From Roughneck Songwriter to Aging Code Monkey: My Pivot Into Programming at 37

Cover photo by Ian Schofinski Kurt Vonnegut famously said: ...The arts are not a way to make a living. They are a very human way of making life more bearable. I didn't listen. I wanted both. Social Distortion and Youth Brigade did it in the classic punk documentary, "Another State of Mind". They crisscrossed the country in an old, beat-up school bus. They chugged beers, played shows, and got the girls and it all worked out. I mean, Social D plays the Ryman now when they pass through Nashville. That's pretty good considering they came from such humble beginnings. Youth Brigade? ...hmm, I'm not sure, they probably broke up. Well, I was going to end up like Social D, anyhow, so it didn't matter. Actually, I wasn't hellbent on playing the Ryman or even getting that big. I just wanted to make enough to live on my art alone. My dream was attainable. This was all going to work out (said every musician ever). My folks made it a requirement that I get a college degree, so I went to school but just barely squeaked by. I spent most of my time playing gigs and partying. Fast-forward a decade, and I had made a couple of albums, lived in three different cities, built an adventure van with my Dad, and had done everything I could to make ends meet. I worked as a barback, a dishwasher, a full-time rideshare driver, a caterer, a food runner at a grocery store, a bike renter-outer, a library attendant, an AV tech/stagehand, and a pizza delivery guy. All to fund a music "career" that never seemed to grow legs or gain any kind of traction. When the pandemic hit, I made the hard decision and decided to hang it up. Fancying myself as a lifer, this decision did not come lightly and took a fundamental shift in self-identity. Like Henry Hill after he joins the Witness Protection Program at the end of "Goodfellas", I went from being a musician to an "average nobody. I was going to live the rest of my life as a schnook." The truth is, I had begun to see the writing on the wall. Some of my favorite musicians were still working days jobs and spending all of their free time making records that few people would hear. Saving up money just so they could tour across the country to play for small crowds. Coming home with an empty bank account and not much to show for their efforts. Just a sore back from sleeping on couches and floors and street cred from indie kids who were excited to see that these old salts were "still our here doin' it". I was on the road to sharing that fate. The thought of being a purist and sticking with it no matter the cost seemed very attractive to me for many years. Now, as a man who wanted to start a family some day, it made me realize how unsustainable that lifestyle would be long term. I'm an all or nothing kind of guy, so I quit. After stumbling across ethical hacker, Heath Adams', YouTube channel, I moved back to my hometown in Western Kentucky, sold my van, got the CompTIA A+ and landed an entry-level Help Desk role at a local MSP just as I turned 34 years old. I was set on following in Adams' footsteps and studying hard to become an ethical hacker. Yes, I would be joining the professional workforce - the world that had seemed so sterile to me as a roughneck musician. But now I had discovered this subversive entry point of ethical hacking. Adams and his colleagues get paid to legally break into buildings. I mean, what could be cooler? Three months into my new career, I was studying for the Network+, and trying to make it to the next level. A position opened in sales around that time, and a member of the sales team reached out to me. Sold on my current path, I said "thanks but no thanks". Shortly thereafter, the CEO of the company pulled me into his office and again proposed the entry-level sales role. I thought about it over the weekend and did some research. Turned out tech sales, specifically SaaS (Software as a Service) sales, could potentially lead to earning an amazing living in under 5 years. And it didn't require experience to break in. Having developed a reputation at my current job for being personable, dependable, and working my ass off, I figured I would be a shoe-in. I didn't have a passion for sales or the sales process, but then again, I never had a passion for IT before I had gone down that path, either. The passion had developed over time. The line from Mike Rowe "Never follow your passion, but always bring it with you" rang in my head. This line of thinking was antithetical to everything I had believed as a musician. Like many, if not most, in the west, we believe you should "follow your passion". Blindly, I may add. You mean, the fervor and zeal you have for one topic can actually transfer to another topic? It's all in your attitude? Who knew? This thought had never occurred to me while I was "following my passion" by driving 200 miles to play to 5 people for tips and a hot meal, but it did occur to me now that I was making moves in my early career. Through SaaS sa

May 8, 2025 - 03:51

From Roughneck Songwriter to Aging Code Monkey: My Pivot Into Programming at 37

Cover photo by Ian Schofinski

Kurt Vonnegut famously said:

...The arts are not a way to make a living. They are a very human way of making life more bearable.

I didn't listen. I wanted both.

