Creative Craig and His Incredibly Captivating Career

I’ve written much about the realities of American job satisfaction. I’ve routinely pointed out the growing sense of discontent in the traditional workforce, and that fewer people are truly passionate about their work. The ability to be creative is often associated with increased job satisfaction, so you can imagine how someone of that leaning would feel when forced to spend their days filing paperwork.

Last week I had an incredibly thought-provoking phone conversation with an old friend. My friend is one of the lucky few who are excited to jump out of bed and face the work day. But not only that, he’s also secured another foundational pillar of life satisfaction: financial security. I came away from this conversation with thoughts swirling in my head, and a clearer picture of what lies ahead for me as my corporate career comes to a close. 

Craig (not his real name) is now a very successful photographer. His work has appeared on the cover of very popular magazines, and he’s been featured in many more high-profile news and entertainment publications. He’s taken photos of some of the biggest names in entertainment and fashion, and worked with many of the household name brands. 

Creative photographer
Not Craig. (Source: Pexels/Kaique Rocha)

And he’s done nearly everything I tell people not to do. I’ve said chasing your dreams is probably a bad idea, and for most of us out there, I firmly stand by that notion. 

Craig got an English degree at an expensive out-of-state school. After a touch of globetrotting, he then moved to an insanely expensive city to pursue writing and photography, two creative career paths that generally don’t pay particularly well. For most people, add a touch of salt and you’ve got a recipe for financial ruin. 

But Craig is different. Craig could probably be successful at anything, and I wanted to understand why he’s a cut above the rest. 

Mr. CC Meets Craig

Craig was a senior at my high school when I began my freshman year. As such, that made us unlikely friends. But we were die-hard skateboarders, and that community in my North Carolina hometown (circa 1999-2000) was small and tight-nit. 

I was heavily involved with filming and producing a series of videos to capture the growing skateboarding subculture of the area, and Craig was one of the best skaters around. Plus, he was an incredibly likable guy. We formed a friendship around skateboarding, underground Bay Area hip-hop, and general — but reasonably innocent — teenage debauchery. 

Craig immediately left an indelible impression that being smart is cool, a rare teenage sensibility. He talked about actually reading magazines (I usually just looked at the photos), discussed unassigned novels that he enjoyed, and stressed the importance of nature — especially a good swimming hole.

The Importance of the Creative Role Model

Craig moved away the following summer to attend an out-of-state school on the other side of the country. I can’t say for sure what led to what — there were a lot of less-than-desirable events conspiring at once in my high school years — but in Craig’s absence, I sort of started to unwind the positive influences he had unknowingly instilled. 

I stopped skateboarding. A new group of friends came into my life, ones that valued a good party over a good book or other creative pursuits. I put on tens and tens of pounds as consumption increased and exercise fell to nearly zero, setting the stage for nearly two decades of very difficult lifestyle correction.

Related post: I Was Really Fat Until I Fixed It 

It eventually took moving away to college and resetting my life to gain back the positive values Craig had instilled in my teen years.

skateboarding screen grab.
The old skate days. Screen grab from video.

2019 and New Creative Forces

Fast-forward to about a month ago, fall of 2019. I’m feeling reminiscent of the old skating days, and naturally, I begin to wonder what some of my old friends are doing nearly two decades later. In classic creeper style, I google Craig. I’m expecting to sort through pages of alleged criminal convictions or maybe Youtube videos of an 18-year-old West Texas quarterback of the same name, with a “hell of an arm.” 

Not so. Craig is the top-rated search result for his name, and he’s no slouch. He’s apparently a rather successful photographer living in the big city, working with big names of fashion and entertainment. Holy shit! I haven’t heard from or spoken to Craig for the better part of two decades, so this really catches me off guard. 

I feel so happy. Without a Facebook account or any other personal social media presence, I really don’t know what the hell people have done with their life. And I generally don’t care. Live and let live. 

But every once in a while I get the urge to look into the path of someone else’s life, and the results are generally of a typical variety. Person A usually works in a whatever job, has two kids, married. etc. The standard path. Occasionally the results are more depressing, but it’s generally just standard.

To see that Craig has gone and achieved relative success on a sounds-great-but-probably-won’t-pay creative career path is so exciting for me to see. But my next thought is that Craig would hate this website. Here I am telling people to not chase their dreams. But Craig chased the dream, and chased it well. Craig is different though, and after a hour-long phone conversation, I remember why.

The Grind of the Creative Dream

During our phone conversation, Craig impressed upon me two important points of a creative pursuit: 

  • No one is born an artist. You must become one.
  • You have to know how to market yourself.

