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.

Stephanie Marchant

If I could go back in time, I would definitely had started my business sooner. I would have focused on photography and business in college and not getting a Masters in English. I was not focused on what I wanted that early in life. I envy anyone who was and made it happen. I started my business almost 15 years after moving to Texas in 1999. So sometime in 2013. Digital photography had already taken off and photographers were a dime a dozen. Read more>>

Ryan Mills

I’ve started multiple businesses but we’ll focus on my current one, “Four-M”. I always wish I had started my businesses earlier, but of course the knowledge and resources all come later via trial-and-error. I started my business out of necessity as being an LLC had more benefits than a contractor at the time. Had I started my business sooner, I would have had more time to reap those benefits and create workflows and practices around that type of operation. Read more>>

Justine Vargo.

If I could go back in time, I would have started my business exactly when I did. At the time, I had no idea what I wanted to do with my life or my career. My boss at the time, tossed me into a Graphic Design position where I had to teach myself everything! I took the time to learn everything I could and in no time, my work was being noticed by entrepreneurs and businesses all around San Diego. Within 2 years, I was able to quit my job and start my own Graphic Design business. I think if I would’ve started any earlier or later, I wouldn’t be who I am today nor would I have the success I have today. Read more>>

Shaina Styles

My past professional jobs taught me so much and I learned many things about the business on many levels. I didn’t start my business too early or too late as I believe timing happens when it is supposed to. Fast forward to now, I am able to implement all the knowledge I have gained from past experiences. Read more>>

Jim Skelton

If I had a chance to go back a few years with the knowledge I have now, I would have started my business many years earlier. Firstly, and probably the most important at this point in my life (48 years old), I would have been able to work more easily at a younger age, with a younger body. Knifemaking is fairly physical work, and it wears particularly on your neck, back and other joints. Even though you’re not doing hard labor like lifting very heavy objects, craning your neck over for hours on end, or hand sanding a steel blade for a day-long session isn’t fantastic for your joints as you put on a little age. Read more>>

Nicole Vasco

If I could go back in time, I would have started my copy and content writing business much sooner. Years ago, as a new stay-at-home mom, I was excited to get the chance to be the mom I always wanted to be, but I always had the desire to work from home while raising my children. Becoming a mom didn’t dim my ambition for wanting to work, earn an income, and feel impactful in the world. It actually increased my desire to want more because the world saw me as just a stay-at-home mom. Read more>>

TiaMichele Walton

My business is one of vulnerability. Walking around on the beach in a bikini is a scary thing to do. Modeling my own pieces is scarier. I built and created Taste Swim to share my story of empowering myself to love myself freely, feel good in my own skin, and share that self-love experience with all of my customers. I couldn’t have done that at a better time in my life. I don’t necessarily think I should have started my business sooner. I do wish I loved myself the way I do now, then. Read more>>

Taneisha Bernal

There is a saying that says nothing happens before it’s time. While I wish I had started my business sooner, there is no time like the present. I started my business in 2019 right before the pandemic. While working a corporate job, I was able to balance both which was not easy. Looking back the only thing I would change if I could was pouring more into myself and my business and less in corporate. In corporate you are building another persons brand while making them wealthier, which leaves you with little or no time to focus on your goals, dreams and family and often times you are just seen as a number and isn’t valued for your qualities, skills and talent. Read more>>

LaTonya Johnson

If I could go back in time, I would have started my business sooner than later. My grand parents were Entrepreneurs. My grandfather was a Carpenter who built the house I grew up in. My grandmother was a beautician. All of their 5 children had a talent that allowed them to have a second income alongside of their regular job. Read more>>

David Chaumette

Looking back, I wish that I had started business earlier in my career. For years, I played it safe — working in large law firms on a path that was easily followed and largely prescribed. The signs that I needed to do something different came early, but I ignored them. I tended to enjoy my work with small clients the most. And there were other aspects of “corporate” issues that I did not enjoy. All of it was more performative than impactful and it was not really for me. I needed to leave the law, but I didn’t know how or when. Read more>>

Tom Steward

Looking back, I couldn’t have started my creative career sooner or later. As a child, I was acting in theatre. As a high-school student, I was acting and writing plays and poetry. When I got to college, I kept all that up and produced theatre while co-hosting a radio show. Then I abandoned it all to pursue a career as a scholar in Film & Television Studies, completing a Masters Degree and PhD and then teaching in universities for a few years. When I moved to the US, I decided to act again and writing naturally followed. Read more>>

