Max Deutsch
38 min readNov 8, 2017


On September 1, 2017, I asked myself the question: With only one month of practice, can I freestyle rap continuously for three minutes?

On September 29, 2017, after 11 hours of practice, I found out that the answer was yes.

During the month of September, I documented my entire learning process in a series of 30 daily blog posts, which are compiled here into a single narrative. In this article, you can relive my month of insights, frustrations, learning hacks, and triumphs, as I strive towards monthly mastery.

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…

As I discussed yesterday, this month, I’m trying to improve my freestyle rapping abilities (effectively from scratch), so that I can continuously freestyle for three minutes.

It’s not exactly clear yet how I can best improve my rapping abilities, but I have a few ideas that I will iterate on throughout the month. In particular, I’m currently thinking about my training in two parts:

1. Writing

While there are likely exceptions, the best freestyle rappers are usually prolific writers of rhymes. In other words, it seems that writing is often the best way to build up a lexicon of rhymes, ideas, and punchlines that can be used within a freestyle.

Thus, especially at the beginning of the month, I plan to spend a significant amount of time writing rhymes, instead of freestyling them.

To be clear, I’m not pre-writing freestyles that I will later just regurgitate. Instead, I’m using the writing process as a more controlled way to strengthen the freestyle-oriented patterns in my brain.

In the same way, an improvisational jazz piano player might practice by learning or writing new licks, not so they can pre-prepare an entire solo, but so they can pre-explore certain possibilities and better understand the relationships between notes, etc.

Simply, this part of my training is designed to build up my freestyling vocabulary.

2. Metronome training

Like in many previous challenges, I plan to use a metronome to structure much of my practice this month.

By using the metronome as the beat for my freestyle, I’ll be able to build my freestyling abilities and confidence at a slow tempo, and then ramp up the speed in a controlled and measurable way.

I’m not yet sure what my target metronome speed is, but I suspect it will be something like 100 BPM.

Simply, this part of my training is designed to practice deploying my freestyling vocabulary within an optimizable framework.

As I continue through the month, I’m sure this plan will develop further and take on more parts. But, for now, this seems like a good starting place.

Since this month’s goal is more artistic and subjective than most, I’m mainly propelled by my taste in the art of freestyle, more so than a particular quantifiable metric. In other words, my goal this month is to close my “Taste Gap”.

Let me explain…

The Taste Gap

This idea of the Taste Gap was first introduced by radio host Ira Glass. He explains:

Nobody tells people who are beginners — and I really wish somebody had told this to me — is that all of us who do creative work … we get into it because we have good taste. But it’s like there’s a gap, that for the first couple years that you’re making stuff, what you’re making isn’t so good, OK? It’s not that great. It’s really not that great. It’s trying to be good, it has ambition to be good, but it’s not quite that good. But your taste — the thing that got you into the game — your taste is still killer, and your taste is good enough that you can tell that what you’re making is kind of a disappointment to you, you know what I mean?

…And the most important possible thing you can do is do a lot of work — do a huge volume of work. Put yourself on a deadline so that every week, or every month, you know you’re going to finish one story. Because it’s only by actually going through a volume of work that you are actually going to catch up and close that gap. And the work you’re making will be as good as your ambitions.

In other words, the ultimate creative goal is to cultivate the skills necessary to produce art that you yourself can appreciate and enjoy (where this appreciation is based on a particular taste for the artform).

This is exactly how I feel about my freestyle challenge: I have a particular taste for the freestyling artform, and would love to develop the abilities to create this specific kind of art.

The problem is that my taste for freestyle is extreme and difficult to fake…

The Two Artistic Strains of Freestyle Rap

In general, in my mind, there are two main approaches to freestyle rapping, which are nicely demonstrated in the video below.

In the video, Lin-Manuel Miranda (of Hamilton fame) and Tariq Trotter (lead MC of the Roots) engage in a friendly rap battle as part of the “Wheel of Freestyle” bit on Jimmy Fallon’s Late Night show.

Lin perfectly represents the first approach to freestyle rapping: Punchline-driven Freestyling. This style of freestyle rapping relies on a standup comedy-style set-up and punchline structure.

Typically, to effectively deliver a punchline, the desired punchline (and specifically, the last word of punchline) is determined, then a rhyme for that last word is selected and used in the set-up. In other words, for a punchline to land hard, it needs to be thought of first, but rapped second, rhyming with the set-up that was thought of second, but rapped first.

Punchline-drive freestyling can be effective even with very minimal or basic rhymes, as long as the last word of the punchline lands smoothly. The challenge of this style of freestyling is quickly crafting the perfect punchline while simultaneously rapping the setup.

On the other hand, Tariq better demonstrates the second approach to freestyle rapping: Rhyme-driven Freestyling. This kind of freestyling doesn’t require such a strong payoff or punchline at the end of a stanza. Instead, this type of freestyle packs its punch sonically, built from a stack of complex rhymes.

In other words, within this approach, the listener’s satisfaction is usually more evenly distributed throughout the stanza (rather than spiking at each punchline) and tied to the depth and complexity of the ongoing rhyme scheme.

This type of freestyling is a little bit more self-involved, caring less about using the medium as a narrative vehicle and more about fully exploiting the medium itself.

