WritingWriting Tips

Six Months a Freelancer: What I’ve Learned

On January 16, I launched my freelance writing career after a truly abysmal 2016 rife with turmoil and heavy soul-searching. Six months later, what have I learned? Has anything changed?

A hell of a lot, actually.

Milestones and Metrics

Number-crunching to track the pace of my freelance writing

Before starting this post, I estimated that I’ve written around 25 paid articles for clients (check out my portfolio to read some of them!). Funnily enough, upon counting how many articles and posts I’ve actually written for clients, that number is…25. And while I’m not going to count the exact number of words written, I’d estimate it’s around 30-40000. The average word count for each article I’ve written is 1500, with the lowest around 800 and the most I’ve written clocking in at a whopping 3200 words.

I’ve been asked to do 0 rewrites (a fact I’m rather proud of).

I’ve never missed a deadline or submitted work past an agreed-upon time.

Money-wise, each client has paid on-time and with zero issue. This means my clients are not only awesome, but that my onboarding process works in ensuring compatibility between clients and myself.

I’ve made as much money as I initially expected, though nowhere near my total earning goal. But I’ve been managing to pay my bills on time, so that’s a huge achievement considering the short length of time I’ve been freelancing.

Lessons I’ve Learned Over the Last Six Months

• Freelance Writing is a Business

It’s easy to think that freelance writing is a side hustle or a hobby. It certainly can be, and for some people, it is. On the other end of the spectrum are those, like me, who treat freelance writing as their career. Think you can’t make a living writing freelance? You’re wrong, and there’s a hundred people I can refer you to as proof that freelancing is a bona fide career.

But just because I can sit at home in front of my PC wearing PJs and writing for a client at 2am doesn’t mean I’m not doing real work. Yeah, there’s no office to show up to bleary-eyed and tired at 7:30am wearing a suit and a crooked tie, but there’s real work to be done and real people expecting that work to be finished by an agreed-upon deadline that they’ve paid me real money for.

Freelancing means no more ties.
I hope I never have to dress like this for 48 hours a week ever again.

Sound familiar?

Freelancing operates in the same way your local grocery store does. Where you hand over money for milk, clients hand you money for content. It’s a business. If you don’t treat it as such, you’re gonna fail.

Ever since I was little, I’ve been accused of being “too serious.” I’ve never seen anything wrong with that. That mindset continued with me since day one of my freelance career.

Running my freelance writing career as a business means a few specific things, all of which has contributed to my current level of success, and will continue to help me find even more:

  • Treat clients like people – they’re not dollar bill dispensers. They’re actual people.
  • Be respectful and honest. In the same vein as treating clients like people, treat them as you would a close friend or family member. Don’t lie to them, don’t oversell yourself if you can’t deliver, and if you make a mistake, own up to it, say sorry, and explain how you’ll rectify the situation. Chances are they’ll understand.
  • Be firm. Don’t act like an employee. In fact, ditch the whole employee mindset. While it’s important to have a strong client:writer relationship, you’re an expert being hired to perform a service. Clients don’t dictate how you run your business, but your business should be run in a way that’s conducive to producing quality work delivered on time. This was the toughest lesson for me to learn in terms of being firm about my pricing and writing methods.

Acting as a business owner first, writer second allowed me to bring credibility to what it is I provide: quality content writing. By choosing to act the way I do, with a professional demeanor and business owner mindset, I demonstrate to prospective clients that I’m the real deal. It shows clients that their money and trust are respected and appreciated and that the services they’re paying for will be fulfilled to a professional standard.

• Always Be Marketing

As a freelancer, I am my own “brand” so everything I do represents that brand. If I go on a drunken tirade on Twitter at 3am on a Thursday, that has the potential for severe negative repercussions for my brand – my business, not just myself. People, including prospective clients, don’t see such tweets as representing “Daniel Mattia” but as representing “Daniel Mattia: Freelance Writer.”

That doesn’t mean I can’t have a personality, though. I’ve learned a lot from Jorden Roper. Jorden doesn’t shy away from her unique, honest, and blunt personality, but she’s still professional about it – all while demonstrating that she’s a real human being, not a word-producing robot.

Before stumbling upon Jorden’s site, I would’ve never considered letting my personality show the way Jorden does. When I first started freelancing, I was all business, all the time. I was a word-producing robot.

I had no personality. Emails to clients? Tweets? Bid proposals? No personality.

“To whom it may concern,

My name’s Dan Mattia and I’m a freelance writer.

I’m interested in writing about spaceships for your company.

