Substack Writers at Work, hello!
The goal? To stop feeling like we have to beg people to upgrade to paid. Below are six smart strategies to keep in mind when asking people to upgrade to paid.
I know. I know. You dislike (hate?) asking people to upgrade to paid. You know you deserve to be paid for your hard work but can’t stand having to do the asking.
But part of your job is writing “copy” that inspires your subscribers to pay. As a bartender (many moons ago), I didn’t like washing glasses in that gross, sudsy water, but it was part of my job. (Slash from Guns n’ Roses once threw up on my bar, but that’s a story for another time.)
That means you have to get very good at asking people to upgrade, a.k.a. writing calls to action (CTAs).
What is a CTA?
Until a few years ago, I didn’t know what “CTA” in business-speak meant. (In Chicago, the CTA is our transit system.) Even the words “call to action” didn’t really help. And when I did know, it seemed salesy and sleazy and nothing I wanted anything to do with. I liked writing for The New York Times and leaving all that up to their sales department where it belonged.
But a call to action is really just what you want your subscribers to do at the beginning, middle, or end of your post.
A CTA is the button and the copy around the button asking us to do something.
Below I take you through 6 strategies that convert on Substack…
Conversion strategy #1: One ask per post
Substack gives us a lot of choices.
And more.
Many of you just use them all. Why not give your subscribers everything?
Because most of us live in a chronic state of decision fatigue and we don’t want to tire our overburdened prefrontal cortexes on your Substack.
When we see a slew of choices, we do nothing and leave.
Conversion Strategy #2: It’s not about you or your Substack
Asking them to upgrade should be about them, not you or your Substack.
Take Apple’s Think Different ad campaign. This has a long and fascinating backstory, but the important part is that it never mentions the word computer. It’s all about the person/consumer and how an Apple computer will turn us into brilliant renegades the likes of John Lennon, Maria Callas, Miles Davis, and Albert Einstein—if we have an Apple computer.
In just two words, the Think different ads tell us what we want, need, are missing, and will get with an Apple desktop computer. It’s aspirational, yes, but that diminishes its power in making the person/consumer, not Apple, the focus.
’s Popular Information does something similar. His short description/tagline/call to action is Independent accountability journalism. It tells us what we want, need, are missing, and will get by subscribing. It makes us the main player, not Judd Legum’s Substack. At the same time, it highlights the core of his Substack—what I call your Substack’s DNA.Conversion Strategy #3: Maybe don’t use Substack’s default CTA in a caption
Here’s the default subscribe-with-a-caption on Substack:
(Did you skip over it? Worth noting—because if you did, your subscribers likely do too.)
There’s nothing wrong with this CTA; it can work, but it’s all about you, not them. It says, If you read this, you should support it because if you don’t I won’t be able to do this anymore. You support me.
It’s also everywhere, and people become inured to it and just skip over it.
And it’s not terribly compelling.
Conversion Strategy #4: Try different CTAs to see what works
Yes, some people have the same CTA on every post for years, but people acclimate to the same wording over and over and start to tune it out. (Hence, ad campaigns, plural.)
We can repeat ourselves—people are busy and may need to be asked multiple times—but we also want to interrupt the pattern. (The current thinking is that it takes four to twelve asks before someone “buys” but that’s a marketing stat for buying stuff, not paying for a Substack.)
Give your CTA a chance. Try it for a month and then try another. If you keep changing, you won’t get a clear picture of what’s working and what’s not.
Conversion Strategy #5: No need to beg
The only time you need to beg is if you’re offering a Substack you know is mediocre—or don’t have confidence in your Substack.
How do you avoid this pitfall?
Answer these two questions:
What aspects of my Substack are way above mediocre?
What aspect of my Substack is a little mediocre and could be strengthened?
Don’t be mean; get curious.
Write both down.
Now do one thing to strengthen what you wrote for #2.
Conversion Strategy #6: Make your subscribers’ lives easier
You can think of asking to be paid as selling or making your subscribers’ lives easier. Tell us what you want us to do. Don’t expect us to guess.
Many of you are borderline passive-aggressive, getting upset when subscribers don’t upgrade even though you haven’t told them that’s what you want them to do in a way that’s clear and strengthens your relationship.
Selling is a relationship and a conversation, not a transaction.
It’s all about making it easy for people to take the next step.
To recap:
One CTA per post (or two)
It’s not about you or your Substack
Don’t use Substack’s default CTA; create your own
Try different CTAs to see what works
No need to beg
Make your subscribers’ lives easier by clearly asking for what you want
—» Complete the to-do below to put this into practice. Reading about it isn’t enough.
For the next year, we’ll focus on growing your paid subscribers. You’ll have the support and expert guidance you need. So give it time and go all in.
To Do: Be compelling, not salesy
I love the word compelling for this. Compelling means evoking interest, attention, or admiration in a powerful way.
Writing a compelling call to action comes easily when you know your Substack.
