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.

Brandon Douthitt

Growing up in school playing an instrument, whenever I would express that I wanted a potential career in music I was always met with responses like, “Are you sure”?, “Musicians have a hard life”. “Make sure you have a backup plan”. Being a musician/creative can be an incredible journey filled with both highs and lows. On the upside, there’s the thrill of creating something unique & pushing boundaries of music, the joy of performing for an audience, and the sense of connection that music fosters. There’s also the freedom to express yourself and explore your creativity without the constraints often found in traditional 9-5 jobs. However, the path can also be challenging. It often involves financial instability, long hours, sacrifice, and the pressure of competition. Rejection and criticism can take a mental toll too. The uncertainty of gig schedules and income can lead to stress that a regular job might not. Read more>>

Crystal Elaine Hilton

In my teens, I jumped into the service industry, thinking a steady paycheck would bring me some peace of mind. At first, it was exhilarating. I was finally making money and felt like an adult. But after a few months, the reality set in. The repetitive tasks drained my energy and creativity. I felt like a cog in a machine, powerless and overworked, longing for the freedom to express myself. No matter how much I earned, it never felt like enough; the joy I sought was absent, buried under the monotony of everyday tasks. Each time I quit, I would take a step back, using that space to heal and reset. I found comfort in the downtime—time to socialize, explore my passions, and live without the constraints of a conventional job. But that cycle would inevitably repeat. I’d find another position, convinced it would be different, only to feel that same creeping dissatisfaction returning. It was a pattern I couldn’t escape, and I started to wonder if it was worth it. Read more>>

Cesar Pita

I often think about what it would be like to have a standard job, especially when finances are uncertain and bills are due. I’ve experienced both managing well and not knowing if I could cover the next payment. When delivering artwork to offices, I sometimes picture myself working in those spaces. But then I’m reminded of the time constraints a regular job would have and make it harder to carve out time for my art. Early on, after graduating, I struggled with this balance. I felt secure in my job, but also anxious and frustrated. My mood was somber, and I became irritable. Over time, I realized that my creative process is essential for my mental well-being. Without it, I lose my sense of expression and challenge. Art is what drives me to get out of bed and engage with the world. Now that I’ve had a bit of time to stabilize my boat, I’m able to see the importance of continuing to full heartedly create artwork. I’m confident in saying I’m far happier as an artist. Read more>>

Wyatt Slaughter

I think this is a really important question, and I think being an “Artist” comes down to the way you think, the way you feel about things. As a kid, you may be an Artist before you even know it, which means from a young age, you’ll probably deal with unhappiness and depression, like me. I think no matter what, that feeling of depression will always be there, you just have to learn how to deal with it. I do sometimes think about having a regular job, a few years ago I used to work at a trampoline park as a sales manager, but while I was there I always thought about other ways I could be spending my time and energy, but I never acted on them, and it slowly killed me, I felt like I was supposed to be doing something else. Now, as I look around me and see other people still living that life, I’m grateful I’m no longer in that world, I would rather be broke, in another country, trying to do something that matters, then work for someone else, and that’s exactly what I’m doing. Read more>>

Sarah Lynn

I am happy most of the time doing comedy. There are definitely difficult moments. Running shows every month is a ton of work and stress. I have cultivated an amazing audience and space, and I always stress out about maintaining it. I get scared of the possibility of losing money. As a producer I have to think about more than my own enjoyment of doing it; I have to think with business sense and make sure the shows I’m producing are sustainable. I do many jobs part-time, and I’m happier that way, I love having my hands in many different things that all contribute to the world in different ways. It keeps the pressure off one thing to be my sole life sustainer as well. Read more>>

Phalecia Young

Am I happy as an artist? Most days. Just like everyone else, I have days where I’m frustrated, sad or indifferent. Feeling those emotions helps me to create art. Art is therapeutic. Whatever I’m feeling can be expressed by the stroke of a brush, the colors in my palette and each line that I draw on canvas. Do I wonder what it would be like to have a regular job?. Absolutely not. I have degrees in human services and a master’s in alternative medicine. I worked in those fields for many years before deciding to become a full time artist. Although I appreciate how that experience helped me to become who I am, I couldn’t see myself going back to working a 9 to 5. I love the freedom that I have as an artist. Read more>>

