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How to write, grow, and monetize your newsletter (from people who have done it themselves)

Only 3 things matter when it comes to a newsletter:

• Content

• Growth

• Monetization

Anything that doesn’t tie directly back to one of those buckets is noise. I learned that lesson after spending 100s of wasted hours on other things.

If you’re starting or getting serious about a newsletter, Jack Raines and I are running the 3rd round of The Newsletter Playbook.

Last year, we taught ~100 students across two cohorts everything we know about launching, growing, and monetizing newsletters. I’m more proud of the 9.1 rating than anything.

Today, we’re opening enrollment for up to 30 students for our August cohort. If you want to take your newsletter to the next level and avoid the costly mistakes we made, check it out.

If you’re reading this newsletter, you probably want to become a better storyteller. That can mean many things — script writing, making videos, giving speeches, writing novels, convincing your boss to give you Friday afternoon off.

But storytelling is like exercising. The more you put in, the more you get back. Don’t confine yourself to one practice.

So, here are 3 practical ways you can practice storytelling daily:

Homework For Life

In Storyworthy, Matthew Dicks lays out his practice called Homework For Life:

• Divide a journal or spreadsheet into two columns, Date and Story.

• Each night, write down one story from that day but don’t spend more than five minutes on it.

You can keep it simple. For me, the story can’t be more than three sentences and needs to be as informal as possible. No second drafts allowed.

The practice helps you remember little moments that would otherwise slip past your memory. Then, after a while, those little moments turn into the building blocks of larger stories.

The Story Response

I bet you get asked “How are you?” or “What’s up?” every day.

If you’re like me, then way too often you respond with some variation of “fine” or “good.” Whew. Not sure there could be a more boring response.

I have a challenge for you.

The next time you get asked how you’re doing, respond with a story. Tell them about your trip to the gym. Or about your dog. Or about your crazy neighbor.

You may feel awkward at first. I did! It’s unnatural to break the normal rhythms of conversation. But once you do, it’s an instant way to both practice your storytelling and have more interesting conversations.

Copywork (Story Version)

If there’s a hack to becoming a better storywriter, it’s copywork. Hunter S Thompson, Jack London, and Ben Franklin did copywork to improve their writing. They’d sit down and copy, by hand, their favorite writing.

You can do the same practice. Take your favorite author. Find their best work. Copy it, word for word, by hand. Let your brain feel the writing.

Last week, I copied page 11 of George Saunders' A Swim in a Pond in the Rain:

When you do copywork, your brain starts to pattern match. You see how great writing ebs and flows. How stories begin and end. How the author keeps you around.

Here are a few places I recommend you do copywork on if you’re interested in practicing these specific mediums:

• Blogs: Morgan Housel’s Why You Believe The Things You Do or Derek Sivers’ Bronze

• Books: Ruta Sepety’s Salt to the Sea (historical fiction), Murakami’s Kafka on the Shore (fantasy), or Yuval Harari’s Sapiens (non-fiction)

• Speech (transcripts): MLK Jr’s The Other America or David Foster Wallace’s This Is Water

You’re looking for writing that resonates with you. When you find it, make a note. Then come back later and copy it.

As David Perrel says, “Imitate, then innovate.”