I am going to do something I rarely allow myself to do. I am going to write without first thinking about what I will say.
You see, I have learned over the years to write masterfully. That is not to say all of my writing is masterful, merely that I know how to do it, and when I don’t, the fault is entirely mine. Mastery, you see, is the culmination of myriad small moments of inspiration, a lifetime’s work so to speak. However, the more important aspect of mastery is knowing what not to say, how not to write, which brush strokes to omit. We achieve mastery not because of what we do, but because of all the mistakes we avoid.
That, my brethren, requires thought.
So I will write this essay on mastery in a less-than-masterful way, so that I can get at the aching core that burns me, and that I might finally say the words in the right order. There is ample time later to remove that which I should not have said. But this is about feeling, and I know that is the case because I am typing this better when I close my eyes than when I open them. A lifetime’s writing has taught me that is when I am my best–when I trust and then do.
When Tracy Chapman was 24, in 1988, she, a relative unknown, stepped onto the stage of Wembley stadium with an acoustic guitar and began to play. The crowd, as English football crowds are want to do, had begun chanting some thing or the other and it seemed to rattle Tracy a bit. She was used, by then, to people’s not giving her their full attentions. She’d reached the level of success she had by being a busker around Harvard University. Uni students usually don’t have full attention to give, and if they do, it’ll almost certainly not be to someone on the street who’s playing for money. So Tracy began singing “Fast Car” anyway, and she didn’t elevate her voice. She sang in her normal quiet way, competing for attention with the rowdy crowd. Her voice broke.
Then she shut them all the fuck up.
(The audio in the YouTube video, above, is quiet. You may need to turn up the volume on your device. )
It was a small moment of inspiration, a whisper of mastery to come. Over the years, she sang the tune hundreds of times. It was her signature tune, after all. The tempo slowed, her voice deepened, but the same Tracy was there in the song: quiet, rebellious, aching. What was missing, however, were the cracking vocals, the wavering notes, the fear. She owns the song now, and even when she joined Luke Combs on stage to sing “Fast Car” at the 2024 Grammys, it was her song. Luke was there, and good, but Tracy? She herself had nothing to prove.
Dizzy Gillespie once said, “It’s taken me all my life to learn what not to play.”
I’m guessing if you bothered to click on this post, then you’ve seen or heard that saying somewhere. What people don’t tell you when they quote him is the context of the statement. Dizzy was speaking of mastery, specifically, mastery of his instrument and his music. Such mastery was important, he said, “… because when you think of something to play, you must say it quickly because you don’t have time to figure how, chords changing so quickly.” Mastery, then, relies on experience. Dizzy broke the complex world of playing masterful improvisational bebop jazz into six skills: the instrument, style, taste, communication (with an audience), chord progressions (technical know-how), and rhythm.
So why does mastery take a lifetime? Surely there are prodigies who can learn these skills quickly. I would agree that yes, prodigies can. And I would even go so far as to suggest that one must show precociousness in one or more areas to have any hope of one day being a master of one’s craft. (This assumes one has the opportunity to be precocious, which I’ll talk about later.) In short, being a prodigy doesn’t make you a master, but it’s likely you’ll never be one if you never had a prodigy’s gifts.
But don’t confuse the two things, because they are NOT the same. Think of a prodigal athlete, for instance. If you weren’t born with elite athleticism, like being bloody tall, or some elite athletic skill, like shooting a basketball, then it’s unlikely a lifetime’s work will see you reach the Hall of Fame for your sport. However, there are probably more prodigies who never reached the Hall than there are HOFers who never worked hard or those who didn’t show evidence of innate talents early on. Mastery takes a lifetime’s work. Those athletes in the Hall of Fame likely worked harder than all of their skilled comrades irrespective of natural gifts.
If you aren’t among the most dedicated people in your discipline, you will NEVER NEVER NEVER achieve mastery. I won’t hedge this. I know of no one who reached the pinnacle of their work without being more dedicated, more detailed, more prolific, more self-educated, and more determined to get there. God makes you capable. You make yourself successful.

Let’s go back to Dizzy for a moment. He broke jazz mastery into its six base elements. How long do you reckon it took him to figure out what those elements were? Answer: his whole life. By the time you know what is required to reach mastery in your field, you’re already a master. If you think you know everything, then you absolutely do not. The last thing you will ever learn in a field are all the “unknown unknowns.” These are the things that no one realized were even part of the equation.
It’s just a small matter of time to learn all the things people tell you to learn. Even when they tell you “no one knows” a thing, they are at least aware of what needs to be probed. But real masters have learned the things that others didn’t even know counted.
As a street photographer with 55 years’ experience, I know the most important aspect of shooting street is to convince people on the streets that you are a pro. Once they believe you are acting in a professional manner, they stop paying attention to you. Only then can you position yourself to be in places where good compositions happen. I can teach you composition, but I cannot teach you how to know what one looks like in a fraction of a second. Your brain does that without your conscious intervention. Teaching it to do so is based on tens of thousands of repetitions. Getting the opportunity to make a great composition on the street requires not creeping people out in the first place. Those things take a lot of time.