Jingjing Fang

I’m truly honored to be a creative artist. I used to work full-time in the design industry, where I received six years of professional education. While my design skills, focused on aesthetics and human-centered approaches, stood out during my studies, they often clashed with the realities of the industry. In my job, despite my training in creativity, I found it challenging to apply those skills due to market downturns and the industrialized processes of many companies. Although I had a stable full-time position, I often felt that my talents were underutilized. Recently, I had a moment of reflection about my career path. I was working on a project for the TV show The Masked Singer (Seasons 10-12), where I was involved in set design and virtual production. As I was immersed in this creative process, I briefly considered what it would be like to have a regular job again—one with predictable tasks and routines. Read more>>

Kelsey Hall

I am so happy to work daily as a creative. I have had a regular job in a creative industry, and I’ve had a regular job in a corporate industry. Both were incredible experiences, but neither filled my cup like the one I have now, building my textile business into something I am so proud of. I look back fondly on the days where a lot of things were taken care of by my employer – health insurance & paid time off, for example. Any time tax season rolls around I question all my decisions that brought me here, but I get always get through it and I always feel very accomplished and capable after I do. How cool is that? I check in with myself regularly and know that where I am in life right now, it makes sense for me to push on and see what I can make out of my business, but I hope to feel no shame if I ever decide to move on and get a job elsewhere. I’m fully aware that it would be a lot easier in a lot of ways, and different seasons of life calls for different priorities. But for now, if I were to weigh the perks of being employed elsewhere against the happiness I feel daily when I get to work, it’s a no brainer that I am where I should be. Read more>>

Eryi Wang

I feel so lucky to be an artist. It allows me to be creative and share my thoughts with the world, and it’s also flexible. It lets me work on multiple projects at once and enjoy long-term joy and fulfillment. I’ve had so many jobs before—full-time, part-time, customer service, teaching, wedding planning, office administration, and more. All of those jobs taught me valuable lessons: how to communicate in a work environment, time management, leadership, and so on. I believe all of this helps me now as an artist. But do I want to have a regular job? I think not, although I do think about it once in a while. The last time I considered it was when one of my friends told me how she could finally take a vacation after completing a large project at her company. She said she wouldn’t think about work at all and would enjoy the vacation as much as possible. Read more>>

Serena Potter

In recent years I have found myself reflecting on how fortunate I am to be an artist. Making art is not just something I do, it is who I am. Being an artist gives an adult permission to have fun, to play, to be silly, to explore, as a means of trying to make sense of our experience, to process physical and emotional pain, to share joy and wonder, to create modern mythologies. Am I happier as an artist? I have not had a full time job as something else (I worked in retail management right out of college, anyone remember Mediaplay?) since my 20’s, so don’t have a lot to compare it to, but I am generally content. I like the routine of my life. My husband and I both work from home, so we go out to our favorite coffee shop every morning, will talk through our plans for the day, current projects, or painting ideas, or our next travel, or our goals, or our girls or what we are reading, or just check in and ask, are we happy? Then we head out to walk a trail, run errands, or keep appointments, head to the gym or pilates, come home, make lunch, then he goes to his office and I go to the studio. We meet up again for dinner and walk the neighborhood, chat with neighbors or their dogs or cats. Read more>>

Marina Nazarova

Yes, I would say I am a happy artist. I learned to be one. I suppose it’s a choice, and at one point, I decided that I wanted to be someone who enjoys creating and even sees it as a blessing to have this passion and the ability to make something with my own hands. Painting is a truly magical process, and the experience of being in that flow feels entirely beyond this world. So, I focus on celebrating that choice rather than dwelling on the financial frustrations that come with this career path in times. That part can be figured out and resolved. At some point you start making a living with art- you just have to be patient. For a long time, I wondered what else I could have done to lead a more financially secure and stable life. I was constantly searching, but I always returned to painting. I worked other jobs—retail and administrative roles at various points. Those were temporary jobs, of course but as a vocation, I never wanted to do anything else. I never imagined myself as a doctor or a marine biologist, for example. It’s always been painting. Nothing else seemed to have purpose or meaning for me except creating art. Read more>>