Importantly, these types of freestyle rapping aren’t mutually exclusive, and ideally can coexist for the ultimate freestyle rap. (In their written work, both Lin and Tariq use both approaches simultaneously and effectively).

But, of course, it’s not easy to leverage both approaches within a genuine freestyle, so it’s very normal for an artist to optimize for one approach or the other.

In the video, check out how Lin and Tariq optimize for the different approaches…

While I like both performances, in this case, I prefer Tariq’s (even though Lin had a better reaction from the crowd). I’m just a big sucker for complex rhyme schemes, and I appreciate this part of the artform the most.

Basically, my taste is aggressively skewed towards rhyme complexity, wordplay, and sonic performance, which means I much prefer to develop my rhyme-driven freestyling abilities this month.

The challenge is that there is very little gray zone for complex rhymes — either it rhymes or it doesn’t. Punchlines are more generous — you can have a bad punchline, an okay punchline, or a great punchline.

As a result, I think it would be easier to fake the punchline-driven rap, even if my punchlines were mediocre. (This is not to say that good punchline-driven rap is easier… But that rhyme-driven rap is less forgiving).

Nevertheless, the Taste Gap that I want to close is on the complex rhyme side of the spectrum, so it will be interesting to see how this taste affects my progress this month.

Yesterday, I described the two styles of freestyle rapping: The punchline-driven approach and the rhyme-driven approach.

Both styles require the near-instant ability to find sensible rhymes while simultaneously rapping, so I’ve been training this rhyme-finding ability for the past few days.

Here’s my process:

  1. Set a metronome to 60 BPM (my current practice tempo). I’m using the built-in metronome on Google’s search results page.

2. Next, use to generate random words.Specifically, generate five words at a time, all of which should have two syllables.

3. Finally, start rapping, incorporating each of the five words into the freestyle. Importantly, each of the listed words needs to be the punchline rhyme (i.e. the second rhyme of the rhyming pair), so a set-up rhyme needs to be crafted first. This requires very quick thinking, which is ultimately the capacity I’m training.

All together, here’s the result:

This is certainly an improvement on my video from a few days ago. In fact, there are a few moments that are half decent (and also some moments that aren’t).

Over the next few days, I’ll ramp up the speed of the metronome and see if I can keep up.

Side note: I seemed to have developed a tic, where I constantly use the word “spitting” in reference to “spitting rhymes” (i.e. freestyle rapping). I’m not sure if this is a bad thing or something I should try to avoid, but I thought I should at least acknowledge it.

In the past few days, I’ve filmed two videos of me freestyle rapping (this one and this one). In both videos, rather than calmly crafting rhymes into the camera, I hyper-concentrate, bulge my eyes, and half scream into the microphone.

In other words, even though my freestyling is getting better, my persona as a freestyle rapper is certainly not.

Not that I need to be cool when I rap (that seems like a wildly ambitious goal), but at least I could have a reasonably normal voice and demeanor.

There are two approaches I can take to develop a more tolerable rap voice:

  1. Continue practicing without worrying about my “rap persona”. As I get more comfortable, I will relax and ultimately find my voice. Basically, I just punt on this part of my performance right now.
  2. Force myself to practice with a calmer demeanor immediately, likely inhibiting the speed of my rhyme crafting in the short-term, but requiring my brain to quickly adapt to the new circumstances.

While I need to suspend my disbelief a bit more for option #1, I think I’m going to stick with my current approach and focus purely on the rhymes.

I have plenty of time to get comfortable and relax into my voice, and if I don’t, maybe I should just embrace my less traditional rapping voice. After all, Eminem committed to his naturally nasally voice, and that seemed to work out for him.

Then again, Eminem is an incredibly crafty freestyler, so he has that going for him. I’ll just need to keep working, so I can have that going for me as well.

Today, I reviewed the footage from the past week of my freestyling practice sessions, and have found particular sets of rhymes that I naturally tend to lean on more heavily.

These sets of rhymes are centered around the self-referential and very hip motifs of “I am a good rapper” and “Watch me as I flow so good”. While these sentiments aren’t the most profound, they make for reasonable freestyle filler.

In particular, I seem to be relying on six main sets of rhyming words. Here’s how I’ve been using them…

1. “I’m spittin’ it, hittin’ it, rippin’ it, flippin’ it”.

I usually break out this set of rhymes if I want to add in a quicker, punchier line or two.

2. “You knowing, I’m flowing, never slowing, keep it going”

Ironically, I use this set of rhymes as a flow maintainer, giving me time to think about where I want to take the freestyle.

3. “I’m spittin’ it smarter, hittin’ it harder, taking this rhyme farther”

This set of rhymes has more space to breath, helping me slow back down from a fast section.

4. “I’m taking it faster, after, all of the laughter…”

I keep finding myself using some line like this, but still haven’t figured out how to make this set of rhymes make sense.

5. “Let me teach you a lesson, did I mention…”

This setup has potential, but I can’t seem to resolve the line to anything substantial.

6. “At the end of this challenge, I’ll be spittin’ with talent, on Jimmy Fallon”

These rhymes are a bit softer, but with a little vowel-bending, it’s no problem.

