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The Most Untalented Talented Person I Know: Notes from a Middle-Class Musician

Turns out you can play thousands of gigs, raise a family, and still be asked when you’re going to ‘make it.’
Nick Di Gregorio

I’ve been a professional musician since I was about 15, which means I’ve been paid to play music in public since then and dove straight into making a full-time living playing since I was 21.


You’ve definitely never heard of me.


The locals in my small town I play weekly barely know my name. I’m a middle class musician—I make enough to support a family and be screwed over by the government, but not enough to utilise the tax benefits of the wealthy.


I live in a world where I’m constantly told that because you’ve never heard of me, my career isn’t valid. It’s usually the subtle backhanded compliments:


“Wow, you’re actually very good. Keep going, you’ll make it,” or


“You should go on insert shitty music competition show.”


Because being famous.



It’s a strange thing—spending your life doing something that everyone has an opinion on, yet being discounted simply because they don’t know who you are. I’ve never met anyone who doesn’t hold a set belief about what music is. But what most people miss is that their definition—the thing they think of as real music—is often just a gossamer-thin sliver of what music truly is across the broader spectrum.


It’s not just the non-music listeners. I’m including myself—and every genre, every little musical community niches there is. If you’re sitting there thinking, “Not me, I love everything,” it usually means you’re unaware of the vastness and thinking too small. That same person won’t be able to sit through one set of original Aussie jazz music. Or they’re thinking only in our Western music tradition. When was the last time you listened to Tuvan throat singing? 


The obvious example at pub gigs is the classic:


“How can you not know this ‘random song’ by the artist ‘I’ve never heard uttered and have never heard since?’”


With the underlying implication being that I’m the one missing a trick. This happens at nearly every gig—it happened to me last night.



Pop songwriters often talk about their corner of the industry like it’s all that matters—that mass-produced bangers are the only meaningful form of music, simply because they sit at the centre of the bell curve. Meanwhile, classical and jazz musicians often operate in a world completely disconnected from popular culture—there’s a 50/50 chance they’ve even heard of Ed Sheeran. Some of the most technically impressive musicians I know barely crack a few thousand streams on DSPs like Spotify or Apple Music.


Singer-songwriters and country artists often treat lyrics as the main purpose of music, to deliver a message that’s always either unclear or too on the nose—but always delivered with passion.


DJs and public curators create a vibe—they think about music in terms of movement, energy, and how it feels on a dance floor.


Everyone’s musical identity is shaped by invisible forces: what you listened to growing up, what era you came up in, the scene you’re in, your instrument, your city, the radio, peer pressure, even deep psychological wiring…


Like my own crippling need to be self-sufficient in everything I do.

Very little music ever changes the course of my life—but sometimes it does. When I was about 11, my teacher gave me a compilation of jazz guitar—Barney Kessel, Tal Farlow, that kind of lineage—and I was knocked over when I heard Martin Taylor’s ‘Here, There and Everywhere / Day Tripper’ (his album ‘Artistry’ is still my top 10). I loved his solo guitar chord melodies, the independence of parts, the freedom of playing anything you wanted, over any tune, with limitless possibility. That mindset—what everyone calls “jazziness”—infected my playing, no matter the style.


Classical musicians notoriously hate improvising. A lot of pop, metal, and singer-songwriters play the same song the same way every time. I prefer songs to be an outline, with space to move—but I also cringe at overextended jams. A 12-minute, 3-chord blues makes me want to die.


These are psychological things. Our personalities shape how we approach music. Our taste affects how we hear. Are you a dancer? Are you a watcher? Are you a thinker?



Playing solo guitar and the interdependence of standalone performance made me crave small group playing—groups where every member holds a different, crucial role. I saw bands with two guitarists strumming the same chords, the exact same way and still find it painful. I like it when less is more.

I love trios—guitar trios, piano trios, Ben Folds Five (still a trio) killer nasally harmonies.