Here’s some samples of my writing. My website is available at https://danmattia.com

Let me know if you’re interested.

I look forward to hearing from you,

Daniel Mattia”


Seeing Jorden’s wildly successful freelance career and how she let her personality work for her helped me realize that I was going nowhere by acting like a robot.

Don't be a freelance writing robot
(Original image (C) Orion Pictures)

Everything I do online represents not only me personally, but my brand and business as well. That’s not a bad thing.

My personality is who I am and what allows me to bring a unique angle to everything I write. Embracing that personality, just as Jorden has, is as much a selling point as my writing ability.

I’ve actually had clients respond positively about “jokes” and funny lines I’ve put into the first drafts of articles. I was hesitant about doing this at first, but when I take time to think about the why of it, it makes sense. No one wants to read boring content. If a piece doesn’t engage you and keep you engaged, you’re going to get bored of it and click somewhere else. How does boring content serve my clients?

It doesn’t.

Letting my personality shine in each piece I write brings added value to my clients. Almost anyone can write bland and dry content, so why hire me if that’s all I’m providing, right?

Freelance writers that inject their personalities into their work all bring something different and unique to the table. Putting your personality into a piece, even subtly, brings value to your clients and helps your work stand out.

One client in particular has allowed me almost free reign when it comes to the voice and tone of the blogs they hire me to write. The subject matter of these posts has a high potential to be dull, not only in writing, but in reading as well. However, because I’m allowed and encouraged to write the type of article I’d enjoy reading, my client’s articles are not only informative, but fun and engaging, too.

So when a prospective client sees my blog or Twitter, they’re given a sense of who I am as a person. Yeah, I can write well and I’m serious about my business, but I’m also a fan of nerdy memes and dad jokes.

And who doesn’t want to hire a guy who’s got some lame dad jokes ready to fire off into an article?

• Create an Onboarding Process

When I was in the beginning stages of establishing my freelance business, I came upon the term “onboarding” during my research into established and successful freelance writers.

Prior to this interpretation, my only experience with onboarding had been a new hiring process I was partly responsible for implementing in a past job. The idea was to bring new hires through a five-week crash course that introduced them to different aspects of their job responsibilities, identifying areas of strength and weakness in order to properly place them in a position that was best-suited for them.

A cornerstone of my business is working with clients I’m compatible with and that are compatible with me. But how can I tell unless we’ve worked together already?

Through an onboarding process!

My onboarding process, then, serves two purposes:

  1. Determine the compatibility between a client and myself
  2. Help me learn as much as I can about a client so that I can best serve them

Determining compatibility goes both ways. I want to ensure that I’m a good fit for the client and can write content for them the way they want it to be written. If I don’t have the expertise to be comfortable enough to write about a subject even after heavy research, or I’m unfamiliar with the type of content they want, I may turn down the project or refer it to another freelancer.

The “tagline” of my freelance business, at the time of this writing is, “I make it MY business to help YOUR business succeed.” This isn’t just some lame way of enticing clients to work with me.

I truly mean it.

While I’m not an employee of any of my clients, I want to do as much as I can to ensure I can speak on their behalf, with the knowledge and expertise that I can accurately represent the company and its services or products through the content I’m hired to write for them.

To accomplish this, I have a short questionnaire I send as part of the onboarding process. This form asks questions about the target audience/market, type of “voice” the client wants me to write in, major dos/don’ts for the project, type of style to write in (Oxford comma, no Oxford comma, AP style, etc.), relevant or proprietary market research or data, and focus keywords.

I also perform intensive research into the company to get an idea of pain points I can help mend, and to get a consumer/outsider perspective. I need to know who I’m writing for, with the who being the reader.

I also link to my FAQ page and offer to answer any questions the client has about, well…anything, really.

Open and honest communication is key throughout every stage of working with a client.

The Downsides and Pitfalls of Freelancing

• Finding Clients is Hard

I was an insurance agent for a short time in my fairly recent employment history. While I excelled at learning about all aspects of life insurance and Medicare, I was total garbage at sales. The successful agents at the company were older, and those few my age who found success were ridiculously outgoing and extroverted.

The older agents had the benefits of having larger and wider networks to sell to or ask for referrals from. They had siblings and friends with kids and grandkids, former employers and coworkers, and people from clubs and organizations they belonged to for years.

I had a couple of 20-something friends just as poor as me.

That meant all of my prospecting for clients was through cold calling leads provided by my company. Anddddd I’m absolutely abysmal at speaking on the phone.

It wasn’t a good time. Great job, but not meant for me, at least at that stage of life.