Social Distortion and Youth Brigade did it in the classic punk documentary, "Another State of Mind". They crisscrossed the country in an old, beat-up school bus. They chugged beers, played shows, and got the girls and it all worked out.

I mean, Social D plays the Ryman now when they pass through Nashville. That's pretty good considering they came from such humble beginnings. Youth Brigade? ...hmm, I'm not sure, they probably broke up.

Well, I was going to end up like Social D, anyhow, so it didn't matter. Actually, I wasn't hellbent on playing the Ryman or even getting that big. I just wanted to make enough to live on my art alone. My dream was attainable. This was all going to work out (said every musician ever).

My folks made it a requirement that I get a college degree, so I went to school but just barely squeaked by. I spent most of my time playing gigs and partying.

Fast-forward a decade, and I had made a couple of albums, lived in three different cities, built an adventure van with my Dad, and had done everything I could to make ends meet. I worked as a barback, a dishwasher, a full-time rideshare driver, a caterer, a food runner at a grocery store, a bike renter-outer, a library attendant, an AV tech/stagehand, and a pizza delivery guy.

All to fund a music "career" that never seemed to grow legs or gain any kind of traction.

When the pandemic hit, I made the hard decision and decided to hang it up. Fancying myself as a lifer, this decision did not come lightly and took a fundamental shift in self-identity. Like Henry Hill after he joins the Witness Protection Program at the end of "Goodfellas", I went from being a musician to an "average nobody. I was going to live the rest of my life as a schnook."

The truth is, I had begun to see the writing on the wall. Some of my favorite musicians were still working days jobs and spending all of their free time making records that few people would hear. Saving up money just so they could tour across the country to play for small crowds. Coming home with an empty bank account and not much to show for their efforts. Just a sore back from sleeping on couches and floors and street cred from indie kids who were excited to see that these old salts were "still our here doin' it". I was on the road to sharing that fate.

The thought of being a purist and sticking with it no matter the cost seemed very attractive to me for many years. Now, as a man who wanted to start a family some day, it made me realize how unsustainable that lifestyle would be long term. I'm an all or nothing kind of guy, so I quit.

After stumbling across ethical hacker, Heath Adams', YouTube channel, I moved back to my hometown in Western Kentucky, sold my van, got the CompTIA A+ and landed an entry-level Help Desk role at a local MSP just as I turned 34 years old.

I was set on following in Adams' footsteps and studying hard to become an ethical hacker. Yes, I would be joining the professional workforce - the world that had seemed so sterile to me as a roughneck musician. But now I had discovered this subversive entry point of ethical hacking. Adams and his colleagues get paid to legally break into buildings. I mean, what could be cooler?

Three months into my new career, I was studying for the Network+, and trying to make it to the next level.

A position opened in sales around that time, and a member of the sales team reached out to me. Sold on my current path, I said "thanks but no thanks". Shortly thereafter, the CEO of the company pulled me into his office and again proposed the entry-level sales role.

I thought about it over the weekend and did some research. Turned out tech sales, specifically SaaS (Software as a Service) sales, could potentially lead to earning an amazing living in under 5 years. And it didn't require experience to break in.

Having developed a reputation at my current job for being personable, dependable, and working my ass off, I figured I would be a shoe-in.

I didn't have a passion for sales or the sales process, but then again, I never had a passion for IT before I had gone down that path, either. The passion had developed over time.

The line from Mike Rowe "Never follow your passion, but always bring it with you" rang in my head. This line of thinking was antithetical to everything I had believed as a musician. Like many, if not most, in the west, we believe you should "follow your passion". Blindly, I may add.

You mean, the fervor and zeal you have for one topic can actually transfer to another topic? It's all in your attitude? Who knew?

This thought had never occurred to me while I was "following my passion" by driving 200 miles to play to 5 people for tips and a hot meal, but it did occur to me now that I was making moves in my early career.

Through SaaS sales, I could potentially change my life in a shorter amount of time than if I went the straight technical route. If I went into real, outbound, software sales, I could out-hustle everyone else to make it to a place where financial freedom would begin to feel attainable. No more eating open-faced tuna sandwiches cause I couldn't afford the other slice of bread. Those days were about to be over.

For the next two years, I worked as an Account Manager at my MSP job while making my plan to break into SaaS sales. I took a course, paid money for a personal coach, and got my foot in the door at a major cybersecurity firm in Austin, TX after undergoing a grueling interview process (I'm learning that the interview process is potentially worse for devs...lmao).

