The Art of the Ask: How I Doubled My Paid Subscribers and It's So Easy...
And why asking is a skill you can learn!
Before you decide this is clickbait, complete transparency: I did more than double my paid subs. Larger accounts probably laugh at my excitement, but I don’t care! The numbers are small yet indicative (more below), and I’m grateful for all subscribers! Okay…
For the longest time, I felt awkward asking for paid support. You probably know that feeling too. Many of us grow up absorbing the idea that we should be grateful, quiet, and not make things about money. I internalized all of that, even after years of running my business and teaching creators how to advocate for themselves.
Then something small shifted.
I realized I needed to heal my relationship with asking.
I started adding one gentle, honest ASK at the end of my Substack posts. Not in Notes. Not in Chat. Only at the very bottom of my long-form newsletter publication posts, where readers were already receiving something worthwhile in their inboxes.
And here is what happened next.
💥 Quick gratitude moment to Booklinker and GeniusLink, my exclusive sponsor, two tools I actually use and love💥 (affiliate link).
Asking helped me grow immediately. No ask for most of this year, and then I got brave and started asking. You can see the jump below starting in early October.
My paid subscribers went from 6 to 14, even up to almost 20 at one point. Small numbers. Not a dramatic income leap. I’m not retiring, buying an island, or splurging on an extra latte from this.
But it was still more than double. And that small bump matters, not because of the money, which is, of course, helpful and lovely, but because of what it represented. My content didn’t change. My traffic didn’t magically increase. I didn’t run ads or chase trends.
I simply asked.
And people who were already reading said yes.
This was a clarity moment.
The Real Power of Free Subscribers
I also want to be clear about this (and the good girl in me wants to say, “I’m not bragging!’ and I’m not. But it’s okay to celebrate our wins)…
I now have more than 10,000 free subscribers I’ve collected over a decade, in various forms, but I started here two years ago with about 1800 subs (none paid).
How? Booksweeps, Written Word Media, and now Book Throne offer reasonably-priced subscriber growth options.*
*Not a sponsored promo. I like them, they work, sharing.
Read here how I’ve intentionally grown as an author.
That number is as meaningful as the paid total. Free readers are the heartbeat of this community. They show up. They read. They reply. They share. They help the work travel farther than any algorithm.
Think of it this way: Paid is helpful. Free is essential.
Chasing paid subscriptions at the expense of everything else often leads to burnout and a sense of scarcity. I’ve seen creators spiral when the paid number stalls, even while thousands of free readers continue to show up with enthusiasm and care.
It’s like having 399 5-star reviews and one 1-star—that’s the ONE we remember. It’s human nature. Think of paid vs. free this way:
Paid does not equal more love or validation.
Paid does not equal more impact.
Paid does not equal higher value.
Paid simply means someone wants to contribute financially. Free means someone wants to be part of the community.
Both are necessary. Both matter. Both are valid forms of support. And it’s not a competition.
This newsletter will always be free; I offer paid tiers to anyone who can support. I never expect to be paid. Maybe I need to change that, I don’t know. But I’m happy that you’re here, reading, no matter how you got here.
Why Asking Works: What the Research Shows
Most readers are not sitting there thinking, “Please don’t ask me for anything.” They’re taking in your words, learning, connecting, processing, and often thinking, “I’d support this if I knew how.”
This is backed by actual research.
In Heidi Grant’s TED Talk, “How to Ask for Help and Get a Yes,” she explains that people are far more willing to say yes than we assume, and that clarity increases the likelihood of support.
Nazia Ahmed’s TED Talk, “Asking for Help,” explores how asking is a human strength, not a weakness.
A 2024 study on subscription-based crowdfunding found that willingness to pay rises when people see clear invitations and a visible community of previous supporters.
The message: Clarity creates opportunity. Invitations create momentum.
Many creators forget this because online spaces can often feel foreign or unwelcoming. That tightness in your chest when you think about asking is usually old conditioning, not the reality of your present moment.
Readers get to choose. You’re not obligating anyone. You’re offering a door. And let’s be super real: not everyone can afford to support us monetarily, and that’s okay, too.
What Asking Looked Like For Me
Here is the exact type of sentence I started using:
“If you value my work and want to support it, would you become a paid subscriber? Your support helps me continue creating resources for readers and creators.”
One sentence. Calm. Clear. Direct. Includes The Ask.
This aligns with findings from the research paper “How to Ask for a Favor,” which shows that clarity, narrative, and gratitude dramatically increase the likelihood of yes.
The foundational paper “Crowdfunding: Motivations and Deterrents for Participation” also notes that belonging, trust, and shared purpose drive people to support creators.
If you want a deeper, creative look at the emotional side of asking, Amanda Palmer’s book The Art of Asking is a thoughtful companion.
Asking isn’t just awkward. It sits at the intersection of being a creator in a precarious economy and growing up in a world that punished you for taking up space. No wonder it’s so hard!
You Don’t Need Courses, Free Gifts, or “Magnets” to Earn Support
Something I emphasize for creators all the time: You do not need to launch a course, design a freebie, or create a “lead magnet” to justify asking for paid support.
Stuff is great, but you can offer value through your writing. You can show up consistently. You can be honest. That alone is enough reason to invite support.
