33 Lessons Before 33

33 Lessons I Learned Before 33

Every year I get a little older, I try to get a little wiser. I wrote 30 Lessons Before 30 and 32 Lessons Before 32 as a way to reflect on what I've learned and share the ideas that stuck with me.  (I guess I didn’t learn anything at 31 😅) This year was a big one. I got engaged, built my business to a new level, got back into running, signed up for a 10-day wilderness survival expedition, and had a lot of the threads from the last few years start to come together.

Here are 33 lessons I've learned before turning 33.

1. Lagging Indicators Are Everywhere

Today's results are the product of decisions you made months ago. This is true for your body, your business, your relationships, and your playing. If you've been doing the right things and not seeing results yet, keep going. The lag is real. And the flip side is also true: if you're coasting on good results right now, the bill from bad habits is already on its way.

2. Your Window Is Shorter Than You Think

This September, I'm flying to Haida Gwaii, British Columbia, a remote island chain known as the "Canadian Galápagos," for a 10-day wilderness survival expedition with my brother. We'll spend five days training with expert guides before being dropped into the wilderness with minimal supplies. No firesteel. A safety net hours away. We'll eat only what we catch, build shelter from scratch, start fires by rubbing pieces of wood together, and spend three days in complete isolation on a remote inlet, all within a region that has one of the densest black bear populations on the continent.

We could have pushed it off another year. But between careers, relationships, and life changes, windows like this close faster than you expect. If there's something you've been wanting to do, stop waiting for the perfect time. It doesn't exist.

3. Do the Misogi

The concept comes from a Japanese purification ritual: once a year, do something so difficult that completing it becomes one of the defining accomplishments of your year. Something that demands everything you have and leaves you genuinely changed on the other side.

The survival expedition is mine. The kind of thing you look back on and say: that was the year.

You don't have to go to the Canadian wilderness. But you should have something on your calendar this year that you're genuinely training and preparing for, something that, when you tell people about it, they immediately ask "wait, you're actually doing that?"

4. Retention Beats Acquisition

Most people, in business, in learning, in life, are obsessed with new. New information, new techniques, new material. But the math almost always favors retention over acquisition. If you're losing 8 members a month, you need 8 new ones just to stay flat. Fix the leak first.

The same principle applies directly to learning an instrument. Chasing new licks and new patterns while your old ones are still shaky is the musical equivalent of a leaky bucket. The players who sound the most fluent are the ones who deeply own what they have, not the ones who know the most material. It's always easier to protect what you have than to replace what you lost.

5. Preparation Is Respect

Real commitment shows up before the event, not during it. I've been running consistently to build the endurance I'll need in Haida Gwaii. I've been studying wilderness survival, learning plant identification, investing in the right gear, and putting in the physical work and study months in advance. By the time I step off that boat, I want to have earned the right to be there.

This applies to anything worth doing. Winging it is disrespect for the challenge and for yourself. The preparation is the commitment. Journey before destination.

6. Willpower Is a Design Flaw

If your system requires willpower to work, it's already failing. Willpower is a depleting resource. It runs out, gets overridden by emotion, and disappears the moment life gets hard. A well-designed system doesn't ask for it.

This year I launched the 90-Day Jazz Blues System in CGA, and something unexpected happened. With so many members working through the same material together, posts started getting 100, sometimes 200 comments. Members were checking in on each other, celebrating breakthroughs, pushing each other forward. Nobody had to motivate themselves in isolation. The system created the momentum, and the momentum built the identity. When your environment is set up correctly, showing up stops being a decision and starts being just what you do.

7. First Impressions Compound

The first 48 hours of any new experience, course, community, or habit, disproportionately determine whether someone stays. At Chase's Guitar Academy, I personally listen to every new member's playing and give them direct, specific feedback. For most members, it's the first time a professional guitarist has ever responded to their playing personally and told them exactly what to do next to improve. That moment sets the tone for everything that follows. Invest heavily at the beginning. How someone starts shapes everything that comes after.

8. More Can Be the Enemy

This year I realized I had created a problem by trying to do too much for my students. New courses, new lessons, new classes, all of it genuinely good, all of it adding up to something overwhelming. When people feel overwhelmed, they don't push through. They quietly disengage. I had to learn that restraint is part of the job. Keeping students consistently motivated matters more than giving them everything at once. Progress requires a path, not a pile.

9. Fulfillment Shifts. Let It.

A few years ago, nearly all of my fulfillment came from performing. This year, the deepest satisfaction comes from creating new ideas for jazz guitar education and watching someone else have a breakthrough using those concepts. It's seeing that moment when a student finally unlocks something they didn't think was possible. Don't hold onto an old source of meaning just because it used to be the main one. Let it shift. Something better might be waiting.

