How I Would Make My First $100,000 As A Writer Starting Over In 2026

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Today, I want to explain how I would make my first $100,000 as a writer if I was starting from scratch.

I’ve made millions of dollars as a writer over the last 10 years. And I’ve monetized my writing in almost every way possible:

Ghostwriting
Self-publishing
Digital products
Group coaching
Paid newsletters
A writing SaaS product (Typeshare)

But if someone took away my audience, I had no email list, and no one knew who I was, here are the steps I’d take to reach $100,000 per year as a writer as quickly as possible.

Let’s dive in!

Step 1: Write for free, first.

Yes, this is the first step to monetizing as a writer in the digital age.

Why?

Because if you don’t write for free on social platforms first, you don’t know:

Who you’re writing for
How your writing helps them

It doesn’t matter how “talented” you are as a writer, if you don’t understand these two points you’ll never be paid well as a writer.

There are lots of very talented writers who don't make a lot of money (for example, Nobel prize-winning writers who make minimum wage) and there are very mediocre writers who make tons of money.

Here’s the difference:

The awareness of who they are writing for.

Because if you don’t know who you’re writing for, then people will never consume your free stuff. And if no one is reading your free stuff, you’re never going to be able to make money from your writing.

So the first step is to write for free on:

LinkedIn
Medium
𝕏/Twitter
Facebook
Instagram

In short, publish your ideas where your writing will get distributed by an algorithm.

This helps you refine and clarify your ideas and thinking. Because if you don’t go through this process first, it doesn’t matter which writing business model you choose or the product you create.

You won’t be able to make money as a writer because you won’t be serving the reader.

Building digital products
Offering a service
Delivering a paid newsletter

It all starts with writing for free.

Step 2: Double down on what’s working.

This is the whole game of making a living as a writer in the digital age.

In Ship 30, when we teach people how to start writing online, we explain what to look out for when you hit “Publish”:

How many people liked it?
How many views did it get?
How many people commented on it?
What sort of comments did you get? (Questions vs surface-level comments)

All of these are signals for you to notice what’s working and what’s not.

The success I've seen in my writing career has come down to making the decision to follow the data:

When I started writing on Quora in 2014, I wrote a lot about health and fitness (I was into bodybuilding at the time).
Then, from 2015-2016, I wrote about broader categories like life advice—which led me to becoming the most-read writer on Quora. I was getting surface-level reach, but no insight on where to take it.
It wasn’t until after 2018 that I saw whenever I published something on writing, people would ask thoughtful questions and want to know more.

I woke up to what the data was telling me.

The answer was screaming in my face.

I didn’t have to stare out the window and try and figure out my “life purpose” when it came to writing.

All I had to do was follow the data.

So I started to write more posts about writing & writing online and phased out the life advice content.

From this, I eventually ended up writing *The Art and Business of Online Writing—*a book that’s earned $250,000+ since I published it. This book became the foundation of Ship 30 for 30 which became the fastest growing and largest writing program on the internet… and the rest is history!

And all I did was double down on what was working.

The same is true on the services side—double down on what’s working for you.

In the beginning, you might not necessarily know which service you want to provide.

The solution?

Do a bunch of different projects. You’ll get a huge ROI just by learning whether or not this is something you want to do more of.

In the beginning, here are all the services I provided as a writer:

Brand strategy
Social content
Social media strategy
Thought-leadership articles

And while I was doing all of these I kept asking which one I enjoyed the most, how long each took me, and how much I could charge for each service.

This helped me figure out which one I found myself enjoying more and which would be the most profitable.

From this, I found my sweet spot:

Ghostwriting 800-word thought-leadership articles for Founders and CEOs—where I got to learn from their industry takeaways and insights.

Plus, I was extremely efficient at writing these—I’d written thousands of articles on Quora and for Inc. Magazine (again, this goes back to the importance of writing for free in Step 1 above).

In the end, doubling down on this niche led me to:

Ghostwriting for 300+ industry leaders
Employing a team of 20+ staff at my agency
Scaling this agency to $5,000,000+ in revenue

In short, the learning process of anything in life comes down to try lots of things and then double down on the ones that are working.

Step 3: Position yourself as an expert.

First of all, you’ll only get to this step in Year 2 at the earliest (and probably more like Year 3 and beyond).

I've been at this for a long time. And I often see people look at other writers and creators who are further along than them, who they think of as experts, and believe they’ve always had it like this:

A large audience.
A successful podcast.
A profitable business, etc.

But this couldn’t be further from the truth.

