How to Start Freelance Writing: Advice From a Six-Figure Freelancer

9 min read
Freelancing, How To's, SEO/Content Marketing
By: Maddy Osman

I’ve been freelancing since my early college days. It all started with a project my then-boss didn’t have time for.

For me, this effectively sanctioned my pursuit of paid projects outside of work. I definitely stumbled through the process of dealing with my first freelance client but luckily, didn’t completely mess it up.

This early freelancing experience taught me an important lesson:

I have a skill that people are willing to pay for. Even outside of a traditional employer/employee relationship.

From there, I went on to graduate. I worked two sales gigs as a foot in the door to my real dream job: marketing. I ate up every opportunity I could find to grow my existing knowledge — including light freelance assignments.

Eventually, one of my freelance clients, turned mentor, helped me see that I had it in me to support myself doing the things I like to do most, full-time. He became my first really big client, giving me enough work to cover my basic needs, and enough time in my schedule to do work for other clients, too.

Fast forward to today…

It’s been over three years now that I’ve been freelancing full-time and I’ve gotta say, this freelance thing ages like a fine wine.

It gets a lot better… over time.

I’ve managed to achieve a rare and beautiful work/life balance. But it took time and hard work. It involves continuously challenging myself to get outside my comfort zone.

Here’s what I’m trying to say:

If you put in the tough work now, you’ll be that much closer to your dreams, with just a few years or months to go.

On my journey to finding success, I’ve shared a lot of the lessons learned along the way for various clients and freelancing publications, which you’ll find below. I love mentoring new freelancers — I also co-founded an in-person meetup for locals: Freelancers Union Spark Denver.

I put this all-in-one guide that you’re reading together because I wanted new and growing freelancers to have a resource to consult at any stage when they learn how to start freelance writing.

The following represents my best advice for how to start freelance writing — some of my favorite pieces to write:

Scaling Up From a Side-Hustle to Full-Time Freelancing

Please don’t quit your job to freelance without a solid plan.

You may be fantasizing about leaving in a fit of rage, when you just can’t take it anymore.



I get it.

But unless you have some published samples to demonstrate your abilities, an emergency fund to cover a few months of rent as you wait for clients payments to process, and ideally, a couple clients lined up, the first few months of working for yourself are going to be a rude awakening.

So for the love of God, at least consider my advice for building a freelance writing side gig that you can scale up when the time is right:

Sales 101 & How to Pitch

I can’t think of a better test run for the entrepreneurship side of freelancing than an entry-level job in sales. I learned so much by starting my post-college career with a sales job at Groupon.

My #UnpopularOpinion for new freelancers to learn how to properly support themselves?

Put in a few months (to a year) at a sales-driven organization and work your way up from warm leads sales (people proactively reaching out to your team to inquire about making a purchase) to cold calling sales (reaching out to people who may have never heard of your solution before).

There’s nothing quite like the pressure of a sales manager and metrics to teach you essential closing and follow up techniques. A sales job will also help you learn how to maintain a consistent pipeline of work opportunities.

My Skillshare class, How to Negotiate a Six-Figure Freelance Salary can help you understand the most important sales techniques you should practice if you want to make bank as a freelance writer.

Here’s some of my best sales advice that you can use to find success:

How to Create Urgency

On that note, these were all written for my client Cirrus Insight, a multi-purpose sales productivity tool:

Freelance Writing Pitch Template

Freelance writing involves a special kind of sales: pitching topics to editors and brands.

An effective freelance writing pitch includes the following:

Here’s an example of how this might look written out:

It might seem like I overdid it a bit in this pitch but check out what my recipient said in response! Oftentimes, going the extra mile in your pitch is what sets you apart from others, who might just send a quick note with a sample and call it a day.

Make it as easy as possible for someone to see you as their future writer by connecting the dots in your pitch.

When I first committed to learning how to start freelance writing, I applied for a staff writing job at Search Engine Journal. At the time, I honestly was being a little too ambitious — I didn’t have a lot of experience or published works to show off (or learn from).

Although I didn’t get the job, they really liked me and invited me to be a contributor (check out my first article about duplicate content on LinkedIn and Medium). I’ll be honest with you: I don’t make any money writing for Search Engine Journal. But all the business it’s helped me to win justifies the time spent on creating quality content.

