How to Self-Learn Content Writing: 9 Steps From a Freelance Blogger

Learning to write blog content online completely changed my life. 

In 2021 I made the jump from full-time sales rep to full-time freelance blogger. 

And all of a sudden, I had freedom. 

I could travel, work when I wanted, control my schedule, and secure time to explore my interests and work on my passion projects. 

Over the last few years, thanks to freelance content writing, I’ve been able to:

  • Airbnb-hop around the US for a year with my fiance (month-long stays in 11 cities). 
  • Read for more than 2 hours a day. (I finally had the energy and time). 
  • Frequently take afternoons off to go hiking. 
  • Spend more time doing the things I love, like writing fiction and seeing friends. 
  • Build and grow a blog. 

Perhaps best of all, I was getting paid over $100 per hour to do creative work I deeply enjoyed.

Since writing online has brought me so much joy (and money), I want to share how to learn the skill, so that it may bring you some as well.

What to Expect from this Guide

Today, I’ll focus on teaching you the craft of content writing, with an emphasis on blog and article writing. The guide will be directed towards people who want to freelance the skill or create a blogging business with it. 

That said, many of the things you’ll learn about how to learn content writing can be applied to almost any long-form online content (e-books, case studies, etc.,)

The goal of the self-education roadmap is to help you become a writer who can craft engaging, helpful, unique content that clients want to pay you for and that people want to read. 

I’m not focusing on the business or marketing side of freelance content writing or blogging. I’ll do that in another post, although some tips will inevitably seep into this one. 

Start with learning how to learn the skill. 

After all, the best way to sell yourself as a content writer or to create a great blog, is to become a good writer. 

That said, I’ll give you nine steps for systematically teaching yourself how to write content online, in an affordable manner. 

The Key to Writing Strong Blog Content: Before I begin, let me give you one piece of advice that really helped me — your main focus when writing blog content should be to anticipate the reader’s questions and provide clear and detailed answers. That’s it. If you can do that, you’ve accomplished more than half the task. 

The 10-Step Process to Teach Yourself Content Writing

Here’s a summary of the 10 steps to go from novice writer to paid wordsmith: 

  1. Pick a Topic Niche You’re Interested In
  2. Set up a Blog and Start Practicing 
  3. Consider Taking an Online Course
  4. Immerse Yourself in Great Blog Content 
  5. Learn the Fundamentals of Blog Writing That Stands Out
  6. Read These 3 Books on Writing
  7. Study the Basics of SEO (can be done in a few hours)
  8. Start Getting Feedback on Your Blog Posts
  9. Learn Some Copywriting Techniques 
  10. Continue Writing, Reading, & Learning

Read on to learn them in-depth. 

Keep in mind that many of these steps will overlap. 

Some will never be completed. Take writing and reading. You’ll do those for the rest of your life should you choose to master this craft. 

Also, note that people learn differently, so think of this as a helpful template rather than a baking recipe. 

I’m simply sharing some tactics of self-education in writing that have worked for me and other content writers I’ve studied. I’m not Stephen King or Charles Dickens’ ghost, so take my advice, along with pretty much any advice you get about writing, with a grain of salt. 

Writing, even when it’s for a landscaping company’s blog, is primarily a solitary, personal, and artistic endeavor. 

And to reach stratospheric levels in an art you must learn to hear, trust, and follow your innermost feelings and ideas. 

Last thing — remember to try out different learning techniques to see which are the best fits for your personality and needs. 

If, for example, you’re like me and dislike most writing courses, focus on reading books and studying great articles. 

Alright, enough self-conscious disclaimers. 

Let’s jump into the steps to become a self-taught content writer who gets paid for their skills. 

1. Pick a Topic Niche You’re Interested in

This is important so strap in. 

To write consistently and authentically over the long term, and thus get the practice you need, you must write about things you actually give a damn about. 

Also, this saves you from mistakenly teaching yourself that writing is a chore. 

I don’t care if it’s gardening, golf, environmental policy, video games, history, dogs, personal finance, sales, cars, political philosophy, or action figures.

It can be several things. The goal is to get you writing about stuff you find interesting, stuff you have something to say about. 

Look at what you like reading and talking about. That’s a good place to start. 

Do You Have to be an Expert in Your Topic?

