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.

Yiting Nan

I attended a recent high school reunion with some of my classmates and the thought of what my life would be like if I had pursued a non-art major like the rest of them crossed my mind. However, as the only one in our class who pursued an art career, I feel incredibly grateful for where I am now and the work that I have been doing. Read more>>

Michael Badejo

I have had my times with playing professional sports and then being released and going back home to work. Of course I want to play the game of football for a very long time, so when I get sent back home to go work it just motivates me to remain humble and to keep working because the man upstairs is creating a plan for me. Read more>>

Kim-Vi Tran

I feel that I can offer a unique perspective on this, as I’m currently working a full-time “regular” job as a Data Analyst on top of my full-time “creative” job as a Live Wedding Painter. I can confidently say that I am very happy doing both! I really enjoy the balance that the two careers offer me. It feels as if both sides of my brain are exercised daily, and when I tire of painting or looking at numbers, I have the option to pivot. Read more>>

William LaVant

Would I say I’m truly happy as a “Creative” in what I do? Hmm, there are happy moments when you see what you’ve worked so hard for pay off eventually. It may not always exceed my expectations but some impact is better making no impact at all. To be honest, I actually did work regular jobs in my teen years but, once I seen that I can make more in a day’s work with what I do on my personal time than the amount I’d see on a regular check from the 9 to 5, i automatically knew the 9 to 5 scene is not for me. Read more>>

Margrethe Aanestad

I feel happier and as a whole individual, being creative as an artist. It is who I am. It is not possible for me to not make, to not be in those processes which feels so crucial and meaningful. I have experienced not making art, in a period over years earlier in my life, having other jobs, doing curating etc, and that genuinely proved this was wrong and unhealthy for me. So there is no way around not actually making. Read more>>

Christian Clark

I can’t imagine myself doing anything else. In fact I’ve tried doing “anything else.” I’ve had my fair share of “regular” jobs, but I simply couldn’t do them long term. They didn’t feed my soul, and they drained any time and energy I had to put into making music. It’s a shame society determines someone’s value based on how much money they make. Read more>>

Harrison Freeman

I think a lot of artists struggle with choosing between a consistent paycheck and doing what they might consider to be more fulfilling work. I actually have a regular job and I have plenty of time to do my art as well. You can have both. I’ve been with the same company for over 10 years. Read more>>

Ali Valentine

Overall as an artist, I am happy and fortunate to do what I love. Like most things in life, there are ups and downs and you have to stay up on top. There are many struggles and barriers you need to push pass through, but then cause you to grow. Not only as an artist, but as an entrepreneur, you need multiple sources of income. Though I do music full time, I also have a regular job that helps support my music. Read more>>

Felisitas Stella

I definitely ask myself this question pretty often, especially as someone at the beginning of her career and not really knowing where the next gig or connection will take me. I am at the point of my life where things are changing in spectacular, messy, and unpredictable ways (i guess this is what being in your 20s feels like). I am learning so much about myself, my music, and the people around me in ways that ive never done before. Read more>>

Latik McNeil

Though it has taken some time to come to this conclusion, I don’t think I’d be happier doing anything other than being a creative. It has been not only a dream, but a goal to live life as a creative, on my own terms. When i was really young, like 10 years old, i already had a plan in mind that i wanted to be an entertainer, who graduated with a degree in video game design from GA Tech, and would be running from president while rocking braids like Lil’ Bow Wow. Read more>>

Baz Gillen

I am so happy that I’m fortunate enough to say I’m a working musician, (at the moment), but I believe the last time I subconsciously pondered whether or not my creative pursuits were worth chasing was in my music theory class this morning. I’m currently a jazz major at MSU Denver, and while I love the program, I think its extremely valid to ask yourself if your art can sustain you in our costly world today, particularly if you’re spending lots of money in pursuit of a debatably worthless degree, (in terms of a guaranteed success in the job market). Read more>>

Emma & Jeremy Bearden & Boyd

We find that we are happiest when we have the space, both mental and physical, to create. However, things start getting tricky when making a sustainable living comes into play. We both currently have or have had “regular” jobs. We have found it very difficult to maintain a work-life balance when the work we prefer to do (creative work) isn’t enough to sustain us. Read more>>

Kelcey Ledbetter

So let’s just say, I’m happy for the most part. It’s hard to define happiness from this perspective because not only do I do music, I also work a regular full-time and a part-time job. Now let’s back up to 2020 because that was when I tried the route of doing music full-time and was hit with reality quickly. I was back in school and I made the decision to quick my full-time job two months before the pandemic started and immediately felt the devastation of having no job and no other streams of income coming in; Read more>>

Sarah Pirkle

Right before the pandemic I was considering switching careers, looking into other skilled trades that I had been drawn to before I fell into getting paid to play music in my early 20’s. I didn’t get my paperwork in order to attend my 2nd year of nursing school, I took up playing the fiddle as I was working and saving $$ to go back to school, but music took over my life, I got a few paying students and it just grew from there. Read more>>

Jeremy Davis

As an artist and creative, happiness in the pursuit of something intangible can be somewhat elusive. The intangible being success. Of course, the idea of success depends on how you define it, and that can change as you move through life. I always wanted to work for myself when I was younger, but I didn’t have a clear idea of how that would work or what exactly I would do. Read more>>

