How NOT to Get the Freelance Job – and What to Do

How NOT to Get the Freelance Job - and What to Do

After posting some open job positions here at Men with Pens, we received a slew of applications. People were really excited to have the opportunity to work with us.

I even noticed a woman tweeting she’d wet her pants if she was hired.

Kind of flattering.

In most part, I had a lot of fun reading through applications and learning more about people. There are some interesting folk out there, from quietly professional to boldly courageous, and whether they fit the profile or not,  it was nice to “meet” some of our followers and readers.

There are some, though – this really means there are a LOT – who applied for the jobs but did so in a way that guaranteed their applications hit the trash can. So many, in fact, that I decided to write a post about it.

Here’s a list of what to do – and much more importantly, what NOT to do when applying for freelance work:

DO read the job ad. No, really. Read it. The whole thing. Top to bottom. It isn’t just there to look snazzy. A job ad is there to give you useful, helpful information so that you can see if you’re a good match and to help you apply in a way that doesn’t annoy the hell out of us. Like, say, emailing us to ask if this is the right email to email us at, when the email you should use to apply is written on the job ad.

DON’T show you’re lazy. I know. This is tough, especially for freelancers, because we all pride ourselves on being able to make our own schedule in our pyjamas. (Playtime hours: 8. Work hours: 1) But try to hide it. When the job ad says email us with information and samples, don’t tweet us and say, “Just click here.” If you can’t do as we ask, why should we do as you ask?

DO follow instructions. If the job ad says, “Use the word ROCKINSOCKS in your subject line and send samples or links,” don’t send an email with a subject line of “Responding to your application,” and then tell us samples are on request. Because we won’t. Request, that is.

DON’T point to a really bad website. Speaking of links, if you have an ugly website with horrible copy that doesn’t reflect your skills, please don’t tell us. That way, you’ll have a much better chance of us thinking you actually can write or design. A poor-copy website with a tacky, broken design is kind of like pulling down your pants – at the wrong time.

DO be sane. Yes, I know, this is especially difficult for most freelancers and entrepreneurs. We’re a special kind of unique breed and sanity isn’t the norm. However, if your application reads like you forgot to take your meds (or should double your dose) that’s… really, really not good. We like fun, crazy people – just not that kind of crazy.

DON’T squee. Flattery gets you everywhere, they say, but moderation is key. Applications that start with “Ohmigod ohmigod ohmiGOD!” and proceed to gush on about how fantastically awesome our site is and how you hang on every word we write and how you’ve been stalking us for years and how you just… well…. thanks, but no thanks. Really.

DO make sure you can do the job. Initiative is nice, and we understand that there are diamonds in the rough out there. That said, don’t apply for internet jobs when you just came online, have no skills, no experience, but can definitely learn everything as you go along. (Hint: You’re not applying for a paid position, you’re asking for a free apprenticeship.)

DON’T have low self-esteem. Any email that begins with, “I probably don’t have enough experience,” “I’m not sure I’m what you’re looking for,” or even “I’m sure you probably have much better writers sending in their resume,” pretty much forces the reply, “You’re right. Thanks for applying, and best of luck to you.”

DO take a chance. So you may not have as much experience as the job posting asks for, but so what? If it says 3 years’ experience and you have one kick-ass track record but only 16 months under your belt, you might still be the perfect fit. You never know if you don’t try. Sighing that you wish you could apply is silly – take the damned chance and do it.

DON’T use “I”. One of the best applications I received was all about me. No, really. Every single sentence in this application was all about me, James, the busy entrepreneur. The extensive, gripping, hooking pitch focused entirely on my problems, my needs, my desires and my goals. This person understood me and my pain, and I was nearly begging her for the solution – surely she had it, if she knew me so well?

And that’s the key to winning a job, people.

There are plenty more do’s and don’ts on what makes for a winning job application and how to get eyes on yours. What extra tips can you think of on what you should do – and what you shouldn’t – when pitching for the gig?

Want even more great advice on how to pitch clients and win jobs? Check out these:

Our very own eguide, Write for the Web, lets you learn how to start your own freelance writing business so you can start pitching for those gigs – and win them. Get your copy today.

