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.

Jisoo Jeong

I love being a creative artist and am grateful that people feel various emotions, such as sadness and happiness, while watching my artworks. I have studied Fine Arts since I was a child, and I never doubted that I would want to do anything else for my future other than painting. However, there was a period when I was overwhelmed and burnt out, trying to figure out if I really wanted to keep drawing for the rest of my life. The answer was no. There are many different ways to express art, and I decided to explore some other fields that I love more. I tried holding an exhibition, teaching students in art class, working in graphic design, and even creating sculptures. That’s how I became a production designer now. So if you are feeling the same way and questioning yourself about whether this is the right path, I’d say take a break and consider trying out some other similar fields that you can enjoy. Don’t stress yourself too much; get confidence, be patient, and keep pursuing your art, and people will love it! Read more>>

Bridget Zhong

Currently I work full-time as a painter’s assistant for a well-known contemporary artist in Brooklyn. On the weekends I work at a tattoo studio in Queens. Although I have a crazy working schedule, I am very happy doing what I am doing right now because making creative work keeps my mind fresh, and nothing is better than doing what you’re passionate about while earning money from it. It just never gets boring that way. My full-time job has a similar work schedule as a regular office job, but it is a lot more flexible than the latter. I was very lucky to have supportive colleagues and bosses who have the same education background but have been working in the industry way longer than I have. I was able to learn a lot about painting and tattooing from them, and I am very grateful for that. Read more>>

Mindy Milburn

I am definitely happy during this work- it is not easy but being an artist is something that is hard to turn away from. I did stop singing and performing for several years after my children were born and although I was and am very happy being a mom, my desire to perform and create music was always in the background. I have to work everyday to strike a balance between my family life and obligations and the time I devote to progressing the band forward(social media posts/engagement, booking shows, coordinating the band, making costumes, etc) because sometimes it becomes very overwhelming trying to do it all. Read more>>

Sommer Roman

I am happy living the life of an artist/creative. Would it be easier to have a “regular job”?… oh yes it would! But in my opinion living out one’s true purpose and who we we’re made to be and do what we’re made to do is worth all of it’s weight in gold and I would never trade that. Obviously for me that is being an artist, which has been a path I’ve really had to forge by myself. Though I might daydream of the ease of having a more straight forward career, nothing in my soul really wants a different path. It’s taken a lot to get to where I am living and working as who I was made to be and that brings deep contentment. Read more >>

Amy Wilderson

I am incredibly happy being an artist. When the youngest of my five children headed off to college, I contemplated getting a ‘regular’ job working for someone else. But I realized that it would mean keeping my art practice on the back burner, which I had done while homeschooling my kids. Considering the level of regret I know I’d have in doing some kind of work other than art, combined with wondering “What if I just put myself out there as a full-time artist” was too great to ignore. Read more>>

Karma Hydra

Having been on both the freelance artist and 9-5 corporate sides of the fence, I realize that I’m not merely pursuing creativity as a career-creativeness is my natural state of being, and regardless of whether I have a regular job or am a full-time artist, expressing my innate artistry is a given. It’s that expression that gives me happiness and joy: painting, performing my music to an audience, collaborating with new artists, and helping business people create visuals for their brand. The freedom of freelancing grants many privileges, but the stress of unexpected challenges and unpredictability isn’t for the weak. In moments of weakness, I’ve given in. The monotony of a “regular job” can be boring and uninspiring, but financial stability can provide a means for personal artistic projects. Read more>>

Carlos Beltran Arechiga

My artistic practice and need to create are embedded in my DNA and the time I spend in my studio every day affords me a space of possibilities for growth where I contemplate and deal with our human condition. The act of painting presents a problem to be resolved and a sort of negotiation between the medium and myself. Although I don’t always “win” I do cherish the small victories, when a work surprises me and reminds me of my childhood and a time when all things were possible. Read more>>

Jack Dauncey

This sounds a little pretentious but I sometimes envy people who are unburdened by the urge to create. Everyone’s time can be bisected into a work life and a personal life, and if you don’t hate your job and have friends and family that love you, you’re pretty much set. But people who are hungry to write, paint, act and sing also have creative lives: a third category which eats into the other two, and makes things a whole lot more difficult. I think of all the time I could’ve spent brushing up on Spanish, traveling abroad, and meeting new people if I wasn’t so damn interested in making cartoons. Read more>>

Zak St. John

No doubt, being a musician has its difficulties and stresses. Including, but not limited to: not knowing when your next paycheck is coming, when work is going to happen and the fact that YOU are your own business in most cases. And then there are the real world/adult concerns. Insurance/medical care, retirement, investments, and being a good partner to your significant other, are all examples of things that tend to fall in place easier for a non artist/creative. And I can definitely see why other people prefer a set schedule and routine at a 9-5 job, Monday – Friday. Read more>>

Chris Naoki Lee

I’ve grappled with this question in different moments of my life, to be honest. Particularly in my 20s, especially at a time when the industry viewed me as a trope or a punchline, I definitely questioned my purpose as an artist. “Is this what I really want?” “Is there space for someone like me?” Many of my closest friends aren’t in the entertainment industry, so when I saw them getting promoted or finding financial success when I was still trying to make ends meet between closing that late night bar shift or scrounging for ancillary side gigs, it made me wonder… Read more>>

Joshoo/ Josh Shpak

I am very happy living as a creative, but the freelancer lifestyle (in any field) is hard! I worked in a touring band for much of my early music career, where, even though we didn’t earn much, I was on payroll. I’ve been freelance for 3 years and the stress of not knowing where or when your next paycheck is coming is certainly anxiety producing. I also live in Los Angeles, which is a very expensive city. My current gig touring with Peter Gabriel is the first time in 3 years where I’ve had the stability of income to let some of that anxiety go and I totally get why people would run to regular jobs after this feeling! As for now I’ll be sticking to freelancing because I appreciate the flexibility and my current bachelor-lifestyle can handle the uncertainties. Read more>>

Stephanie Diani

Yes and YES. I love my job, I love 99% of my job. Which is to say I love the act and art of making of photographs in collaboration with subjects; creating a safe space for people to be themselves, or someone else, in front of my camera; solving logistical issues and overcoming practical obstacles; creating amazing light. It’s all incredibly fun. Read more>>

Kiyotaka Tsutsumi

I’m generally happy. However, there are moments, albeit occasional, when I feel the opposite of happiness, like when I’m not in the best state of mind, lacking motivation, or when I find myself overly concerned with others’ opinions. During those times, I sometimes think that having a regular job might be less stressful. Read more>>

Viveca Chow

When I grew up, creativity was not always celebrated in my culture. I remember being in Kindergarten and was asked to draw a “sun, tree and flowers” on a piece of paper in class. I finished early and decided to add a smiley face to my sun. I was a happy kid and thought it would be a nice touch to my piece. I immediately got in trouble because I “didn’t follow the rules.” After this incident, my parents transferred me to a school that nurtured my creative abilities and they were never shy of unconditionally supporting me in my endeavors as well. Read more>>

Thee Vibe Creator

I am 100% happy being a professional DJ, I have often times wondered what it would be like to have a regular 9-5 and I have tried it but I learned very quickly that I am not good at working for other people it never served me any real joy but when I am able to DJ and having control over the energy in the room I feel like I am truly in my calling. Read more>>

Aaliyah Warren

I am very happy at where I am at in my career. I make a living off of rollerskating and being a “influencer” basically. Not everyone can say they make a living off of doing something they love. At the same time I do question what it would be like to have a more normal career. Who knows, maybe I will go back to school so I can give my more knowledge and opportunities in the future. Read more>>