PM Lowe

Over time, I’ve based all my happiness in music. Now, as I’ve gotten older, music is still a driving force and while it does make me happy and free to create, I’ve learned to spread that happiness across over things I do, because we all know what makes you laugh can also make you cry. Read more>>

Jacob Bryner

I will always feel like I am an artist first. There are certainly times where I’ve wanted to have a (for lack of a better term) “normal” brain when times are tough. One that doesn’t feel this nagging urge to create but simply looks to go do a simple job, get paid and then come home and relax and just play a video game or watch a show on Netflix. Read more>>

Elizabeth Bergeland

Not particularly. But I think I’m an incessant melancholy type and would likely answer the same no matter my occupation. (I used to work as a designer in bridal and can confirm the same overall sentiment then) haha. I think that being an artist is definitely romanticized and people tend to have this idea that there’s a lot of freedom and joy and spirit inherent to the art-making process. Not to say that that isn’t the case for some people, or that I don’t experience joy or happiness along the way, but I find the process to be a bit more fraught for me. Read more>>

Christina Davis

I have been very blessed to have extrememly supportive family and friends. On social media, I’ve seen a lot of small business owners talk about strangers supporting them more so than their family and friends. I’m grateful that isn’t my story! My family and friends are the reason I am still in business today. They believed in me and the vision God gave me. I didn’t have to ask for their support, they just did it. Having total strangers to you support you is great, however, there is no comparison when people you love, and admire support your dream and/or vision. Read more>>

Carrie Madrid

Asking my friends and family to support my nonprofit was a little uncomfortable at first. I wasn’t even sure I knew what or how I was going to help cancer patients financially, but I knew I had to try. Once I explained my own experience, vision and mission, everyone I asked for support happy supported me starting the nonprofit and most have continued to financially support as well. Read more>>

Michael Payne

Asking friends and family to support my business has been essential to me on this journey. The area I chose to use as the launch pad for taking photography from a hobby to a business is a small but tight-knit one. Competitive paintball whether on a regional or national level is so interconnected that once you’ve been present in it for a significant amount of time you develop an unbelievable amount of friendships, acquaintances and contacts. Read more>>

Akiko DuPont

Word of mouth is is almost everything for my business so asking friends or family that believes in what you do to spread your word/works has been very important. Of course, before asking anyone, you’ll need to believe in yourself/ feel confident enough and love what you do! Read more>>

Angel Jordan

Benefits of Asking Friends/Family to support your business: Emotional support: Friends and family are more likely to show emotional support for the business owner. They may be more understanding and empathetic toward the challenges and struggles associated with starting a new business. Access to networks: Friends and family often have a wide network of contacts that could potentially benefit the business. They may be able to provide valuable connections or introduce the owner to potential customers, investors, or industry experts. Read more>>

Ty-Vaun Hoskins

People give up early in business and damage relationships because they are too focused on getting support from people they already know like friends and family because that is the easy part . I pride my business by the phrase ” Everyone is NOT going to support your business, good thing you don’t need everyone ” . You have to understand that the people you have relationships with you already know what value they can bring to your business so you have to take a chance at the unknow which is networking and meeting new people . Read more>>

Andy Burns

Oh, most definitely! Hence why I created the brand The Unconventional Black Hottie! As a black woman, The struggles of black women in society are often overlooked and underestimated. As a result, many black women feel the pressure to conform to certain stereotypes and expectations that are placed upon them. This can be especially true for unconventional black women who don’t fit into the traditional mold of what society expects from black women. Read more>>

Cee El PEN

Just the name of my show gets mischaracterized .Let’s be clear the name of my show is 3 words not to ever be combined it’s Puss Cee Talks!People Immediately have questions or challenges me on what it says and how to say it lol… So just for the record the name of my show is “PUSS” my name is Cee and my guest come to talk to me! I cover a wide variety of topics from parenting,friendship,a lil bit of sex and relationships. Read more>>

Matthew I Mosley

Due to the content I use to convey my metaphors combined with the esthetic of my overall brand, alot of ppl at first glance don’t take me seriously but of course that changes once they see the skill set n hustle I put into my career What I learned is if u work without the need of validation you’ll always go far Read more>>

Izzy Lugo III

I think that understanding that the mischaracterization of my work has been evident throughout my career to date. My journey to this point of my life has been people trying to fit me in the box that they think I would be great at–without asking me first. I’ve learned to speak up for myself in these situations and be my own biggest fan, even when there are doubters. Read more>>

Rachel Strickland

Living the self-employed freelance artist life is very different from having a “regular job” although that will mean vastly different things to different people. There are many amazing benefits, and sacrifices, to having a more conventional professional career path, and vice versa. Read more>>

Kelly Stuck

I am happy being a creative, and like anything I think the happiness comes in waves. There are moments that I can’t imagine doing anything else, truly. Being an artist feels so right, but there’s a balance I’m trying to keep… I can’t believe I get to draw for a living. I have the privilege to capture memories, to celebrate creatures that we hold so dear in our hearts, to use my hands in a way that is fulfilling to me. Read more>>