Finding clients as a freelance writer is similarly difficult, but I don’t have a compliance department to worry about. I can prospect for clients however I see fit, so marketing is entirely up to me.


Marketing is entirely up to me!

Marketing as a freelance writer is my responsibility

No one provides you with a list of leads when you’re a freelance writer. You need to either purchase a list (of dubious quality) from somewhere, or brush up on your Google-fu to find companies and publications willing to pay you to write for them.

Or you can use a site like Upwork or Textbroker and “bid” on projects. (As an aside, I had a very bad experience with Upwork. And content mills like these are usually a race to the bottom where you’re paid peanuts. Use them sparingly and as a very last ditch effort, if at all. They generally put you into an “employee” mindset, but I’m rambling. This is a post for another day.)

Or you can utilize SEO and social media to have clients come to you.

Of course, the best option is a combination of marketing efforts (except using content mills).

Cold emailing prospective clients found by searching

niche + "write for us"

on Google is the go-to method for most beginning freelance writers. Then you simply send a cold email introducing yourself and pitching your services to the potential client and…wait.

Like with cold calling, cold emailing is a numbers game. The more you email, the more likely it is you’ll land a client.

Unfortunately, I have some crazy anxiety about coming off as annoying by cold emailing. I’ve gotten a little better, but I have a long ways to go. Ideally, I’d like to send 20+ cold emails a day.

I have had some moderate success finding clients organically through Twitter and LinkedIn. Simply engaging with my desired clients and posts and content they share has helped build relationships that later led to them becoming clients. This is definitely my preferred method of finding clients, but it’s a little tougher to predict and control than cold emailing.

• Staying on Top of the Game

Things are always changing in the content writing scene. SEO best practices change and evolve, different types of content emerge, and aspects of your niche progress and develop.

When I’m not writing, I’m reading. My latest read has been Hey Whipple, Squeeze This: The Classic Guide to Creating Great Ads. I’m pretty confident with my content writing skillset right now, so I want to focus on the copywriting side and Hey Whipple was recommended to me.

I’m also subscribed to a few different newsletters from people I consider mentors in the freelance writing game, as well as some SEO updates, tips, and advice newsletters.

READ: 3 Resources to Help Freelance Writers Start Writing
Resources to help freelance writers start writing

It can be difficult to find the time to keep educating yourself as a freelance writer. Afterall, it’s time you’re not making money. The payoff is worth it, though.

Increasing your knowledge, your expertise, brings added value to your clients. Knowledge that should play a role in the prices you quote to clients.

Staying on top of the game increases your marketability and helps you to better serve your clients. While it might be tough to set time aside to learn when you could be spending time getting your name out there, it’s part of the game.

• It Can Get Lonely

My last job was at a grocery store where I was friends with most of my coworkers. At the insurance agency before that, I was friends with agents all over the office, and both of my bosses were always available to talk to when I had an issue, problem, or question.

Know who my coworkers are in my home office?

My cats are my freelance coworkers.
The most needy managers ever!

As much as I love my cats, our conversations are pretty lackluster. That, and they make me do all the work. I can’t even get them to answer emails for me.


I’m not the biggest people person, but even still, it’s nice to have someone to bounce ideas off of or commiserate with. It took me awhile to realize just how much I needed to have some sort of correspondence with colleagues.

Twitter’s been a great tool for finding people to talk to and share trials and tribulations with. I’m also part of a couple of forums and Facebook groups dedicated to freelancers and writers. Not only have I made writing friends(!), but I’ve learned a lot from participating in these communities and interacting with like-minded individuals.

I’ve even shared a few of my own resources that I’ve come up with over the past six months, such as a contract template freelancers can use that (I think) covers all the important bases.

RESOURCE: Sample Freelance Writing Contract Template

There’s value in networking with other freelance writers. Sure, I guess in a way we’re all one another’s competition, but there’s no point in being at each other’s throats for fear that we’re costing each other business.

That’s ridiculous.

In fact, almost all of the freelance writers I’ve met and spoken with have been incredibly generous, helpful, and chock full of advice and well-wishes. The truth is we’re all in this together and chances are one freelance writer writes in a different niche than the next, so we’re not really competing with each other for the same clients.

And each of us brings something different to a client: our unique voice.

Like I mentioned earlier, I inject my personality into each piece I write. Chances are your personality’s much different than mine, so you’d appeal to a different client than I would.

The point is: the positives of connecting with fellow writers vastly outweigh the possibly non-existent negatives you think might exist.

So get out there and make some friends!


Fake it til you make it, as long as you’re actually working towards making it.