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Post by James Chartrand

James Chartrand is an expert copywriter and the owner of Men with Pens and Damn Fine Words, the game-changing writing course for business owners. She loves the color blue, her kids, Nike sneakers and ice skating.

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  1. You know what? Reading between the lines here seems to imply (to me at least) that all of these “don’ts” could be redefined as “Things that MenwithPens are NOT”

    Perhaps the secret is to getting a job is to emulate the EXISTING team. That way your applicants would play it cool, be slightly cocky 😉 and show their smarts… without squeeing or ignoring instructions.

    My advice to jobseekers in general: Research the company and then present yourself as the *missing* member of the team!

  2. As well as all these points, I don’t like it when applicants are over familiar. They may have been a fan of the blog for years and think you’re like family but acting like it in a job application, it’s a no no for me personally.
    .-= David´s last blog ..The new MP30 music projector from Australian Monitor has arrived! =-.

  3. Yeah, see? I would have loved to apply, but you asked for 3-5 years’ experience–which I don’t have yet. But at least I READ the ad to see that, huh? (Of course, if you change your mind….)
    .-= –Deb´s last blog ..Who Are You Talking To? =-.

  4. @Deb – Yes, but this post also says ” If it says 3 years’ experience and you have one kick-ass track record but only 16 months under your belt, you might still be the perfect fit.” Most companies ask for a wish list but will look beyond that for a candidate they think is suitable.
    .-= David´s last blog ..The new MP30 music projector from Australian Monitor has arrived! =-.

  5. My two cents: If you’re offered a job but can’t accept for any reason,
    outsource it if you’re allowed. That way, you still look good to the employer.

  6. Excellent post James! Funny too …

    You want to capture someone’s attention! Hard to do that when folks are taught to hide their talents. I say let them rip and if it’s a good match so be it. You never know unless you try.

    Thx, Giulietta the Muse
    .-= Giulietta Nardone´s last blog ..I’ll Always Love You =-.

  7. Mark W. says:


    The next time you put out a call for job openings, you’ll be able to refer to this post. Tell them they have to read the comments too. Read everything. It’s Okay to read it two or three times if necessary. With that being said, I wonder if it would make a difference. There are times to blaze trails, be the individual, etc. and other times it’s also necessary to be able to follow directions. I’m thinking teamwork, boundaries, schedules, and guidelines are all necessary for MWP to be a successful outfit. Also I like your mention of putting it on the table and letting the person or people in charge of recruiting make the decision if the applicant is a good fit for the organization.


    .-= Rhodester´s last blog ..Why we love cats and dogs =-.

  9. Kind of funny, I just posted a position for a researcher and had a similar array of applications. I needed one person and got 91 emails… A couple of amusing ones.

    Don’t spell the clients name wrong. Someone wrote an email to “Mr. Bangamon.” It immediately went to the trash bin.

    Do use flattery. They guy who ended up getting the position started with “I enjoy your funny tweets.”

    Don’t ask for “a lucky break.” You’re not applying for a lottery ticket.

    Do include testimonials. Even if they’re not exactly related to the job you’re applying for, it’s nice to see that you can at least get someone to say something nice about you.

    Don’t use canned answers. No one can give 110% effort on every project… it’s a mathematical impossibility. But telling me you work like your “buns are on the frying pan” gets the point across and shows a little personality.
    .-= Henry Bingaman´s last blog ..Why You’ll Never Swipe Your Way To Copywriting Success =-.

  10. @Henry – Before I posted a job ad and publicized it, I did some direct headhunting. That was an experience all in itself:

    Some didn’t want to apply until they’d raised their rates. (huh? but… huh?)

    Some said they were gung-ho and excited!… but took 7 days to reply with no explanation.

    Some used canned responses – and it was so obvious I had to shake my head.

    Good additions, btw!

    @Rhodester – Well, it was the sample article that included the porn star in a bikini. I’m partial to full nudes, myself.

    @Mark – Yeah, good essentials there, and good suggestion for next time we expand!

    @Guilietta – Aye! If you’re skilled and talented, STRUT IT. Best advice right there.

