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.

Lindsey Paulson

Starting a consulting business wasn’t originally in the cards. I have always loved operations, systems, and processes and was able to channel that love into my career for Marriott International for years. Hotel operations, business operations, and property management operations are all a love of mine. I was able to pivot my role during Covid to construction operations and work as the Chief Operations Officer for a local construction company. Read more>>

Cheyenne Canton

I’ve had my business for years now , while still working as a chef in restaurants. One day , i decided to put in my notice and focus on taking my business & myself more seriously. At the time i was getting booked a lot and wanted to put my all into it and i knew i couldn’t do both. I wish i started taking it more serious 2018, i think i would be ALOT further in my career and avoided a lot of mistakes. But in the year and a half of going all in, i can truly say everything happens when it’s suppose too. Read more>>

Cherrelle Allen

I started Wow Just Wow out of a pure, unadulterated love for fragrance. It wasn’t a calculated business move; it was a passion project born from countless hours spent dreaming up new scents and envisioning a world filled with the intoxicating aroma of soy wax. Starting later might have meant missing out on potential market trends or opportunities. But starting when I did allowed me to build the brand with a solid foundation and a deep understanding of the industry. Looking back, I wouldn’t change a thing. The journey has been filled with challenges, but the rewards have far outweighed the obstacles. It’s been an incredible experience to watch my dream grow into a reality. Read more>>

Ronnie Wylder

There are certain aspects of my career I wish I had jumped on way sooner. I was always focused on the branding and visuals rather than learning to produce my own music, play piano/guitar. I solely focused on my vocal skills, which has definitely paid off, but I do wish I had given my focus to other sides of music as well. I started singing in 2016 after my first of five spinal surgeries. I began getting professional gigs in 2019. In 2023 I was a full-time musician.  During that time frame I moved out of my parents house, worked 2 jobs, got married, and ran a band in the middle of it all.  Sometimes, I regret not doing things sooner, or wish I had done them differently. Through it all I’ve learned to accept that it is all a part of the journey. We are meant to be exactly where we are in this moment, all we can do is learn going forward, and know that it is never too late to try something new. Read more>>

Phoebe Ritchie

Of course I wish I had started earlier! I think we all wish we had a jumpstart on the things we find out later in life are important to us. I keep meeting people who started when they were 10 or younger. It’s incredible – they’re the unicorns of the industry that apply for entry level positions with a decade of experience that we all thought couldn’t exist. Personally, I was late to the game. I joined a choir at the end of high school and again in college, but I didn’t realize music could be anything other than an hobby until after I graduated. Most people had industry knowledge, a functional understanding of theory, and connections by then so I didn’t have a group of people to be excited or build out ideas with when I realized I wanted to pursue writing. The upside of that is that I was forced to learn a lot of it on my own, which gave me a lot of independence down the road! Read more>>

Michael Pereida

My start in music was different than most I would say. I always loved words & was heavy into writing. Whether that was poetry, short stories, journaling, love letters,(that never were given to the girls I liked) cause I was shy lol, My sister Bianca is a vocalist, my other sister Mercy was always doing the latest dances in the 80’s & 90’s, & my parents loved music. I first started performing with the Purple Bee Crew around 2000. They would have jam sessions at clubs & would call me up on stage to freestyle on the mic while they created live improv music. I would come up with chorus ideas & then make up verses on the fly to fit the song idea. We did this for years & still do to this day, when our busy schedules permit. Read more>>

Alexia Benson

Last August, I made a decision that changed the trajectory of my entire music career — moving across the country to Austin, Texas to build an in-home studio and pursue my musical ambitions as an independent neo-soul/rnb artist. I left behind my career as a classical composer and opera singer, prestigious grant opportunities, a network I established over many years, and skills I spent nearly a decade harnessing. You may wonder, why? I’ve always been very passionate about learning many musical styles. I took the classical composing route to challenge myself to write music with live instruments and complex, longer lengths. As an opera singer, I learned how to use my voice to sing powerful arias and smooth, lyrical lieder.  Read more>>