Christina Doelling

I personally know very few other professional artists, which is telling. It’s a tricky business, and isn’t for everyone. One can’t go from new and inexperienced to successful and profitable overnight, without significant luck and contacts. For most artists, it takes persistence, patience, a huge amount of trial and error, and being realistic with your goals. For me, there have been years that offered fewer opportunities and were less profitable than others; those were the times I sometimes questioned my choices and wondered, should I give it all up, and just get a regular job? I always circle back to “no”. I worked as a creative in the corporate world until my early 30’s, and honestly, I could never go back to that kind of environment. The structure, the hours, the commuting, the fast pace, the constant sense of urgency and the stress that I felt, would not suit me now. There is more peace for me being an artist. I really enjoy the solitude of working alone. My studio is in my house so I can control my work environment. I like being my own boss, deciding when to paint, and what I want to do. It’s a simpler life, yet far more empowering, being an artist and being responsible for everything that it entails. Read more>>

Deja Hood

“Two things can be true at the same time.” I can’t recall the first time I heard this phrase, but it’s something that I reflect on constantly. I am always thinking about my happiness in artistry because it’s not all sunshine and rainbows. Most days, it is hard, exhausting, and questionable. Not to mention, artists are underpaid, undervalued, and underrepresented, and as a Black Woman from Chicago, I am no exception. And yet, art is the most beautiful calling that found me.  Over the years, I have joked that art saved my life, but it is the truth. The creativity, the people, the opportunities, the stories all have grown me as a person and as an artist. Art is where I feel the most alive and free. I have found my tribe, and I can not imagine my life without it.  Read more>>

Kata Baron

I juggled multiple jobs over the years—waitressing, I was a preschool teacher, and a Sephora salesman and makeup artist. Through these experiences, I realized I wanted to do things my own way, even if it meant taking the longer, more challenging path. Being in control of my art and creative vision ignited a passion in me. There were moments in the past 15 years when I wondered if a conventional job would be easier, but doing things on my terms has always been my priority. In 2022, I herniated two discs in my back, causing chronic sciatic pain that left me unable to work or even walk. It was a life-changing experience, especially as someone self-employed. I didn’t know if I’d ever be able to do makeup again and thought my career might be over. I faced a choice: trust myself and fight for my passion or surrender to my injury and settle for a desk job. I chose to bet on myself, even if it meant taking the harder road again. Despite the challenges, I wake up every day excited to work. That fire is still alive, and it reminds me of the Frank Sinatra song ‘My Way.’ Whenever I feel uncertain, I listen to it, and it reminds me why I chose the unconventional path. My favorite verse sums it up best: ‘Through it all, when there was doubt, I ate it up and spit it out. I faced it all and I stood tall, and did it my way!’ Read more>>

Willa Lucille

After I graduated high school in 2021, I went straight into working full time. I had planned on going to school for music, but things were complicated. Covid-19 cases were still high, most colleges were online, and I would be paying completely on my own. So, instead, I dived into work, juggling multiple jobs in an attempt to afford my first apartment and save in order fund my aspiration of purchasing a vehicle to live in and travel North America full time. I spent the next three years working, letting music sit on the back burner until my need to create boiled over. I can look back now and say I lost my creativity and my purpose. Flash forward to present day; I purchased and converted a short school bus this spring, and I’ve moved into it full time. I’m currently in Omaha, Nebraska visiting my family before officially hitting the road. Just yesterday afternoon I was sitting in my mother’s living room, sending out countless emails and Electronic Press Kits to venues across Colorado in an attempt to book shows. It had been days of no responses. It was incredibly frustrating. Read more>>

Patty Ihm

This is something that I think about every day. Many of my friends and peers are at an age of retirement, where they are considering what their “next chapters” will look like. We are longtime foster and adoptive parents, still with young children with high needs. Raising them has been my “job,” and retirement is not on the horizon. If I had continued classroom teaching, I believe I would have similar pursuits (writing, beekeeping, hobby farming) to look forward to in retirement. As my life is now, though, work and parenting are inextricable. Though the days can be long, I am happy just being open to what they will bring, and I am grateful for every space I find to fill with my creative pursuits. Read more>>

Dolly Whitley

Being a creative isn’t always linked to happiness, is it? I’d say it’s more of a compulsion. There are many times when creating does make me happy, but even when it doesn’t, I’m still an artist. It’s a way of being. That being sad, I do monetize my passion, and that can prove very challenging at times. I work a lot of hours and that doesn’t always translate into consistent income. I do look for “regular” jobs fairly often actually, because the weight of having to earn income from creativity can be soul sucking at times. There is so much behind the scenes labor that most people do not see or appreciate. I also think art is seen as a luxury when the economy is struggling. That is completely understandable but it directly impacts my ability to keep doing what I do. Read more>>