You don’t have to be an expert in the topic, though some prior knowledge helps, as you’ll be able to write from the hip, aka without research, and thus practice the art of letting it flow, an ability every writer must hone (of course, you can still do that after reading about the topic).  

But really, if you aren’t an expert in the niche, that’s more than okay. Sometimes it’s an advantage. 

Honestly, I often find the articles I write that I knew nothing about beforehand are my best. 

I find that curiosity and the thrill of exploring a question I desperately want the answer to fuel my research and writing. 

One caveat — you should know enough about the topic to know that it’s actually something you’re going to be interested in for the long haul, especially if you’re creating a blog around it. 

Another thing — you can always switch your topic. This isn’t a life sentence. The great thing about freelancing is that you can write a few posts in another niche and use those samples to get your foot in the door. 

Where sticking matters the most is probably in creating a blogging business. 

This is Primarily Your Practice Topic 

Remember that this topic is your practice topic. It’s where you’ll cut your teeth. it doesn’t have to be the one you get paid to write for. 

For example, when I started out I knew I could get clients by making my niche sales because I had worked in the industry for two years. The problem was, after a few posts, I lost interest. 

On the side, where I really learned, I wrote like 15 articles on a personal development blog that went nowhere but served as a practice ground. And I wrote a whole bunch of unpublished short stories and crappy essays as well. 

Then I got my first client in the sales space and made that my niche because it paid well and I needed clients. 

By then, I was well practiced and saw writing as fun even if it was on a topic I wasn’t super passionate about. And I was disciplined enough to write both for my clients and for myself, them in the morning and me in the evening. 

I think if I’d only written about sales and tech to start I would’ve burned myself out or failed to learn the fundamental skills of content writing. 

So, focus less on profitability of the niche right now and more on picking a topic that you’ll be excited to write about. 

Ideally, the topic you pick will do both, be enjoyable and capable of earning you a living. 

These days, you can make money writing online about almost any topic using a blog or social media if you’re creative with marketing and monetization. 

Freelancing is a bit different. It might be hard to find a company that wants to pay you as well as you’d like to be paid to write about action figures, though they are out there.

If You Need Money ASAP  

If you’re really in need of money, and want to learn content writing and get your skill up to factory-grade level so you can get your business off the ground, then the niche I always recommend is B2B writing. They typically pay the most for content marketing. 

But this article is about learning to write good content, not to start a business. So let’s get on with it. 

2. Set up a Blog & Start Practicing (1,000 words per day)

Set up a blog and start writing. Don’t worry about the blog’s design. This is your practice ground. 

Though it could grow into a profitable blog one day, right now your focus should be on writing every day, ideally for 1,000 words (a significant yet achievable goal). 

I write in Google Docs and then publish on WordPress. Some people use other writing tools. I don’t think it matters much for beginners. Writing frequently matters.

As for the blog, you can buy a domain name from GoDaddy (search for a .com and find something relevant to your niche but not too restrictive — if you turn this into a real blog business you want to be able to expand into different territory). 

You can set up a blog up pretty quickly with Bluehost hosting. I use the Acabado theme because it’s easy to set up and is focused on displaying the blog posts. 

If you need help setting up a blog read this: how to start a blog

Why a Blog Over Medium?

I like publishing on a blog rather than Medium because you own the content and can make it into a business that gains organic search traffic. You own the land you write on, you don’t rent it. 

However, some people like publishing on Medium because of the virality of the platform. They get instant feedback on their ideas and writing from strangers (though I’m not sure if this is good for the beginning writer learning to trust and follow their intuition). 

Personally, when I’m learning a new form of writing, I like to do it alone for at least the first few months, to work in obscurity. 

This allows for freedom to make mistakes. 

Regardless of where you publish your content, aim to write 1,000 words per day. Do this for enough days in a row and you’ll improve.

How Do You Write 1,000 Words Per Day?

How you get to 1,000 words is up to you. I do it in one 2 hour sitting. 2-3 hours in the morning seems like the sweet spot for most writers. 

But I don’t know your process and, if you’re reading this, neither do you. 

You have to figure out what writing routine fits your personality and lifestyle, what leads to your best writing.

And the only way to do that is experiment — to write, day after day. 

Philip Roth wrote one page a day, all day, alternating between writing and reading sessions. 

Murakami writes for four hours every morning. 

