10 Tips for Kicking Ass as a Freelance Writer

Kick Ass!

Want to be the greatest, most in-demand, kick-ass freelance copywriter ever? It’s not about the basics, like knowing how your spellcheck works or being a grammar god. You do need those, but being really good at the basics only gets you to “competent.”

Not great. Not kick-ass. Just competent.

So what’ll take you to the next level? What’s going to make you fantastic? What tricks help you hook your readers, get clients clamoring, and bring you the success you want?

Here are ten tips to steal from top kick-ass writers — so you can give them a swift kick and be a contender.

1. Readers don’t care about writing mechanics

Some of the most in-demand writers aren’t all that good at the kind of “good writing” your Grade 5 English teacher liked.

Many of the most successful copywriters don’t have degrees. They break all the rules. And no one notices. Readers just don’t care.

No, you don’t want to turn in copy full of typos. But you need to write in a way that readers care about.

Readers care about being touched on an emotional level. A few words resonate, they read a little more and then they’re hooked. They’re in the grip of the story, the persuasive content and the message that’s reaching them.

No emotion? No readers. It’s that simple.

2. Readers want to be interested

You might think your job is delivering information. But it’s not. Your job is to get people to read the next word.

Your job is to get the reader interested — and that means you need to be interesting.

Writing is more than words. It’s a performance. Think of public speakers. The best ones don’t just talk; they get up and walk around. They wave their hands. They make jokes. They get excited in the right places and pause at the perfect moment.

Give your writing some life, and give readers a good show.

3. Readers want to feel they’re great

People don’t care about you if you only care about yourself. Not many people are impressed by claims of greatness these days. Boasting about how great you are (or how great your client’s product is) won’t work.

Help readers and customers feel like they’re great. If they feel you genuinely like them, then they’ll feel better about you. And they’ll start coming back for more.

4. Readers like personality

When readers notice someone fun, interesting or engaging, they pay more attention. They want to be entertained.

The best characters in TV and movies show how it works. They use strongly-drawn personalities to reach audiences and get them paying attention.

Don’t believe me? Picture your two most memorable high school teachers. Think about everything you know about them.

Now picture the two main characters from X-Files.

Case closed.

5. Readers like secrets

Be confident about bonding with readers and customers. Don’t be afraid to show the real you, with all your quirks, flaws and passion. That spark of life makes you more real. No one wants to deal with a façade.

Mention the little details that make a big difference. Give someone a ‘secret.’ Sometimes just hinting at an interesting confession, or admitting that you have to have a blast of Eric Clapton with your morning coffee, does the trick. Your readers will feel trusted and important — and that’s a good thing.

Just beware — there is such a thing as too much intimate information. Giving a few personal details doesn’t mean you don’t have boundaries.

6. Clients like a great business experience

Being a kick-ass writer means you need to know how to get and keep customers. You need to be smart about marketing, prompt with replies, friendly with your service, and ready to give the best customer experience ever.

That’s what clients want — a great experience. Frankly, you’ll rarely hear a customer say, “Great use of alliteration in the third paragraph. Oh, and love your ellipses!”

7. Readers like confidence

Your self-assurance, confidence and determination are big factors to your success. No one likes wimpy uncertainty.

You have to have confidence. It has to show in every word of your work. That may mean hiding your terror of goofing up deep down inside, but if that’s what it takes, do it. The more you step up, the more confidence you’ll gain and the more it’ll show in your writing.

8. Readers like something different

Kick-ass freelance writers have their own edge. They’re distinguishable. They have to be, because in a sea of sameness, they need to find ways to make people pay attention.

So what’s your winning difference? What’s your edge? Go ahead — break a few rules and find ways to zig where others zag. Find something that you can call all your own, and make yourself stand out as special.

9. Readers like you to be humble

No one likes snotty people who think they’re better than everyone else. And it’s often easy for creative types to get that inflated ego going on.

No one’s perfect. Everyone makes mistakes. Keep that ego in check, don’t get too lofty about your skills or self-worth, and accept that sometimes you suck — because everyone does. Acknowledge your shortcomings gracefully.

10. Everyone likes you to tell it like it is

Skepticism is one of the hallmarks of today’s age. Honesty is the name of the game. In fact, it’s one of the most commonly appreciated qualities these days.