    @Poch – Hmmm… “if you’re allowed” being the key. If someone who worked for me outsourced without my knowledge, they’d be out of a job pretty fast, I’d think 🙂

    (Momentary tangent… what IS that bigass pink box Comment Luv’s displaying before my eyes? PINK?! On MwP?? I need to talk to Jeff about this…)

    @David/Deb – To be fair, a lot of people don’t want to risk offending the potential employer by not following instructions, so they see 3 to 5 and accept that they don’t meet the criteria. So I do appreciate the nod of respect in that direction.

    But believe you me – there are often applicants with 10 years experience who couldn’t do the job. That means employers have to look to other ‘best fits’ – and it just might be the person who’s only been at it 6 months.

    @David – Familiarity I don’t mind, but that’s a personal preference. I’m a pretty casual person overall and tend to get a little turned off by formality. But I do agree to be careful of how much familiarity shows through – a job application is still a job application.

    @Peter – That’s excellent advice. Flip the coin and look at what the company ISN’T about. Then pitch everything they are about. Had someone listed everything Men with Pens stands for and matched up with its philosophies and beliefs, I definitely would’ve looked twice, because it shows this person *knows* us – and would clearly be the perfect match.

  11. The reason why I mentioned ‘if you’re allowed’ was that I was
    offered an exclusive job and the employer requested that I keep
    the offer private between us. Because the offer required programs
    I don’t use, I politely declined and didn’t outsource the excellent

  12. Oh god, I hate to be the haughty grammarian, but …

    This sentence in the fifth paragraph/stanza —

    “There some, though – this really means a LOT – who applied”

    — is incorrect. Seems like “They’re” makes more sense.

    Just blame it on Dragon Naturally Speaking even if you don’t use it. That’s what I do.

    “That damb computer software. Why just last week it replaced a perfectly good singular possessive mixture of Old English and Pig Latin with some possessive plural crap mixture between Old English and Pig Latin. I mean, come’on! Get it right fella.”

    (I won’t apologize for being right but I will apologize for being anal.)

    Which brings me to my next point, I’m trying to promote recognition of analism as a disease. We analists don’t mean to sound judgmental or condescending. (Why doesn’t judgmental have an “e” after the “g”? Seems wrong.)

    More accurately, most of us don’t want to seem judgmental or condescending. But, I know this one PhD candidate, she works in a library. She consistently rips everything I write to pieces. And she always does it with a smirk. We only know each other online and have never seen each other face-to-face, but I know she’s smirking. She’s a smirker if I’ve never haven’t unseen one. (That’s right, a triple negative.)

    YEAH — THAT’S RIGHT JEN! If you’re reading this I’m talking about you! You … you stupid smirker. Why don’t you go put a book back on the shelf or something. Or just, go work on your Dewey Decimals or something. Smirking smirker. I hate you.

    (I secretly love you.)

    Maybe Men With Pens can join the fight against Analism? Come up with a clever tag line for the cause. Something that ends with ” … because an anal is a terrible thing to waste.” would be great.

    Thanks for sharing your knowledge, Men With Pens! Keep up the good work. Love ya. TTYL! KIT! Have a great summer! L8R. WWJD? WTF?

  13. @Matt – Thanks very much for catching that typo (and the tip on blaming Dragon). Also, good luck with Jen – may you both end up in each other’s pants and prove yet again that love on the internet does indeed happen.

    Or something like that.

    While I’m at it, I’d like to fondly suggest that you step away from the coffee. Really. I highly recommend it. You’re starting to sound like me at 7am after I’ve had about 12 espresso-mud mugs.

  14. Susan Johnston says:

    James, this is a great post for all freelancers or job applicants, and I’m glad it went beyond the typical “common sense rules that freelancers forget or choose to ignore” post. I especially liked the last piece of advice (“don’t use I”), because focusing on the recipient can be a really effective technique in copywriting. However, in my opinion, i has to be used carefully so it doesn’t cross that line into seeming too presumptuous.
    .-= Susan Johnston´s last blog ..Guest Post: Writer’s Block is a Lie =-.

  15. Thanks for the post, James! Since you’re offering advice as a prospective freelance hiring person, can you please expand on the following?