For the longest time, I had no clue what “Fake it til you make it” meant. I wrote it off as a hollow cliche.

But you know what?

It works.

I’ve been writing all my life, with very few periods that I didn’t. I have excellent command of the English language, my grammar’s exceptional, and I hardly ever make spelling errors. I understand the necessity of researching topics I don’t fully know and I know what it takes to properly fulfill a client’s writing needs. I know how to run my freelance career as a business.

I may have only been freelancing for six months, but I don’t act it.

Fake it til you make it.

Whether you’ve been freelancing for a week or for 10 years, you need to have the confidence to properly represent yourself and your abilities. That means waking up every morning and telling yourself you’re a business owner working to grow your business and your income, even if you haven’t had a client in a month…or ever. Even if you’ve just overdrafted your bank account.

You need to take the reins and say, “This is my business and this is my career. When I’m working, I’m a professional. I can do this.”

Throw all the other BS away.

I know it’s easy to get down when you’re not finding interested clients or you’re writing about a dull subject like vacuums. Or when you’re waiting for invoices to be paid and your client hasn’t answered you in a week and your thoughts are swirling around wondering if you’re getting stiffed or if they simply forgot or their business is going under and everything’s on fire and how are you going to pay your bills or eat.


Most businesses fail within the first two years. Those businesses that are still functioning after a two year period tend to be successful. But of those failed businesses – restaurants, retail stores, service companies – how much money was sunk into startup costs?

I’ve spent less than $100 in the six months I’ve been running my business. If I had to quit freelancing today, I’d be right back where I was when I decided to start freelancing, except I’d be armed with the knowledge of running my own business and everything that comes along with that.

Over the last six months, I’ve asked myself a few times if I can pull this off. If I can make my freelance career successful enough to support me and my financial goals for the future.

Each time, the answer is a resounding yes. I love what I do in a way I’ve never loved any other job. I finally feel like I’ve found my calling, so after reaching the six month milestone, I know I have what it takes to continue building my business and finding success.

This is the right choice for me. And hopefully, if you’re considering freelancing or you already are, I’ve helped you evaluate your own freelance career and figure out what steps you need to take next.

What are they?

I want to hear about them! Your successes, failures, and thoughts on my own experience over these last six months.

Give me a shout on Twitter or leave a comment below about how your freelance career’s going!

17 thoughts on “Six Months a Freelancer: What I’ve Learned

  1. Awesome article Dan! Thank you so much! As a brand new freelancer I found your article tremendously encouraging! Continued success to you as you grow your business!

    1. Thank you Celia! I’m glad I could encourage you! Freelancing is definitely a worthy path to take so it’s awesome to read you’ve embarked on the same journey 🙂 Thanks for the warm wishes and I wish you success as well!

  2. Thanks Daniel, I too am new at this, and am currently struggling to write faster (it is taking me waaay longer to write 2k word posts for my main client than I am charging her for). Any advice on how I can speed it up?

    1. Hey Scot, thanks for reading and commenting!

      How long does it usually take you to write a 2000 word piece? One method that’s helped me in terms of speed is putting an outline together and filling it with all my research about whatever topic I’m writing about. This creates a sort of bare-bones structure I can easily build upon when it comes time to actually write the piece. Invest a little upfront time in figuring out the skeleton of the article and it’ll shave some time off coming up with a first draft.

    1. Thanks for the reply Elna! It’s really reassuring to have evidence from someone of your stature as to the whirlwind feeling of the beginning months. It’s definitely been overwhelming at times, but I, too, feel like it’s all laying the foundation for an exciting and lucrative career as I grow and evolve. Thanks for stopping by!

  3. Daniel. Thank you for this post. I found it helpful as I start my own journey freelancing. It is good to know what to expect six months from now.

      1. Thank you! Also I’ve spent a lot of time in customer service as well and one of the things that made me nervous about starting a freelance writing career was ” how can I sell my retail background?? How will clients find value in that?” Your about page spelled it out for me. I was just making it super complicated. Lol. Sell what experience you have in the best light possible and market it like crazy. Someone will bite eventually.

        1. Exactly. Don’t worry too much about needing to find a niche, either. It helps to have a specific area of expertise, especially in the beginning stages, but don’t obsess over the urge to specialize if it means it’ll cost you projects and clients in the long run. If you can write about one topic, chances are you can write about others, too, as long as you’ve got the research chops to back up your writing. Most of freelancing is just throwing yourself in and floundering around a bit until you catch your groove. As long as you keep your eyes on the prize of finding success, you’ll eventually figure out all the intricacies.

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