Some writers write at night. Some in bed, some at a desk. I bet there’s one who writes upside down, or on a horse, and does pretty well for himself. 

I do one 2-hour session in the morning and one 90-minute session at 4 pm (this gets me 2,000 words). 

The only way to figure out your ideal process for getting 1,000 words onto the page is to try different routines and see which works best for your unique web of temperament, desires, motivations, and life obligations.  

The reason so many people say do it in the morning is because you can get it done before work when your mind is at its freshest. 

The reason I do it in the morning is because I’m anxious the entire day until I finally write, so I like to sit down and get to work early. It’s like having an interview at 4 pm. Who wants to wait? 

Obviously writing is more fun than an interview, but it’s also more important to me, and as Steven Pressfield says in The War of Art, the more important something is to us the more we fear it.  

The reason to go for 1,000 words is that you have to get comfortable generating words and ideas. That’s the essence of online content writing, expressing yourself clearly on the page. 

It’s also an attainable number, while still being something to be proud of. 

A General Blog Post Writing Process to Follow 

  1. Pick your article topic and title.
  2. Research the question.
  3. Create an outline. 
  4. Research to fill in the outline. 
  5. Write the rough draft. 
  6. Rewrite the draft. 
  7. Edit for flow, succinctness, and coherence.
  8. Edit for grammar and publish. 
  9. Look it over in a month and realize you aren’t writing up to your standards and need more practice (I don’t think this step is ever gone from the process, even from Hemingway’s A Farewell to Arms). 

Like your routine of writing, this might not be the best process for you. And each type of article might require a different process. 

For example, one where you know your shit you might just be able to write 1,000 words of a rough draft ASAP then go back and add in headers to create an outline and do research to fill in gaps. 

Again, you’re going to have to experiment with a lot of different processes to learn your process. 

Writing is exploration, not just of the topic or story, or of your unconscious that reveals itself onto the page, but of yourself and how you best work. 

To make writing 1,000 words a day a habit, consider using the Jerry Seinfield technique, where he gets a calendar and marks X for every day he does it, trying not to break the streak. 

You won’t want to break the chain! 

Okay, onto the next step. 

3. Consider Taking an Online Course 

Courses can be helpful to learn the structure of the different types of content you might want to write, from an e-book to a how-to guide, as well as various online writing techniques. 

I enrolled in Location Rebel Academy early in my freelance writing journey. 

I’m not sure how much it helped me improve my writing, but it certainly taught me how to start a freelance writing business — how to pick a profitable niche, market myself, etc., 

What helped me improve my online content writing was reading good online content. Since I wanted to write blog posts, I read a lot of blog posts, with a student’s eye. 

4. Immerse Yourself in Great Content Writing (& Study it)

Humans learn well from observation and imitation. 

Before books and courses people used to learn things by watching other people do them, and then copying them. 

Monkey see monkey do. 

Watch a man throw a rock at a lion enough times and try to imitate him over and over, iterating on your mistakes, and someday you’ll get pretty good at hitting a charging lion right in the eye. 

This same approach to learning, according to Francine Prose in her book Reading Like a Writer, is how many of the great writers learned their craft. 

A lot of it happens by osmosis. The lessons of good writing seep into you as you spend time reading. 

You’ll read a lot of content and find that your blog posts are naturally looking more and more like something a pro would write. 

You’ll find your rhythm, structure, and prose are improving, just from reading content you admire. 

But you can also make the unconscious conscious by analyzing blog posts you love, aka reading like a writer. 

You can identify and consider the significant choices and techniques the writer has used to create the piece. You can notice an effect and figure out how it was achieved. 

How to Read Like a Writer for Blog Posts

Reading like a writer looks a little like this: 

“Wow, I read that intro and was so hooked. Why? What did the author do to get me so hooked? What techniques did they use?” 

Then you analyze and find some principles .

“Oh, I see, they mentioned a highly controversial claim.” 

And then you think about how to apply that to your own writing. 

“What if I did that in my new blog post about squirrels? I could claim you should capture and neuter every squirrel you see!” (hopefully you apply more effectively than this). 