Get to work.
Back to Dizzy. After decades of playing in front of and with people, he summarized everything he learned into not just six categories, but effectively into a few groups that can be applied anywhere.
- Know your tools. Whether it be a trumpet, paintbrushes, basketballs, or cameras, know how they work, how to handle them masterfully, and what to do with them in all situations. If you can’t handle your tools masterfully, you aren’t a master. If you need expensive tools to do (occasionally) great work, you probably aren’t even consistently good yet.
- Eliminate steps that don’t help. Masters learn how previous masters operate, but they always look to improve. They don’t play phrases that don’t the improve the song. Why would they? They don’t make passes that don’t lead to better shots. Why would they? They don’t take photos that can’t be fixed in editing. Why would they?
- Know what a masterful work looks and sounds like. If you don’t know what is good, you can never be good. If you can’t tell a boring reference photo from a great one, how can you make a great painting from it? If you can’t recognize great literature how can you write it? Musicians have to know elements of good music–rhythm, chord progressions, time signatures, pitch, etc. Photographers and artists have to know what great compositions are. Those who don’t, no matter how skilled, won’t become masters. If I know what to do, getting there is just a matter of reps. If I don’t know what to do, all the reps I take may simply be reinforcing my mediocrity.
- Know how to communicate with other agents of your success. For Dizzy, it was with the audience and the other players. But it was also with composers, arrangers, and recording engineers, with sound and lighting guys. Mastery is a cooperative exercise. I write books, I take photos, and I make paintings. None of them are good unless the people who see them agree. To become a master, I must learn what moves humans in an artful, consistent, and masterful way.
Life creates many shortcuts. Few will ever take you where you’re trying to go. Achieving mastery isn’t as simple as doing something 10,000 times or for 10,000 hours. However, keeping that mindset is the best way to get you on the right path. I think it’s highly unlikely you will ever spend that much time doing anything for which you have no natural gifts, so don’t spend time wondering if you’re talented enough. Being a prodigy is only cool when you’re a kid. After that, it’s all about the work. If you find yourself 8,000 reps into a skill that you think you’re learning to master despite never having been a prodigy, you’re wrong. You were. It’s just that no one told you. That spirit inside you spoke the words, however, which is why you are still at it. Greatness persists; mediocrity gives up.
Discovering you have prodigal talent takes a lot of good fortune. If you never get in a music class, you may never learn you could have been the next Dizzy. Even if you do, there is only one first chair and the world often forgets that chairs two through ten are still freaking awesome. Sadly, there are fewer opportunities in the world than there is talent. If your heart burns to be an artist of some kind (or any of a million other pursuits), learn what greatness looks like, how it is achieved, and then sit down and do the work. Don’t assume you can’t. All assumptions we make about ourselves prove to be true, with reinforcement.
I’m not especially religious, but I am very spiritual. I might not believe in your God, but I pray to mine at least daily. And after most of a lifetime, I’ve come to believe that the God of Artists, whoever that is, won’t put anything to your heart that you aren’t meant to achieve.
If you want it, make it happen. Today is a good day to start.










Dad used to teach guitar and for his more advanced students he taught a bit of jazz. Using recordings of Dizzy, Miles, Ella and Duke, he tried to instill what jazz was and how to get there. So many times while working at his studio I overheard Dad telling a student “too many notes” “keep it simple until you feel it.” At some point all of them would say that he (Dad) was so effortless and just knew EVERYTHING there was to know about creating good jazzy work.
EVERY time, he corrected them, saying that ‘the day I wake up thinking I know it all is the day I quit playing. ‘
The videos were emotional for me. I felt her fear and also her determination in that first vid. The second video is celebrating HER, alongside a white man who sings county music and who was giddy sharing the stage, sharing her anthem. Like a kid. 🥲 Thank you, Bill.
I enjoyed your lessons today.
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Thanks so much for reading and commenting! It was great seeing the two videos on Tracy and feeling the difference within her. It’s what led me to thinking about how one becomes a master in the first place.
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shiboof@oldpostie.bluesky.social here…..
😉👏
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That’s some piece of writing, Bill! A lot to think about.
I particularly like it that you said, “If you don’t know what is good, you can never be good.” As you say, you have to hear it or see it first, as the case may be.
But it’s not just about when you want to do start to undertake something creative. I’m sure you’d agree that we can apply that sentence of yours also to a general education in the arts, because if you’ve never been exposed to what is good, you can never know what the good stuff is out there to be appreciated, in the first place.
It’s not for me to judge, of course, but I often feel sorry for those I see, who, for some reason or another, have missed out on these things while growing up.
https://bsky.app/profile/andrew75862.bsky.social
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I agree with you. I pointed this toward the arts, but I could have just as easily written about the business world. Achieving a master’s level takes work, attention to detail, a positive attitude, and openness. It kind of doesn’t matter what you’re trying to master.
Thanks for reading it and commenting!
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