When times are good it’s easy to feel like entrepreneurship is the only path for you, but what about the times when your hit with multiple crises at once? We wondered if all entrepreneurs have moments when they wonder whether they should have gone with (or stuck to) a more standard job where they worked for someone else.

Heather Thompson

I have been an independent contractor or business owner almost my whole life! I have so many ideas that it is really fun for me to be in a place to implement them. Yes, I absolutely have days that I wish I wanted and had a ‘regular’ job so I did not have the concerns of retirement, sick leave, and a steady paycheck. However, I have been doing this so long that I might feel like part of my being was cut off! There are definitely challenges as a small business owner, but part of the beauty is pivoting and creating a new and more amazing business. So, yes. I am happy. Small business is a place you can create and apply what you learn. The success of the business does not always look like what society deems as successful and you do get the opportunity to dig deep within yourself and really find what you want and what you stand for. It can humble you, empower you, knock you to the ground, and test every ounce of faith in yourself. In that, we as small business owners have the great opportunity to grow, to change, to love ourselves, to believe in ourselves, and to trust that no matter what we will be ok. In this, my faith has absolutely become stronger. Read more>>

Jourden Gomes

I believe I’m happiest as a business owner, but yes, I do occasionally think about going out and getting a regular job. Every now and then, the days where I am at home all day long, with no one to talk to except my 1 year old, feel endless, and at times, are incredibly lonely. Those days make me wonder what life would be like otherwise. Just a few weeks ago, I was running myself into the ground, working on craft market preparations, because I had booked myself in two pretty major ones and was working around the clock to get things done. I got pretty burnt out, and my husband, Chris, and I contemplated very briefly if I should maybe put my business to the side for a little while and get a part time or full time job. Ultimately, the answer was the same as it always is, absolutely not. Read more>>

Shelby Ford

I am absolutely thrilled to be an artist. Art has been my lifelong passion, and while I’ve faced challenges in pursuing a creative career, I’m convinced there’s no other path I’d rather follow. Regardless of my role or job, I’ve always been driven to create art. It’s an integral part of who I am, and I’m committed to it for life. Since launching my paint party company, I’ve found immense joy in sharing my passion with others, and I couldn’t imagine doing anything else. While the phrase “starving artist” exists for a reason, and it’s true that AI, plagiarism, and mass-produced art pose challenges, I firmly believe in the power of authentic creativity. At my events, I often meet talented individuals who may have studied art but hesitated to pursue it professionally. To them, and to anyone with an artistic spark, I say: embrace your talent! Participate in shows, join craft markets, and encourage your network to support your art. That first sale is an incredible confidence booster, and the rewards of a creative career are immeasurable. Read more>>

Rebecca R. Levy

Being a dancer, choreographer, and artistic director is still very much work. While it’s a deeply personal and creative process, the reality of leading Jacksonville Dance Theatre inside of a capitalist society means that the work must also function as a product. Each performance, piece of choreography, and artistic vision needs to be of the highest quality, and there’s the added pressure of ensuring that people are willing to invest in the experience, whether by attending a performance or supporting the company. There are moments when the idea of having a “regular job” does cross my mind—usually when I’m feeling the weight of responsibility as an artistic director. Sometimes, I wish someone else could step in and take the lead, even for a moment, or I feel the burden of carrying the company’s future on my shoulders. But even in those moments, I never take the privilege of being an artist for granted. The opportunity to create dance, to choreograph, and to guide Jacksonville Dance Theatre is something I’m profoundly grateful for every single day. Read more>>

