Why most Substack writers struggle to make a living (and how to fix it)

For the last week, I've been sharing tactical strategies for creating and selling digital products to your newsletter audience.

We've covered product types that work best for writers, the weekend creation system that lets you build products quickly, and the an email launch sequence that converts your readers into customers.

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But today, I want to step back and talk about something more fundamental – something that bothers me when I think about the thousands of talented writers pouring their hearts into their work but still struggling to make ends meet.

Here's the hard truth: most writers are thinking about monetization all wrong.

I see the same pattern play out again and again. A writer starts a newsletter with passion and enthusiasm…

They commit to publishing consistently. They focus on growing their subscriber count, hoping that once they hit some magic number – 1,000, 5,000, 10,000 subscribers – they'll finally be able to make a living from their work.

They look at the success stories – the writers making $20,000 a month from subscriptions – and think that's the only path forward.

So, they keep writing. Keep promoting. Keep hoping that subscriber growth will somehow translate into financial security.

And while they're waiting for that subscriber count to reach critical mass, they're:

• Working side jobs they don't love

• Taking on clients that drain their energy

• Feeling guilty about not spending enough time on their newsletter

• Wondering if they'll ever be able to make this work financially

I know this cycle intimately because I lived it.

I spent months pouring everything into my newsletter while still working with my “day job” clients that left me drained. I'd check my subscriber count, watching it inch up by a few people each day, doing the depressing math in my head about how long it would take to reach "enough" paid subscribers to replace my client income.

At my lowest point, I remember sitting at my desk late one night, finishing up a client project that I resented, looking at my latest newsletter stats, and feeling a wave of frustration. At the current growth rate, it would take nearly two years before I could live off subscriptions alone.

I couldn't keep going like this for two more years. Something had to change.

That's when I had the realization that completely transformed my approach to newsletter monetization:

The subscription model alone is a painfully slow path to financial freedom for most writers.

Think about the math: Even if you charge $10/month for your paid tier (which is on the higher end), you need 1,000 paying subscribers to make $10,000 per month.

With average conversion rates between 5-10%, that means you need 10,000-20,000 total subscribers to hit that income level.

How long will it take you to reach 10,000+ subscribers?

For most writers, that's years of work – years of financial struggle while you build toward that goal.

But here's what changed everything for me: When I created my first digital product and made around $2000 in a weekend, I realized I didn't have to wait.

That single product, sold to my modest list of ~1,200 subscribers, generated the equivalent of what 202 monthly paid subscriptions would have.

In other words, that single weekend product instantly had the same impact as growing my paid subscriber base by 17x.

The traditional "subscriptions only" approach to newsletter monetization isn't just slow – it's unnecessarily limiting. It forces you to put all your eggs in one basket, pinning your hopes on gradual, incremental growth rather than creating multiple revenue streams.

This realization doesn't mean subscriptions aren't valuable. They absolutely are – they provide predictable, recurring revenue that grows over time. But relying on subscriptions alone is like trying to fill a swimming pool with a garden hose when you have access to a fire hydrant.

Digital products are that fire hydrant.

They allow you to:

1. Generate significant income quickly, even with a small audience

2. Serve different segments of your audience at different price points

3. Create multiple streams of revenue that don't all depend on continual growth

4. Escape the content treadmill where you're constantly creating to justify subscriptions

But perhaps most importantly, they give you the financial breathing room to build your newsletter the right way – without the pressure to compromise your vision or take on work you don't love just to pay the bills.

Since that first $2,000 weekend, I've created multiple digital products that collectively generate four to five figures each month – all while continuing to grow my subscription revenue as well. I’ve been able to take on less “day job” clients and my newsletter is consistently growing.

But what matters more than the money is the freedom it's given me:

• Freedom to write about topics I truly care about

• Freedom to publish on my own schedule

• Freedom from the anxiety of watching subscriber numbers

• Freedom to build a sustainable business on my own terms

I've now helped hundreds of other writers implement this same approach, and the pattern is consistent: those who add digital products to their monetization strategy reach financial sustainability 3-5x faster than those who rely on subscriptions alone.

One writer went from making $230/month from subscriptions to over $4,000/month in combined revenue within 60 days of launching her first digital product.

Another was able to quit his day job six months earlier than planned after his product launch generated three months of living expenses in a single week.

The question isn't whether adding digital products will accelerate your path to newsletter profitability – the data is overwhelmingly clear on that point. The question is whether you're ready to break free from the "subscriptions only" mindset that's holding so many writers back.

If you're tired of the slow build, if you're feeling that same late-night despair I felt when looking at your growth numbers, if you're ready for a more direct path to making a living from your writing – then digital products aren't just an option, they're the solution you've been looking for.

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The Six-Figure Digital Product Masterclass is designed specifically for Substack writers who want to escape this common trap and build a more sustainable, profitable business around their writing.

When you join today, you'll get access to:

• The complete system for creating profitable digital products specifically for newsletter audiences

• Templates, swipe files, and frameworks that make implementation simple

• The exact strategies I've used to generate $5K+ monthly from my newsletter through digital products

• Step-by-step guidance for creating your first product in a single weekend

Plus, when you join before Wednesday at midnight, you'll also get these special bonuses:

1. 5-Day Digital Product Sales Launch Training for Writers — This method ensures your product sells by properly prepping your newsletter audience beforehand

2. Six Figure Digital Product Brainstorming Template — This template helps you mine your existing newsletter content for product ideas your audience will actually pay for

The sign-up cart for the Digital Product Masterclass closes for good on Wednesday at midnight, so if you're ready to transform your newsletter from a slow-growing side project into a profitable business, I recommend you check out all the details now:

Keep Writing, Wes

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P.S. When I talk to writers who are hesitant to create digital products, the most common objection I hear is "I don't think I'm expert enough yet."

Here's what I've learned: You don't need to be the world's foremost authority to create a valuable product. You just need to be a few steps ahead of your audience on a specific journey they want to take. Your unique perspective and approach are precisely what make your products valuable.

In the Masterclass, I'll show you how to identify those areas where you have more than enough expertise to create a product your audience will love.

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P.P.S – Tomorrow, I’m writing a new post answering a bunch of questions I’ve gotten from subscribers about digital products.

Today, in the Chat I asked subscribers their toughest questions around how to create and sell digital products for writers. Be on the lookout because I bet you have some of the same questions, too.