10. Reigniting Someone Else's Dream Is One of the Best Things You Can Do

Most of my students are guys in their 40s, 50s, 60s, and even 80s who picked up jazz guitar years ago and at some point put it down. Helping them get back to it and actually get good reignites something in both of us. Never underestimate the power of helping someone believe in themselves again. It might be the most meaningful thing you do this year.

11. Let the People You Love Be Who They Are

I got engaged this year. One of the biggest reasons it works is that Rachel and I give each other room to be fully ourselves. She knows the Haida Gwaii expedition matters to me and she supports it, even knowing what it involves. That kind of trust is a daily practice, and it works because we both know it is a practice. Love someone enough to let them be exactly who they are.

12. Intentionally Shrink One Thing to Grow Another

Every week I release a new YouTube lesson and run a live class or artist masterclass. Every day I give personal feedback on student videos, answer direct messages, and plan and film entirely new course content, including the upcoming Phase 3 Master Improvisation Blueprint. That output is only possible because I took fewer performance gigs this year. You can't grow everything simultaneously. Sometimes the most strategic move is subtraction.

13. Turn Your Limitations Into Selling Points

My YouTube channel is built around jazz guitar. Posting outside that niche confuses the algorithm and gets suppressed. Instead of fighting it, that constraint became part of the pitch: inside CGA, you get the depth and personalization that a broader platform like Truefire can never offer. Tailored feedback, direct access to me, and a curriculum designed specifically around mastering jazz guitar playing.

14. Build the Free Thing That Leads to the Paid Thing

I recently created a free community, the Jazz Guitar Vault, as a place where guitarists can get real value before ever paying for anything. Free PDFs, backing tracks, mini-courses, and a community of players at every level. The goal is to help people until they're ready to go deeper. For some players, jazz guitar is a casual hobby and the free resources are plenty. For those who want to make real, consistent progress, that's where the right system and expert guidance make all the difference. When they're ready, the door is open.

15. Stop Spelling, Start Speaking

In any skill, there's a stage where you know all the "letters," the theory, the rules, the individual pieces, but you're still spelling words one letter at a time instead of speaking fluently. In jazz, I've identified 9 Essential Jazz Patterns that make up 95%+ of the melodic language used by the greatest improvisers in history. Nine. That's it. The bridge from spelling to speaking is learning how those 9 patterns combine into real musical phrases, the same way a handful of common words combine into everything you say. If your playing, your writing, or your cooking still feels mechanical, you're probably still spelling. (Read the full blog post here.)

16. Integration Over Accumulation

"Perfection is achieved not when there is nothing more to add, but when there is nothing left to take away." — Antoine de Saint-Exupéry

I originally built a course around 31 Essential Jazz Patterns. Then I realized I could simplify it down to 9, with zero information loss. I researched hundreds of transcribed solos, mapped every possible combination of those 9 patterns, and documented specific examples from master jazz musicians in real recordings. That became the Master Improvisation Blueprint. Mastery in any field is about going deeper into fewer ideas and exploring their combinations, not endlessly collecting new material. Most people think the answer is more. Usually, it's fewer things understood more completely.

17. A Strategy That Works at Level 5 Fails at Level 1

What works for an advanced player is often useless, or even harmful, for a beginner. This is true in music, business, fitness, and every other skill. Most frustration comes from applying the wrong strategy to the right goal. Know what level you're actually at, and find the approach appropriate to it. There's no shame in being a beginner. The shame is in pretending you're not. Check out my full post on the 5 Levels of Improv, what I call the Improv Ladder, here.

18. Systemize What Everyone Else Teaches Randomly

In creating my Master Standards Blueprint curriculum, I analyzed over 100 jazz standards chord by chord to figure out the optimal learning sequence, so that each new tune builds directly on the last. Most teachers pick the "important" standards and list them arbitrarily. When only 13% of the chords overlap between two supposedly related tunes like Autumn Leaves and All the Things You Are, you're basically starting from scratch each time. A deliberate sequence changes everything. Whatever you're learning or teaching, look for the system hiding underneath the convention.

19. The Curriculum Is the Product

A collection of great lessons is not a curriculum. The order matters. The connections between concepts matter. What you leave out matters. Spaced repetition and review need to be built directly into the sequence, not left to the student to figure out. The role of a great teacher, or a great curriculum, is to lay out the path. The student's only job is to walk it.

20. Long-Term Thinking Is a Competitive Advantage

Most people optimize for the day or week. However, if you optimize for this decade, you're playing a different game entirely. The decisions that feel slow now, building a content library, deepening relationships with top jazz guitarists, refining a system, are the ones that compound into something nobody can replicate quickly. Think longer than your competition and you'll outlast them.

