Pursuing a creative or artistic career can certainly be fulfilling, but it’s far from certain. Over the years, we’ve heard about the struggles from thousands of artists and creatives – it’s incredibly challenging and it can be tempting to wonder – what if you hadn’t pursued this path. We asked artists and creatives from across the community if they’ve every had those doubts themselves.

Victoria Haallman Hamre

I am definitely at my happiest working creatively! I’ve always dreamt of becoming a comic book artist or an illustrator, and as a child I couldn’t think of anything cooler than making books similar to the ones I used to read. Now I am lucky enough that I get to be both a comic book artist and a children’s book illustrator, and I have loved every minute of it! Being a freelancer obviously has its challenges, as it is often unpredictable and financially precarious, and I do sometimes envy my friends who have a stable income, colleagues to chat with, as well as other perks that normal jobs offer. This was especially prominent when my friends were starting out in their careers, as their experience was so different from mine. Read more>>

Danielle O’day

I have been pursuing my creative career for a little over ten years, and my answer to this question has changed in correspondence to a deeper understanding of living authentically and maturity in said creative pursuit. Now, let’s navigate this discussion as I feel it has several different facets. The first time I caught myself day dreaming of a closet filled with business casual, a 401k, and water fountain chit chat with colleagues was simply when my business was not doing well. The bakery brick and mortar opened summer of 2018 and it barely had time to learn how to walk before covid shut us down for months, and a high percentage of other local restaurants for good. Read more>>

Andrea Rullo

I am happy doing what I do as an artist and creative. There have been times when I’ve thought about giving up my path and pursuing a more traditional job, simply because what I do is not always easy. It’s natural to have tough periods, and I believe that’s just part of life. Despite these moments, I am still here, continuing to do what I love, never having given up in any meaningful way. The reason I haven’t walked away is because I truly love what I do, and what I love most about it is the freedom it allows me to have in my work. Read more>>

Ryder Tam

I have a bit of a unique perspective in that I worked a “normal job” as an engineer for years before pursuing comedy. I was a guidance, navigation and control engineer working as a contractor for the US Space Force. I specialized in orbit analytics, and I launched three satellites that are still in orbit during my time in the aerospace industry. During that time, I did improv and sketch on the side, producing my own shows with my comedy partner Gabe Valdez under our duo TVunscripted. I would fly out to Chicago and LA regularly to take classes, but it was extremely challenging to keep up with a career job and comedy. Eventually I quit engineering to focus on comedy full time.  Read more>>

Krunal Patel

The thought crosses my mind now and then, especially when I’m knee-deep in a challenging project. I remember one particular night vividly—it was around 2 a.m., and I was in the studio, surrounded by sketches, material swatches, and my laptop glowing in the corner. I was trying to piece together a concept for my corporate interior project. I was exhausted, my coffee had gone cold, and I thought, Wouldn’t it be easier to have a job where I could clock out at 5 and leave my work behind? Read more>>

Stephen Tenebrini

I’m definitely happier as a creative, though it comes with unique challenges. People often don’t understand that being a Creative Director involves serious strategy and problem-solving, not just making things look good. Straddling both commercial and fine art worlds can also be isolating – fine artists sometimes look down on commercial work, while industry professionals focus heavily on advertising awards, which isn’t my priority. I occasionally wonder about having a more structured 9-to-5 job, but I know I wouldn’t find the same satisfaction. The creative freedom is worth the trade-offs. Read more>>

Kenneth Borner

In the vibrant world of creativity, where every note and lyric felt like an extension of his soul, Big Wordz found happiness as a creator. It was a world he molded with his hands, crafting art and building a brand that resonated with others. His artist name was not just a label—it was an identity and a testament to his passions. Yet, in quiet moments, curiosity about a more conventional path would occasionally surface, like a whisper in the back of his mind. He pondered what life might be like with a regular job. He considered the structured routine, the predictability, and the days filled with tasks set by someone else. But he knew from experience what it was like to have a regular job—a different world with its own rhythm and responsibilities. Read more>>

Ciara Bird El

I really love this question because I think it actually crosses my mind at least weekly, if not every few days. I absolutely love being a creative and getting paid to make art. It’s something I’ve done since I was a child and it is amazing that I can support myself and my children doing something that comes so naturally to me. …Yet on the flip side, I personally am not yet replacing my contracted income from my own personal creations, passion projects, etc. I specialize in creative direction— being commissioned to create visuals for existing brands, or to hold space for new brands to explain what they would like or need and bringing that idea into reality through identity design, brand styling and mood boards.  Read more>>