Jordan Pastor

Being an artist as a profession was always a dream that I felt was not achievable. As a young adult, life & the universe had other plans for me which ultimately led to living my dream. Let me elaborate! Drawing was something I loved doing since 2000. I always found it therapeutic and seeing how people react was extremely fulfilling to me. Fast forward to the present, that is the exact feeling I chase when I bring my art to events.  Throughout the journey, I stopped drawing from age 17-20 until my girlfriend (now wife) convinced me to pick it up again. I graduated from Sacramento State University with a degree in Marketing, while working various manual labor jobs as a forklift driver, etc. After college, I thought the car industry might be a viable path for me, so I started selling cars at the local Chevrolet/Cadillac dealership. Although I was pretty good as a salesman, I hated the feeling of selling something I wasn’t passionate about. Than I thought to myself, “If I can sell a car that I have 0 attachment to, I can definitely sell art that I am passionate about” which led me to apply to a small convention called Vacacon and the rest is history! Read more>>

Isa Rocio

I think the ironic thing about working as a creative—at least for me—is that you’re constantly teetering along the line of feeling blessed to be so embodied in your creative gifts and drive, while also feeling that constant outside pressure to prove that pursuing any creative path is ‘worthy’ in the eyes of society. I wonder about once a month if I would be happier working a regular job. Not because I’m unhappy pursuing what I’m passionate about, but because there are constant reminders that working as a creative is risky and requires a lot of grit, especially when we live in a world that is so expensive to live in! But no matter how often I wonder if it would take the stress off of me to just get a regular, high-paying job, and put my creative pursuits to the side, the thought of not having that outlet and giving up on myself seems more misery-inducing than toughing it out and holding onto determination. Because at the end of the day, money is one of the only initial downsides of pursuing a creative career—I say initially because we also live in a world where the sky’s the limit to how successful you can be as an artist, thanks to social media—and I would much rather commit to creating and sharing my art at the risk of not living the most financially abundant existence, than make this existence all about money and miss out on the beauty that is art. Read more>>

Abby Goodman

I began working as a freelance artist when I moved to New York, and have always been fortunate finding work in the creative field thanks to the tight community of artists here. The flexibility and freedom of this work lifestyle has always appealed to me, so I never gave much thought to having a regular 9-5 type of job, with the only exception of wishing I didn’t have to pay for health insurance out of pocket. I like knowing that when a job ends, I can have concentrated studio time to get lost in the process, working as long or late as I want without interruption. Being a freelancer also means having autonomy to take jobs that interest me, instead of having a set routine, and I have specifically chosen jobs where I can learn a new technique, or advance my artistic endeavors in some way. I have had an eclectic roster of professional work experiences, including metal sculpture fabrication, decorative painting, package prototyping, various teaching positions, Imagineer/ Theme Painter for Disney Hong Kong, and Retail Mall Design and Development in Dar Es Salaam, Tanzania. When I returned to New York after working for the year in East Africa, a friend recommended me for a contract position in the Design department at the Metropolitan Museum of Art, so I spent that next year in awe, enjoying privileged access to treasured works of art and antiquities. All of these experiences have enriched my life, and influenced my practice. Although there has been a lot of uncertainty in this path I chose, the personal and professional rewards have made for an interesting and fulfilling life journey. Read more>>

Hoda Ramy

As an artist living in New York City, I’ve often romanticized the hustle—the city that never sleeps, the energy, the endless inspiration. But lately, it feels like I’m caught in a survival cycle. Once a nurturing ground for artists, NYC feels like a devouring mother. The cost of living rises relentlessly, and the pressure to keep up with bills has turned my passion into a chore. I remember a night not long ago. It was past midnight, and I was at my desk, racing to finish yet another scene for a project. My apartment was quiet, except for the hum of my computer. I felt disconnected from the work in front of me, with scenes blending into each other, and I had no time to savor the creative process or appreciate what I’d made. The joy of creation had been replaced by the constant rush to meet deadlines to keep afloat in a city that demands so much. I paused and thought, What if I gave this up for something more stable? A corporate job with reliable paychecks and clear-cut tasks suddenly seemed appealing. No more late nights agonizing over details that might go unnoticed, no more financial uncertainty. Just a predictable routine and a steady income. But then, I asked myself: would that stability fulfill me? Would the creative spark that defines me wither away in a sea of trivial tasks? Read more>>

