This title may have surprised you, but I’m dead serious about this. I have never failed to tell this to any one of my students. There are no exceptions to this. Every musician should indeed learn at least 1000 songs. I’m going to lay it out clearly for you why you need to do this.

Perfection, the Enemy of Excellence

The typical way they teach people to play an instrument has to do with playing a very small amount of difficult songs. I’ve seen people take a year or more to learn only one very complex piece. This is 99.9% wasted time in the sense of your long term development as a musician and as a creative person! This person should have learned a few hundred simple songs in that same year instead. That piece of music would no longer seem so complex. They could then turbo-learn that one song! 
It’s extremely counter-productive to obsess too much over the tiny details. It’s so much better to get the job done and fix it later if necessary. This is especially true in music. It’s better to be able to get through it and move on to something else. The details will naturally get cleaned up more and more with time, as you improve in all aspects as a musician. This is an error that is way too common, even in advanced musicians. 
This is even more the case in group situations. In today’s world there’s this kind of false stigma about “playing covers”. The problem is that nobody has ever been successful as a band without a huge repertoire! I have never seen a band that only plays original music that sounded any good, and I mean that absolutely! They ALWAYS wind up sounding like a bad copy of the music they most like to listen to. Avoid this trap at all costs! Both individually and within a group, you should always be striving to make your repertoire as big as possible.

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Learn How To Learn

It’s all about the meta-learning. When you learn a lot of songs, you always wind up learning how to learn them faster and better. This is a lot more important than you may think at first.
If you find yourself working as a professional musician, you can count on one thing. You will be often called upon to learn a lot of material in a very short amount of time. This is one of the main things that separates serious pro musicians from amateurs. And what prepares you for this rigor is having already done the same in your practice regimen. 
The truth is, as a pro musician, you almost never have to play anything hard to play on your instrument. But, it is very common to have to learn a lot of simple music in a very short time. Your practice routine needs to reflect this. 
Another strategy is to learn patterns that apply to many different musical settings. 


The Big Picture

A famous person once said (very true): “the majority of the ideas you have are going to be stupid and wrong”. This is painful but necessary advice for us, especially those of us working in music. We love to think that everything we create is special and beautiful, but this is not reality. The reality is: we are going to have to write 50 or even 100 songs to write one good one. It’s also important to know the musical past so that we don’t wind up imitating it. 
1000 songs may sound like a lot. But this is because these days, technology does a lot of stuff for us. This has led to some very low expectations among musicians. Even 50 years ago, this was pretty much the norm for any serious musician. And, all the artists who conquered the world back in the day have 1000 or more songs in their repertoire. This is actually one of the key elements that successful artists share. 
I can honestly say that not one person who ever took my advice on this matter has ever regretted it. 

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