Learning to sing at a ripe age of 22 was also about freedom & independence initially. Gigging as a soloist meant I didn’t have to rely on flaky-as singers.


Even your instrument shapes your brain. String instruments have physical patterns. Piano players see vertical harmony laid out clearly. Wind players think horizontally. What you play becomes how you hear. In my own playing, single notes hold less nuance in my brain—which is something I’m working on in the practice room.



I never got into rock or heavier music like most guitarists who loved AC/DC, Brian May, or Black Sabbath. Most other guitarists I talk to started music because of their favourite band. I didn’t.


I was pulled into the classical world through that tiny, tightly knit Australian guitar lattice-brace scene. I was surrounded by orchestral musicians and pit players in musical theatre. I was accepted and shunned in equal measure by different jazz communities in Melbourne, Perth, London. I studied jazz guitar seriously, explored free jazz in New York, played cruise ships, and from then to current day am in the working musician grind.


I met gospel players with monster ears and zero theory. Theatre singers who could pin a room with one note. Lyricists who moved people without knowing what a 9th chord was.


I started singing with the intention of becoming a soloist—and letting fate decide whether I’d sink or swim. (Luckily still swimming.)


In London, I explored the broader “music industry.” I met hundreds of musicians. Some were burnt out. Some were thriving. Almost none of that had to do with their actual ability.


“You don’t have to be famous—or even understood—to live a meaningful life in music. But you do need clarity, resilience, and a relationship with music that’s deeper than public validation.”

Music is super weird in the sense that what you’re hearing from someone in a performance is very different from how they’re actually creating it—internally, subconsciously, emotionally.


I’ve met players I assumed had studied at some top-tier school because their playing was clean and expressive—only to find out they’ve come to music like the way a child learns to speak. Word by word and actually speaking it with others. Then growing into a person who can’t read but can swindle you out of thousands of dollars and happily convince you to hand them the shirt off your back.


It threw me through a loop because, truth is:


I’m the most untalented ‘talented’ person you’ll ever meet.

In 7th grade music class, I took an aural exam: “Is this in 3/4 or 4/4?” I couldn’t tell the difference.


I clawed my way into having better ears—hours and hours of transcribing. Still, basic things trip me up. I’m the person who learned Italian by reading and writing, but then got to Rome and couldn’t understand a word. I knew the grammar. I couldn’t converse.


Practicing jazz taught me: your ears must be connected. Now people say “so talented,” but really—I just chose to get better at something I was extremely ungifted at.



Jazz always held a freedom to me. Real understanding with execution. Not jazz as a genre, but jazz as a mindset.


It revealed the underbelly of how music functions, and then gave me permission to mess with it. To be and react with the moment. To let the music go wherever it can. That’s the lofty goal anyway.


I apply it to every genre. Every song. That mindset has served me—and sometimes hindered me—well.



Lately, though, I’ve been asking harder questions—the kind that keep me up at night:


• If the music I make is never heard, is it still worth making?

• What music do I create when no one is watching?

• How do I want my son to experience music?

• If I’ve already reached the peak of my career, would I be content?

• What am I actually practicing for?

• Would I be happy with the art I’ve made so far?


(Hard no on that last one.)


I want my son to feel the beauty and awe of mastering something. It’s never just about music—it’s about the joy of doing something that takes time, patience, and persistence.


I’ve sacrificed a lot to live a life in music. And to be honest, I’m still trying to figure out what’s actually important.


The way I came to music, it seemed like there were multiple clear paths: do this, and then that will happen. But my journey has felt more like starting on a road, spotting a gap in the bushes, running through it, finding a new, slightly different road, picking up new tools and lessons along the way—and continuing like that, until the map starts to feel imaginary. A tapestry of roads leading essentially nowhere, because the paths are made up. And the road is just time, carrying you closer to the journey’s end.


But I know this:


The best people I’ve met in my life have come from music.

And I want music to keep connecting me with people who are curious, kind, and built to care.

 
 
 

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