M2M Day 305: Attempting to freestyle rap continuously for three minutes

This post is part of Month to Master, a 12-month accelerated learning project. For September, my goal is to continuously freestyle rap for three minutes.

Today, I start a new month and a new challenge: With only one month of practice, can I freestyle rap continuously for three minutes?

Why freestyle rap?

I tried to think of the challenge that I would be the most uncomfortable and embarrassed to post on the internet, and then picked that.

Publicly freestyle rapping is definitely pushing me way outside my comfort zone, and will be quite apologetically horrible in the beginning, but this is exactly what makes this challenge fun and worthwhile.

Why 3 minutes?

Three minutes is the typical length of a radio song, so it seems like a nice benchmark. Of course, most rap songs are 50% hook and 50% pre-written verses, but still, three minutes seems reasonable.

Defining success

Freestyle rapping is more of an art than anything else, and, as an art, doesn’t have clear criteria for objective “success”. Thus, the best I can do is define the rules of the challenge so that they align with what I want to be able to do.

To complete this month’s challenge, I must fulfill the following three criteria:

1. My freestyle maintains continuous flow for three minutes. Continuous flow means that there are no hiccups or awkward breaks in my freestyle, just a smooth constant flow of words for 3 minutes.
2. My freestyle isn’t completely nonsensical. The rap is glued together by some sort of loose narrative or meaning. (I may choose to use a random topic generator to seed my rap. In this case, my freestyle should build its narrative around these generated topics).
3. My freestyle rhymes. I value “flow” over rhyming, but it’s very hard to have a long sustained flow without a liberal use of rhyme. In other words, I should aim to land each line on a rhyme, but this isn’t an absolute requirement. With that said, a failed rhyme is a very good way to interrupt the flow, which I’m strictly not allowed to do.

These three criteria are highly subjective, so I will do my best to judge myself as neutrally as possible. At the end of the day though, I have a taste for what good freestyle rap sounds like, and will measure myself against that.

My starting point

Other than a few casual freestyle attempts at summer camp ten years ago, I’m starting from scratch.

Here’s a short video of today’s attempt, rapped over a free beat from YouTube. In the video, you’ll see that I don’t yet have flow, the rap is completely nonsensical, and my rhyming is simplistic, so I still have plenty of work to do.

While this is a bit painful to watch, it can only get better from here…

Read the next post. Read the previous post.

Max Deutsch is a product manager at Intuit, the creator of Somebody.io and Rightspeed, and the guinea pig for Month to Master.

If you want to follow along with Max’s year-long accelerated learning project, make sure to follow this Medium account.