Please, before you build the course, write the song

Taylor Swift could make millions teaching songwriting, but she's a billionaire because she keeps writing songs

Taylor Swift could make millions teaching people how to write songs.

She could launch a six-week cohort on bridges, hooks, metaphors, turning heartbreak into narrative, and writing songs that feel diaristic without becoming small. She could charge $4,000 for it. People would pay. Heck, I would pay.

But the reason Taylor Swift is Taylor Swift is not that she teaches songwriting. It is that she keeps writing songs.

This sounds silly but take one look at YouTube and you’ll see what the hustlebros are doing. On the internet, the fastest way to monetize a skill is often to stop practicing it and start packaging it. Learn to write, paint, code, make videos, shoot film, and before the thing has even had time to become yours, the internet will suggest the next step: make a course. Put it on Skillshare. Build a paid community on Skool/Circle. Turn the practice into a product.

Teaching can be beautiful. The problem is, the internet makes the flashy course landing pages look like the mature form of a craft, when often it’s just the earliest escape hatch from the slow, humiliating work of getting good. Monetizing early is the cheap move. The expensive one is staying with the work until it’s powerful enough to carry its own weight.

The course was the shortcut

I know the temptation because I have been tempted by it.

When I uploaded my first video about painting, I had grandiose visions of the YouTuber I was about to become. I was working as a reporter (which paid pennies), and YouTube looked like a trapdoor out of the “default” path. I could quit my job. I could travel. I could become the thing every internet kid secretly wants to become: a full-time creator with a life organized around saying “hey guys welcome back to a day in the life”.

The roadmap presented itself: I would record myself painting once a week. A few years later, if I just kept going, I would be set.

There was one tiny problem. I was not very good yet. My sketches were squiggles at worst and rudimentary at best. My videos were fine, in the way early videos are fine when you’re learning in public. I was hoping my family would give my videos 5 likes.

I was on the slow path of the roadmap, but I still hit the coveted milestone of being monetized after 18 months and more than 130 videos. It then took a few more months to get my first $100 in AdSense. The arduous uphill climb made the shortcuts look hella attractive.

Around then, I noticed that many successful YouTubers had Skillshare classes. That seemed to be the move: get good enough at something, then teach it. Package the skill. Turn the practice into a product. I started wondering whether painting tutorials might be my path too. I even made little mini-tutorials as practice.

I won’t pretend I was above the temptation. I was very tempted.

But eventually the course idea made me feel strange. Who was I to teach painting? I was still learning how to see negative spaces. I still felt clumsy with the paintbrush. Selling people my knowledge would have required pretending I had arrived somewhere I had not arrived. Impostor syndrome made me put the course down.

The art I made instead

After I stopped trying to turn painting into a business model, I missed painting, so I painted because I loved it. I painted Hong Kong street signs, trash cans, parks, piers, taxis, friends. I painted because I wanted to capture the city in my sketchbook.

Then I saw another possibility. Paul Millerd was gifting Good Work to people, and I realized I did not want to sell a class. I wanted to make a book. I wanted to bundle the art itself into the prettiest, bestest object I could make and give it to people.

I made In Plein Sight, a collection of my Hong Kong sketches. I borrowed a friend’s scanner. I licensed a font. I asked a friend to edit the foreword. A few weeks later, I unboxed 300 copies in my living room.

What I felt most clearly was pride. I had taken painting from nothing, from clumsy marks and shaky sketches, and spent enough time with it that I could make something real. The book was evidence that I had adopted a whole new skill from scratch and gotten decent enough at it to make something beautiful.

It felt different from selling a course. (I did end up selling some copies, but the money was not the point). The point was the painting. The point was the book. The point was that I had made something beautiful enough to hold tangibly in my teeny tiny hands.

The book felt like a gift because it made no claim on the person receiving it. I was not asking them to become a better painter, sign up for a system, or believe in some promised version of themselves. I was just saying: here is something I made because I learned how to make it. And I hope you enjoy the Hong Kong scenes as much as I do.

Be good, then be useful

The danger of monetizing too early is that it changes the motivation of the craft.

Instead of asking, “How do I get better?” you start asking, “How do I make this useful enough for other people to buy?” Teaching can solidify your learning, and usefulness is not bad. But if you make the turn too early, you freeze your current understanding into a product. You start performing competence instead of pursuing it. You become useful before you become good. And because usefulness is rewarded faster than mastery, it can become the ceiling.

A craft-first year is not glamorous. It is a year of consenting to be bad. It is sketching every object you can see, writing bad paragraphs, making ugly paintings, and staying with the work long enough to push through the phase where your work just sucks. Ira Glass calls this the taste gap: that awful period when you can tell the work is not good yet, but you cannot yet make it better. Working through the gap is where the craft starts forming.

