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.

Michelle Hamilton

Like a lot of entrepreneurs, I’ve wondered what it would have been like if I had started sooner. But looking back, I honestly feel like I started my business at the right time for where I was in life. Before launching, I spent years building my skills and learning through different experiences. Read More>>

Lisa Schafer

Because facilitating freedom for others (like tutoring through my step-by-step process to forgive the unforgivable) is all about answering God’s call to do so, I obviously wish I’d have started sooner. I’ve always felt like the Lord wanted me to serve other women, but it took years for me to find clarity of purpose. Read More>>

Chris Pantier

You would have had such an easier road prior to Covid. LOL I’ve been on the air now for over 30 years, but about 15 years ago I was working at a radio station and one of the Voice Legends I have always loved listening to (He was the station voice for a ton of stations) passed away. Read More>>

Ebony Little

If I could go back in time, I’d keep everything exactly the way it was and wouldn’t change a thing. I would not have been able to open and operate my business without years of management, service providing, administrative, accounts payable and receivable experience that I gained during my decade span in the corporate America world. Read More>>

sherrie bennett

I was in my 40’s when I first started taking pictures of as a hobby because I was working in healthcare as a CNA. I wish I found the passion sooner because so many stuff, I missed out on taking pictures of like my older grandchildren growing up. Not sure if doing it sooner would make me what I am today. Read More>>

Amy Steinhour

I 100% wish I had started sooner. For many years I worked as a Physician Assistant, always employed by someone else or by a larger organization. I was deeply invested in the success of the places where I worked. I poured my heart, energy, and countless hours into helping those businesses grow and succeed. Looking back, I realize I was essentially building other people’s dreams. Read More>>

Whitney Fernald

If I could go back in time, I think I would have started my photography business sooner. Photography has been a part of my life for as long as I can remember. When I was about 10 years old, my mama sent me to a photography summer camp at Ijams Nature Center. Read More>>

Jasheana “Jae” Hamilton

I love this question so much!! (lol) as I grow, I reflect a lot on my most recent job experience and where I was mentally in that chapter of my life. I most definitely would NOT change a thing. I went from working the most random jobs!! I held two jobs majority of the time during my early 20’s. Had dreams of being a nurse. Read More>>

Tamara Perry

My business, Flavorables by Tam, came from a genuine love for fragrance and creativity. I’ve always been drawn to scents and When I finally decided to start creating fragrances and sharing them with others, it felt like stepping into something I had been preparing for my whole life. If I had started sooner, I believe I would already be even more established today. Read More>>

Travis Sigler

I started my business at age 24 when I was working for Dark Horse Comics/Things From Another World here in Milwaukie, Oregon. Life wise I would say it was pretty early on compared to a lot of people. I think in our twenties we are still figuring out who we are. Read More>>

Bryce Beck

I started my creative career in 2017, but it definitely didn’t begin as some grand plan. At the time, I was deep into my corporate career—working as an accountant at Verizon after graduating from FAU and starting my professional life with PwC. Read More>>

Elizabeth Coachman

As a child, I gravitated towards both art and biology. My father encouraged my interest in the former by providing me with a variety of art supplies and a beautiful drawing table that I use still. I attended Moore College of Art in Philadelphia as an advertising art major and discovered that much 1960s graphic design work required tedious hand lettering. Read More>>

Arik Grant

It was a long process, and there was no true, standalone ‘epiphany moment’. As a child I had art talent and the ability to write well. I was constantly praised for it, and told how I’d go somewhere, make money, be famous, that sort of thing. Read More>>

Mike Retland

I wish I could go a back and start my music career sooner. Growing up I was always in a house where someone was involved in music. All my brothers and sisters played an instrument and or song, was in plays, or in choir but I was to deep into sports that I always thought I couldn’t start. Read More>>

Benjamin Schneider

I wish I’d started sooner, but not where I thought I’d be going. When I was 6 years old, I fell in love with theater. I wanted to perform, and nothing else mattered. That passion took me through community theater, college acting programs, and eventually to a master’s degree in directing and arts administration. Read More>>

Olga Ziminska

Growing up, I always knew I was meant to tell stories. I dabbled in poetry, short stories, and even completed my first manuscript in high school, but I knew that wasn’t the right time for me to push this as a career. I attended community college before transferring to a university where I achieved my Bachelor’s in English with a concentration in Creative Writing. Read More>>

Jessica McEachern

If I could go back in time, I would have released children’s books and recorded music sooner. I would have released children’s books and music while I was in college. At the time, I was focused on completing my undergraduate and graduate degrees. My children’s book, When I Grow Up, was published in 2017. My first single, Scared to Love, was released in 2018. Read More>>

Kristen Dorsey

Although I dearly wanted to go to college after high school as an art major, there were four kids in my family, and money was tight. I began to explore alternative ways to get an art education and enlisted in the USMC for a four-year tour of duty that included a year in Okinawa, Japan. Read More>>

Josh DiChiara

Honestly, I go back and forth on this. Part of me wishes I started sooner, just because of the reps. Content creation is one of those things where you only get better by doing it, and I definitely had that awkward phase on camera. If I had started earlier, I probably would’ve gotten past that quicker and built confidence faster. Read More>>

Olivia Robinson

I began my healing journey in my twenties, around 2023. At the time, I had been working in corporate for nearly ten years. I loved getting dressed up each morning and heading into the office. That routine felt like stability, like success, like the life I was supposed to want. Everything shifted after a car accident in Chicago while visiting family. Read More>>