You can do this for the different aspects of content writing: 

  • Intros (what principles underlie a strong opening?)
  • Overall structure (how many words do they use in between headers?)
  • Content elements (e.g., bullet lists, additional reading boxes, etc.,)
  • Hyperlinks (when do they hyperlink? How does it help the reader?)
  • Closing (how do they sell their call to action?)
  • Sentences (are their sentences short or long? How do they make them flow?)

It’s best to do this analysis on your favorite content, stuff you really admire and would love to emulate. 

Some of my favorite blogs that I’ve studied are Location Rebel, HubSpot (for B2B), The Art of Non-Conformity, and The Art of Manliness. 

Another way to think of this is breaking an article down to its bare parts (what makes it work) then building it up into your own article. 

If you want to read more about how to learn writing this way, check out the book Stealing Like an Artist.


It’ll help you be more creative and become a better learner. 

5. Learn the Fundamentals of Content Writing That Stands Out

Okay, you’re writing and reading every day, slowly improving your craft.

Now it’s time to learn some best practices of content writing that will help you take it a step further and learn some skills to stand out from the other freelance content writers and bloggers. 

  • Great titles. 
  • Blog post scannability.
  • Competitor research. 
  • Sourcing quotes from experts. 
  • Authentic voice. 
  • Generating original ideas.

Let’s quickly go over each. 

Clickable Titles

Titles should grab the attention of the user and convince them that your article will answer their question or satisfy their interest. 

If you can write a great headline, you can win traffic to a post even if it’s in the 3rd or 4th slot in the Google search engine results. 

Some great blog title types that work:

  • Lists: “10 Ways to Surprise Your Husband This Valentine’s Day” (people love lists.)
  • How-to: “How to Read a Novel Like a Literature Professor (5 Key Steps).” 
  • Guide to: “The Ultimate Guide to Dressing for a Wedding: Everything Groomsmen Need to Know.” 
  • “Search query”: If the common keyword for an article is “why read old books?” make the title “why read old books? 7 reasons to consult the dead.” 

Sean Ogle, whose content helped me a lot when I got started, has an article on 15 types of blog titles that’ll help you get the fundamentals of this important skill. 

Blog Post Scannability

The next thing you should learn is how to write for the 3-minute or 30-second reader, the people who want to scan for quick answers to their questions.

Here are some elements to include to make your blog posts scannable: 

  • Headers: Try to go no more than 200 words without a header. Also, build hierarchies. If H2 is the overarching topic like “How to Build a Tree Fort”, make the steps H3s. 
  • Plenty of Lists: If you have a list of three or more things, create a bullet list rather than separating them by commas in a sentence. If it’s a step-by-step, use a numbered list. 
  • Quotes: Quotes from reputable sources are great ways to break up the text and provide value to the reader. 
  • Answer Targets: An answer target is a short 2-3 sentence bolded answer to the main question the searcher is asking. Check out the 2nd paragraph in “what is an autodidact” to see what I mean. 
  • Images: Relevant images help break up the text as well. Try to include one every 750 words or so. Original photos, images, and screenshots are best but stock images work well too. 

Include a healthy mix of these elements and your posts will have higher engagement rates and read times. And your readers will leave satisfied. 

Competitor Research

When writing a blog post, your goal is usually going to be to rank number 1 in the search engine results page of Google or Bing for a specific query. 

A good way to figure out what your blog post needs to have in order to rank number 1 is to analyze the current #1 ranking article and identify what it’s lacking and how you can outshine it.

For example, the number one article for the keyword “how to self-study sociology” might have a list of tips, but not an actual systematic step-by-step guide for getting where the reader wants to go. Thus, if you write a step-by-step guide, you can potentially outrank them. 


The rise of AI automated content will make content writers with strong voices who pull from personal experience even more desirable than they already are. 

You’ll be a designer brand in their niche. 

People travel to Tuscany just to get their handmade leather. 

A reader will no doubt click your link over someone else’s if they find your content to be more authentic, personal, and considered. 

If you write about stuff you’re interested in and care about, authenticity will take care of itself. 

If you want something to focus on to improve the skill, here are two: 

  • Draw from your personal experience. 
  • Give your opinion. 

People love this stuff, and robots can’t very well provide them.

Sourcing Quotes

If you want to make your content stand out, consider interviewing real people like a journalist would and then putting their quotes into your blog content to back up your points. 

I did this the other day for a client in the B2B space. 