Since I naturally find these six sets of rhymes while I freestyle, rather than immediately expanding into new sets of rhymes, I should first further flesh out my options within these sets. That way, when my instincts naturally kick in, and I find myself repeating some version of these lines, I’ll be able to keep them going for longer.

So, today, I headed over to and found additional rhymes that I could use in each category. (Note: My natural ability to bend vowels seems to be pretty good, so softish rhymes are fair game.)

Here’s what I’m working with now…

1. “I’m spittin’ it, hittin’ it, rippin’ it, flippin’ it”.

Hittin’ it, spittin it, whippin it, flippin it, rippin’ it, shippin’ it, grippin’ it, drippin’ it, licorice, ridiculous, conspicuous, gibberish, hit or miss, meticulous, hideous, triplets,

2. “You knowing, I’m flowing, never slowing, keep it going”

Flowing, going, knowing, showing, slowing, throwing, blowing, owning, Boeing, snowing, bowling, rolling, patrolling, strolling, hoping, scoping, stolen, trolling

3. “I’m spittin’ it smarter, hittin’ it harder, taking this rhyme farther”

Smarter, farther, harder, father, darker, parlor, martyr, armor, charmer, farmer, partner

4. “I’m taking it faster, after, all of the laughter…”

Faster, laughter, pastor, after, blaster, master, plaster, disaster, rafters

5. “Let me teach you a lesson, did I mention…”

Mention, lesson, blessing, dressing, messing, testing, texting, guessing, pressing, impressing, depressing, obsessing, professing, progressing, flexing

6. “At the end of this challenge, I’ll be spittin’ with talent, on Jimmy Fallon”

Talent, challenge, Jimmy Fallon, talons, patent, combatant, scavenge, gallons, Woody Allen, Alvin, Calvin

The next step is to practice freestyling within each category over and over, hopefully strengthening the synapses between the already wired words and the new rhymes.

I’ll try to post a video tomorrow demonstrating exactly this.

Today, let’s start with the video (6 minutes of decent, nearly continuous freestyle rap) and then I’ll discuss afterwards…

A few things to mentioned about the video:

  1. Since Day 1, I’ve already drastically improved my freestyling abilities (as hopefully demonstrated in the video). I think most of this progress can be attributed to the fact that I’m just more comfortable letting anything come out of my mouth. As a result, with much less filter, occasionally decent new ideas are formed mid-freestyle.
  2. To keep this freestyle moving forward, I leaned on the groups of rhymes that I practiced and fleshed out yesterday. I will continue building out a strong set of “filler rhymes” that I can use to augment the rest of my performance.
  3. The piano is great for performance, but is less good for serious practice. Because I have control over the tempo while at the piano, I’m able to flex the tempo as needed to help me more successfully land my rhymes. With a metronome, I don’t have this luxury, which is actually better for building up my freestyling capacity.

If I can get this much better in a week, I’m excited for what’s to come…

Yesterday, I freestyle rapped on video for 6 minutes. It wasn’t perfect, but it was mostly solid and reasonably sensible, which was a big jump from just a week ago.

Given that I’ve only been practicing a few times per day, in increments of 5–10 minutes, it’s surprising how much progress I’ve made.

I would argue that this level of freestyling was in me at the start of the month, and all I have done in the last week is slowly chip away at my inhibitions.

In fact, I suspect most people, if challenged, could easily rap a comparable freestyle, but are also held back by the mental block of “not wanting to look stupid”.

This is a universal pattern across acquiring any new skills: Most of the progress is made simply by mentally allowing yourself to fully commit to whatever it is you are trying to do, overcoming the self-preservationist mental barriers that originally impeded you.

Often times, this mindset shift is all you need to get to the desired level of competence. (This was the case for my backflip challenge, for example).

In the case of this month’s challenge, while this mindset shift has helped a great deal, my ambitions are a bit higher, and so, I’ll need to augment my new mindset with more rigorous practice.

In particular, I will need to start lengthening my practice sessions, forcing myself to explore new material, rather than mostly recycling the same material in each of my 5-minute sessions.

During these longer sessions, I’ll need to deliberately use a range of constraints to force myself into new creative territory and to isolate different parts of the freestyling process.

I still need to figure out exactly what these more structured sessions will look like, but it’s clear that they are necessary. I’m not going to get too much more mileage out of my mindset.

Over the past week, I’ve practiced freestyle rapping to the unexciting drone of a metronome.

By using the metronome, my hope was that I could more precisely adjust my practice speed and more scientifically track my progress, which I have: The metronome has been a great tool to help train my brain to fire faster in real-time.

The problem with the metronome is that it’s boring. It doesn’t provide any of the color or musical interest that a normal rap beat or backing track would. As a result, although I might be getting faster, I’ve started to become comfortable flowing over the metronome.

Last night, encouraged by a friend, I tried rapping over an instrumental, and found that it was strikingly different to rapping over the metronome.

Because the instrumental has its own musical ideas, I needed to change the flow of my freestyle to fit into the instrumental’s rhythmic world. Not only did this force me to explore new rhythmic possibilities, but, because of these new rhythmic constraints, I had to find new ways to spin lines and land on my favorite rhymes.

In other words, the instrumental forced me to explore new territory and new possibilities, breaking me out of my metronome rut.

