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.

Breanna St. Clair

Yes. I wish I could have done this sooner. It was a huge risk, I quit my day job, moved my family to another town to open this gym. But it was the best and most rewarding decision I’ve ever made. I wish I had done it sooner. Read more>>

Aiesha McKenzie

I believe in divine timing, so I started exactly when I was supposed to do it. If I had started the business any earlier, I would not have had the experiences that equipped me with the knowledge that contributed to my successes. I had already owned three business before this one, and I needed to learn what I learned from them. Read more>>

Tréja London

It has been about 10 years since I’ve started my business. At that time I recently graduated photography school and I was working 2 part time jobs. One job was working fast food and the other job was with a large photo company that specialized in hospital photos of Newborns. Read more>>

Danny Arguello

I started my business during the height of pandemic in 2020. Imagine at that time I had been coaching basketball for 9 years and had an informal education on how to properly train high level athletes. I never would have thought to be a basketball trainer prior to 2019. Read more>>

Anaia Ward

I started my business in 2018, I was a sophomore in college when I got the urge to start doing nails seriously. I initially started doing nails for fun in elementary school on myself and my friends would pay me to do their nails as well but back then I did not see nor have the push to pursue this professionally. Read more>>

Gail Hulnick

I finally finished my first novel when I was 55. After decades as a broadcast journalist, a child caregiver, and a media consultant, I stopped circling the runway on the first goal I’d ever had. I studied writing, and made it a priority to put the final period on everything I started: a chapter, a scene, a page of dialogue, a short story. Read more>>

Candice Luebbering

I wish I had started my business both later AND sooner and while that statement seems an impossibility, I promise I do understand how time works. Launched without a plan as a side hustle while finishing up graduate school, my business was a creative escape. Read more>>

Shreena Shah

If I could go back in time, I don’t think I would start my business any sooner or later. I began exactly when I was meant to. I started my business at a phase in life where I was balancing motherhood, rediscovering my identity, and craving a creative outlet that was truly mine. Read more>>