If you want to create courses or digital products, great! Do it! That can be wonderful. These tools are helpful if you’re intentionally building passive income or diversifying revenue.
But they also take time, energy, testing, setup, customer support, and emotional bandwidth. Nothing is ever truly passive.
Bottom line: The absence of those extras does not make your work less valuable.
You do not need to perform more labor to earn the right to ask. You do not need a funnel to deserve support. You do not need a “resource library” to validate your writing.
Sure, courses and extras can help you scale. But you don’t need them for The Ask. And you certainly don’t need them to deserve support.
The Art of Asking: Think of It as an Invitation, Not a Demand
You’re not saying, “Pay me or else.” You’re saying, “If this work matters to you and you want more of it, here’s how you can support it.”
Think of it this way:
☕️ The Coffee Shop
You don’t walk into a café and feel bullied by the tip jar. It’s simply there. It gives you a choice to say thank you.
📚 The Library
Libraries are free. They run on community support. People donate because they believe in the work.
🎨 Art Supplies
Creativity costs time, energy, and emotional depth. Support helps creators keep going. Asking isn’t taking from others. It’s inviting collaboration.
Crafting Your Ask: Try One of These Today
Here are a few options to put at the end of your next post:
🥰 The Warm Invite
“If my work is useful to you, would you become a paid subscriber? Your support truly helps.”
✅ The Practical Approach
“Do my posts help with writing, marketing, or your creative life? A paid subscription helps support this work.”
💃🏻🕺🏻The Community Approach
“Did you know that this space grows because of your engagement? If you want to help sustain it, you can join as a paid subscriber.”
🤫 The Quiet Confidence Approach
“Would you like to go deeper in supporting my work? Paid subscriptions are always welcome.”
One or two sentences are enough. I also recommend including a gratuitously darling pet picture. Here’s Pip. He works for snackies.
When Asking Feels Uncomfortable
If asking brings up anxiety, you’re not doing it wrong. Reframe: It means you care about your readers, content, and integrity.
A few reminders:
Readers get to choose.
Asking is neutral.
Your work has value.
Keep the ask at the bottom.
Keep it separate from vulnerability or trauma.
Keep it simple.
Clear boundaries make asking feel safe.
Why This Matters Beyond Money
Learning to ask for support is one of the most grounding acts of self-respect in a creator’s life. It strengthens confidence, reinforces that our work has value, and shapes our relationship with your readers. It also creates collaboration between creators and supporters, which is fantastic.
And sometimes, it simply feels good to let people say yes.
Your Turn
Try adding a gentle ask at the end of your next post. Not a pitch. Not pressure. Just an invitation.
See what shifts.
If you’re still reading this far, try this exercise: Ask yourself these three questions:
How am I holding myself back from growing?
What can I do today to recognize the importance of my subscribers?
Where do I find inspiration?
🙏 And if you want to support my writing and help me continue creating resources for readers and creators, can you become a paid subscriber? Free is always appreciated. Paid keeps the work sustainable. 🌻
Both are welcome. Both matter. As do you.
I suspect monetization on Substack depends heavily on genre. I’ve actively looked for serialized fiction stacks carrying a “bestseller” badge and, so far, I haven’t found any. Despite positioning itself as a platform for writers, Substack doesn’t seem especially well-suited to serialized fiction.
I think there are a few reasons for this, some of which are related to user behavior and not Substack per se: The serialized format asks for sustained emotional investment over long gaps. When readers have to wait a week or two between chapters, momentum fractures. Character attachment weakens. And in practice, serialized fiction on Substack ends up competing directly with Kindle Unlimited, which offers immediate access, binge reading, and complete story arcs on demand. In a market conditioned for instant gratification, that’s a hard hill to climb.
For that reason, I plan to stop publishing serialized fiction here once my current serial concludes. Stories that would have been new serials will become books instead, where the format better supports immersion and long-form payoff. On this platform, I'm instead leaning into essays, short stories, poems, and one-shot letters that build relationships with my readers.
What does appear to perform well on Substack’s fiction bestseller lists are two very specific categories: erotica and “how to write fiction” stacks. The few fiction-forward exceptions I’ve seen tend to publish standalone short stories in the 2K–5K word range, which aligns better with Substack’s newsletter rhythm and reader expectations.
Based on my own admittedly informal trend analysis, fiction stacks—particularly serialized ones—aren’t optimally positioned to thrive on Substack as a primary monetization channel. That doesn’t mean they lack artistic value or audience interest, but the platform’s strengths seem to favor immediacy, insight, and completion over long-form narrative continuity.
I love this. But I must confess. I have been asking. I asked creatively. I asked to tip my coffee jar. I asked implicitly. I asked nicely. I asked when I wrote something that substantiated my worthiness to ask. I have been asking but it hasn't panned out. I do have paid subscribers but they converted when I offered my support, my assistance, my unconditional help. But of late, even that isn't working. I blame substack but I am also looking at me. I am overanalyzing. I am repurposing my offerings. I am trying new things.
All this to say I that I have failed at asking. I loved your post because it reasserts the positivity in asking. So I will continue to ask. I will learn to ask better. Thanks for your thoughts.