For the first year, maybe the first three, optimize for output instead of income. Keep a secret sketchbook if you need to. Make things no one sees. Make things that embarrass you. Make things that prove you are still in motion. The internet will ask you to turn your half-formed understanding into a product. Refuse, at least for a while. Let the craft have its ugly, traumatic childhood.

A counter-existence: Write of Passage

Not all courses are bad. Some courses are good. Some courses change your life.

Write of Passage changed mine. I learned how to write online. I met other online writers. My life trajectory changed because I started writing on Substack. So no, I do not think “course” is automatically a dirty word.

But Write of Passage felt different for three reasons.

First, the teachers still shipped the thing. David Perell was still writing his newsletter, and the newsletter was good. The mentors and editors had their own newsletters too. Nobody had stopped writing to sell writing. The work was still very much alive.

Second, the course was built around the craft, not around the teacher. Instead of one guru broadcasting into a room, it was a community of people each deep in a different facet of the work: Charlie Bleecker taught us how to make writing more personal and descriptive. Michael Dean taught us how to structure an essay. Vicky Zhao taught us how to notice ideas ambiently in life. The structure pointed back to the writing, not to a personality.

Third, the business model did not feel like an escalator. A big ick for me with online courses is the endless upsell that resembles multi-level marketing: the entry-level course, then the advanced course, then the accelerator, then the more expensive inner circle… Write of Passage had a community membership (that only happened twice in its lifetime apparently) that helped people keep the habit going, but the community feel was still there.

That is the distinction. Teaching is good when it comes from overflow. It gets hollow when it becomes extraction. The question to ask of any teacher is simple: do they still make the thing, or do they only sell the map?

(Though Write of Passage did eventually shut down because it didn’t make enough money so maybe that’s a lesson there too…)

Don’t ask your newborn craft to pay rent

There is an obvious objection here: what if you need money?

If you need money, your craft probably isn’t where to find it. Go into sales. Get a job. Do something where usefulness and compensation are already aligned.

Don’t write poems to make money!

Money is not dirty. But desperation is a brutal editor. When the work has to feed you before it has learned to stand, you will keep bending it toward usefulness, urgency, marketability, and proof. Sometimes that creates a business. But often it prevents the craft from becoming anything deeper than a storefront.

The practical middle ground is less romantic but a lot more realistic: make money from a completely separate job, then protect a small part of your non-work time where the craft is allowed to be beautiful before it has to be useful. You don’t need a very high-income job, by the way. You just need enough. Enough depends on your life, your bills, your appetite for risk, and what kind of time sacrifice you are willing to make.

If you are struggling to have a meal tomorrow, I would not tell you to write poems as your money strategy. Write poems if you want to. Write poems if you need to. But if the poems are supposed to save you financially, that is probably not the smartest survival plan.

Do not ask your newborn craft to pay your rent.

When money becomes okay

Money becomes less dangerous when it arrives as a consequence of the craft instead of becoming the reason for the craft.

If people start asking you to teach, that is different from waking up one day and deciding your fragile new obsession needs a funnel. Demand is a signal. It does not have to be a command.

Even then, teaching is not free. It spends the same substance the craft spends: time and energy. If you genuinely love teaching your craft to others, teach. But know the trade. Taylor Swift could have had a very different career if she spent half her songwriting time teaching songwriting and half her time writing songs. Maybe she would still be successful. She would probably still make millions. But she makes billions, and writes bangers like The Last Great American Dynasty, because the time keeps going into the songs.

All you have is time. Spend it on the thing you actually want to get better at.

Protect your craft

I want you to become protective of the thing you make.

Your craft is not just raw material for a funnel. It’s a place where your attention goes to become sharper. It’s a place where your taste catches up with your hands.

Do anything else if you need money. Sell something useful. Get a job. Build a service. But please do not automatically turn your craft into a course just because everybody else is on Skillshare, Skool, or Circle.

Before you teach the thing, make the thing. Before you sell the roadmap, see how far the road takes you.

Please please please, before you build the course, write the song.

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Update log:

• 👩‍💻 New job hard launch - an AI workflow of mine was featured in an Every article on Friday

• 👋 Set up a Hermes agent finally, and I’ve named it Baymax

• 🤓 Met Wyndo for the first time IRL! It’s been ages since we first met in the WOP halls

• 🍙 Picked up a musubi on the way home and realised this might be one of the last few times I can do this

• 🖨️ Figured out how to bulk-print photos on my Niimbot B21Pro by bypassing the app and going straight from the Terminal

• 📓 Made a little zine maker so you don’t have to do the Canva rotation math: https://beckyisj.com/fun/zinemaker

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