Selling Your Stuff on Substack (Even If You Suck at Sales)

A confession, a reckoning, and the start of a real sales engine.

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I could have titled this post “Seven Secrets to Sales Success on Substack,’ but it would have been Bs. Unfortunately becoming good at sales doesn’t happen with secrets or steps, or over a weekend with a downloadable checklist.

For most of my life, I’ve said:

“I suck at sales.”
With my whole chest. Proudly, even. As if that let me off the hook.

But now? That mindset won’t cut it.

Because if you’re building something successful on Substack — a business, a body of work, a new way of earning — sales can’t be the thing you keep avoiding.

No more tucking it behind “generosity” or hoping your brilliance speaks for itself.
It’s time to build something stronger. More grown-up. More sustainable.

It’s time to build a sales engine.

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🧱 The Four Pillars of a Sales Engine

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🧠 1. Mindset: Sales isn’t the enemy

This is the one I’ve resisted the longest.

Most writers don’t think of themselves as salespeople. We think we’re above that.
But in the world of solopreneurship? That’s just not going to fly …

Because:

• Something paid for is valued more and gives the creator credibility. .

• No one wants to give their best work away forever.

• And we deserve to be compensated for the time, energy, and brilliance we put in.

The “I suck at sales” story feels true, but it’s just that — a story.
It’s one I’ve lived for years. But now I’m choosing a different one.

Because avoiding sales means avoiding growth.
And we didn’t come all the way to Substack to stay stuck.

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🔧 2. Skill: Sales isn’t magic — it’s practice

Sales is a skill. And like any other skill, it can be learned.

That practice won’t make you perfect — but it will make you skilled.
That’s how anything works, right?

• You write → you get better at writing.

• You lift weights → you get stronger.

• You sell → you get better at selling.

Not every attempt will work. Some launches will flop. Some DMs will be ignored.
But if you keep practicing? You get sharper. Braver. Calmer.

You also get more solid in yourself. Because real sales skill includes mindset control:

• How do you stay steady when you hear crickets?

• How do you keep offering when your brain screams “No one wants this”?

• How do you detach your worth from your conversion rate?

This is the part no one talks about in the “tripwire funnel” world.
But it’s the foundation for everything.

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🧴 3. Offer: You have to believe in what you’re selling

Here’s the thing: if your offer is wobbly, your sales will be too.

I don’t mean it has to be perfect. But if you:

• Don’t trust that it helps people

• Aren’t proud of what it includes

• Secretly wish it didn’t exist...

...then yeah, it’s going to feel like pushing a wheelbarrow full of shame uphill in a headwind.

This pillar is about creating something solid. Something you:

• Believe in

• Want to talk about

• Would buy yourself if you were your reader

Confidence in the product takes pressure off the pitch.

This is something we’ve been working on in my Inner Sanctum.

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🧩 4. System: Sales needs structure

Even with the right mindset, solid skills, and a great offer — if you don’t have a system, you’re starting from scratch every time.

This is where I feel most at home.
Creating The Substack Creator System was easy for me. Because I’ve written courses professionally for years.

But sales? That’s been my nemesis.
The one thing I’ve never felt like I could crack.
The thing that kept me working for wages instead of building something on my own terms.

A sales system is what brings all the pieces together:

• Audience building

• Relationship nurturing

• Offers at the right time

• CTAs in the right place

• Pathways from free reader → paying fan → long-term customer

Without it, every sale feels like a fluke.
With it? You create repeatable momentum.

And the hard part: it’s not linear. It’s a dance. 💃

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So what’s next?

I honestly don’t know, (yet).

Yes, there’ll be a series . But I definitely won’t be writing it from the top of the mountain. I’ll be writing it from halfway up the damn thing, shoes muddy, hands scratched, still figuring out which direction is north.

But here’s my promise:

I’m going to figure this out.

I’m building my sales engine in public — and if you’re a “sales tragic” like me, I hope you’ll stick around.

We’re not here to hustle harder. We’re here to build something solid.
To get our work out into the world.
And to finally feel good about getting paid for it.

Get on board now before your audience gets tired of free content.