’t wait to tell a friend. Starting sooner would have changed everything about me and my journey. Read more>>

Trust Noone

Honestly, if I could have started my career as a rapper earlier, I definitely would have. A lot of these rappers coming out the gate and going viral are 21, 22, 23 years old and I just turned 25 in February of this year, so sometimes I feel late to the game already. I think that’s just me being hard on myself though, I mean 25 is just a couple years off and a lot of other rappers that are already running things and at the height of their careers are in their 30s. Read more>>

James Cox

I do wish I started my podcast earlier than I started it in February of 2020. I had seven prior podcast I created before we (Blake Moseley, co-host) and I founded “When Words Fail Music Speaks” Podcast. For a short run through of the past podcasts I’ve created are…. “James VS the World” where I would talk about my life living with Cerebral Palsy. “2nd Hand Banter” Where me and my friend John would discuss random topics”. Read more>>

Chrissy Goobache

I started working as a singer, songwriter and performer early, at the age of 3. I went and recorded my first professional song at the age of 14 in the studio, but I never took it seriously. It was always a hobby until the age of 22 and 8 years of my life passed by where I had wasted my time on things that weren’t sustainable. So, to answer your question, yes. Read more>>

Katelynn Corll

I was incredibly fortunate growing up, because I’ve been surrounded by music for as long as I can remember. All three of my older brothers started taking piano lessons at a young age, so all I wanted to do was learn, too! I was able to start taking piano lessons myself when I was 5, and I just fell in love with music even more from that point on. Read more>>

Meghann Jordan

Being that hindsight is 20/20, of course I wish I would’ve started earlier. That being said, I wouldn’t have had the life experience that led to the songs I’ve written so who’s to say? Read more>>

Tiffany James

Life is interesting. There are so many twists and turns that happen as you find your way and especially as you follow God’s calling and purpose for your life. For me, it started young. I was always drawn to different things, and now when I look back, I can see that they were all related to social justice advocacy in some form of another. Read more>>

Brooklyn Borders

I wish i would have started my creative career sooner, just because i was doing such fun things at a young age it would’ve been cool to document it all!! Read more>>

Ryan Semple

For the most part, I try not to dwell on the past. Rumination of the what-ifs is of no positive gain. But, there are times that I wish I had made the decision to pursue a creative career sooner. Mostly because it means I would’ve gotten more time under my belt. Read more>>

Yuliya Gabriella

I have always been a creative person, but I never considered pursuing a creative career until later in life. When I was younger, I was more focused on pursuing traditional academic and professional paths. However, as I gained more life experience and exposure to the creative industry, I began to realize that I could turn my passion for creativity into a fulfilling career. I am grateful for the experiences that led me to where I am today and excited to continue growing and developing as a creative professional. Read more>>

Karo Kozak

This is a really interesting question because I used to be mad at my parents for not putting me in acting as a kid. Growing up all I wanted to be was a child actor. I used to always say I would’ve had it so much easier. Looking back now, I am forever grateful I got to have a “normal” childhood because everything I got to experience shaped me into the actress I am today. Read more>>

Amber Rose

Andres says: “I think the time i started listening to music and playing it was perfect for me in shaping my play style. I was 15, and was into bands like system of a down and blink 182, different styles, but a wide variety. Any sooner or later would’ve gotten me into different artists, and different styles i assume, but it’s tough to say.” Read more>>

Chanta’ Johnson

Looking back, I wish I had started my nail enthusiast journey sooner. I began experimenting with various nail polish colors, designs, and techniques at home in 2015. I frequently watched online tutorials to improve my skills. Over time, my interest in nail art grew, leading me to share my work on social media platforms in 2020. I received positive feedback and encouragement from other nail enthusiasts, which motivated me to attend nail art events. Read more>>

Casie Farrell

If I could go back in time, I wish I would have started my DJ career at least 10 years ago. Not very many people know this about me, but I started my DJ’ing journey at the age of 35, YES, 35! 3 years later, looking back, my biggest regret is not starting sooner. While I have been active in the club world since I was 16 years old, I didn’t start getting involved in EDM music till 2016 when I went on a trip to Berlin, Germany, where I went to the infamous Tresor night club. Read more>>

Michael Coppage

Yes. When I graduated from undergrad (Memphis College of Art) I planned to go to the Peace Corps. While I completed the application process and waited for my travel dates I worked as a substitute teacher for the Chicago Public Schools. My departure date was pushed back multiple times and I decided to apply to graduate school. Eventually I was accepted to PAFA (Pennsylvania Academy of the Fine Arts) and gave up my interest in the Peace Corps. After graduating, I moved to Ohio where I would begin my international travels for the next 10 years. Read more>>

Mai Ty

I think the best time for me to start my career in music was exactly when I did. I have no regrets really. But don’t get me wrong, I definitely have moments where I wish I was the young new artist on the block, but I wouldn’t have had the confidence and perspective back then that I have now. Read more>>

Asa Lecourbier

I’ve been drawing since I was five and started taking it serious at fifteen. I wish I was more consistent in my earlier years but its irrelevant to what I’m doing now. Read more>>

Tyler Garrett

I definitely wished I would’ve started my creative career much earlier. I loved to draw when I was younger, I would look at pictures and draw a copy without tracing, usually portraits. In retrospect, I was actually very good, much better than I am now. But when I got into middle school the comparison dilemma started to really affect me. There seemed to be so many people who were better than me. Read more>>

Maxxi

If I had known then what I know now, sooner would have been ideal. I let fear, trials, and tribulations of life stop me from consistently pursuing a creative career instead of pushing past being uncomfortable and utilizing the time and resources I generously had in between my struggles. That’s not to discredit who I’ve grown into, and the knowledge and experience I’ve gained. I sincerely believe I’m right where I’m supposed to be. Read more>>

Lisa James

I had always wanted to be a kindergarten teacher since I was a little girl. I got married at 18, moved 1400 miles from home, and never went to college. Three years after being married, I got pregnant with my first baby, followed by two more babies (every other year). Within five years at age 26, I had three little girls. I couldn’t go to college. Fast forward ten years, I was separated from my husband. Read more>>

Lola Darzens

There will always be a part of me that wished I had started sooner however, when I catch myself thinking that, I always remind myself that I would not experience the true happiness that my career brings me now without my background. I went to business school after high school and dropped a lot of my creative interests. I always say that I learned the hardships of the business so I could enjoy the glitter of the show. Read more>>

Steven Holliday

I think once we all find something we truly love we always think back to “I wish I started this 10 years ago.” However I believe that things are supposed to happen when they happen. You cant rush the creative process. Even if it take a decade to get where you are comfortable, that decade is filled with hard work, humiliation, and experience that is paramount in guiding you into the person that you eventually become. Read more>>

Christopher Rubano

Trash Goblin formed in February 2020 — three weeks before the entire world would go into lockdown. It is a reflection of who we are and where we are in our respective journeys — and it could not exist if we had met earlier in life. It has been an island of community in a sea of isolation, and catharsis in a time of madness. Read more>>