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.
David McIlroy of How to Write for a Living joined me to talk about writing, building a business on Substack, and the friendships that make showing up more fun. Somewhere between the publishing advice, the jokes, and a chat that practically turned into its own party, I was reminded that the best thing we build on Substack might be the people we find along the way.
📓 Field Note 006
I’ve been on Substack for years, but until this year, I didn’t really have friends here.
I had publications, I had articles, and I had subscribers.
What I didn’t have was a group of people I looked forward to seeing every time I logged on.
Then I started going Live and somewhere between the conversations, the ridiculous comments, and trying to keep up with everyone in the chat, Substack started feeling different.
I was still building a business, but I wasn’t doing it alone anymore.
I Spent Years Publishing Before I Found My People
During Conversation 006 of The Publisher’s Desk, I sat down with David McIlroy, the Substack Bestseller behind How to Write for a Living.
David’s been on Substack since 2023 and I’ve been here for years too, but 2026 has been completely different for me.
I started taking Notes more seriously, I started going Live, and I started having conversations with people I’d previously only known through their writing and those conversations turned into friendships.
People like Chris B. Writes, Rob Riker, Danielle Wright , mary beth kaplan🪶, Robyn Levin and Duncan The Sage, and others have become part of my everyday Substack experience.
Some of us talk outside the platform now.
A year ago, I didn’t have that.
Now I can log on, see someone I know going Live, jump into the chat, and end up laughing at something that has absolutely nothing to do with publishing.
I didn’t realize how much I was missing until I found it.
Building A Business Can Still Be Lonely
Here’s the part I don’t want to gloss over.
This year, I also went all-in on Substack.
I’m running three publications, and I don’t have the steady income of a regular job right now.
That’s stressful.
When you’re building something that needs to make money, every day can start feeling like another day you need to produce something.
Another article, another Note, and another reason for someone to subscribe and sometimes I feel like I’m constantly on the edge of burnout.
I admitted that to David during our conversation, but here’s what’s interesting.
This is also the most fun I’ve ever had on Substack.
How does that make sense?
I’m working harder, I’m taking bigger risks, and I’m thinking about income and how to make this business sustainable.
And somehow, I’m enjoying the platform more.
The work didn’t suddenly get easier. I just have people to share it with now.
David Reminded Me Why Lives Matter
David told me that Substack has made him enjoy being online again.
I loved hearing that.
Because how often do you hear someone say the internet has become MORE enjoyable?
He talked about how Lives changed his experience on the platform.
Reading someone’s articles is one thing, but seeing them laugh, stumble over their words, make a ridiculous joke, or get distracted by the chat?
That’s different.
You get to know the person behind the publication and the people watching get to know each other too.
During our Live, the chat was moving so quickly that David and I could barely keep up.
People were asking questions, answering each other, and making jokes.
At one point, David commented on how active the chat was and I realized something.
The community wasn’t waiting for us to entertain them. They were having their own conversations.
Sometimes It’s About a Baseball Cap
David told us he sometimes joins other people’s Lives just to see if he can distract the person speaking.
He’ll leave a funny comment and watch them try not to laugh.
Which explains a few things about his behavior in my other Lives. 😂
We also learned why he wears a Cleveland baseball cap.
His wife, Christine, bought it because her name starts with C.
Apparently, David didn’t even realize the C represented Cleveland until someone shouted, “Go Cleveland!” at him in a hotel.
You can’t make this stuff up and that’s exactly why I love these conversations.
We can talk about writing, business, subscriptions, and publishing strategies all day, but sometimes the thing that makes someone memorable is a story about a baseball cap or a joke in the chat or discovering that someone you’ve been reading for months is actually hilarious.
Those are the moments that make people feel like friends instead of profile pictures.
Showing Up Looks Different Now
Another part of our conversation stayed with me.
I used to think showing up for my publication meant publishing another article.
If I promised a certain number of posts and didn’t hit that schedule, I’d feel like I was falling behind, but now I’m going Live.
I’m collaborating and I’m having conversations that turn into articles, Notes, and new ideas.
David and I talked about how a Live can become several pieces of content afterward and Danielle brought up something I’ve been thinking about lately: a Live can be the main thing you publish that week.
You don’t necessarily need to write another article on top of it.
Just because I didn’t publish another written article doesn’t mean I didn’t show up for my publication and sometimes, the conversations themselves are worth more to me than another item checked off my publishing schedule.
I Almost Missed What Was Happening Right in Front of Me
When I started The Publisher’s Desk, I wanted to have conversations with interesting people about writing, publishing, and building a business and here I was, hosting David McIlroy, a Substack Bestseller joining me from Northern Ireland.
That alone was pretty cool, but what I keep thinking about afterward isn’t his bestseller status.
It’s the people who showed up, the familiar names in the chat, the questions, the jokes, and the way everyone seemed genuinely happy to be there.
David even pointed out that the activity in the chat said something about the community around my publication.
I hadn’t really thought about it that way. I was so busy trying to keep up with the comments that I almost missed what was happening right in front of me.
People weren’t only showing up for the content. They were showing up for each other and somewhere along the way, I became part of that too.
Conversation 006 Takeaway
→ You can build a publication on your own, but the people you meet along the way can change what building it feels like.
I’m still figuring out how to make this business sustainable and I still have three publications to manage.
And some days, I’m still wondering how I’m supposed to keep up with everything, but there’s something I didn’t have a year ago.
People I look forward to seeing.
People who make me laugh when I’m supposed to be working.
People who remind me that there’s a whole human being behind every publication.
I spent years building my Substack. I didn’t realize I was also looking for my people and now, when I open Substack, I don’t feel like I’m walking into an empty room.
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 006 of The Publisher’s Desk: The Best Thing I Built on Substack Wasn’t An Article
I’m super grateful that David pulled up a chair at The Publisher’s Desk.
Your turn: Has someone you met on Substack changed your experience of being here?
Tell us in the comments. 🙌
About David McIlroy
David McIlroy writes How to Write for a Living and helps creators build confidence, consistency, and traction on Substack so they can get paid for doing what they love.
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 and David McIlroy
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