So when you write, be open, honest, and transparent. Don’t treat people like dummies, don’t try to pull the wool over their eyes, and don’t sneak around with questionable tactics. People sense when they’re being sold, and they can smell a scam a mile away.

What do you think it takes to be a kick-ass writer? Which techniques and tricks have you used to get ahead in your own career?

Do you have the The Freelance “X” Factor that leads to a lucrative copywriting business? Click here to find out!

About the Author: James Chartrand is a kick-ass freelance writer breaking all the rules over at Men with Pens. Click here to get James’ book, The Unlimited Freelancer. It’s your ticket to unleashing your freelance business.

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Reader Comments (70)

  1. says

    Awesome tips. I’ve just started getting serious in my freelance writing career, so this post is extremely helpful.

    It makes me sad as a writer though to think that people don’t care about basic grammar online. While breaking the rules will make your content interesting, I still feel like it has to be built on that solid foundation, ya know?

    Number 8 is my favorite. I always try to create content that makes people go “well that was different” in a good way. :) Great post.

  2. says

    Great post. Don’t know whether I’m kick-ass or not but what makes a great writer for me is an intense empathy with the reader.

    The reader always comes first. Not the client, not the brand guidelines, not grammar – the reader.

    Beyond this, it’s about having an intuitive feel for language, not being afraid to play with words. Too many writers are too restricted in their styles and approaches. It means that everything they write ends up sounding the same (and the same as 99% of the other copy that readers have to endure).

    Finally, it’s about understanding what the client’s business needs (not just what they say they want) and being able to convey this to them effectively.


  3. says

    Knowing how readers think and respond is SO helpful. It’s not worth being a writer if no one reads your work. Any tip to make my message more clear to the reader is wonderful!

  4. Liz says

    I thought good writing was about offering people stories, insights and information in a unique, compelling way. If making the reader ‘feel great’ was a goal for, say, Vonnegut, he failed pretty miserably.

    Some of the best writing is difficult to read because it asks tough questions and uncovers disturbing revelations. When “edge” is more important than authenticity, writing turns into marketing copy…Some of your tips are relevant, but as a whole, this tone of this article turned my stomach. I think it was all the cheese.

    But this is exactly why I’m switching to social work…I love truly meaningful writing too much to start running around “unleashing” some freelancing schtick on everyone.

  5. says

    Liz, this post (and this blog) is geared towards writing for business and and marketing… so of course some of that involves marketing copy, along with business-related content.

    I wish you well with your shift to social work, but I can’t understand why you took time to even leave this comment. I mean, what was the point?

  6. Liz says

    Brian, a coworker sent me the link to this article, which doesn’t explain that it’s primarily geared toward business content. It just said freelance writing. I actually work in journalism, which maybe sheds some additional light on my bitter tone.

    In retrospect, yeah, kind of silly to comment in the first place.

  7. says

    I liked this article.

    I can totally relate to it because I hate when people try to impress me with big words and unrecognizable vocabulary. I do not like having to dictionary.com just to find out what happened to Michael Jackson.

    PS: This article was worth the time to read. :)

  8. says

    Really good post. When it comes to copy, for me 3’s the key.

    Because it seems that copywriting’s all about selling. And to sell someone you need to build rapport and you need to focus on your prospect/customer with empathy.

    “People don’t care how much you know until they know how much you care.”

    And the other big one for me was put yourself into your writing. Inject some personality. Take off your writer’s hat and put on your P.T Barnum hat.

    In our current info overload, it’s the only way you can even get noticed.

    Gotta go kick some ass…

  9. says

    @Jason, I like your approach a lot. The whole client needs thing gets tricky. They’re paying your invoice. But if it doesn’t work for their customer, it doesn’t work. You raise a great point about what the client thinks they need vs. what they actually need.

  10. says

    Bravo. Another way to kick ass is to write with attitude and high energy, the hipper the better. Just like you did here. Yeah, you gotta stay humble, but you can actually come off humble with a kick ass attitude… again, just as you did here. With so much stuff out there, attitude and wit and style is the best way to differentiate yourself. Especially if the work has a marketing agenda – your clients want to get noticed, and for them we need to write to be noticed.