My client wanted tech founders and sales leaders to give some advice on how to hire your first sales manager, so I tapped into my network, and used Help a B2B Writer, to source some quotes. 

I’m going to start doing this for Knowledge Lust as well, interviewing real people with experience in self-learning skills and subjects. It’ll make the articles more valuable and be super interesting for me. 

If you’re worried about asking people for quotes, don’t be. Most people love that you consider them an expert and are happy to share what they know. 

Generating Original Ideas

Generating original ideas for blog post topics and writing usually comes down to reading and living. 

If you live what you write about and consume content in your niche, you’ll have things to say. 

I spend a lot of time in self-directed study, and I read a lot about autodidacts from the past and present, and every few months I tackle a book about learning or education. 

So ideas for articles are always visiting me — in the shower, on a walk, while writing. 

Sometimes when I write I have an idea for another article and open a tab immediately and just title it so I can save the idea for later. 

This brings up an important point: idea capture. 

Keep a notebook or use your notes app on your phone to capture your ideas. 

A big way to gain a competitive advantage in idea generation is to read more real books. 

Not many people do that anymore. They consume a lot of fast food information, and just end up saying what other people are saying. 

Want an even bigger advantage? Read old books. This is going to make your content writing even more original, because very few content writers spend time reading the classics. 

Also, you’re going to want to read outside of your niche. 

Let’s say you’re writing about sales. Perhaps you’re interested in history, literature, and science. Go read books in those genres. It’ll give you ingredients for creative association. 

You’ll come away with an anecdote about a persuasive king, and you can use that to show the effectiveness of a sales tactic you’re writing about. 

You’ll gain new ways of talking about your topics. 

For example, you could describe some trend in B2B sales using language from astronomy, thus making the sentence more vibrant, original, and, if you’re doing it right, clear. 

6. Read These 3 Books on Writing 

Craft books were helpful for me as a beginner freelance content writer. 

They gave me some techniques to try out and experiment with. And they taught me other best practices for how to approach writing work. 

Here are 3 books that helped me early on in my content writing journey: 

  • Deep Work: This book taught me how to devote blocks of time (90-120 minutes) to deep focused writing work, and why that’s a key to success in this economy and a fulfilling life. 
  • Everybody Writes: Here I learned the fundamentals of solid marketing writing and how to capture and engage a reader. 
  • Bird by Bird: This book taught me helpful mindsets for thinking about writing, like “the ugly first draft,” which is where you assume your first draft will be shit, but that it will contain some gems, and can be polished. This helps you face the blank page. 

I love learning from books because every piece of advice in them has been extremely well considered. The writer spent hundreds of hours thinking and writing about the topic of the book. 

Extra Book: You might also want to consider picking up a copy of Mastery by Robert Greene, the guy who wrote 48 Laws of Power. It’ll help you chart a long-term plan for mastering your craft. 

7. Study the Basics of SEO

Most marketers hiring freelance content writers want them to have some basic SEO knowledge, so that’s what you should focus on getting — basic knowledge.

For example, here’s the first job posting I opened up on ProBlogger: 

Interlinking, article structure, tags, and keyword research are not that hard to learn. 

In fact, I’ll just tell you how to make an SEO-optimized post right now: 


Usually, clients want you to link out to a few authoritative websites in your niche. My clients often ask me to link out to companies with URLs ending in .edu or .org. 

Linking out to external sites with lots of authority is an indicator to Google’s algorithm that your post is trustworthy and thus valuable to the reader, so it’ll rank higher. 

Clients will also want you to include internal links. 

These are links to their own blog posts that will keep readers on their website, thus improving their user engagement and SEO rankings, while also serving to create a good experience for the reader. 

Article Structure

You should use short paragraphs, about 1-3 lines for each, because this keeps people on the page. A block of text can be intimidating and cause more dropouts. 

You should also aim to make articles scannable by including bullet point lists, numbered lists, images, and headings (H2, H3, H4). 

Try not to go more than 200 words without a content element that breaks up the text. 

Keyword Research

Keyword research is the act of finding relevant keywords that you can rank for on a search engine. Read more about the skill here

In most cases, if you’re a freelance content writer, your client will include a few keywords in the content brief to include in your copy. 

So you really won’t have to do too much keyword research, aside from maybe figuring out the intent behind those keywords. 