Having lived in Austin as a musician from 2012-2013, it was a tough pill to swallow to have to move back across the country and leave my family again. But I had to work a hybrid role as an Sales Development Rep to get started. Once I got my feet wet and became an Account Executive (full-cycle sales rep), I would move back this way and work remotely. That was the plan. So, I sold my house and moved across the country.

But it didn't work out.

I was crushing at first, but then I began missing quota!

Oh no, everything I had worked for was slipping out of my hands!

The interview process had gone so well that I had two managers fighting over me. And now, here I was. From potential golden boy to looking at a Performance Improvement Plan.

I was in disbelief and would call my dad and cousin, both of whom are in sales, and ask them for advice and vent to them until they were probably sick of me. I felt like I was working around the clock to turn things around, but it was becoming a desperate situation.

Missed quota numbers turned into meetings with the managers. Meetings with the managers turned into official emails, tracking the downhill slide which eventually led me out the door.

The truth is, sales was never a good path for me in the first place. Yes, I am personable. Yes, I work hard. But long, sustained periods of being engaged with people all day every day wore me out.

60+ cold calls a day (sometimes 100), meeting after meeting, doing the same tasks over and over. It's mentally stimulating but in a completely different way than the technical side. You have to be "on" at all hours of the day. I knew that going in but figured I would get used to it and end up enjoying it. Instead, it filled me with dread.

I chose a severance package over a PIP - I was done with sales. Through a loophole, I was able to get on unemployment through the state of Texas which helped me finish out my lease.

In May 2024, after seeing the writing on the wall of my sales job, I began looking into programming. After a lot of soul searching I decided I wanted to go back to the technical side of things but actually become a builder. I didn't want to go back to Help Desk as I would be completely starting over from square one. And, frankly, the idea of spending two hours troubleshooting one person's MFA did not sound appealing. I also wanted something that had unlimited potential where I could gain the skills to build anything I could imagine.

So, beginning in May, I went through some minor programming stuff on Udemy and Free Code Camp, took my severance in July, and landed on The Odin Project in September of 2024.

I finished out my lease in Texas, said goodbye to all of my amazing friends and headed back to Kentucky where I am currently typing this in my childhood bedroom.

My parents were supportive and kind enough to take in their 37-year-old, jobless son while I make yet another major pivot in life. But this one is for good.

As Billy Joe Shaver said, "I'm just an old chunk of coal, but I'm gonna be a diamond someday."

I am 7.5 months into this journey and it has been one of the most challenging, rewarding, and interesting things I've ever done.

The Odin community is fantastic and I'm no longer spending four days attempting to debug an event listener (probably shouldn't speak too soon there).

I've been building small projects and, while the knowledge has slowly been compounding, I know this learning journey never ends. Which is something I love about it. Also, the creative aspect is immensely rewarding. Designing a simple sign-up form with '70s-style block font that looks like it was ripped off the Ramones first album cover. Writing a surprisingly complex logic puzzle to come up with an Earthbound-inspired Tic-Tac-Toe game. Fun, frustrating, and rewarding all at once.

I love being in flow, I love the problem solving and introspection required, as well as the vast ocean of information right at your fingertips. The areas of discipline within the programming field are practically limitless. And, frankly, I just like esoteric, weird crap. It also scratches that itch. And all you need is a laptop. That's pretty dope in my book.

Programming reminds me of making a record in a sense. The work is done privately in a flow state, there are tons of small decisions to make in the process, and you finally release it to the world just to start on the next one.

Once I'm employable, I'm going to move back to Nashville and settle down. This ol' hoss is ready to grow some roots.

It has been a whirlwind life so far. I definitely have walked a crooked path but it feels I am finely about to wind up where I'm going. For now, at least. There's always another path to walk down. That's just life.

If you're learning like me, keep the faith. It's hard but we can do it. My hair is thinning, I'm going gray on the sides, and I'm creeping up on 40.

My youth has faded, but my drive and perseverance is alive and well. In fact, it's stronger than ever before.

The truth is, I never imagined that I would be studying to become a programmer. Not in a million years. But I'm finding that the creativity, the unlimited potential, and the rebellious spirit of field, really scratch that itch.

All right, enough jabbering. Time to go build something.

Sam

PS: Here's an old song I wrote. It's inspired by a guy who burnt down my Mom's high school on purpose:

"Firebug Ronnie" by Sam Hadfield