    Anybody can sound credible, but not everybody can grab a reader by the throat. It’s the art of attitude, married to the craft of strategic writing.

  11. says

    I like your distinction between competent and kick arse. Kick arse is the way to rise above the line.

    For me, I like when a writer can make an old song new, or demonstrate relevant thought leadership.

  12. Maggi Deroian says

    These are great tips, thanks James. I look forward to reading more of your work as I try to break into freelance writing.

    I’d add an important key: know your audience and channel of communication, and tailor your writing style accordingly. For example, proper grammar may be more important if you are writing a formal newsletter or your readers include copy editors than it would be for a blog post targeting 20-year old skateboard enthusiasts.

  13. says


    Tellin’ it like it is. These tips are worthy of any freelance writer – be it copywriting or whatever. Applying these principles builds a foundation for success. I know I try and incorporate them into my daily writing existence – including my blog.



  14. says

    I would say you hit that nail squarely on the head with those 10 tips.

    I think the best writers out there probably have a laundry list of personality quirks that the shrinky dinks don’t have labels for.

    I would also guess very few of those guys have much if any formal education. Which would lead most of them to having great salesmanship skills other wise they would be garbage truck drivers.

    And as far as tip number 11 in order to become a great writer you have to write and it doesn’t hurt to get out and find some of the great works of great writers and re-write their stuff with a good old fashioned pencil.

    You’d be amazed what you can gleen from that exercise.

  15. says

    I like number 7, which of course can be applied to just
    about anything.

    Got a speech to do? Wondering if you really know what you’re talking about? If you begin to wonder, your audience will sniff that out a mile away. If you got to give the impression you know your stuff even if you don’t know as much as you should–so be it.

    Confidence is half the battle. The rest will follow in place. People aren’t inspired by the timid. I’d argue, they’re also not as forgiving.

    They showed up to see you speak, not to put your tail between your legs.

  16. says

    That was one well crafted post. I think it’s very important to look at how we put together our work with the customer in mind. As that saying goes, “the customer comes first” is so true. You write with considering them and what they will be looking for, they will come back for more. It becomes like a cycle. If you please one person, they refer you to someone else – and on and on we go!

  17. says

    Telling it like it is, writing with humour, having a crazy personality and caring for my readers has helped me build a great community around my blog. I still have a lot to learn but I think I have a decent foundation to start with.

    Helpful post. Thanks James.

  18. JeffM says

    James this is an amazing message. Everything a blogger – or any writer for t’internets come to that – needs to ‘get’ about communicating with an audience, delivered in a single post. I always give your stuff the total read-through, and this is a classic.

    Tip o’hat to ya.

  19. says

    Hey everyone – late to the party, but no less happy to be here.

    I enjoyed writing this article. I think there are so many elements of writing that really have nothing to do with writing at all that truly make a difference.

    You can have your work read, enjoyed, appreciated… You can impact people, create change, increase sales… You can get readers, links… You can do so much that it’s worth the effort to go beyond just good writing.


  20. River says

    As Groucho Marx said, “I’ve had a perfectly wonderful evening. Unfortunately this wasn’t it.” Some posts to this blog are valuable, informative and interesting. This wasn’t one of them. Yawn.

  21. says

    There is more to it ummm like building a rapport with readers and being truthful and honest in your appearance and more then anything making them depend on you ( the most difficult yet the most powerful achiever)

    But neat tips James….Thanks for posting :)

  22. says

    How about admitting when you’re wrong or when your opinion has changed? These days there’s barely an industry I can think of that stands still … if I were never to acknowledge a new or different approach I think my readers would be missing out on a fair bit of useful information! Not only this, admitting you’re wrong builds trust.

  23. says

    Great tips. I especially love #2 “You might think your job is delivering information. But it’s not. Your job is to get people to read the next word.”

    I wish I could always work for clients who want engaging, dynamic copy that follows these excellent rules.

    But the truth–apropos of Jason’s and Sonia’s comments? Some internal marketing directors, CDs and other clients don’t REALLY want great copy that focuses on customers’ needs and core desires.

    Sometimes they specifically ask the copywriter to craft egotistical, organization-centric content–the kind of boilerplate that uses words like “world class,” “cutting edge” and “next generation.”