Jesse Hinson

I don’t know that I have a concrete answer to this question but it is something I get asked a lot. There are elements to pursuing a career in the arts that are wonderful but simultaneously soul sucking. For as long as I can remember making art has been pretty much the only thing I have ever put any genuine effort, time, and thought into. When I started applying to colleges as a teen, the idea of studying something that wasn’t art felt like a daydream because, as far as I was concerned, I didn’t have another choice. I had absolutely no idea what that would look like as a tangible career or a way to make money, but I knew it’s what I wanted to do. And I loved it. I loved art school (generally wasn’t a great student, but I digress). Trying new things, learning new skills, just surrounding myself with the things I love to do. Art school also gave me a lot of life lessons, experiences, and creative problem solving that doesn’t happen in other areas of higher education. Read more>>

Lauren Washington

I’ve always said I’m an actor because it’s the one thing I love most in the world. It’s the only thing that makes me wake up every day with a smile on my face, and the only thing I could do for hours on end and still be like, “No, seriously, I could do this all day”. I’ve had a lot of “regular jobs” — bagging groceries, phone banking for charities, being a secretary (I’m basically the queen of administrative work), and even a fitness instructor. I did it all, and it was always just so I could keep acting. I started acting in 6th grade when my family moved to the suburbs of Illinois, and my mom was still figuring out the new school schedule, so she was a little late picking me up. After school one day, a teacher asked if I wanted to audition for a play, and I was like, “Sure, why not?” I ended up with a background role, but the second I stepped onto that stage under those lights, I was hooked. From then on, I was either in a play, rehearsing for a play, or directing a play pretty much every single day until I graduated college. So, my entire life has been dedicated to this craft. Because of that, I can’t really imagine doing anything else. Read more>>

Lux Fatale

I’m absolutely happier as an Artist. Most of my life I’ve had a ‘regular’ job, and while that’s necessary for many creatives as a vehicle to make the art they love, I was forced into making this work about 2 years ago. I was lucky enough to come across a contract opportunity almost as soon as I was let go from my ‘regular’ job, which launched me into freelancing. At the time I was still freshly grieving the loss of my father who had only passed a couple months earlier. There were big shifts in my life and I felt like I needed to make this work. My first job into freelancing full-time was with Smosh (a youtube comedy improv channel for those who aren’t familiar), I’m a huge fan and was incredibly stoked to make art for them. I did two merch designs and had weekly check in’s with their marketing team to follow up on design updates. I remember being so filled with joy like, “Wow, I’m actually doing this”. I would see cast members walking by who would wave during our zoom calls and I just thought that was so cool. The designs came out pretty well, I was very proud at the time with what I had come up with and couldn’t wait to see it launched on the website. I was very nervous and the project was a lot of work but it was that excitement that overpowered the immense anxiety of wanting to impress my first official client. Read more>>

Baolu Chen

I would say I’m learning to be happy again after music became not just a passion but a way of life. When I have a lot of deadlines and feel pressured to write something, I start to wonder if it would be better to treat music as a side hobby instead of a career. That way, I would feel freer to create whatever I want, rather than forcing myself to produce something on demand. I also wouldn’t need to worry about the financial impact of turning down offers. I could write purely because I love what I’m writing about, not because I have to. Read more>>

Xuewei (eva) Hu

It was during early pandemic when I encountered a job interview, which made me realized that I need to pursue a creative outlet. During the early uncertain period of time, I had just lost my job as an assistant stage manager on one of the biggest projects I’d ever been a part of—it was a dream role, and suddenly, the pandemic brought everything to a stop. With the industry at a halt, I found myself asking, “What now?” Desperate for stability, I began searching for any job that was hiring. Eventually, I landed an interview at a language institute near my home. The role involved preparing students for language proficiency tests, drawing on my five years of experience living in the U.S. and some previous tutoring work. The interview went well, and I received an offer almost immediately. Read more>>

Gabe Shaddow

I’m happiest when I’m creating—it’s where I feel the most alive and in tune with myself. As an artist, there’s a deep sense of purpose in bringing ideas to life and sharing them with the world. That said, I’d be lying if I said I’ve never wondered what it would be like to have a regular job. The last time I had that thought was during a particularly challenging period. I was juggling multiple deadlines, navigating unpredictable income streams, and dealing with the pressure to stay innovative. One night, after a long day, I sat on the couch feeling completely drained, staring at my computer screen, and wondering what it would be like to have a 9-to-5 job where I could clock out and leave the stress behind. I imagined a life with predictable hours, a steady paycheck, and the simplicity of focusing on one task at a time. Read more>>