As a result, today, I practiced by rapping over a number of different instrumental backing tracks. For each track, I started with the same few lines, and then let the track take me where it wanted to, arriving at very different destinations for each.

By training in this way, and forcing myself into musically “uncomfortable” situations, I’ve discovered how to extract a lot more mileage out of my favorite lines and rhymes, as well as found new lines and rhymes that I can use to build out my freestyle foundation.

The lesson here is clear: If you’re getting into a bit of a rut, it’s usually best to intentionally and systematically disrupt your comfort.

Yesterday, I stopped practicing with a metronome (as my backing track), and instead started using a diverse range of instrumental tracks. By introducing this variability, I forced myself outside of my metronome-based comfort zone, challenging myself to rap within the new musical constraints of each beat.

Today, I wanted to continue my use of constraints as a mechanism for creating more diverse freestyles, and, to do this, I turned to the board game Apples to Apples, incorporating the random phrases of the cards into my practice.

Here’s what that looked like…

It’s tempting for me to want to present very polished freestyles, which would require that I start consolidating the topics I rap about. But, it’s far too premature to do that, and it’s much more important that I use these first few weeks of the month for exploration, even if it doesn’t necessarily sound like I’m making measurable progress.

The more exposure I get to different freestyling scenarios, the tighter my final freestyle will be.

So, I need to ignore my ego, and continue putting myself in strange, new freestyling situations.

Today, I spent my practice time once again constructing freestyles around a list of randomly generated words (via Like the past couple of days, I used these random words as a forcing constraint to guide me into new, exploratory freestyle territory.

After today’s session, I’m finally started to see how this is all going to come together. Here’s the process (for mastering freestyle rapping) as I see it:

  1. First, you need to lower your inhibitions through practice, fully committing to whatever comes out of your mouth. It’s very hard to freestyle with a filter.
  2. Next, by using a range of different constraints, you need to explore a diverse territory of freestyling topics, rhymes, punchlines, etc.
  3. By practicing with constraints in this way, you start building up and strengthening independent pockets of freestyling ideas. Within these pockets, you begin strengthening connections between sets of rhyming words, etc.
  4. Over time, and through more exposure, these independent pockets of ideas start to overlap and connect, as you find natural bridges between the pockets. These bridges allow you to smoothly transition from one well-tuned pocket to the next, creating a seamless freestyle.

Currently, I’m in phase #3, slowly building out more and more pockets of ideas. However, while I was freestyling today, I found my first bridge between two of these pockets, tasting #4 for the first time.

The more pockets I create, the more options I have for bridges. (This is important because the number of bridges seems to correlated highly with the smoothness and seamlessness of the rap).

Interestingly, for each pocket that I add to my repertoire, the number of possible bridges increase exponentially. In fact, we can use a formula from Graph Theory (the mathematical study of graphs, where graphs are the structures used to model pairwise relations between objects) to perfectly show this relationship:

# of bridges = 0.5 * (# of pockets) * (# of pockets -1)

In other words, if I only have 2 pockets, I can only have 1 bridge. 10 pockets and I can have 45 bridges. 25 pockets and I can have 300 bridges. 100 pockets and I can have 4950. It grows very quickly.

Therefore, the best investment I can make right now is in the number of pockets at my disposal. To do this, I will continue with my exploratory freestyling…

In the past twelve days, something has become apparent: It’s very hard to hide while freestyling rapping.

Essentially, in order to effectively land rhymes within a freestyle, you need to source your words directly from your subconscious. Any filter between your mouth and subconscious will prevent a smooth, flowing freestyle.

As a result, there’s nowhere to hide: Everything that comes out of your mouth is raw and unfiltered, which can be a scary proposition, but also a fascinating one.

Sometimes, my conscious brain will shutoff, and I’ll do the freestyle equivalent of daydreaming, only realizing many minutes later that I was rapping the whole time.

In other cases, I can get a similar effect, but my conscious brain will still be observing what I’m saying, which is often quite interesting and revealing. In these cases, I get a very clear look into the weird world that is my subconscious.

In fact, many of my freestyling sessions have been highly therapeutic: I’ve been able to rawly address the topics that are buried a bit deeper in my mind, which is not something I expected when I entered the tough guy world of rhyme-spitting.

Today, I split my practicing into three 7-minute sessions. During each session, I turned on an instrumental track, generated 50 random words (via, and started freestyling, incorporating the words into my freestyle.

In a performance, I would typically spend longer with each word and the associated tangents (i.e. filler rhymes), but, for today’s sessions, I tried to keep my meandering to a minimum.

Here’s the first session of the day. It took me about 10 words to get fully warmed up.

You’ll notice that I’m often overextending myself in the video, trying to find one too many rhymes for a given word.

This is by design: Since this isn’t a performance, I don’t need to land each line smoothly. Instead, I’m essentially forcing myself to extend each word until I hit failure, and then move on.

By straining myself in this way, I’m forcing my brain to adapt and improve. After all, this is how learning works…

Today, I want to give you another inside look at one of my practice sessions.

Unlike yesterday, rather than focusing on developing my pockets of rhymes, I focused on the rhythmic aspects of my flow. In particular, I tried to push my syllables per second to its breaking point.