    It happens. A lot more than you might think.

    So while prospecting for more like-minded clients, you sometimes have to grit your teeth—and write the copy your clients want.

  24. says

    Great article, and I think a couple of other things that cannot be stressed enough in this day and age is to be entertaining to the reader, and not be a flake to your clients.

  25. Tariq says

    I have been reading ur blog since 3 months, but commenting for the 1st time. This blog is so awesome. But if you have given an example of the points then it would be easy for a writer ‘how to write better’. Keep it up, thanx.

  26. says

    I liked this post a lot. The points you raise are all relevant. I agree about breaking the rules when writing but agree that there must be some levels of gramma. Nothing worse than reading something online (or in a book for that matter) that hasn’t been proofread.

  27. says

    Amen on #2…I’ve been finding this to be more and more true even when I’m reading fiction. If those first couple of pages don’t pull me in, why should I keep going? Check out Donald Ray Pollock’s Knockemstiff for a great examples of opening stories off with a bang.

  28. says

    Thanks for the info … just started a blog and was thinking as I am not a professional writer nor have any training I should look into taking a class or something but you steered me in the right direction … as I noticed most health care info blogs, artricles, and sites are boring (to most) … sure as a Doctor I like them, but I want my patients and general public to read, enjoy, and share my content and your advice is awesome thanks !

  29. says

    There’s nothing like tugging at the heart strings to sell products. And the strings of all the other emotions.

  30. says

    @ Dr Jon – I think any content in the world can be great, kickass stuff if the writer just puts the passion and excitement he or she feels right into the words. There’s nothing better than reading content from someone who LOVES the subject!

  31. says

    I like your style James, you got something different here.

    Confidence is the most important part, I believe. If you are not confidence about yourself, you won’t make many mistakes that will teach you many things. So be confidence and go make more mistakes 😀

  32. says

    HOLY Cow James,

    I know you wrote that as a helpful article for Freelance Writers, but, what you wrote is also 10 Incredible Marketing Concepts. Substitute “Buyers or consumers or prospective clients” for “Readers” and you have a very accurate guide for marketing today. Buyers certainly don’t care about the sellers claims to greatness, “What’s it going to do for ME?” asks the prospective client. And they most certainly don’t give a hoot about the “mechanics.” ‘This NEW computer will calculate 10 terabytes of data per nano second. Ok, can I play my game on it in 3 D?”

    This is brilliant James, and I will be pointing people who want some actionable marketing ideas at this post. My favorite of course is #10, and yes, I do my best to tell people like it is. Excellent ideas.


  33. says

    Just great, to me what is pretty important is personal style blended with the important arguments that you specify above. Though i agree to everything, i think that the most important thing was not mention and that is marketing. This is always the most important thing to do in whatever means it is possible. A separate article like “Freelance Like Real Madrid Markets” would probably be nice :) (weird title wanting to stress out the importance of marketing to freelancers too, hope it’s find Brian :)

  34. says

    This is perhaps one of the best posts I’ve read on the subject in months. Great job James. I especially like the part about revealing secrets and being interesting/different.

    Too many people try to copy others instead of being themselves.

    Also, being real means you don’t have to hide anything.

  35. says

    Great advice. The thing that leaps out at me though is the balance between being confident and being humble.

    Too many writers (and I include myself in this) veer dangerously close to arrogance when they’re aiming for confidence. Obviously these two go together like kids toys and broken glass, so you’re running the risk of putting forward a contradictory personality.

    If it comes to the crunch, I say confidence trumps humbleness every time – so if you can’t balance the two, always go with authoritative.

  36. Ken says

    Be open minded. I read this article with ease, but I could not even finish reading your comment.

  37. says

    The way I started my freelance writing career is to start small. I initially posted articles on websites with no gatekeepers such as Ehow.com. I built a following there, and only then did I start applying for writing jobs. I recently got approved to write for Examiner.com. I’m now the Home-Based Business Examiner.com for Phoenix. I’m planning on moving on to applying to more writing jobs that pay more soon.

  38. says

    Those are really good points. Also, don’t be afraid to give away your very best information to your customers right away for free. It will really increase trust, and lead to easier sales.

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