Mastering Rap by Mandeep Singh (Medical Student, KCL)

Chris Lovejoy
6 min readAug 5, 2018

About 3 years ago, I developed a deep interest in learning to rap well. I emphasize the word ‘developed’ because up until this point, I was waiting to passively discover a passion which would somehow carry me towards expertise.


The main initial ingredient — from my experience — needed to produce expertise is authenticity. Authenticity is essential because any serious undertaking of a new skill will necessarily face you up against failure and self-doubt. The new skill needs to be important enough to make this tolerable. With rap, I reached a point where I needed to know my thoughts to overcome a heavy bout of stasis, and rap allowed me to do this whereas my primary musical outlet — the saxophone — did not. If I started rapping to impress people, I would not have cared enough to move through the many stumbling blocks.

This initial phase of learning is relatively stumble-free. Starting to write is an exhilarating experience. There’s a certain beginners luck as you first see your thoughts coalesce into meaning on a page, and I found the emotional salience of this often lead to surprisingly good writing. Strong feelings and good writing go hand in hand. With authentic motivation to learn the skill, this was therefore an easy period of development. However, it is short-lived. Eventually, you find yourself with a strong feeling but lacking the tools to express it. This is the first major stumbling block and you must ask yourself a question: do you have something you want to say enough that you are willing to put in the hours needed to make the craft work for you?

Maximising control by starting with easy subject matter:

You will not always be able to say what you want to say. There are many reasons for this. Strong feelings are fleeting, difficult to pin down and often come along at inopportune moments, such as when you’re in the middle of an important meeting. Strong feelings also take a basic level of linguistic fluency to express coherently. Babies feel extremely strongly but make relatively poor rappers. You therefore cannot rely on inspiration and feeling to learn the craft. You must use discipline so that your pen is sharp enough to actualize inspiration when it sporadically comes.

How did I start doing this? I needed a larger, more stable target on which to practise than my thoughts and feelings. I chose mundane objects and events. My thinking was “The better I can describe the outside world beautifully, the better I will be able to describe my thoughts and feelings”. And so I started writing small sketches about mundane objects and situations regularly. They were tiny (4–8 bars) and only for me. This meant that each ‘practice session’ had a low entry threshold. Using mundane situations is useful because they are your situations. Shakespeare never wrote about the man sitting opposite him on the central line so you cannot compare your sketches to his and get disheartened. Here’s an example:

“I’m on the tube

In front of me is some dude bopping his head

To music no-one can hear.

Probably not even him

He’s got no headphones in

Wearing some red shirt thing

with flanneled collars

Shall I holla? Or get the next verse in?”

This is much less intimidating to write about than the Middle Eastern conflict, for example. By all means, writing about hefty topics is important but can be frustrating at the start. Writing a verse like this every day, however, is a much less heavy — and equally productive — commitment. Many of my best verses were stumbled upon by starting to describe something totally useless. It settles the self-doubting, neurotic mind, allowing what you truly care about to be lifted to its surface by the constraints of writing in rhyme. You may notice it happening quite soon into the exercise.

Utilise mundane pockets of time to overcome non-creative limitations:

Rap is both spoken and written. Eventually, your writing becomes increasingly rhythmically complex and your mouth will struggle to keep up. For this purpose, I started reciting my verses with a pencil in my mouth whilst doing mindless tasks such as household chores, or walking my dog. The wonderful thing about rap is that it can be done at any time and so life becomes far more purposeful. Missed my bus? Awesome. 10 more minutes to practise that verse I couldn’t get down two days ago.

Studying vs. listening to music:

Alongside output, it is important to develop how you listen to music. This naturally started happening as I wrote more and more. I even started ‘enjoying’ music I don’t particularly like. It’s useful to be mindful that even if you despise this music, someone somewhere listens to it otherwise it wouldn’t be out there. What about it could make it resonate with someone? The delivery? The cadence? The emotion? It’s fun to figure out!

Even more importantly, if music resonates with you, figure out why. I believe that if something strikes you emotionally, there’s an element of your truth in that artists expression. If a rappers line makes you want to move, learn it and repeat it until its cadence in locked into your body because that is the rhythm your body is aching to produce. If a piano melody hits you, sing it until the same thing happens. Music is all rhythm, melody and harmony. You can learn to rap from a saxophone solo if you want to. It’s a matter of how you pay attention, not what you pay attention to.

Create competition:

It is important to surround yourself with people who are working on the same skill. This will put healthy competitive pressure on you to keep going, as in a big enough group there will be someone who is at your skill level or similar. I did this through my university rap society and by performing wherever possible. Rapping about how you’re better than your peers is also a great and fun muse to work on.

Break down your limitations:

If you’re not improving, take a step back and really examine why. I’ll give you an example. I went through a phase of losing the “catchiness” of my verses. They felt more like rambling sentences and thoughts than crafted, musical verses. Upon close examination, it was because I got comfortable enough with rhyming that I could write a decent verse fairly mindlessly.

To overcome such limitations, make it harder for yourself. When you’re not getting stronger at the gym, you either up the reps or up the weight. Similarly, to get past this bout of stasis, I decided I would find a beat and sing out a rhythm. I would then write a verse using only that rhythmic. This forced me to think about the musicality of my words as a priority again, and my writing improved dramatically.

In summary, it is the desire to learn must be authentic. Start by writing often and little, and on subjects which do not paralyse you by their sheer scope. Use non-creative time to iron out the mechanics (i.e. enunciation, breath control) of rap. Do not take in the work of others passively, but study it and aim to learn something from every song you listen to. Most importantly, when you feel yourself becoming comfortable, make it harder for yourself. But writing is a very, very personal thing. As you start writing, you will undoubtedly figure out your own way of getting around problems and growing. As long as you’re authentic, curious and can tolerate failure, it will be a very rewarding journey indeed.



Chris Lovejoy

Data Scientist + Junior Doctor in London, Cambridge medicine grad, striving to improve healthcare through technology and education.