As a result, about 20% of what I rap today is complete nonsense, 30% is mostly nonsense, and 50% is in English.

You’ll notice that my flow also hits a few bumps as I try to find my way, but overall, I’m happy with this exploration of new rhythmic ideas.

Listening back to this session, there are some lines that, at the time of rapping them, I thought were gibberish, but actually turn out to constructed of real words and reasonably topical ideas.

This is a fascinating realization: It means that, in some cases, I can formulate the rhyme and rap it simultaneously (where, up until this point, I would need to first formulate the rhyme, wait for the right moment, and then rap the rhyme).

I don’t think it’s possible to get to 100% real-time rhyme creation, but I am curious what percentage is possible. For example, when Eminem freestyles, what percentage of his rhymes are crafted in real-time? I’d love to know.

Anyway, it seems like my brain is slowly getting the hang of this.

Today, I took a break from freestyling.

Over the past few days, I’ve noticed that I’ve started to reuse the same kinds of lines, rhymes, and motifs over and over.

While this isn’t necessarily a bad thing — since it means I’m starting to build a functional freestyle toolkit — it does make it harder to explore new territory. In other words, the gravitational pull of this “toolkit” is keeping me creatively grounded.

So, today, I decided to take a break and give my mind time to shed some of its habits.

Back in March, when I was learning to play improvisational blues guitar, I took this same sort of “creative refresh” break, and found that even one day off allowed me to return to the craft with a renewed creative energy.

I’m hoping that tomorrow I’m able to tap into this creative energy, and take my freestyling in a new direction…

In the past two weeks, I’ve built up a lot of freestyling confidence, allowing me to fully commit to each line of the rap.

However, this confidence has only existed within my apartment, when I’m completely alone and in control of all the conditions. In other words, I’ve never freestyle rapped in front of a group of people before.

But today, this changed.

Tonight, I had a group of friends over to hang out, and eventually the conversation found its way to freestyle rapping. While I was unsure if I coulddeliver in this group setting, I decided to volunteer a demo of my progress, which the group eagerly wanted.

As soon as the beat kicked in, my fear subsided and I was completely locked in: For four minutes, I put on one of my best freestyle performances yet.

Overcoming fears has been one of the most satisfying parts of the entire M2M project, and tonight was no exception. I definitely rose to the occasion.

One thing I took away from tonight: If you want to know how well you’re prepared, see how you perform under pressure. If the pressure makes you better, you’re well-prepared. If the pressure crushes you, you have some more preparation to do.

My training is definitely paying off: It felt good to be prepared.

Through practice, I’ve accidentally stumbled on a great freestyling trick using the word “it”. The best way to explain the trick is through a few examples…

Take the following list of words: options, threatened, passage, matrix, dependent.

Seemingly, as far as rhyming is concerned, these words have very little in common.

However, they do share one quality — they all end with the same vowel-sound (of the letter i). Because this vowel-sound is the same as the sound in the word “it”, these two-syllable and three-syllable rhymes can be reduced down to one-syllable and two-syllable rhymes respectively.

In other words, when I’m freestyling, I can greatly reduce the complexity of the rhyme I need to find, just by using the word “it” to rhyme with the last syllable of these kinds of words.

So, for example, here are some suggested lines for the five words above:


Every time I’m on the mic, I straight-up rock it // For every word I have a rhyme, infinite options


Every time I’m on the mic, I straight-up get it // For every word I spit, other MCs feel threatened


Every time I’m on the mic, a crowd, I amass it // Every word I spit cuts through like a passage


Every time I’m on the mic, I straight-up take it // I bend these vowels back like I’m Neo from the matrix


Every time I’m on the mic, my title, I defend it // I’m spitting straight from my brain, not at all dependent

You might be unconvinced that these soft rhymes work, so here’s a recording of the lines I wrote above. It doesn’t have the best audio quality, but it should get the job done…

Bonus tip: The words “this” and “in” also has the same vowel sound as the word “it”, so this same trick works with both of these words as well.

I most often use “it”, but sometimes “this” or “in” sounds better (based on the ending sound of “s” or “n”) or makes more sense in the line.

For example, I would probably choose to use “in” as the end rhyme for the word “threatened” from above (potential rhymes include “get in” and “let in”).

Over the past week, I’ve almost exclusively practiced freestyling with the help of a random word generator.

As a result, I’ve been exposed to a much wider range of words, allowing me to find broader patterns in the English language that I can exploit during my freestyles (like this one).

However, since my freestyles have been structured around lists of random words, their narrative arcs have been less than inspiring. In particular, I haven’t at all practiced carrying a story or punchlines through from one couplet/stanza to the next.

I’ve been purely focused on the art of rhyme, and not on the art of storytelling.

From an interest perspective, I’m more fascinated by rhymes versus stories (as I mentioned on Day 3 of the month), but I also don’t think I should completely neglect the fact that freestyle rapping is a wonderful means of storytelling and creative expression.

So today, I untethered myself from the random word generator, and practiced freestyling more cohesive raps.

In particular, I turned on a long instrumental, and then just walked through my apartment, effectively freestyling a tour of each room. In this format, I not only needed to successfully land rhymes, but I also need to select what I wanted to rhyme about (which isn’t something I’ve had to do while using random words).