I’ve talked about my approach to leveraging bylines in detail on the Clients from Hell podcast, but here’s the TL:DR;

Writing guest posts for high authority blogs can be great inbound marketing for your business, in addition to providing samples that you can leverage to get well-paying gigs. Guest posting can also be a great way to build backlinks to your freelance portfolio website, which will help you to come up in relevant searches.


If you’re unsure where to start reaching out, Theme Circle put together an awesome guide for where to guest post, organized by topic and authority (measured by domain authority, which is important for SEO).

Just as with building up your freelance client roster, the key to success is a good pitch:

Job Boards with Occasional Gems

This is a good lesson to learn early on:

You’re not going to make six-figures freelancing if you exclusively pitch to publicly posted jobs.

I really have a problem with the fact that most job board postings aren’t transparent when it comes to payment. You’re expected to spend time customizing the perfect pitch, but oftentimes, your efforts result in an invite to write a free test piece. It only goes downhill from there.

Yeah… no thanks.

But there are some hidden gems if you stay on top of job board postings. I started writing for Sprout Social after responding to a job post I found on ProBlogger.

Here are my best job board-related resources to help you with how to start freelance writing:

Facebook Groups: to Get Feedback, Enjoy Camaraderie & Share Opportunities

As a freelancer, you miss out on the opportunity to lean on coworkers when you have a problem to work out or just need a break from the grind.

I’ve found the following Facebook groups to be especially useful for finding online “coworkers” and getting feedback for how to start freelance writing successfully:

Where to Learn More About SEO

The modern freelance writer needs to at least have an awareness of SEO.

My Skillshare class, SEO for Bloggers & Solopreneurs, provides a straightforward process for conducting simple keyword research and effectively implementing keywords within a blog article.

These articles represent some of my most relevant SEO tips for freelance writers:

And 6 DIY SEO Tips for Small Business Owners

I’d also recommend keeping up with these blogs to learn the basics and stay fresh:

Write Good Copy

Becoming a writer truly is a never-ending process. You can always keep working to be better at your craft.

If you’re looking to skill up fast, check out Copyhackers’ Tutorial Tuesdays: 20 minutes each week dedicated to becoming a better copywriter.

Here are some of my best writing takeaways from learning how to start freelance writing:

Check out my best advice for creating a solid foundation with my Skillshare class, How to Write a Kick-Ass Blog Outline. While you’re at it, check out my most popular Skillshare class, with 700+ students, How to Write a Kick-Ass Blog Post.

Freelancers Writers to Follow (At Minimum: Their Email Newsletters)

These freelance writing, ass-kicking ladies inspire me:

So if you want motivation to constantly be striving for the next level of what you can achieve when you learn how to start freelance writing, I encourage you to sign up for their newsletters and pay attention to their ideas and processes.

On that note…

If you’ve enjoyed this article so far, sign up for my newsletter, where I share my best content marketing tips.

How to Get Clients, Then Make (More) Money:

Everyone fakes it until they make it in some areas, but I only ever feel confident raising my rates after I’ve taken on projects and clients that push me out of my comfort zone, teaching me something new.

Here are some of my other best tips for getting more clients and making more money:

If you need a tool recommendation, the following advice for how to start freelance writing digs deep into my favorites:

Accounting & Bookkeeping Basics

Here’s another lesson I want you to take into learning how to start freelance writing:

If you’re not good with numbers, or organization, outsource your bookkeeping and tax preparation as soon as possible.

It was the best thing I ever did. These tools and resources helped me then — and now:

How to Deal with Difficult Clients

Oh, the stories I could tell you about dealing with assholes…

Here are the most important things to do from early on to protect yourself and your valuable time:

Repeat after me: these are non-negotiables.

I’m hoping that this specific advice for how to start freelance writing will save you from the worst offenses:

How to be a Good Boss (to Yourself)

To find freelance writing success, you must first get in control of yourself.

You have to learn how to find a work/life balance. You have to learn how make time to enjoy the perks of freelancing (traveling, taking a nap, wearing yoga pants, etc.) without completely taking advantage of them (to the point where you miss deadlines).

It’s a delicate balance and this advice for how to start freelance writing involves my best tips for self-management:

Business Growth: Scaling to the Next Level

I didn’t hit six-figures until I hired contractors to help me run various aspects of my business.

Once you’re ready to level up (or ideally, right before), check out my best advice for outsourcing various aspects of your freelance writing activities:

You’ll also want to check out my Skillshare class, How to Grow Your Business with Virtual Assistants. It takes less than an hour to get through and you’ll come out of it with an action plan to hire virtual assistants.