Becoming The Artist

Some folks who fancy themselves the creative type feel that they should produce high art right out of the gate. Whether that’s music, food, photography, or painting, many are not willing to put in the years of work to build a broad base of experience, unwilling to compromise on their “aesthetic.” 

For example, in Malcolm Gladwell’s best-selling book, Outliers, Gladwell contends that the Beatles became the Beatles because they were willing to play over 1,200 times (!) at all-night shows in Hamburg, Germany. Hardly the rock and roll dream…until it was.

Or perhaps the story of one of my personal favorites, the late and great Anthony Bourdain. In his classic breakthrough novel, Kitchen Confidential, Bourdain hilariously recalls the years of drudgery in countless crappy New York kitchens. While culinary school students might dream of taking the helm in a swanky uptown restaurant, Bourdain caustically reminds of the grueling reality of his pre-CNN days. After all, it was his writing, not his food, that first brought him mainstream attention.

Craig’s early years as a professional photographer were spent doing any assignment he could snag, running endlessly as a photojournalist for a major news publication. It wasn’t necessarily creative and it wasn’t art. Photojournalism wasn’t the kind of work he longed to do. Eventually, after building a wealth of experience and a name for himself, he began to slowly shift into his preferred realm of artistic photography.

To this day, he says he’ll come and take pictures of your dog if asked. But of course, he’ll make little Sophie look damn good. Many of his colleagues spent those formative years only in search of gigs that fit their image as an artist, missing out on crucial technical and professional experiences.

The Unknown (and Poorly Marketed) Creative

Many creative luminaries live in obscurity, only to be discovered posthumously. Tragically, legacy doesn’t pay the rent. I asked Craig, “There’s lots of people who take pretty pictures. How are you so successful in a crowded field?” He laughed, and then humbly replied by reminiscing on the addictive element of hustle when he moved to the big city after college. 

Craig knew early on that he wanted to be close to the action. So, instead of being overwhelmed by impressive and abundant competition, he used that energy to propel his own career. Craig reframed the competition as a motivating force to up his own game, clearly showing his propensity towards a growth mindset. Craig wasn’t demoralized by the abundant “talent” around him, and he didn’t move away to be a bigger fish in a smaller pond.

city crowds
Don’t let the competition get you down. (Pexels/Pawel L)

Be Likable

Craig did not go on to tell me that being likable was key to his success. He’s not the kind of guy to boast, after all. But unless the core of his character has dramatically changed since the early 2000’s, I remember how Craig had a way of warming up to everyone.

So many people in this world go through life with a distaste for certain groups of people. You know, a general dissatisfaction of a people simply based on broad classifications, such as political party, country of origin, or even something as simple as the county in which they reside. I.e., “those folks in Murphy County are nothing but a bunch of toothless hicks,” or “I really don’t trust people with dimples.” 

Some of us can’t see past even simple ideological differences. We fail to recognize and appreciate the core similarities shared in the human experience.

Craig could hold a civil conversation with teachers, greasy skate rats, angry property owners, responding police officers, and five-toothed creatures from deep in the shady Appalachian hollows. More importantly, he could make them all smile. There’s little doubt that his approachability has been instrumental in determining who gets the job. 

None of us are too good for anyone else, and it’s easy to stir the pot. Find a way to make your enemies smile and you will always be a step ahead.

Financial Independence is Only Part of the Equation

Yes indeed, Craig is an example of the relative few who have made a career out of something they love. Well, sort of. Even Craig professes that he now treats photography as a career, and rarely carries a camera for fun. He even still skates to this day, but only recreationally. Craig is glad he didn’t pursue professional skating (he had a chance in that world too). Because, as he claims, turning a hobby to a job waters down the experience.

This conversation got me thinking a lot. Long before my corporate geology days, I too had a penchant for creative endeavors. As a child I drew and painted endlessly. In my skating days, video production became my new obsession. For my college years and early 20s, it was food and music. Today I’m writing.

Let’s be real, I’m not necessarily looking for a new career, at least not in the traditional sense. And you, dearest reader, aren’t here because you want to hear me talk about career changes. You are probably here because of the intrigue of financial independence. Ah yes, that gooey buttery cookie dough that might seem like the elixir to all life’s problems.

Oh, financial independence is fantastic, don’t get me wrong. I’m very happy to be where we are financially, but it’s not a panacea. People who are financially independent still get sad, stressed, and angry. After all, money still doesn’t bring happiness, even if you have it for all the right reasons.

The Time is Coming

I’ll be leaving my job soon. I haven’t said much about it here, but the reality is starting to sink in.

My goal is to find that next project that brings me satisfaction like Craig has found in photography. I don’t believe my obsession with climbing is going to cut it, at least not entirely.

Where would you dedicate your best efforts if a paycheck wasn’t a factor?


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