This was a very fun exercise that forced my brain to operate in new territory — not only in the context of freestyling, but I also observed things about my apartment that I’ve never consciously noticed before.

It’s interesting how interpreting the world in a new way (i.e. through freestyle rapping) actually helped me experience my world in a new way.

I guess that’s the whole point of learning new skills in the first place…

I have a bit of a problem:, the site I’ve been using to inspire my freestyle raps, is currently broken and not generating random words.

Today, as a result, I needed to turn to a new site for my word generation. Sadly, this new site doesn’t let me specify the number of syllables in the random words (I’ve been selecting “two”), so I had to cope with everything from one-syllable words to four-syllable words.

Additionally, this new site uses many different, more obscure words (versus

Theoretically, neither of these changes should be a problem if my freestyling skills are generalizable…

…but my freestyling skills aren’t generalizable (at least, not fully so), as I found out today.

It turns out, I’m much worse using this new site. Not only do I find the three-syllable and four-syllable words difficult, but I’m also oddly finding the one-syllable words challenging. I’m also generally less quick with all of these new words.

Using this new site, here’s what I sound like…

Despite my freestyling decline, this actually a really happy accident: In my mind, as of yesterday, I thought I was getting insanely good at freestyling, when instead, I was just getting more and more used to the two-syllable words on

I’d guess there are at least 5000 two-syllable words on, but I’ve practiced enough, where I’ve seen many of them.

Before today, I was in the mindset of “I’m pretty good at this point, let me just polish things up before my final performance”, which would have incorporated (it still might).

However, by being forced to use a new site today, I discovered a number of new weaknesses in my freestyling skillset that I’ll be able to address over the next two weeks.

In other words, I’m going to continue my aggressive upward climb towards freestyle mastery, rather than prematurely finishing the climb in an effort to polish my current skills.

I’m glad this unexpected “problem” allowed me to see that 1. I have so much more time left in the month to significantly improve, and 2. I have so much more room to significantly improve.

It’s a good thing I was forced outside my comfort zone. After all, this is the only way I’ll truly come face-to-face with my limitations, giving me a target to aim for and the hunger to keep going.

For the past few days, my brain has had trouble leaving freestyling mode

Whenever I hear a “nice-sounding” word, wherever I am, my brain automatically tries to find a rhyme. It’s like a reflex now.

Today, when I was grocery shopping, every brand name I saw instantly became the seed of a mental rhyme. I spent about 15 minutes too long shopping just because I was going up and down the aisles seeing if any product or food names could stump me.

Here’s a short reenactment of my mental dialogue in Whole Foods today:

Wild Atlantic salmon? More like “Styled, frantic jammin’”

Unsweetened Applesauce? More like “One weakened rapper boss”

Kashi Organic Cinnamon Harvest? More like “Watch me pour magic, sinner gone artist”

Clearly, I was having fun, even if it was mostly nonsensical.

My brain has just been craving rhymes…

Even while typing this post, I can’t help but hear each line in a sing-songy, rhythmic kind of way, just yearning for a nice couplet resolution, which I reflexively provide via my newfound general quickness at finding (mostly reasonable) rhymes.

I’m not sure, outside of freestyling, if these rhyming skills are very practical, but I’ve never really concerned myself too much with practicality. Interacting with the world in this way is a ton of fun, and that’s good enough for me.

Two days ago, I mentioned, my favorite site for, well, generating random words, is no longer functional. As a result, I’ve tried to find other websites that are equally as good for training, but I haven’t yet found anything that is as useful.

Thus, I decided that I might as well build my own website for freestyle rap training.

I haven’t fully acted on this idea yet, so we’ll see if it actually happens, but I did take the first step, compiling a list of the 10,000 most common words in the English language.

When I say “I compiled a list of the 10,000 most common words in the English language”, what I actually mean to say is “I found this great Github repository, where someone else has compiled a list of the 10,000 most common words in the English language”.

Not only that, but they’ve broken this list into three sub-lists of short words (1–4 characters), medium words (5–8 characters), and long words (9+ characters).

I’m only interested in the medium and long words, which together are 7,717 words, so I’ve deleted the short words from my list.

The next step is to identify the number of syllables in each of these 7,717 words, so I can parametrized my tool in this way.

Until then though, here is my very first freestyle based on the top handful of words on the list:

I’m not sure exactly what the end result of this mini-project will be, but I should have a few minutes each day to work on it, so stayed tuned…

In yesterday’s video, I attempt to make the words music and future rhyme, and somehow, by swallowing the “c” in music and the second syllable of future, it almost works.

This is a fairly extreme example, but, the more and more I practice freestyling, the more I realize that basically any two words can rhyme with the right pronunciation.

First, it’s very easy to make two words with the same vowel-sounds, but different consonants, rhyme. Simply, swallow the consonants and emphasize the vowels.

In fact, this was the very premise of the “it” trick: For example, in that post, I showed how threatened and get it can rhyme, just by emphasizing the two shared vowel-sounds (“eh”-“ih”).

This same trick is used by Eminem in Lose Yourself (and ever other song), where he rhymes “arms are heavy” with “moms spaghetti” by swallowing the letter r in arms (so it sounds like ahms and mahms).