Neena Allen

On my journey as an artist I am finding happiness in the everyday moments. The role of the artist is not to create only when we are happy, but to express our authentic life story & feelings at all times in hopes it will resonate with someone. We ask questions through our work that most do not have the courage to ask themselves. My career path has been long & winding, but I’m grateful for it because it’s led me to where I am today. I earned my degree in business management and ignored my creative side for quite a long time. I would attend our schools fashion shows, but did not think I fit into that crowd so I never thought of joining these fashion organizations. After graduating I thought that I wanted a 9-5, I worked in job recruitment, education & many other industries. I realized a “regular” job always seemed to stifle my creativity. I make art to connect artists together, to keep community & humans in the present moment through radical authenticity. For me, I found this difficult to do in a office job environment. This past August I took a chance on myself and put in my 2 weeks at a 9-5 I was working in Chicago. I knew I wanted to create for a living and I could figure everything else out on the way. My main focus was devoting my time to creating clothing & styling and I’ve made a lot of progress so far. I’ve connected with so many different artists in the Midwest, just finished a sewing course & even created a collection for a Chicago Votes fashion show! Read more>>

Mataya Britton

Although I’ve always been a creative person, whether that be making movies and writing scripts for my friends or playing pretend at every chance I got, the first thing I remember wanting to be was an opera singer, followed by an astrophysicist, and then a forensic anthropologist–pretty much every career available, at some point or another. Drastically different, I know. I would find myself watching a movie and being completely enthralled with the career of the lead character for a period of time. So it’s safe to say my mind was changing all the time. It wasn’t until I was in high school that I realized I didn’t actually want to be a doctor or a paleontologist, I just wanted to play one on screen. Even though the thought of following my passion was constantly playing through my head, it scared me to death. Leaving my hometown and moving to another country to pursue an improbability seemed beyond my reach. So when I graduated high school I enrolled at my local university for a bachelor’s degree in Archeology. I somehow managed to convince myself that digging in the dust for ancient artifacts was my path and although I found it fascinating, it wasn’t for me. I remember waking up one day, two weeks before classes started, and just knowing something was wrong—within a matter of four hours I had replanned my life. Read more>>

Heather Harman

I am very happy as a creative. After spending almost 30 years working in the corporate world, I don’t have to imagine what it would be like to have a “regular job.” Actually, “regular job” is a term that I, myself need to stop using when referring to what I do and what I used to do. I find that thinking that way diminishes the work I do now and draws a line in the sand of what the world as a whole, family, friends, former coworkers and others deem to be normal. I think we all need to change our way of thinking when it comes to the arts. It is hard work and in many ways creatives must work harder than those in “regular” jobs to survive. Climbing off my soapbox now… :) That said, I am trying to do everything I can to go back to the corporate world. While I have always been artistic and even went to school in a creative field, I never imagined I could live as an artist/photographer. Once I took the plunge, I felt like I was finally doing what I was meant to do and becoming who I was meant to be. Read more>>

Mira Scirica

Am I happier as an artist? I feel like I am much happier being able to work as creative than I ever would be at a regular or standard job. I think I knew that at a young age that I never wanted to have a desk job or a typical 9-5, the idea of laboring my life away for something I wasn’t passionate about was never something I wanted for myself. I actually remember wanting to be a Marine Biologist for the majority of my childhood and teens but realized I was pretty bad at biology in high school and that it wasn’t just swimming with dolphins it was a much more scientific career! Back when I lived in North Carolina, I was studying to get my degree in Psychology as I’d grown very passionate about mental health but dropped out a few months into the pandemic to pursue cosmetology through the Aveda Institute and a career in the makeup industry. I am glad I had that bit of experience and knowledge with Psychology because as I’ve realized throughout my years in the industry, makeup is a very intimate experience and my makeup chair acts as a safe space for all my actors and models and more often than not their time in my chair is also their time to really talk about anything troubling them in life. Working as a Freelance Makeup Artist really gives you a taste of other careers, it’s not all fun and beauty! It’s being a business owner, an accountant, a manager, a therapist, a script supervisor, a consultant, and so much more. Read more>>