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.

Sandra Hunter

I started my business, empowerHER, at age 65 after 19+ years in academia as a professor of English and Creative Writing. For nearly two decades, I watched my female students graduate, enter the workforce, and face the same systemic gender and race bias that women have struggled with for generations. It struck me that there was no place of transition, no safety net between the educational institution and the start of a young person’s career. I decided I needed to do something about it. Read more>>

JT Penderville

Starting a business can be very scary! When I decided to go full time with my videography business, Penderville Films LLC, I was approaching my 15 year anniversary at Carnegie Mellon University! I thought for many years, CMU would be my lifetime career. I was on a pretty great trajectory. I started there in 2007 as an intern for the School of Computer Science. I quickly worked my way through 3 months of paid, part-time work, and then got hired on as a Video Technician full time. My job was to record classes for distance education. I spent 11 years at SCS before I accepted a promotion as the A/V Distance Communication Manager for the Electrical and Computer Engineering department, where I spent 4 years before deciding to leave it all behind, so to speak. Read more>>

Danesha Artis

I’m going to say yes in this case? Almost every creative always wishes they started earlier than they did, but more often than not? We usually have our own reasons. For me, it was all down to lack of self esteem and fear.

I’ve been drawing ever since I was younger, but I didn’t refine it until I got to college. And even then? I just thought my work was okay. Nothing to truly write home about and surely not worth anyone purchasing it. It took a lot of urging from fellow creatives to get me to step out of an honestly well built comfort zone. Can’t tell you how many times I’ve stepped out of it to sell my work and to immediately get low balled or demeaned over the “crime” of asking for payment. Read more>>

Shaurya Kapoor

I’ve been singing since I was 4, but growing up in Faridabad, India, without any musician friends around me or any professional musicians in my family or circle to look up to, I never really saw music as a viable career option. It was always something I loved deeply, but it didn’t seem realistic. Read more>>

Daphne Winters

I started my voiceover journey in January of 2024, but I wish I would have started it when my husband suggested it to me.

In December of 2021, I finished my masters in biology and applied to a ton of jobs between December of 2021 and March of 2023, but hadn’t had any luck finding something in my field. Sometime during 2022, while I was trying to figure out what to do for a career, my husband and I were driving home from a vacation. During that 12 hour drive, I asked my husband what I was going to do. We were listening to an audiobook together in the car and he pointed at the dash and said, “this.” Read more>>

Nancy Rice Early

I have created art most of my life. For years, I created in the evenings and weekends after the full time job. I didn’t know exactly how to make enough money selling my art to quit the full time jobs. I would get in galleries, and participate in local art fairs and group shows, but the sales were few and far between. Read more>>

Michael Meyer

The answer to that question is difficult. Ideally, yes I wish I could have dedicated full time to being an artist much earlier. I believe I would be further along in my ongoing development as an artist. I say that because, even though I have been drawing and painting since grade school, my knowledge and progress has dramatically increased since moving to New Mexico fifteen years ago. However practically, I started out looking for a paycheck because I didn’t know how to make a living as a fine artist. Initially I pursued freelance illustration work and commercial art jobs. Read more>>

Ashley Farrell

If I could go back in time, I 100% wish I would’ve started my creative career earlier — and more importantly, that I would’ve owned it earlier. I actually did try in high school. I started a YouTube channel, made videos I was proud of, and then promptly got bullied out of it. Like full-on embarrassment, teasing, the whole thing. I was crushed and honestly let that experience dim my confidence for a long time. Read more>>

Kim Clark

I have always known that I wanted to be an artist, but when it came time to pick a career path, I allowed myself to be talked out of pursuing it in favour of something more financially stable. This decision lead to a lot of jobs, and a few decades of a career in the financial services industry. While it provided some monetary security, it gave me no joy. Read more>>

Chloe Amour

I wish I would have started sooner. In porn world, once you start hitting your mid to late 20s, the way you get casted changes bc you’re no longer in the “teen” category. You’re seen more as a “babe” and once you’re around your late 20s and beyond, companies will try to book you as a “milf”. You always have the choice to say yes or no to what jobs you take and want to be casted as. It’s bittersweet, bc when I got into the industry I was 22. I lived in my agency’s model house for about 2 weeks and the other 3 girls staying there were 18 and 19 so I felt old but I knew I wouldn’t be ready to do porn at younger ages. I already felt at 22, that I was “too young” to be doing this until I met other girls in my agency. Read more>>