In fact, Eminem shows that, not only are consonants mostly irrelevant when it comes to rhyming, but so are vowels in many cases. In other words, if the vowel-sounds don’t agree, just change the pronunciation of one of the words so that they do.

For example, in the same song, a few lines later, he rhymes “ready” with “forgetting” by bending the vowel sounds to agree (i.e. “forgetty”).

While clearly not everything rhymes, by swallowing consonants and bending vowels, you can get away with quite a lot.

Today, for practice, I went down my list of common words (from yesterday), and tried to make every pair of adjacent words rhyme as best as I could. I couldn’t make everything work, but the exercise was definitely valuable and helped strengthen this part of my brain.

Give it a try, and see how you do (Hint: It’s not easy to make the words rhyme, but trying to figure out how it might be possible is the purpose of the training)…


Two days ago, on Thursday, I mentioned that I was going to build my own website for freestyle rap training. This was a direct reaction to the fact that my previously favorite training website ( became nonfunctional earlier in the week.

The project has progressed faster than I expected:

On Thursday, as a first step, I aggregated the 10,000 most common words in the English language, deciding to use the 7,717 words that are longer than four characters.

Then, yesterday, I hired someone on to help sort all 7,717 into separate lists based on the number of syllables in each word.

This morning, I woke to surprisingly find that my Upwork hire had completed the project overnight (with about 95% accuracy, which was good enough for me).

Today, with the sorted list in hand, but with limited time, I set a timer for 15 minutes, challenging myself to get my website online before the time expired.

And thus, was born.

Due to the time constraint, the site is currently quite limited, but it does work for what it’s designed to do: Generate random words with a specified number of syllables.

If I have more time over the next week, I may enhance the site further, but, for now, I’m happy with the result.

This weekend, I did something I never imagined I would do: I freestyle rapped in some of the most touristy areas of San Francisco. In particular, I tried to incorporate members of the crowd and people walking by into my rhymes in real-time.

Watching the videos back, there’s definitely plenty of room for improvement, but it’s a good first attempt.

Here’s a video from the first of three spots that I played (Union Square outside the Apple Store, Market Street at the end of the trolley line, and the Ferry Building).

The audio in this video is the best of the three spots, even though it’s still not very good, especially since I was still figuring out how to properly use the mic. But, it should give you a sense of the day.

I wish there were shots of the audience / people I was rapping about, but here we go…

Truthfully, while this was extraordinarily fun, I think I can do much better in this crowd-based format. It’s just not something I had previously practiced for.

Of course, for a first performance, this is exactly how it should be: You should never wait for perfection before revealing yourself to the world. Otherwise, you’ll never end up revealing yourself to the world.

This is of course easier said than done, especially since I’m naturally a very high self-monitoring person. However, since starting this project, I’ve become much more comfortable presenting myself in a more unrefined state, which has not only been fun and fulfilling, but has given me the opportunity to get better faster.

I’m sure I’ll be back on the street again soon, and, next time, will be that much more prepared to work the crowd.

A week ago, the site I was using to generate random words for my freestyle raps ( become nonfunctional. Thus, I decided to build my own website (, which involved paying someone on the internet to categorize 7,717 words based on their number of syllables.

Almost immediately after publishing my site this past weekend, magically became functional again.

It’s like when the forecast is for rain, and this one time you finally remember to take an umbrella, effectively guaranteeing that it will certainly not rain.

Truthfully, I’m happy is back. It is simply a better site than mine (although my site has a larger corpus of words). Still, I enjoyed the mini-challenge of quickly putting my site together.

Interestingly, a week ago, I declared that I was confusing my comfortability with the words on with “good freestyling skills”.

However, now, I’m not sure if this assessment was totally true: For the past week, I haven’t practiced freestyling much tethered to a word list, and returning to it today (first, in the morning with, and then later with, I found it to be more challenging than I remember.

Or, perhaps, my standards for good freestyling has just gone up, making it more challenging to meet my standards.

Here’s a video of one of my sessions with I had filmed this just for my own review, not as a performance, so I’m a little loose at times. Still, I figured that I have the video, so I might as well just share it…

There are some very cool moments in here, and some less cool ones.

In the next few days, with a bit more practice with both and, I should be able to perform a freestyle that remains fully in the “very cool” zone the whole time.

(Side note: Somehow this month’s blog has turned into a saga about word-generating websites. I’m not exactly sure how this happened, but it’s given me a narrative arc to hold on to, so it is what it is).

Today, I didn’t have time to train, but I did have time to turn on a quick instrumental and see just how good my rhyming skills are.

In particular, I picked a high-tempo beat (well, actually, it’s fairly slow, but I rap it double time) and used my own site,, as the source of random words.

Since the corpus is large and inclusive of all types of words, it’s as close as I’m going to get to a fair test of my generalizable rhyming abilities, especially when tried over a fast beat.

So, here we go:

I’d say about 80–85% of the rhymes were solid, and the rest were a bit mushy. Interestingly, most of the mushy words were proper nouns, which makes reasonable sense, given that proper nouns can deviate further from common English word constructions.

Still, it seems that, for most words, especially when excluding proper nouns, I can find a decent rhyme or two in real-time, which I’m quite pleased about.

