How To Sell Every Day In Your Content (Without Feeling Like A Sleazeball)

Even if you're an introvert, shy, and hate selling

I used to think selling was for extroverts with slick tongues and zero shame.

When I first started writing online, I'd create content for months without mentioning anything I sold.

I thought I was being "helpful" by giving everything away for free.

My email lists were growing, sure. But I wasn't making any money.

I was terrified of looking pushy. Every time I thought about writing a sales email, my stomach would twist into knots.

I'd draft it, delete it, then write another "value-packed" newsletter instead.

The result? A list full of freebie seekers who'd never buy anything.

This was back in 2011.

Today, I pitch daily. And it's one of the reasons why I'm making a good living writing for merely a few hours every morning.

So if you're afraid of selling, you might want to spend 4 minutes and 27 seconds reading what follows.

Teaching for free doesn't help anyone

This might sound backwards.

But when you give everything away for free, people don't take action.

I used to write these massive 3,000-word blog posts with step-by-step instructions. I'd include screenshots, templates, the whole nine yards.

I thought I was being generous.

But you know what happened? Nothing.

People would bookmark the post, maybe share it, then move on to the next shiny piece of free content. They'd collect my tutorials like Pokemon cards but never implement anything.

Free content demonstrates your expertise. Sure. But it rarely solves anyone's real problems from A to Z.

People only value what they pay for. When someone invests money, they're invested in the outcome. They actually do the work.

I've seen this pattern hundreds of times. Students who pay $997 for my course get better results than people who get the same information for free. They show up. They ask questions. They implement.

Free content is great for building trust and showing what you know. But if you really want to help people transform their lives, you need to charge for it.

For your own, and your client's sake.

Pitching feels awkward (when you're not doing this)

Most creators try to hide their intentions.

They'll send 10 "value" emails, then suddenly hit you with a sales pitch. It feels like a bait and switch. Like they were pretending to be your friend just to sell you something later.

That's what makes selling feel cringy.

I do the opposite.

In my very first email, I tell new subscribers exactly what I'm about:

"I'm going to teach you how to create and sell online courses. And yes, I'm going to pitch you my products regularly. If that bothers you, scroll down, and feel free to unsub at any time."

This sets the right expectations from day one.

People know why I'm here. They know I have products to sell. They know I'm running a business.

Being transparent eliminates the awkwardness. There's no pretending, no hidden agendas. Just honest communication about what I do and why I do it.

Some people unsubscribe immediately. Good riddance.

The ones who stay?

They actually appreciate the honesty. They know when I recommend something, it's because I genuinely believe it will help them.

Make sales without ever pitching a single product

This completely changed how I think about selling.

Instead of trying to convince people to buy my course, I focus on convincing them of an idea.

For example, instead of pitching my course on creating courses, I pitch the idea that "anyone can create a profitable online course in 10 hours without showing their face."

I have over 5,000 notes in Obsidian. I'm obsessed with ideas. I love connecting them, playing with them, turning them into content.

When your marketing is built around ideas instead of products, everything becomes more fun.

Ideas are easier to sell than products because they don't feel like selling. You're just sharing what you believe to be true.

My daily emails are full of ideas:

• "Most online courses fail because they try to teach everything instead of solving one specific problem."

• "The best way to find your course topic is to look at what you complain about in your industry."

• "You don't need 10,000 followers to make $10,000 a month."

Each idea plants a seed. Over time, these seeds grow into a worldview that aligns with what I teach and sell.

Make selling fun again

Once someone believes your ideas, selling becomes the natural second step.

If they're convinced that anyone can create a profitable online course in their spare time, the next logical step is learning how to do it.

If they believe that most courses fail because they try to teach everything, they'll want to know how to focus on solving one specific problem.

Selling simply becomes an invitation to implement the ideas they already believe.

That way, you're not manipulating anyone.

But you're offering a solution to people who already want what you're selling and are ready for it.

As an introvert, this approach works perfectly for me. I don't have to be pushy or aggressive. I don't have to overcome objections or handle confrontation.

I just share ideas through writing, then invite people to take the next step.

The people who are ready will say yes. The people who aren't will keep reading until they are.

No pressure. No awkwardness. No sleazy tactics required.

Selling doesn't have to feel gross

When you're transparent about your intentions, focus on ideas instead of products, and invite implementation rather than pushing purchases, it becomes a natural part of helping people get what they want.

And the best part?

You can do it all through writing, just like I do every single day.

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PS: If you want my 3 favorite “selling with ideas” templates, click here (it’s free.)