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.

Michelle Lander Feinberg

Honestly, no. My path unfolded the way it was meant to. I had a full, rewarding career before, and that and other experiences shaped me. They gave me perspective, taught me discipline, and helped me understand people—lessons that now feed into my creative practice in meaningful ways. Read more>>

Dallas Ochoa

I do wish I’d started my creative career sooner, but honestly I’m glad I waited.
If I had started sooner, I probably would have gone more into graphic or visual design, instead of something with crafts which I enjoy more. I probably would have been happier with my career overall, but would have had a harder time with career growth. Read more>>

Christa Vail

I will always wish I started my creative career sooner, because I knew from a young age that I wanted to be in the arts. However, as life has unfolded, I know that when I started was the right time for me. I officially started my business when I was freshly 30 years old, in 2023. But leading up to that, I was a solo mom to a toddler and I was very riddled with postpartum depression and PTSD with no end in sight. My creativity seemed non-existent and had been for years at that point. I started making quirky little suncatchers while I worked from home, during my daughter’s naps. Read more>>

Eitan Prouser

Music was a relatively late endeavor for me. I started playing piano at a very young age for fun, but never truly took it seriously. I always had a musical mind and my elementary school music teacher, Laura Deutsch, once told my mother to make sure I never stopped doing music. As a result, for most of my time growing up, my mother always told me to play the guitar. However, I didn’t even begin until I was halfway through my junior year of high school. Read more>>

Darren Paltrowitz

I started early, since I began interning and writing local publications when I was in high school. But the mistake was quitting when a few publications stiffed me on invoices around the same time. And unfortunately that sort of thing happened a few more times over the years, which I would learn is normal for the freelance and creative worlds. Read more>>

Dinah Gacon

I began my creative journey into hairstyling when I was a senior in high school. I began working at 19 and 2 years into my career I met my husband and I kind of put my focus on what I wanted my career to evolve into on the back burner. We moved around a lot for his career and I kept dreaming of someday owning my own salon and mentoring other creatives. I felt like my career really began taking off when I turned 39! I finally had the opportunity to open my own business and begin building a brand. I began independently teaching the craft of hair cutting and grew my business to have like minded stylists join me. I wish I would have began this sooner, but I’m glad I had the time to really hone in on what I wanted with the experience I’ve gained! Read more>>

Jonathan Giles

I think sometimes it’s easy to look back and say what if… When I was graduating from college, I interviewed with Cartoon Network for their internship program. To this day, it’s one of the best interviews I’ve ever had. The recruiter and I—total vibes. At the end, she asked, “If there was any other job you could do, what would it be?” Read more>>

Kris Mayers

Considering I’ve been a musician of sorts since 2009, I definitely wish I started being more creative a lot earlier. I didn’t start getting serious about creating my own music until about 2021, before that I was mostly just playing covers or letting other musicians take the creative lead in other bands. I’ve always messed around here and there but I spent most of my free time playing video games. Of course, I don’t really regret this since I was just doing what I enjoyed more at the time but it makes me wonder how things would have been different. Read more>>

Laura Pellegrino

I never truly stopped creating — I just stopped sharing. Dance was my first language, and in college and beyond, it was how I expressed myself professionally. But my curiosity always went beyond movement. I was fascinated by building entire environments: movement, light, texture, and emotion layered through immersive installations. I explored that in school with tools like MAX/MSP, but life pulled me into a more conventional path after a health shift — and eventually into a career in tech as a Product Manager. Read more>>

Greg Madhere

I knew since the age of 18 I wanted to start my own business. In 2003, I made the leap of incorporating my business, Lowgic, Inc. Back then I was immersed in the technology world and wanted to provide IT services to small companies. Over the years I had some starts and stops, bouncing back and forth between W2 employee life and independent contracting. I didn’t make the choice to go all in with my practice until 2023, and took the chance to rebrand as Lowgic Partners. There’s been a big pivot since then and things evolved as I did. While still geared towards helping small, growing companies, the service focus is now on fractional Client Engagement Management for professional services technology firms. Read more>>