Another one of my secrets for being efficient? Outsourcing various tasks to Fiverr.

Ok, it’s not really a secret. I’ve written about how to do it for two of my favorite clients:

I also get business from Fiverr as one of their Fiverr Pros. Being a successful Fiverr seller has been an easy way to make money each month without getting involved in any long-winded sales discussions. My gigs offer preset packages, so upfront chatter is pretty limited — which means I can just focus on the work.

I Couldn’t Fit These Anywhere Else

…But I think there are some good lessons to learn from them, anyway:

Freelancing Book Recommendations

I strongly believe that part of being a good freelance writer is being a good reader. So start a Goodreads challenge to encourage yourself to read consistently and stay fresh with word choice when writing otherwise boring articles.

A few of my best picks for resources to help you learn how to start freelance writing:

Efficient Self-Marketing

Freelance writers are sometimes also referred to as marketers, and it makes sense. Great copy can sell just about anything.

Just don’t forget that your business needs consistent marketing just as much as your clients.

The following advice for how to start freelance writing will show you how to spend the least amount of time to get the best results when it comes to marketing yourself:

Want to dive a level deeper? I teach a Skillshare class for How to Build Thought Leadership on Social Media that runs through my process for keeping my business top-of-mind with my network (while building it out!).

I also contributed to a Growth Marketing ebook for AND.CO, alongside several other experts.

Finally, if you’re struggling with writing the copy for the service page(s) on your website, check out what I did with my SEO content writing services page to spark your creative juices (and see my transparent pricing structure).

Blogging/Content Marketing Advice

Being a freelance writer oftentimes necessitates a working knowledge of content marketing and blogging best practices.

Here’s some of my best related advice for how to start freelance writing, focusing mostly on creating efficiencies with content efforts:

WordPress for Non-Devs & How to Create an Effective Portfolio Website

I taught myself web design at age 11. That helped me win college scholarship money at a local competition and also led me to my fateful college job (where my boss gave me my first freelance assignment), which was crucial for getting me to where I am today.

Now, I specialize in writing about WordPress, a skill that might also help you while you’re putting together your freelance portfolio or uploading blog articles for clients:

This is really the tip of the iceberg as far as the content I’ve written about WordPress. If you’re hungry to learn more, check out more examples of the knowledge I’ve shared about WordPress in my portfolio.

On a side note: don’t feel pressure to niche down immediately but it does help you get more jobs overtime if you can demonstrate expertise in a particular niche. Just avoid the writing niches that don’t pay well!

Additionally, I put together an in-depth online course that guides you through everything you need to know to put your own WordPress portfolio website together (including guidance for SEO, creating page content, and installing useful plugins). Check it out: Teach Me How to WordPress.

Infographics: How to Start Freelancing

How to Start Freelance Writing: Advice from a Six-Figure Freelancer
Scaling Up From a Side Hustle to Full Time Freelancing
Freelance Writing Pitch Template
Freelancing Job Boards Have Occasional Gems
Where to Learn More About SEO
Accounting and Bookkeeping Pro Tip
How to Deal With Difficult Clients
Freelancing Book Recommendations
Efficient Self-Marketing

Final Thoughts: How to Start Freelance Writing

I’m breathing a sigh of relief as I wrap this up — happily reminiscing about the times that inspired me to write each of these pieces and glad that I don’t have to do it all over again!

Although I’ve covered a lot of topics around how to start freelance writing, I know there are still so many more questions to address. So what do you want to know about starting a successful freelance business? Leave a comment and I’ll share my best tips!


Maddy Osman

The Blogsmith

Maddy Osman is the author of Writing for Humans and Robots: The New Rules of Content Style. She's a digital native with a decade-long devotion to creating engaging, accessible, and relevant content. Her efforts have earned her a spot in BuzzSumo’s Top 100 Content Marketers and The Write Life’s 100 Best Websites for Writers. She has spoken for audiences at WordCamp US, SearchCon, and Denver Startup Week.

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So glad you liked the Infographic! My friends at made it and they did a fantastic job.

To answer your question: when I first started my freelance business, I considered insurance but ultimately ruled it out as something I really needed — especially now that I’m more focused on creating content that goes through multiple rounds of reviews and is approved by the client before it goes live (vs social media where I feel like stuff goes wrong all the time!).

Thanks so much, Nick! Nice seeing you at the Denver Bloggers Club event the other day. 🙂