Going From Humor Writing Beginner to Pro

The five ways to master the craft.

Hey, happy new year!

Before we dive in: comedy book club begins next week, on Jan 13.

The details are in that post. I hope you’ll join.

Now, onto our first Comedy Bizarre post of 2025, inspired by a reader question:

“Also, I have a question: how does one move from newb to pro?“ - Matt H.

Well, that’s a great question. And it’s the perfect question to tackle in a new year’s post.

We’re all excited to crack into 2025 and make it our best writing year yet.

“How do I improve at comedy writing?” is not a question I’ve ever tackled in a single post, so I’ll give it my best shot.

Also, I’ll make today’s post free for all subscribers for the first 72 hours. After that, it’ll be paywalled.

Onward.

For starters, when we talk about going from funny writing beginner to pro, in many ways I think it’s more useful to ask, “how does one go from beginner to pro at any human skill?”

The latter question—though it feels epically large—is actually easier to answer because so many smart people have already answered it. And answering that more general question makes the, “how do I become a funny writing pro?” question far more approachable.

Here are my two favorites books about how human beings improve at things:

The Talent Code by Daniel Coyle

Mastery by Robert Greene

Working on my own craft was pretty heavily influenced by both of those books. So, I’ll draw on those books quite a bit in today’s post.

A few preliminary distinctions are helpful. What exactly does “going from beginner to pro” mean here? Here are three good, related ideas to think about:

• Professional (in the vocational sense): Someone who gets paid money for their trade or craft. In many cases, this means it’s their primary income source or that it creates enough income to sustain them.
  

• Professional (in the skill sense): Someone with a high-enough skill level at a trade/craft/profession that they can land significant paid work. Basically, someone who’s good enough, skill-wise, to be well-paid for what they do.
  

• Mastery: A deep level of understanding and accomplishment in some skill. Or, achieving the highest level of proficiency in that skill.

I don’t want this post to be about making money per se, and I don’t think that’s what Matt was asking about anyway.

So, let’s address the following questions in this exploration:

“How do you become a comedy writing pro in the skill sense? How do you walk the path to mastery?”

I’d argue there are five features in common to mastering just about any craft:

1. Deliberate practice.
   

2. A community of peers that elevates the artist/practitioner.
   

3. Mentorship (of some kind).
   

4. Studying the best of what came before.
   

5. Persistence.
   

(I’d also argue for a sixth one, which I’d call “A vision of where you’re going—one that’s unique to your DNA.” However, I really want to focus on skill improvement in this post, so I’m going to call that sixth one out of scope. We’ll table that bad boy.)

Anyhow, let’s talk about each of these—1 through 5—in turn.

1. Deliberate practice

Deliberate practice is the foundation of skill improvement. It involves methodically performing a skill intensely, repeatedly, and iteratively.

For a writer, this means having a deliberate writing practice. But deliberate practice is the essence of all skill or craft development, whether you’re trying to get great at karate, archery, painting, guitar, salsa dance, stand-up comedy, humor writing, or whatever.

Let’s deconstruct deliberate practice for the writer. This section is mostly my summary of Daniel Coyle’s The Talent Code, plus some of how I’ve applied it in my writing life.

Here are the features of deliberate practice:

1. It’s deliberate: This means you’re working on your craft intentionally, not randomly. When a world-class violinist, soccer player, or MMA fighter are practicing, they have a plan. They have a training regime. They have an awareness of their strengths, their weaknesses, and where they need to be. Their practice (or training) is methodical and thoughtful. Ditto for the comedy writer who wants to grow.
   

2. It’s intense and difficult, i.e. it’s done “at the edge of your ability”: When you grow, it comes from practicing right at the edge of what you can pull off now. I love the phrase “at the edge of your ability” because it so well expresses the subjective feeling of deliberate practice. Practice something that’s too easy, and you won’t grow. This is the equivalent of a guitarist just playing the same song over and over, long after it’s rote. Practice something that’s way too hard, and you get nothing from it. Growth—and brain rewiring—requires practice at that special place where you’re just reaching for something that’s one centimeter beyond your grasp. Your deliberate writing practice should generally feel fatiguing and hard but not impossible.
   

3. There’s quick feedback: Feedback has many sources. It can come from peers, a coach, a mentor, an editor (who accepts or rejects your work), an audience of readers, or even some type of sober self-assessment (though that’s tougher.) The point is that you’re not just working in solitude, throwing shit at a wall, maybe glancing about occasionally to see what it looks like, and moving on. You’re getting feedback and determining, rather quickly and frequently, wether your efforts got you what you wanted.
   

4. It’s iterative: The practice involves some kind of adjustment and improvement on the basis of that feedback. You can’t just ignore the feedback. When you get positive feedback, you mentally note, “ah, so that worked.” And when you get negative feedback you note, “hmm, not so much.” That repeated observation is essential to rewiring and learning. In future iterations, you slightly change your practice on the basis of that previous feedback. It’s that iterative nudge that pushes your ability level upward.
   

5. It’s slow and persistent: Progress at a craft requires sustained, consistent effort over many months and years, not random bursts of flailing around for a month then quitting. Getting really good takes years and years. You have to be patient and persistent because there’s no alternative. The “quick fix” is not a thing.

For a writer, practicing at the right intensity is less tangible than if you’re an athlete or a pianist or someone performing an intensely physical skill. But I do think intensity of practice is something a writer should feel, even mentally, on some level.

Writing the same kind of jokes, or the same kind of stories, over and over becomes boring and unchallenging. On the other hand, if you’ve been writing comedy for six months, and you decide to write an intricate comedy novel that’s deeper and better than A Confederacy of Dunces, you probably can’t handle it: you’re going to overload your brain.

That said, the five features above all resonate with my writing experience. Here’s how I often write comedy pieces using deliberate practice.