How I Went From a Frustrated Classical Pianist,
to a Confident Working Jazz Musician —
And How You Can Skip the Struggle
Hi, I'm Justin Highland. Pianist, composer, educator, and the founder of Play Better Jazz.
Are you really getting the results you want?
Still wondering how to actually get better at jazz piano?
You have watched hours of YouTube.
You have read lots of books.
You have transcribed solos.
Maybe you have taken lessons and felt like it was a waste of time, especially when it comes to what and how to practice.
You have done everything until your brain felt like a bowl of jazz-flavored oatmeal.
And still… your playing sounds more like "mildly confused keyboard player" than confident improviser.
You can play piano — well, even. You’ve got chops. Theory knowledge. Maybe even a degree.
But when it comes time to play — to improvise and create...
Cue the inner panic...
The second it's time for you to solo, your soul leaves your body.
(And probably hides behind the fake plant in the corner of the jam session.)
You don't know what you "should" really be doing, or if it's the right way to do it.
You second-guess everything and are constantly looking for new ways to improve,
but end up overwhelmed with options.
You might feel like your playing sounds stiff or underwhelming. And deep down, when you hit that final chord…
You don’t feel proud. (More like hoping no one heard it.)
It’s frustrating as hell.
You might be coming from a Classical background.
You might be technically solid, can read music, or can play other styles.
But somehow, all of that training did not prepare you at all for jazz piano.
You are stuck trying to turn scales, licks, what you transcribed, and theory into real music...
And yet, it's NOT WORKING like you expected.
Been there, bombed that. Now I help others avoid it.
When I first got into jazz, I was a Classically-trained pianist of 14 years, thrown straight into a university Jazz Big Band with some serious players.
I thought, “Okay, how hard can this be? I’ve got chops.”
Yeah… famous last words.
I'll never forget that first day of rehearsal:
Lead sheets with alien-looking chord symbols were being passed around like candy.
I was nervously trying to build chords I didn’t really know, hoping no one would notice.
My anxiety was climbing by the second.
And I knew Theory. But actually using it in the moment? Ha!
Then we started playing a tune — I was praying I wouldn't get called on to solo.
And then all of a sudden out of nowhere, the director pointed at me and said:
"Alright, now take a solo."
I froze. NOTHING.
My fingers didn't move. My brain short-circuited.
Anxiety. Embarrassment. Internal identity crisis.
14 years of training — all gone in one panic attack.
I walked out of that rehearsal with my ego in a body bag.
That moment hit me hard. REALLY HARD. I realized I had NO IDEA how to play.
How was this possible after 15 years of piano playing?!
I took the scenic route through Jazz Frustrationville, and did what most people do:
I tried absolutely everything:
• Transcribing solos, learning transcriptions.
• Learning dozens of licks.
• Working on every technique I could find.
• Learning lots of theory.
• Practicing endless licks, scales and exercises.
• Reading lots of books.
• Practicing to backing tracks for hours on end.
Yet, I still felt like I was spinning my wheels, making little to no real progress.
AND, battling with myself and if jazz was really for me.
Discouragement, uncertainty, imposter syndrome... all the time.
Sound familiar?
It took years of trial and error, and questioning my life choices...
but eventually I figured it out over time and with serious mentoring.
Not from one “magic method”, but from breaking the bad habits,
simplifying and focusing on what actually matters, and learning
how to think and practice like a real jazz musician and true improviser.
Now I help people shortcut that long, frustrating and chaotic phase.
I’ve taken everything from my 30+ years of playing and 15+ years teaching hundreds of students... and turned everything I know into clear, practical systems that actually work.
You’re in the right place especially if you're coming from Classical, or you’re tired of guessing your way through jazz and are ready for professional guidance that GETS REAL RESULTS.
You're not lacking talent, you're lacking a CLEAR SYSTEM
No more spinning your wheels.
No more “I just need one more videos/licks/transcriptions.”
No more wishing your solos actually sounded good.
I want to eliminate every excuse and mindset that has kept you from real progress and transformation.
I’ll help you break through self-doubt, second-guessing, and frustration — and finally start sounding like the player you have always wanted to be:
Improvising with freedom, joy and confidence.
Practicing with clarity and a clear direction.
Avoiding all the traps I fell into and see so many others do… so you don’t have to.
Step one is easy: Download one of my free guides — if you're new to jazz piano and don't know where to start, The Jazz Piano Jumpstart System, and 5 Ways to Instantly Improve Your Solos, today. And let’s start rewiring your musical brain — without the usual confusion.
And if you’re serious-serious? Check out my complete jazz transformation mentorship program, and self-guided courses below.
(FAIR WARNING: side effects may include spontaneous improvisation and finally enjoying the sound of your own playing.)
• The Beginner Jazz Piano Bluesprint - Go from "Where do I start?" to playing real jazz right away, in just a matter of days. Perfect for Beginners and especially Classical pianists coming into Jazz.
• The Complete Jazz Improv System - Learn the best pro-level techniques, the actual principles of improvisation, and all the ways you could possibly imagine for how to solo like a pro. This course completely cures the fear and doubt of not knowing what to play next, "my playing sounds bad", and never running out of ideas of what to play. Comprehensive, and best for early Intermediates - Advanced players.
• Transcribe Smarter - The RIGHT ways to effectively practice what you transcribe, so you get jazz language to actually come out in your playing, and how to not sound like a vending machine of other player's licks. Eliminate all the common mistakes everyone makes with transcribing, and the practice strategies for getting transcribed phrases to actually stick that you will not find anywhere else.
Who am I?
30+ years of piano (and guitar) playing. BA in Classical piano performance from MSU Denver, Masters in Jazz piano performance from The Lamont School of Music, 16+ years of seasoned teaching experience to hundreds of students, and mentoring students who have gone on to become confident improvisers and real performers.
I have studied with some of the best, world-class, monster jazz pianists like Art Lande (a true piano master), Eric Gunnison (Carmen McRae’s first-call pianist), Glenn Zaleski, Peter Martin (Open Studio), and keyboardist extraordinaire Dennis Hamm, from the Grammy-winning band Thundercat.
I have taught and mentored within professional jazz piano communities, including working directly alongside Noah Kellman.
Click here to see a review of my teaching.
My originally composed jazz EP received world-wide airplay on the jazz radio station 89.3 FM KUVO.
Want to hear me play? You can check out my YouTube channel for videos on lessons and performances. I also release original music with my rock jazz fusion band Inner Stellar on BandCamp.
