So I had a conversation with Sean Wright on a spotlight recently (winner of one of my monthly challenges) about the single article he was most afraid to publish.
You know what? He told me that article turned out to be the best-performing thing he’d written. Can you imagine?
🔥 I’m Speaking at the Substack Success Summit 🔥
The first-ever Substack Success Summit is happening on 11-13th of November and I’m speaking about monetization with 30+ successful Substackers who made it on the platform.
I think this is one of the most important lessons for anyone on Substack right now.
But before that, a bit about Sean…
Sean is 60. He lives in Portugal. Six years in the UK military, then a long career that includes two short films that won seven awards between them (one at Cannes), a feature film you can still find on Amazon Prime, and a professional photography practice he fell into by accident.
Nine years ago he sold everything, packed his van, crossed the Channel, and ended up a permanent resident in Portugal. Now he writes about mental health, overcoming limiting beliefs, and rebuilding yourself at 60.
His Substack is called Rethink and Rebuild. But this is the story worth telling.
The article he almost didn’t publish
A few months ago, Sean wrote an article about setting artificial deadlines to help with mental health. In that same article, he set himself one: write one article a day for 30 days.
He got to 15.
Then he just couldn’t do it anymore.
Imagine where you are mentally in that moment. You announced something publicly. You failed in front of everyone. And you still have 15 more days you can’t deliver on.
Most creators hide. They quietly stop, hope nobody noticed, come back weeks later pretending nothing happened, and then wonder why their audience is quiet.
Sean did the opposite. He wrote an article admitting he couldn’t finish. Why he couldn’t. What stopped him.
That article got a bigger response than almost anything else he’d written.
Here’s why.
Most people on Substack think they have to show up polished. They think they need to have the answers. They think vulnerability is weakness. But readers don’t connect with polished pieces. They connect with the actual truth.
And Sean’s article about failing was the clearest, truest thing he could have written in that moment.
If you ever find yourself in that situation, don’t hide. Write the thing you’re most afraid to write. Readers will meet you there, almost every time.
🔥 Get Your FREE Playbook from the Substack Success Summit 🔥
The Summit Just Dropped A pure piece of GOLD - The Substack Creator Playbook - a total of 192 pages where 100+ creators share how they start, grow, and monetize Substack.
The rebrand
Sean started calling his Substack Sixty and Lost. It felt true. He’d just turned 60, he was figuring things out, and that was his story.
Then readers in the community started telling him, “Sean, you don’t really sound lost when you write.”
So he rebranded to Rethink and Rebuild.
And I love this because it’s a lesson I keep seeing on Substack.
Your readers often see you more accurately than you see yourself. The positioning you start with is your best guess based on how you feel right now. Keep writing, and your readers will reflect back who you actually are.
Sean’s own words: “I’m not really lost. I just thought I was.”
If you’re stuck on what to call your Substack or what to write about, you might be exactly where Sean was. Start writing. Let your readers help you see.
Watch on YouTube:
Rocky earns more than Sean
Rocky is Sean’s dog.
One day Sean wrote a comic article where Rocky “took over the computer” and wrote about all the weird things Sean does. Pure comic relief from heavier mental health content.
Then another Substacker suggested he change his “Buy Me a Coffee” button to “Buy Rocky a Treat.”
He did. And now Rocky earns more on Substack than Sean does.
This is one of the best examples of creative monetization I’ve seen on the platform. Most people put up a “Buy Me a Coffee” button and nobody clicks it. But a dog getting a treat? Everyone wants in on that.
Stealing this idea for a community member. Maybe for my own dog ;)
The human slop problem
Sean and I talked about AI, and he said something I keep thinking about.
When the Substack discourse was about getting rid of AI slop, Sean asked, “What about the human slop?”
Yes, AI slop is real. But bad writing on the internet existed long before AI. The problem has never been the tool. The problem is the writer.
Sean uses AI as an editor. He built his own GPT trained on his own articles. He asks it for honest reviews. He pushes back when it’s too nice. Every idea is his. Every story is his. The AI just refines.
This is how AI should be used. Not to generate ideas. To sharpen them.
Sean’s actual system
Five notes a day, mostly scheduled for US evening hours. Two articles a week, Wednesday and Saturday. All his notes for the full week batched in a single two-hour block on Sunday morning. And he keeps himself six articles ahead at all times, so a bad week never breaks the momentum.
That’s a clean system. And he’s actually doing it, which is the thing that matters.
If you find Notes challenging, here are five free templates you can use to grow your subscribers:
So that’s Sean
I asked Sean what he wanted to leave readers with. He said four words: “Never give up on yourself.”
He’s been in dark places. He’s still here. He’s still writing. That’s why I wanted to feature him. He’s a good example of what it looks like to keep going, even when you fail publicly, even when the numbers plateau, even when you have to rebrand because your readers know you better than you know yourself.
Go subscribe to Sean’s Substack, Rethink and Rebuild. He writes with a kind of honesty that’s rare on the platform.
A few books Sean recommended (my affiliate links):
Can’t Hurt Me by David Goggins (get the audio version, the interviewer asks Goggins questions between chapters)
And if you’re thinking of moving to Portugal, Sean offers one-to-one calls on the visa process because he says too many people get ripped off paying hundreds of euros for things that take five minutes.
Yana
Wanna have your own Spotlight Session?
You can take the place under the spotlight in one of the next sessions and talk about your personal story and your Substack!
All you need to do is:
Be a paid member of my Unplugged newsletter
Аdd yourself to the Accountability Tracker
Every month I choose two winners - one for the Notes and one for the Writing Challenge. Watch all spotlight sessions here.
If you’re still a free subscriber, become a member and get your spotlight session with me!
👉 Start a discussion in the Unplugged community! Get help or simply introduce yourself and connect with like-minded members, and create meaningful connections.
Kickstart Your Substack Growth:
Get Your FREE High Converting Substack Blueprint
Get a FREE 10-Day Substack crash course to grow your first 1000 subscribers
Join my FREE Masterclass on how to start making consistent $5,000/month
Join the One and Only Substack Quest to build a high-converting Substack
Work with me to get your Substack up and growing
Save Tons of Time! Use My Custom GPTs:
The Title Generator that gives me headlines that stop the scroll
The Notes Writer that writes Viral Notes, bringing me and my paid members hundreds of subs
The Writer Pro that turns my Notes into >90% human drafts (here’s the free version).
Or get the bundle with all the tools, now at a very special price ;)
Become an Affiliate:
Earn 30% from each sale. Apply below, I approve everyone.
Apply here for my AI tools & templates
Apply here for the SUBSTACK QUEST courses
Become a sponsor:
Reach thousands of engaged buyers.
More from me:
FREE Daily BiTES: A daily mail with just 3 bullets from the most helpful things I read about writing and making money online with AI
Unplugged: The place to be if you want to grow an AI-powered paid newsletter and create content that sells itself.