Answering the Query

By far, the most important thing you need to know about SEO when writing content is that your job is to answer the reader’s query as clearly and effectively as possible, and in a better way than the competitors on the search engine results page are currently doing. 

That, more than anything, will influence your ability to rank highly in the SERPs. 

Writing for Google’s algorithm is becoming less and less important, because Google’s algorithm is getting better and better at identifying which content is most helpful for its users. 

It’s getting better at awarding rankings to the articles that actually help readers, not those that have mastered interlinking and keyword stuffing. 

Therefore, mainly focus on the reader:

  • What questions do they have? 
  • What information do they need to answer it? 
  • What are they trying to decide and how can you make that decision easy? 
  • What action items can you give them that’ll help them get to their goal today?

If you want to go learn more about SEO, do what I did and read Moz’s beginner’s guide to SEO. You’ll walk away with more than enough knowledge to SEO optimize posts for your clients or your personal blog. 

8. Send Your Blogs to People & Ask for Feedback  

Once you’ve written about 10 blog posts and have gotten some good practice in, send them out to peers who are strong readers. 

They don’t have to be bloggers or writers, though that helps, but they do have at least some ability to judge a piece of writing’s quality and discern what makes it work and not work. 

Once you’ve found your people, I’d start by asking them two simple questions (I got this from Tim Ferriss):

  • Where were you bored? 
  • Where were you confused?

This’ll help you identify points in your writing that are boring and unclear. After your readers have pointed these out, you can figure out why it was boring and unclear, either by analysis or by asking them if they have the answer.  

Then you can go and fix the issue and, more importantly, learn from the process. 

Try to do this with as many articles as you can emotionally handle. 

The more feedback you get the better, provided that it doesn’t destroy your belief in your ability to write. 

After a point, you can start to ask readers to focus on other things, like pacing or scannability. 

Hopefully, some of your peers will rave about the writing and that’ll fuel you to keep going! 

Pro Tip: If you can, find a client who comes with an editor, as this will provide you with feedback on every article you write for them, sometimes in-depth. Revision is often painful and annoying, but it certainly helps you improve as a blog writer. My editor at Selling Signals was great and taught me so much about the craft of blog writing and how to make my writing more compelling. 

9. Learn Some Copywriting Techniques

Now that you’ve produced some content, take some time to learn some copywriting basics to make your writing more addicting to read. 

Copywriting is defined as writing that persuades the reader to take some action, whether it’s to click an ad, sign up for a newsletter, or buy a product. 

Typical forms of sales copy: 

  • Sales pages
  • Email sequences
  • Social media ads
  • Landing pages

All copywriting focuses on engaging the reader and encouraging them to move from line to line, page to page, (slippery writing), and this is at the core of any type of writing, whether it’s a white paper or a novel you’re crafting. 

There are some great courses online for this. 

I personally took Copyhour’s course, which has you hand copy and analyze a great piece of sales copy every day, thus internalizing the rhythm, styles, and techniques of the masters. 

If you like copywriting, you could offer it as a service alongside your content writing. 

You could also read The Boron Letters, a series of letters from history’s greatest copywriter, Gary Halbert. I loved this little book of wisdom. 

Also, if you’re ever going to start your own blog or content-focused business, you’re going to need to learn how to convince people to take action through your writing, whether it’s to click your article or to sign up for an email newsletter. 

So it’s worth learning at least the basics early on. 

Write, Read, & Improve With Consistent Practice

If you continue to study great online content, practice the craft of writing, and learn from your mistakes and experiments, you’ll consistently improve as a blog content writer. 

Remember that you should always be skeptical of writing rules. You’re going to have to do a lot of self-discovery to figure out who you are as a writer.

That’s how you find your ideal writing process, writing routine, learning techniques, and craft approaches.  

I hope this guide was helpful for you. And good luck on your journey as a writer. 

If you’re an aspiring polymath interested in learning other skills and subjects in a systematic way, from philosophy to meditation, check out my self-education roadmaps section of the site. 


After graduating college with an econ degree I realized I was still anything but well-educated. Over the last 4 years, I've been trying to fix that, autodidact-mode — by reading books and engaging in self-directed study across multiple subjects. On this blog, my goal is to share my learnings and help others get a well-rounded education outside of school. Education, after all, is a lifelong process, one well worth the investment.

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