Editor’s Note: Conversations spark ideas. Field Notes are what happens next. They’re not a transcript or a recap—they’re my reflections on the ideas that stayed with me after we pulled away from The Publisher’s Desk. Conversations explore ideas. Field Notes capture what was worth remembering.
Rob Riker of The Creator’s Edge, Danielle Wright of Your Next Sprint, and I celebrated my birthday with a conversation about making money on Substack, having fun along the way, and building a publishing business that works for YOU.
📓 Field Note 005
For my birthday, I invited Rob Riker and Danielle Wright to go Live with me on Substack.
Some people celebrate with cake and cocktails. Apparently, I celebrate by discussing publishing schedules, paid subscriptions, and how to make money online. 😂🎂
And I had FUN, but somewhere between talking about writing schedules, selling offers, and building relationships, something stuck with me.
Before you ask how to make money on Substack, ask yourself what kind of business you actually want to run.
The Rules We Make for Ourselves
Rob talked about how Substack starts out fun.
You’re writing, meeting people, and enjoying the conversations and then you grow.
Suddenly, there are more notifications, more people to keep up with, and more pressure to publish, promote, and sell.
Danielle shared that her Wednesday publishing schedule had started feeling like an obligation. Rob was questioning whether he wanted a fixed schedule at all.
And me? I’m still running three publications and working on staying consistent. 😂
I like having a publishing schedule. It helps me take my work seriously, especially while I’m building newer publications, but publishing another article isn’t the only way to show up.
Sometimes it’s a Live, sometimes it’s a Note, and sometimes it’s taking a conversation and turning it into something readers can come back to later.
I’m not giving up my schedule. Rob might give up his. Danielle is rethinking hers.
And none of us has to be wrong.
A schedule is supposed to help you publish. It’s not supposed to make you dread publishing.
Making Money Doesn’t Require a Massive Audience
We also talked about the pressure writers feel to grow their subscriber count before they can start earning.
I challenged that idea.
Why wait until you have thousands of subscribers to create something people can pay for?
Rob brought the conversation back to a few questions:
What problem are you solving?
Who needs help with it?
And are they willing to pay for your solution?
Those questions matter more than an impressive subscriber count.
Making money online takes work. Having an offer doesn’t guarantee anyone will buy it, but a small audience doesn’t automatically mean you can’t earn, either.
Rob shared how someone discovered him through writing that had nothing to do with his business, followed him, and eventually hired him.
Think about that.
The writing that brought in a customer wasn’t even about what he was selling.
People can connect with you before they ever need what you’re selling. You don’t have to turn every Note into a pitch.
Build Something You Actually LIKE
Here’s what stayed with me after our birthday Live.
I still want to grow my three publications, I still believe in consistency, and yes, I want my writing to earn money, but I also want to keep enjoying the work.
I want room for conversations that turn into friendships, Lives that turn into articles, and the occasional birthday party that turns into a business discussion because if I’m going to spend this much time building something, I want to actually LIKE the thing I’m building.
I don’t need my Substack to look like Rob’s, Danielle’s, or anybody else’s to make that happen and neither do you! Build something YOU actually like!🎉
Conversation 005 Takeaway
→ Build a Substack that supports the life you want, instead of building a life around your Substack.
Make something people value, give them a reason to pay, find a way of working you can sustain, and don’t forget to have some fun while you’re at it.🎉
Continue The Conversation
Thank you for pulling up a chair at The Publisher’s Desk.
If today’s conversation sparked a new idea or perspective, I’d love for you to continue the conversation by sharing your biggest takeaway in the comments.
↑ Listen to Conversation 005 of The Publisher’s Desk: Make Money, Have Fun, & Build Your Substack Your Way
One of my favorite parts of The Publisher’s Desk is introducing you to thoughtful people whose work I genuinely admire.
I’m super grateful that Danielle and Rob pulled up a couple of chairs at The Publisher’s Desk.
Your turn: If you could change ONE thing about how you run your Substack to make it more enjoyable, what would it be?
Tell us in the comments.🎉
About Rob Riker
Rob Riker writes The Creator’s Edge, where he helps creators build real relationships, grow an audience of true fans, and turn those connections into a stronger creative career.
Follow Rob’s work at The Creator’s Edge →
About Danielle Wright
Danielle helps creators turn big ideas into small sprints, make real progress, and party and have fun along the way.
Follow Danielle’s work at Your Next Sprint →
Thank You
Thank you so much for everyone who tuned into this live, your presence is truly appreciated, and to the people who are watching the replay, thank you!
-Jess, The Creator, Rob Riker, and Danielle Wright
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