In fact, if I let myself freestyle around each word more topically, I think I can turn this slightly bumpy rhyming exercise into a compelling freestyle that lands essentially all of its rhymes.

I’ll likely give this a try tomorrow…

It’s almost the end of the month, which means I need to film my final freestyle performance in the next couple of days. It also means that I’ve been reflecting a bit on my progress over the past few weeks, and so have gone back to review some of the footage from earlier in the month.

Here’s the video I shot on Day 1…

Weirdly, in this video, my rapping is worse than I remember, but less embarrassing than I remember…

This is a fascinating observation: It means that my mental reference frame of my baseline freestyling skills has increased enough where 1. The rapping in this video seems comparably worse (naturally), and 2. Perhaps more interestingly, I no longer associate with this version of myself, therefore removing any amount of embarrassment that I previously felt.

I think this is so cool.

The way I feel is as if I visited my parents’ house and found a painting I made when I was age five. Clearly, this painting would be pretty bad… if it were painted by a 24-year-old. But it wasn’t — it was painted by a 5-year-old, so I can just look at the painting without feeling like its “badness” is somehow an embarrassing reflection on me.

This is how I feel about my freestyle rapping, except it’s only been 27 days.

Perhaps, this is generally how I feel about this entire project: As of I’ve grown over the past almost eleven months, I’ve unquestionally disassociated with the version of Max who existed pre-November 2016.

I didn’t intentionally disassociated with this version of myself. I liked this version of myself a lot. But, it’s really striking to think about how different I am now (Many fears, self-beliefs, etc. that I had at the beginning of this project now feel completely irrational and unimaginable).

I’m glad I feel this way. This is how I should feel, and how I hope to always feel as I continue to grow.

But… it’s genuinely the strangest feeling to watch a video I shot less than a month ago and 100% not associate with the person in the video. Weird.

Today, halfway through my daily walk around San Francisco, I finished the audiobook I was listening to, and wasn’t ready to start the next one.

Usually, at this point, I’ll either put on some music (recently, a lot of Lawrence), or will just walk in silence. But, today, I decided I should listen to some rap music for inspiration, ultimately putting on the Chance the Rapper Pandora station.

It’s fascinating to hear other rappers (…yeah, I guess I just grouped myself in with Chance and co.) construct their verses and rhymes. More usefully, other rappers’ verses are a great source of pre-curated pockets of rhymes.

In fact, I can imagine, in an alternate universe, using other people’s music as a major component to my freestyle training — especially since, compared to actually freestyling, listening to music is such a passive, mobile activity and more comfortably indulged in out in public.

I suspect that I could have made faster initial progress if I had front-loaded my month with daily listening sessions, like the one from today.

However, I’m glad I didn’t take this approach: I like the fact that I constructed my own style and rhyming-tendencies that I can now augment with ideas from other artists (versus trying to adapt the tendencies of other artists into my own style).

Since this month’s challenge is ultimately an artistic, subjective challenge anyway, my objective was more about finding my personal style, the confidence, and the competence to express myself via freestyle rap in a way I could get excited about.

Tomorrow, I’ll film my final performance, and we’ll see if this personal style comes through in the way that I hope.

Still, it is amusing to realize that, during this entire freestyle rapping challenge, I only first listened to another artist perform with two days left in the month.

Today, I went back to the piano to accompany my attempt at three minutes of competent freestyle rapping. When I sat down, my hope was to land some solid punchlines, as well as maintain reasonably complex rhymes throughout, all while keeping the flow continuous.

I’m quite happy with the outcome, and feel like I could have kept going for another three minutes. As result, I’m going to officially call this challenge complete!

Here’s the video of my performance…

It’s the last day of September, which means it’s time to look back and see just how much time I spent on this month’s challenge.

Over the month, I practiced in 41 discreet sessions spread over 26 days, with one or two sessions per day. Each session typically lasted between 10–15 minutes, totaling 549 minutes or about nine hours for the month.

On top of this, I spent about two additional hours performing (on the street, for friends, for the camera, etc.).

So, in total, I only spent eleven hours training this month, which is a bit surprising to me: I felt like I was consumed by freestyle rap the entire month.

Of course, these eleven hours don’t count all the little freestyle riffs that played out in my internal monologue while I went about my normal life. In fact, in the past week or so, my brain became conditioned to search for rhymes almost all of the time, so there was definitely some casual “practice” going on as well that wasn’t counted as part of the eleven hours.

Nevertheless, there seems to be two main reasons why this month didn’t require too much training time: 1. A large part of becoming a better freestyle rapper is simply committing to freestyle in a serious and unfiltered way, and 2. In a typical, fully-focused, 15-minute training session, I could work through about 200 rhymes, which is significant, especially since I found the English language to be highly contained in terms of word types and rhyme types. In other words, if you’re practicing in a fully focused manner, it doesn’t take very long to start noticing the clear, exploitable patterns of English.

I genuinely believe that anyone who makes a commitment to seriously attempting freestyle rap can make noticeable progress quickly. Given this, and the fact that freestyling is extremely fun, I’d highly recommend you give it a try…

This post is part of my year-long accelerated learning project, Month to Master.

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