Kevin DelMastro

I didn’t know I’d love playing music and performing like I do. Now I feel passionate about it and love spreading joy through my music. If I had known back then, I would’ve gotten into the profession much faster! I actually loved sports when I was a kid, and the part that I was most attracted to was the adrenaline rush of performing, in this case basketball, baseball, football, or tennis, in front of a crowd. When I played music as a kid, Read more>>

Katie Donnelly

I think about this question a lot – it’s something I write about in my first EP. Being almost 30 in LA in the music industry has given me a lot of perspectives; it has made me feel behind in many senses, but also, with reflection, has taught me that I got here exactly when I was ready. I started writing music from a young age but always thought of them more as poems. I never really considered myself a ‘songwriter’ till I got to college. I was shy, and never wanted anyone (including my mom) to hear me sing. Read more>>

Ogechi Ofodu

I released my 1st track “Blvck + Womvn” on all dsp’s in the summer of 2017 at 19. I was a freshman in Georgia’s state’s film school while working on it. Career wise I had been spoken word poet and author (Lost Negro Records). I actually try not to think about because to me life played out that way when it could and was supposed to happen. I’m involved in several things outside of music and I feel like in having a colorful full life and respecting divine timing, it lessens the perceived irritation not starting sooner. As well as adding to my personal vitality and overall artistry. Read more>>

Tom Falco

I always drew, as soon as I could hold a pencil or crayon. As I grew older, I would draw comic strips, but I would never submit them to syndicates. If I did, I never had a plan. It was more of the journey for me than the destination. I never said to myself, “On this such and such date, I will submit my work.” I would just submit it when it felt right. If I received rejections, I would put the work away for awhile (years at times) and then come back to it again at a later date. Read more>>

Blacc Horus

Gladly pleased with my experience and process along this long prelude for just the beginning. Just a starving 25 year old in Houston,Tx, always the black sheep of the creativity world. I know everyone isn’t going to agree with your terms and morals, but in due time all will play out. I wouldn’t change a thing only because God doesn’t make mistakes and all mistakes are lessons in life. Growing away from hip hop a little, helps out with the longevity of my craft and art. Read more>>

Gregory Gordon

How it all started….back in 2001, I knew I wanted to be an actor my junior year in high school. I was given my first opportunity to be a part of a local commercial for a clothing store called Trendsetters back in Tulsa, Oklahoma. Soon after I had my first son at the age of 17 after graduating high school. I attended Tulsa Community College and studied in the theater program. It wasn’t really what I was expecting so I dropped out after less than a year after trying to balance being a young dad, studying acting, and keeping a job. I realized that acting would have to take a back seat for a while. I knew I would eventually get back to it again. Read more>>

Mike Mike Desatnick

Unfortunately I wasn’t able to attend art school until after a tour of combat in Viet Nam (I wouldn’t recommend this particular approach). Hindsight is always 20/20. Looking back, it would have been nice if I had been become a little more serious about pursuing my are when I was younger. But, maturity is a very important part of becoming an artist and trying to reach your artistic goals. Read more>>

Jennifer Sanders

When I embarked on building and launching the Dallas Innovation Alliance with my partner Trey Bowles, I was working at a consulting firm that focused on clients in the technology, energy, finance and economic development sectors. As I started to notice that these industries were beginning to converge around an emerging concept – smart cities and sustainability – I became fascinated by this intersection. For awhile, I had been trying to figure out what was next for me, I really enjoy consulting and supporting multiple clients, but I was seeking something that closer matched a passion or mission-driven North Star. Read more>>

John Serafinko

I wish that I had started with my current firm a lot sooner than I had. I feel that sometimes people, myself included, allow themselves to believe the myths that families and friends instill in them. “It’s better to have a nine to five job. Business ownership is for “other people”.” “You will never be financially stable. You will work until you can’t anymore.” “Being rich is for other people. Not you.” Read more>>

Gwendolyn Everline

I wish I had started my business earlier because we are going into a recession. I started with a bang and now sales has plummeted. I am forced to rethink and re-strategize my mission. I would have made some changes that would have cushioned the company It can be done and now my aim is finding a market and offer what my customers want Read more>>

Jada Campbell

I have been a licensed cosmetologist since June 2011, fresh out of high school, working under my beautician, Pamela Hall, Desired Images II. She took me under her wing when I was in cosmetology school learning how to be a shampoo technician (that is where you make your tips). I learned so much working with Mrs. Pam from relaxer, semi-permanent, permanent colors etc, it was honestly the greatest experience and rushed me to pass my test on the first round. Read more>>