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.

Chris Chemel

I did try to do stand-up comedy and photography earlier in life. When I first tried photography I was wholly uneducated on the subject and had zero clue what I was doing. That didn’t remove the feelings I had when I saw something amazing, and wanted to capture that image. Read More>>

Tye Harris

I started my business over 15 years ago. I’ve always been in or around the music and entertainment industries but never took advantage of it until I felt like it. Looking back had I taken on the opportunities then as opposed to later I don’t think I would be as far as I am now. Because mentally I was not prepared. Read More>>

Jennifer Schiavone

Looking back, I truly think my timing was just right. I started my business five years ago, at a point in life when my kids were getting older and didn’t need me in the same way they once had. For years, my focus was 100% on raising them and being present for all the little (and big) moments. Read More>>

Abel Hernandez

I opened up my barbershop Mvne society Headquarters at the beginning of this year (February, 2026). Before opening up my barbershop I had a studio for the past 12 years and even though I loved the studio life I felt like it was time to level up and do something that challenged me some more. Read More>>

Courtney Wilder

Jess and I started Tired as a Mother Coffee Co. in 2024. At the time, her kids were 4.5 and 2, and mine were 4.5 and 1, so to say we were in the thick of motherhood would be an understatement. We were both running on little sleep, juggling family life, and trying to balance work experience with raising young kids. Read More>>

Apryl Shue

If I could go back in time, I would start my business sooner. For a long time, fear held me back. Living with a disability that includes chronic and unpredictable health symptoms can be an incredibly vulnerable place to be. Read More>>

Sarah Luque

Yes! Starting my balloon design business was the best decision I’ve made for myself! Even after a couple years, I still love it! I started my business after having my kids. Read More>>

Ema Alagić

If I could go back in time, I sometimes think I would have started my spa business sooner — but only if I had the awareness and confidence I have today. Before entering the wellness industry, I spent more than 15 years in marketing and communication science. Read More>>

Calandra Martin

Looking back, I would have started sooner, much sooner. If I had understood the power and potential of online businesses when I was in high school, I genuinely think I would have skipped the traditional path entirely. Read More>>

Jennifer Otis

I believe I started my business at the correct time because God’s timing is never wrong. I have been blessed to be able to have experience in a few different career fields that are aiding in the success of my business. Read More>>

Francesco Dalli Cani

If I could go back in time I would start my career exactly when I did the first time. Since middle school I always tried to get into the theater club, but funnily enough something always happened last minute and the theater club always got cancelled. However, things changed during my fourth year of High School. Read More>>

Jessica Rangel

I absolutely wish I had started sooner. Before launching Copper & Stone, I owned a housekeeping business. I loved the flexibility, my clients, and the lessons it taught me about running a business. But the truth is, my real joy always waited for me after work. I was constantly creating, whether it was painting, sewing, sculpting, I just couldn’t sit still creatively. Read More>>

Denise Dethlefsen

I wish I’d started sooner. Read More>>

Jessica Glynn

If I’m being honest, there are moments when I think, “I wish I had started sooner.” I always knew I wanted to be a therapist. That calling was there early. The drive, the curiosity about people, the desire to sit with someone in their pain and help them find their way through it- that was always part of me. But life unfolded differently. Read More>>