Ilse Castro Corona

I am really happy to be an artist, I believe I find freedom when I am directing but of course, I have questioned myself about the profession I chose. Theater and film are demanding industries, sometimes you are on set for fourteen hours, and sometimes, you go into a process for several months and it requires all your time and might end up not being what you wanted. People expect you to have all the answers and forget you are also human, you always have rehearsals and most of the time, doing this work represents a lot of financial instability and no personal life. So, many times I have thought about what it would have been like doing a regular job and I have done it and still do it. I train professionals on public speaking and other communication skills which I think might be more of a regular job, but the truth is no matter how much stability a regular job can give me, I will always come back to directing because it gives me much more than it takes away from me. I guess I choose directing not because it is easy or gives me stability but because it gives me a purpose, it makes sense to me. No matter the hours of rehearsal I find some magic in gathering with other people to create fictional universes to share with an audience so they for a moment in time can get out of their life. Directing implies building gathering and community, and beliving in the power of creation. Read more>>

Xuezhu Jenny Wang

As people often say, working in the creative industry is not just a job but rather a lifestyle. When most of your friends are artists, gallerists, and writers, it’s really hard to find the right balance between work and life. Fortunately, I knew very early on that I was drawn to roles with a creative component, so I’ve never had a single moment of doubt that another field would be more suitable for me. However, there are definitely moments when I wish there were a more predictable or straightforward path in this journey. Back in college, many of my friends working in consulting, IT, or finance had job offers lined up months before graduation, while most art jobs don’t necessarily have a recruiting cycle/timeline like that. It was almost impossible to not compare yourself to others and feel lost, especially when you don’t know what you will be doing next month: You could be working at a gallery, as someone’s studio assistant, or be unemployed. I don’t think there is any easy way to reckon with this reality, but it’s important to constantly remind yourself why you made this career decision. The uncertainty is part of what makes this journey so beautiful and full of adventure. Read more>>

Alexis Taylor

Being an artist or creative is an emotional rollercoaster – there are incredible highs and deeply challenging lows. I do wonder what it would be like to have a regular 9-to-5 job at times. During the last production of my song “Seeing Ghosts” I had a lot of roadblocks. The producer I ended up initially hiring ended up delivering a song that was okay, but I felt like the track was missing something. So like the stubborn girl I am, I decided I would try to start from scratch and produce something myself, redoing the song entirely on my own. I had never done something of that magnitude before, and it turned out to be a way bigger task than I anticipated. So I ended up hiring a different producer to redo the entire thing for a third time. Though I had worked with the producer before, I felt defeated right from the start. I started worrying that the song would never be produced the way I wanted to, or sound how I thought it should. That led to a bigger question: if I don’t like the song, and the song never gets heard, what’s the point? Wouldn’t it be easier to have a “normal” 9-5 job where I would at least have a steady paycheck to show for my efforts? There was no way I was going to release a song I wasn’t proud of. Maybe getting a job where you punch in and out wouldn’t be so bad. It would make way more sense than being on this 24/7 grind of chasing a dream that sometimes feels more further away than when I started. Read more>>

Won Kim

I used to have a regular 9-5 type job and it was fine until it wasn’t. Grass is always greener on the other side right? I didnt feel fulfilled as a person working the way I did. I did art part time and whenever I can fit it in. I did like the security of a steady decent paycheck, insurance, etc, but could definitely feel like something was unfulfilled. It started to get bad when I was taking PTO to just be able to finish a project or too tired from the night before working or djing. Work and income comes in waves now and as much up and down there is with going full time and trusting the process, I do sometimes miss the simplicity of having a regulated schedule and a steady income stream. Read more>>

Sarah Whalen

I was lucky enough to make a living from the sale of my works at a very young age. Every day is a blessed day, it is an incredible opportunity, but also a considerable amount of work. I wouldn’t say that these are sacrifices, since it is a passion which can sometimes, if you are not careful, devour your life. But especially when you are young, talent is not enough, you have to understand the artist’s profession and also build your career, in particular a trusted collaboration with art galleries. I sometimes think that if I had to get a job to live, I would never have been able to create works that I am happy to present, due to lack of time. I believe that the life of an artist when you have an ambition for quality and creativity, whatever your talent, requires time and considerable energy. This idea coming to my mind, highlights the fragility of the artistic profession, that circumstances, luck, encounters, courage and energy make the difference… and perhaps destiny if we believe in it… Read more>>

