Is it natural to wonder what life would have been like had you chosen a different path? Is it common? We asked many artists and creatives from all over the country if they’ve ever wondered about whether they should have pursued a more standard career path to see what we could learn from their stories.

Bonny Shilton

I couldn’t be happier working as an artist. Creating art is a big part of who I am and I’m fortunate to be at a place in my life where I can do it full time. There’s not much difference between the art, the artistic process, and who I am as a person. When I wake up in the morning I’m already thinking about what to paint, what colors to use, how to solve the current artistic puzzle. Read more>>

Roukia Ali

This is such a good question! Though I knew I wanted to be a writer since I was four years old and have for the most part never wavered over the years, I have experienced (and still do experience) intense bouts of self-doubt. People are always telling you that you’re lucky for knowing from a young age what you’re wanting to do and keeping at it and seeing results (like an interview with CanvasRebel, oh my god!), but I think they mean that for traditional careers. Read more>>

Ituaje Okojie

I’m definitely happiest as a creative. Balancing Letters To You Blog with a full-time job isn’t easy—some nights I’m editing into the early morning, knowing I have work in a few hours. But honestly, It’s worth it.
There are moments when I wonder what it’d be like to just focus on a 9–5, come home, and chill. But even in the chaos, creating still feels right. It brings together everything I love—food, travel, business, and editing. And every time I post a new video or connect with someone through my content, I remember why I started! Read more>>

Reginad James

I think to be a full-time artist and creative is to sometimes be in a constant back and forth between “I’ll never do 9-5 work again” and then “man can probably make 3x my salary”. To be artist is to live through the hills and the valleys. I’m blessed to have stablish multiple streams of income to make those valleys not feel as impactful, but I’m sure all creative entrepreneurs can testify how unpredictable and expensive things are today. Read more>>

Patrick Mowery

I had multiple regular jobs that’s not for me doing what I love touching stages and crafting full corse meals for people to enjoy to the fullest Is my albums just like a top of the line steak you gonna get hi class every time with my bars I make sure my music is very addictive to my fans that’s why it’s hiphop with a twist I was not put in this world to be a worker I was put in this word to be s creator. Read more>>

Benji Alexander Palus

This is a tricky question, mostly because being happy is not the goal; creating is. Artists struggle. It would certainly be easier to give up on the creative side for a regular paycheck. Financial stress can wear you down like little else. It’s difficult to constantly turn down invitations from friends because you can’t afford a night out, to deny yourself so many of life’s little pleasures, to have to decide if that follow up appointment with your doctor is worth skipping a few meals. Most of all, it’s incredibly stressful to push through a financial slump not knowing when it will end. But, as an artist, the currency that I value above all else is time, not money. I need time to create, and I’m willing to sacrifice all but a bare subsistence to get it. Read more>>

Sophia Jackson

I believe this doesn’t get spoken about enough, especially by artists and entrepreneurs who are forging their own paths. But the truth is, I think about having a “regular job” almost every other day. As a creative, an artist, and an entrepreneur, I don’t think you can help but think about it. It’s part of the journey. The challenges of carving out your own lane are real, and they often bring up questions about stability, predictability, and whether it would just be easier to follow what the majority are doing. Read more>>

Alex Lv

Believe it or not, before diving fully into photography and the creative field, I studied Mathematics and Chemistry for my Bachelor’s, and later did a Master’s in Forensic Science. I thought I was destined to sit in a lab or an office—or maybe open my own pharmacy—living a stable, regular life like my parents had hoped. But looking back, I’m glad I picked up a camera and started experimenting with light and color in my spare time about ten years ago. That simple curiosity quietly shifted the course of my life. Read more>>

Julia Stone

I think for me the only thing harder than doing stand up would be not doing it. As someone who doesn’t like to be the center of attention and isn’t a performer by nature, it’s taken a lot to get to the point of being comfortable on stage. But stand up is one of the few things that makes me laugh out loud and I feel such a sense of community. There’s still a lot of rejection and difficulty so you have to be resilient but I don’t think I could be content having a regular job. Read more>>

Hayley Koning-Bastiaan

I’m jealous of the days when curators and collectors would fund symphonies and works of music. I think with some reframing we can get back to that point. Currently the landscape looks as if shards were floating in space of what once was a viable and respectable art form. That might sound depressing but more than anything it’s existential. It is our duty as artists to engage in creation as a sacred rite, to pick up these broken pieces and rearrange them in a way that’s meaningful. Until music and sound are valued to a greater extent, people like me are going to need a job on the side. Read more>>

Erica Lane

I’m going to reinvent the question, because I exist in both worlds. “How do you successfully practice your artistry while working a full time job?” During certain periods, I’ve worked exclusively as an artist/creative, and in other stages of life I’ve maintained a regular day job. In the last five years, I have married the two and am able to pursue a lucrative career in music while enjoying a rewarding occupation as a church music director. It took me years to realize that I could do both effectively, but the first thing I had to do was place my priorities in order. Read more>>