Eric Hagen

The thought of “should I have started sooner” or not is something I think about often. As a musician, being young is a key selling point. Most artists start out as a young adult, say in their early 20s. The industry expects that. You’ll be hard pressed to find a “successful” artist that started later in life. But there are pros and cons to both. Starting out younger has it’s advantages as far as image and freedom. You’re much more marketable as a young adult. And you also have a lot of freedom. You may not have a career, a spouse, children etc. But it also comes with risk. If you don’t “make it” as a creative, you may find yourself in your 30s or 40s with little to show for it. No career, no savings, no family… Read more>>

Rachel Leibman

I’m a late bloomer. I didn’t start my art career until after I had my first grey hairs. When I was younger, I think I knew I had the talent and creative mindset, but I didn’t have the confidence to take the emotional risks that being an artist required. In college, I was utterly intimidated by the coolness and maturity of the art majors. Next to them I felt like a little girl. So I put art to the side and concentrated on less risky endeavors, at least for me. I got my masters in business and worked in tech as a programmer and analyst for many years. Read more>>

Catherine Matthews

Some might say starting a career in writing fiction at the age of fifty-eight is a bit late, foolish even, particularly if you are leaving a successful thirty-three-year career in public education to do it. I would say it is the perfect time. The journey that led me to become a published author has unfolded at exactly the right pace. In my twenties, I studied science and helped high school students to understand their world. In my thirties, I led schools. In my forties, I analyzed data and systems. In my fifties, I explored my inner and outer worlds. At the time, each pursuit fit exactly the person I was. Read more>>

Big Slime

I Actually Did Started Sooner As Soon As I Graduated High School In 2017. I Purchased Studio Equipment Recording My Brothers And Friends And A Camera To Shoot Music Videos And Short Films, But I Also Was Getting Caught Up In Bad Things So My Mind Wasn’t Focused. So Eventually I Was Incarcerated In 2020 & 2021. While Incarcerated I Wanted To Start A Record Label, Named It, Slimeto Records, And Also Pursue My Career In Videography. Released In 2024 I Started Over Again. Only Thing I Wish Is That I Was More Focused Back Then. But Im Also Glad I Went Through What I Did Because It Opened My Eyes Today. Read more>>

Alahji Robinson

I’m a firm believer of divine timing. Although having experience as a print model since I was a child, I started in the modeling and fashion industry full time in my mid to late 20s. I started runway at the age of 28. I was working part time in a hospital as a Certified Nursing Assistant with no knowledge of runway etiquette. This was almost 3 years after I lost my father, whom I nursed before his passing. I have mixed feelings about if I had started sooner. One side believes that I would’ve been more polished and extremely successful by now, the other side believes that I wouldn’t have the life experience that I have which helps me navigate in the industry. Read more>>

Yang Sun

I have never seriously considered taking a career path in choreography and dance until half way through College. Before junior year in college, I was quite the opposite. I majored in economics and was on my path to find summer internships in investment banking and consulting. Dance, back then, has always been there for me but didn’t take up my main focus. Things start to shift during the Pandemic. Being trapped in remote meetings makes me rediscover my relationship with dance. I used to improvise a lot in cafeteria, river banks, side walks, etc. back in high school years, and the pandemic led me back into my improvisation journey in dance. Only this time, I felt a deeper connection and craved to share and involve more artists in the creative process. Read more>>

Jon Kvassay

I’m not sure if starting sooner would have made a difference. I started kinda late in life, I decided to drop everything at 27 and go to college for Illustration. Honesty, I didn’t have much to drop so it was kind of a no brainer. I think what would have made a difference would have been learning to deal with self doubt and self sabetage early. I spent my late teens and early 20’s mostly focussed on everything but art. I started and dropped out of community college over and over again. I played in a band with my friends for like ten years and it never went anywhere. It was incredibly fun, but I gave it all of my attention. Read more>>