Dawn Tappen

Yes! I am very happy as an artist! I’ve never had what our society might call a “regular job.” I’ve always called myself an artist, and supplemented my income over the years with part-time work as a food server. While I love the creative freedom I’ve chosen, I’d be lying if I said I’ve never wondered about the road not taken. These thoughts occasionally creep in during sleepless nights, when my mind spins through what-ifs. Should I have pursued a more conventional path after college? One with financial security, health insurance, and paid vacations? Read more>>

Abigail Yeung

I am simply happy doing what I do. Sometimes, I question whether I should be doing something else that may be able to contribute to the world. I still would like to do and I plan to do something worthwhile unrelated to the arts and film, such as contribute to environmental protection or healthcare for all. But right in this moment, I need to figure out what to do with my life before I can make myself fully resourceful. I have always known that I was stronger when it comes to the arts. It was always film and music that drove me to where I am today, and with the support of my parents, I am so glad that this is what I am going to be doing for quite a while, if not, the rest of my life. Sure, I have my doubts sometimes about myself and my abilities doing what I do. I worry about the future and what fate has in store for me. I always fear that I should be doing something else with my life. Maybe I need a safety net. But nevertheless, I will never regret challenging myself to step into the world of art and film and exploring the many things and experiences that being an artist and filmmaker has to offer. Read more>>

Torey Haas

This is actually something I thought about recently… when you hit middle age you get a little reflective on where you’ve been and where you’re going haha. My thoughts settled on this: you only have one life (at least as far as we know) and you owe it to yourself to spend that life doing what makes you happy. I was always good academically- I went to Georgia Tech, and while I didn’t study engineering (that’s a story for another day) I could have, and I certainly would be making much more money with a 9 to 5 job as an engineer than I am as a freelance film and video producer- but if I had pursued a more ‘normal’ career route I would just think, “Man, I really wish I was making movies.” Film and video production is my passion, and I’m just happier working on a video project than I would be doing anything else, even if that something else pays more money and is more consistent. Read more>>

Meghan Covington

I have had many different jobs over the years, and many of them were fun, rewarding, and helped me to grow as a human. None of them would be categorized as “regular”, but they did help me pay the bills! At this point in my life, I am so grateful to be able to make a living as a creative. Nothing compares to the deep sense of fulfillment that comes with making theatre, but I do recognize that my success as a theatre artist would not have been possible without my other “regular” career paths. In early 30s I abruptly decided to put my creative career on hold in the pursuit for financial stability. My husband and I wanted to start a family, and I was unsure of how to provide for children while working as an actor. That’s when I started my own business in the fitness and yoga industry – Mind Body Fitness. 3 kids and almost 10 years later, I had built a successful business and learned useful skills (marketing, budgeting, management, and costumer service). While I wasn’t necessarily feeling creatively fulfilled, I was preparing myself for a more stable future as an artist! Read more>>

Gegham Abrahamyan

Had I chosen a different profession instead of being an artist, I have frequently reflected on this, often looking to the skywards and bowing in gratitude for my grace. While art is often created in the solitude of a silent studio, I believe its true fulfillment comes from engaging with and resonating within the hearts of people. If there are no people, the vital interaction between art and the audience is absent; art loses its profound purpose and mission. Everyone faces diverse challenges in life, and though I’m unsure how each person overcomes them, I believe that without being an artist, I might not have persevered. Art has been my lifeline, keeping me afloat through these trials. Perhaps this is why I was destined for this path. I wonder how those not engaged in art navigate life’s tumultuous waves. Yet, in every situation, a light of hope emerges, offering kindness and grace, reaching individuals regardless of their professional pursuits. Read more>>

Michael Keelen

I have mixed feelings about running my own firm, but mostly I really enjoy it, and the benefits certainly outweigh the drawbacks. For example, I previously worked 10 years as a high school teacher, and the level of freedom afforded by that work is very low. I woke up very early to begin teaching very early, and a whole decade was spent doing high stakes, high stress work from bell to bell to bell, and then usually into the evenings. Work like that has tremendous value for students, communities, and even teachers, but the toll from teaching can feel enormous, and the highest levels of pay require lots of expensive education and decades in the field for what will ultimately be higher-stakes, higher-stress positions for pay that is still supremely subpar given the importance of the work. I am happy and proud of the work I did as an educator, but 10 years was as much as I could give that system. Read more>>