Becoming an “expert” takes time. And before we go on, I really want to emphasize here that being an expert doesn’t mean acquiring a specific title, becoming a New York Times bestseller, or waiting for some magazine or some high-profile person to tell you're awesome in public.

This isn’t what it means to be an “expert” writer at all.

Instead, becoming an expert is about crystallizing the frameworks around your writing.

All I'm advocating for, and what I would tell you to do, is to recognize the point on the journey when you start to have some clarity around what you could pay forward to the next person.

As you start writing more you will inherently begin to:

Create your own opinions.
Create your own processes.
Create your own frameworks.

In other words, you will have an understanding of what you do and why you do it.

At this point, it’s a good time to consider how you can again double down on those things for yourself. This means a) positioning yourself as an authority in your niche and b) creating a personal brand for yourself.

Personal branding is an area writers misunderstand, too.

We live in an age where people get “personal branding” wrong.

It isn’t about:

Growth hacking to 200,000 followers.
Posting pictures of yourself on social media.
Being featured on tons of different podcasts for “exposure.”

In reality, the people who do this just have followers and not much authority and haven’t really contributed to their niche or industry.

Instead, becoming an authority is about contributing something new to your industry and space.

Once you’re clear on this, it’s time to consider how you can package this up into a video course, a book, a webinar—some way of sharing this new thinking.

This is how you transition from a “student” of the game to someone adding to the broader conversation where you can pay it forward (and this is exactly what I did with The Art and Business of Online Writing).

One final word of warning:

Please don't feel like you have to have this from Day 1.

Don’t rush this part of the process.

But don't keep kicking the can down the road and avoiding this, especially if everything else is going well.

Don’t cheat us of your contribution—we want to hear it!

Step 4: Create a portfolio of writing businesses.

In this final step, you have to stop thinking of yourself as an individual writer and start thinking about yourself as a small portfolio of writing businesses.

I have generated over $1M as a writer, over and over again, in 8 different business models:

SaaS
Cohort
Services
Consulting
Low-Ticket
Self-Publishing
Paid newsletter
Group/High-Ticket

And now, I’m working on another (fiction books).

But one of the quickest ways to accelerate your earnings is to become a ghostwriter. It’s the fastest way to monetize your talents. You can hit $10k/month+ quicker by landing 2 x $5,000 clients as a ghostwriter over trying to sell digital products at $150 a pop (that’s 66 units per month vs 2 clients, by the way).

But here’s the real reason why I love ghostwriting.

Ghostwriting helps you quickly replace your income.

This means you can quit your job and then start practicing writing full-time which has way more compounding power if you’re trying to monetize your writing talents further.

The services allow you to power level your earnings in the beginning and it also gives you some cash to play with. This is how you start thinking entrepreneurially so you can build a portfolio of writing businesses. Then you can start to build your own digital products and become a “hybrid” agency (and yes, that can mean an agency of 1).

There are two revenue streams here:

You sell writing services to clients.
Sell a digital product to potential clients who then consume the product, find it’s too much to do themselves, and ask you to do it for them (so you can sell more services).

The more services you sell, the more you can reinvest into other streams of income:

Self-publishing
Digital products
Cohort-based products
Group coaching, 1-on-1 coaching, etc.

There are loads of different ways to monetize as a writer.

So, if I was trying to get to $100,000/year as a writer, this is how I would do it.

It’s really important you do these 4 steps in this order:

Step 1: Write for free. Be your own case study and practice on yourself. Monetize with ghostwriting.
Step 2: Double down on what’s working. Then take the funds from the ghostwriting and reinvest in yourself.
Step 3: Position yourself as an expert. In around Year 3 at the earliest, start positioning yourself as an authority in your niche.
Step 4: Create a portfolio of writing businesses. Then start thinking of yourself as a business owner or entrepreneur who runs a portfolio of writing businesses (using services to invest in yourself again).

But before I leave you with this, I want to address the objections I get every time I lay out this roadmap.

3 faulty beliefs writers have about what it takes or “means” to be successful.

If you can master these faulty beliefs, then the steps I’ve outlined above will be 1000% easier:

You can’t just focus on the “art.” You also need to focus on the business side, the marketing side, the sales side, and how these engines power your writing. This is very, very important.
Success is more about the relationship you have with yourself. This isn’t a hard skill issue. Writers hold themselves back because of the relationship they have with themselves and their ability to trust themselves.
It’ll take longer than you think. Someone doing something a couple times and not putting forth enough volume and saying, “Ah, that that doesn't work for me,” or they pitch one person in their industry and that person says, “No,” and they immediately say, “This doesn't work for my industry”. Trust me, this works. You just need to put in more reps.