Getting started sounds so easy – but for millions of aspiring artists and creatives, the uncertainty of the path forward presents a very real challenge. So, we wanted to gather some artists and creatives we admire to open up about their experience and how they think about whether they should have started sooner or waited for a better time.

Ashley Orlando

Everything we go through in life serves a greater purpose. Whether we find that purpose depends mostly on how we look at our past experiences and overall perspective. Sure, sometimes I wish I’d learned how to sing jazz as a kid, or that I hadn’t quit piano, or that I’d picked up the ukulele in my teen years rather than as an adult. Read More>>

David James Strain

If I could go back in time, there are moments when I wish I had continued straight on to earn my Master’s in Fine Arts after finishing my Bachelor’s. I sometimes wonder what it would have been like to become a gallery artist right out of college, with that academic foundation and momentum. Read More>>

Audrey Ingram

If I could go back in time I would honestly have done things differently than what I am doing now. I would have been more serious in my acting career. In 2006 I wanted to become a actress. I met alot of great people during that time but being so young and not knowing the business entirely I probably would have forfeited alot. Read More>>

Aaron Ulfstam

I made my first tattoo about five years ago now. I’ve been working in tattoo shops since 2011 always doing front counter stuff cleaning scheduling stuff like that. I did that in a few different tattoo shops for about nine years. While I really enjoyed doing that side of it. Read More>>

Rylan Benet

Honestly, I think about this a lot. I started creating seriously while I was already deep into my career in digital marketing so I had the structure, the analytics brain, the “strategy first” mindset. But creatively? I was behind emotionally. Starting when I did meant I already knew burnout, bad managers, and corporate chaos. Read More>>

Kelly Wasmer

If I could go back in time, I do wish that I would have started acting sooner, as it has been so rewarding for me in so many ways! However, much of acting is drawing upon lived experiences and emotions, so I feel that there was purpose in the delay. Read More>>

Darrell Smith

If I could go back in time, I’d absolutely start sooner. The vision behind my mentorship and career placement consultation work had been in my heart for years before I took the leap. I was already mentoring young people informally, guiding them through personal challenges, and helping them discover their direction in life. Read More>>

Peter Mitzelfeld

I wish I had started my business sooner, and broadened my marketing skills to include many types of advertising and marketing to go along with my education and other skills training for the business. Read More>>

Lauren St George

Timing is everything — especially when you’re building something that serves a new niche or introduces a fresh solution. Start too early and you’ll spend a lot of time educating people about why your idea matters. Start too late and you’ll find yourself fighting for space in a crowded market. I’ve experienced both sides. Read More>>