🎧 Taylor Swift’s Business Plan for Substack Writers

The art and business of writing on Substack

This post is a companion to the Make Money on Substack: The Business of Writing workshop. Replay available. Find out more here.

🎧 Listen to the podcast version:

This may go without saying, but being a professional writer is hard—financially, mentally, and emotionally. I’ve been one all my life and because I was never willing to make writing a side gig, financial insecurity has been the norm, which, by the way, is terrible for your mental health. 

Substack has changed all that—not just for me but for all writers.

But there’s a problem. As writers, we’ve been conditioned to think that being paid for our work is somehow unartistic. The myths that commerce corrupts “real writing,” that writing should be free, and that “real writers” struggle have been internalized and made us vulnerable, dependent, and entitled.

Here’s the really damaging part of the art vs. commerce mythology: The truth is that having a professional’s money mindset will only help your writing.

Time to get our agency back.

That entails not expecting other people to connect us with our readers and learning from people outside the writing world.

But who?

Substack the T-$wift way

Taylor Swift is a business icon worth $780 million (by last count). The stats around her success—monetary, professional, and, yes, artistic—are ridiculous in the sheer number of them. (Even if you don’t like her or her music, you have to admit she’s a great lyricist.) To give you a sample: over a hundred Guinness World Records, 12 Grammys, the most-streamed female artist on Spotify, named Woman of the Year/Decade and Artist of the Year/Decade on the regular, and Eras Tour generated an estimated $5 billion for the U.S. GDP.¹ None of this happened while she sat by waiting for her music and other people to do it for her. 

Most of all she has a legion of Swifties—fans devoted to her.

Swift isn’t just a marketing genius; she’s sincere. Be a bummer if you want, but I truly believe that. (Full disclosure: I’m technically too old to be a Swiftie, but I legit am one. I even had a fleeting moment of wanting to use only Taylor Swift lyrics in this post.) 

If nothing else, Swift is an inspiration on how to own your career and empower yourself as a writer.

T-Swift’s 5 tips for Substack writers

If you don’t want to earn an income as a writer, by all means, stop reading. If you do, get a pen and take notes.

1. Write for your readers, not yourself

Swift’s lyrics are for her fans, not herself. She makes herself into a character and writes songs her fans will relate to.

Cases in point from the Reputation album: 

• Delicate: “Dive bar on the East Side, where you at?”

• Getaway Car: “I’m in a getaway car, I left you in the motel bar”

It’s highly unlikely that Swift has ever been in a dive bar unless they cleared it of patrons for her to be there privately, which would lose some of its dive-y-ness. She and Tom Hiddleston fled the Met Gala, not a motel bar, which is supposedly what “Getaway Car” is about.

We don’t have to go quite this far, but writers can be so precious about their “creativity.” Writing only for yourself isn’t artistry; it’s ego.

Write for your readers—or at least with your readers in mind. 

2. Fall in love with your subscribers, not your subscriber count

Swift makes you feel like she loves each one of us. And we love her back like a friend. That’s how she keeps us buying her over twenty-two albums (if you count the live albums, etc.).

I say this a lot: For professional writers (and specifically writers on Substack), it’s way more important to keep subscribers/readers than to get them. What’s the point of getting them if they just unsubscribe? 

Love the subscribers you have; don’t just chase new ones.

3. Give more than you promote

Swift is a social media genius. She figured out how to make it about her fans. She mentions them, shares their posts, and likes and favorites their photos. You can be cynical and say that her people are the ones doing this, but I don’t think so. They’re vetting, maybe, but she’s doing it.

This wasn’t always the case. Her early posts are like everyone else’s–me, me, me. 

But now, even when she posts to promote, it’s a thank-you or about her fans. Try that on Notes.

Bonus tip: Substack’s media assets for social don’t connect with people. Do your own.

4. Create surprises

Okay, you can call this a marketing trick along the lines of celebrities visiting hospitals, but again, she seems to genuinely enjoy it.

5. Love cats

This one’s clearly the biggest factor in Swift’s success:

The reclusive Meredith, Olivia (whose net worth is $97 million), and Benjamin Button (a ragdoll like Baby Theo)

Cats, my friends. Love cats.

L💙ve Your Substack

Let’s take advantage of the opportunity Substack presents. The business of making money on Substack is as much about forming relationships with our readers and valuing our work. 

Try this:

• Look at your Subscribers page on the Substack dashboard—not the number, the list. Go down. Read the names. Not the ones you know.

• Imagine them giving you their email addresses.

• Imagine them reading your posts.

• Imagine them paying you to read them. Yes, picture their credit card bills.

• Write your next post to them.

Examples of Substackers who do T-Swift-esque Substacking well—some without trying to—include

• Nishant Jain
  —Watch my interview with him here, during which he talks about how he does it and shares a very different way of thinking about publicity.

• Katherine May
  —A master of community building and speaking to her subscribers.

• Roxane Gay
  —She’s used her financial success to create a magazine to champion edgy writing and emerging writers, particularly people of color.

• david roberts
  —Definitely exhibits an aspect not discussed here. T-Swift is really good at connecting with other artists (minus the Kanye thing) as is David.

I want us all to succeed on Substack—financially, professionally, and emotionally. To do that, we have to own our careers, empower ourselves, produce amazing writing, put it out there, and love our subscribers.

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1. Taylor Swift knows her stuff and learned it young. Her father is a former stockbroker for Merrill Lynch, and her mother was a mutual fund marketing executive.