21. Run Your Own Race (Literally)

I got back into running this year and started working on my mile time. There's something clarifying about a purely individual metric, just you and the clock. No shortcuts, no comparisons, no one to benchmark against except yesterday's version of yourself. If you don't have a physical practice that gives you honest, immediate feedback, find one.

22. Write to Think

Writing forces you to discover what you actually know. Thinking alone lets you stay vague. The act of putting ideas into words demands a level of clarity that doesn't exist in your head until you try to explain it on the page. If you're confused about something, try writing about it. The confusion won't survive the process.

23. AI Sharpens Thinking When You Use It Right

I've used AI extensively this year, for research, organizing ideas, drafting strategies, building systems. But the judgment is always mine. The best way to use it is the same way you'd use a great conversation partner: let it help you think, not think for you. The person who combines good judgment with better tools and better data, wins.

24. Play Long-Term Games With Long-Term People

"Play long-term games with long-term people. All returns in life, whether in wealth, relationships, or knowledge, come from compound interest." — Naval Ravikant

I wrote about this in last year's post, but this year I felt it in a new way. The members of CGA who've been around longest are the ones lifting everyone else. They answer questions, celebrate other members' wins, and set the tone for what's possible. The culture of a room is built by the people who stay. Choose who you spend time with accordingly, and then invest in those relationships for the long haul.

25. Develop Range

Photography taught me that contrast and balance are musical principles as much as visual ones. The same instinct that tells me when a photo needs a shadow to make the light pop tells me when a solo needs space to make the next phrase land. Physical training taught me that consistency beats intensity, that you can't PR every session, and that recovery is part of the work. The broader your range of experiences, the more bridges you can build, for your students, and for yourself.

26. Beginner's Mind Is a Cheat Code

This year I played my first gig on bass, spent a couple months learning Italian to a low conversational level, picked up a sling (not a slingshot, an actual leather sling), and reignited my photography practice during a trip through Rome and Florence. Every time you pick up something new, you remember what it feels like to be a beginner, and that makes you a better teacher, a more patient learner, and a more interesting person. Novelty is fuel.

27. Do Things That Don't Scale

Paul Graham wrote about this for startups, but it applies to teaching too. I give personal feedback on student videos every morning. I respond to direct messages myself. I listen to where members are struggling and adjust the curriculum around it. None of that scales efficiently. All of it is the point. My goal is to get exceptional results for the students I can genuinely serve, not mediocre results for as many people as possible. My commitment to doing things personally is the source of the results.

28. Challenge Doesn't Always Come From Where You Expect

I still love performing. But it's gotten harder to find gigs that are musically challenging in the way that used to drive me. The real challenge now comes from building something, solving new problems, and helping students break through plateaus they've been stuck on for years. When your original source of challenge goes flat, look for where the next one is hiding. It's usually closer than you think.

29. The People Who Stay Prove the Product Works

My longest-tenured members have a retention rate above 97%, essentially unheard of in online education. They're staying because the system works and they're still getting better. When the right people find CGA, there isn't anywhere else that offers what they get here. Some people try it and realize it's not the right fit, and that's fine. But for those it's built for, they stay because leaving would mean giving up the thing that's actually moving the needle. Don't take my word for it, read what members have to say.

30. Invest in the Experience, Not the Story

The survival expedition is not Instagram content. I'm bringing my camera because I love photography and wildlife, not because I need the footage. Some experiences are worth having for no audience at all.

31. Your Interests Are Your Curriculum

Guitar, running, photography, survival skills, language learning, martial arts, cooking, mathematics. Each of these has made me a better teacher, a sharper thinker, and a more interesting person. Every pursuit gives me a new lens, a new analogy, a new way of seeing an old problem. The most dangerous thing a teacher can do is stop being a student. Keep adding new rooms to the house.

32. Everything Requires Maintenance

Your skills, your health, your relationships, your finances, your tools. All of them need ongoing attention to stay sharp. The moment you stop putting in the work, things start quietly slipping. Not dramatically, not all at once, but consistently. Entropy is patient. The question is whether you're paying attention.

33. The Best Year of Your Life Should Always Be Next Year

This year was a great one. I got engaged, grew my business, helped students around the world rediscover something they love, and committed to an adventure I've been training seriously for. The whole point of a good system is that next year builds directly on everything you did this year. The compound effect is real. Keep the process right, and the best is always ahead.

If this post resonated and you want to see the system I've built for learning jazz guitar, check out Chase's Guitar Academy. I'd love to help you get unstuck.