    “DON’T show you’re lazy. … When the job ad says email us with information and samples, don’t tweet us and say, “Just click here.” If you can’t do as we ask, why should we do as you ask?”

    On my resume, I provide links to articles with my byline on the newspaper’s website. I thought it lends a little more credibility. If prospects ask for clips, however, are you suggesting I should attach individual pdfs or jpegs of my work, rather than, or in addition to, the links? Thanks, in advance, for your feedback.

    Phoebe King
    The ‘write’ choice for you SEO content/copywriting needs

  16. @Phoebe – Offering links to online work that’s been published seems fine for me. Since I don’t work in the offline world, though, I’d have difficulty counseling you on how they like things done 🙂

    @Susan – Agreed on presuming – the trick is using common sense. The application wrote, “You’re a busy person.” That’s common sense and easily presumed, since I’m hiring extra hands, and since I own a business. I doubt I’d come back and say, “No I’m not! How dare you!”


  17. “Don’t use I” is crucial. Did more than my share of hiring before a recent move into the world of freelance, and got tired of hearing in interviews about what a great opportunity this would be for the applicant. I was happy to hear that, but it did nothing to answer the core question in any job interview, “Why are you the right fit for this job?” If you want the job, do your homework (it shows me you’re thorough and conscientious), figure out what my needs are, than show me through your answers and discussion of your experience how you can help me. Doesn’t seem much different in the freelance world from what I’ve seen so far. Thanks for the great advice.

  18. Great post! Also half terrifying since we always feel the need to be unnecessarily elaborate. And end up missing the mark.

    Prove that you are worth the work, whether you get the it or not. Be a person who learns from evey experience. Someone who’s eager to learn will always get recommended by me. They might not fit the current position with me, in my company but someone I know might be interested.

    Start with the assumption that what you know is enough and what you don’t is company and position specific. . . . If only I’d read this 5 years ago.

  19. Another great post James.

    The two that really tweak my lug nuts are: following directions and showing some self-esteem.

    I mean there are instructions for a reason; follow them! Also, if you are applying to a job, show some freaking back bone! Like you said for those that start with: “I probably don’t have enough experience” are just defeating themselves. Show you have some respect for yourself and send in a kick butt application or don’t waste your time.
    .-= George Passwater´s last blog ..Don’t Let Robots Take Over – Learn the Secret to Creating Success =-.

  20. All I have to say is… common sense is the least common of all senses!

    Seriously, though. Most of these mistakes can be avoided by taking a step back and looking at the situation from the prospect’s point of view. Surprised at how few people do this.

    BTW, James… thanks for the kind words about our book! 🙂
    .-= Ed Gandia´s last blog ..To Get More Clients, Keep It Simple =-.

  21. Once again you over deliver and show us how it’s done. Thanks for all the great tips, James.
    .-= Tammi Kibler´s last blog ..Write Now – What If Perfect Never Arrives? =-.

  22. James,

    As a manager in a previous life, I understand your pain. After reading through thousands of job applications, it’s amazing how much a little copywriting training would help almost everyone.

    It’s a shame that you got such a pile of people that were just grasping at straws, when in fact, you were really looking for professionals.

    I think that people are in such a hurry to do everything in BULK these days, like we are looking for work on the shelves at Sam’s club, that they aren’t taking a second to really focus on the quality.

    In the end, it’s the ones that really care that will get the brass ring, and the rest will just disappear into the pile of “everyone else.”

    -Joshua Black
    The Underdog Millionaire
    .-= Joshua Black | The Underdog Millionaire´s last blog ..7 Insane Customer Magnets That Even My Dog Wouldn’t Touch =-.

  23. Jack Busch says:

    I loved the last tip–that’s a good one. I think that probably goes for selling anything to anyone. Boasting about how swelltacular you are only impresses to a certain point. It’s like those ridiculously high tech sports drinks. Yeah, that’s great, it’s got electrolytes, carbohydrates, vitamin C3P0 and hypertonic hydreogelogic ultrazords–but is it gonna quench my thirst?

    I also really appreciate the “DO be sane.” It makes me wish there was an emoticon for maniacal laughter. That way it’d be easier to filter out all the cover letters containing such qualities…
    .-= Jack Busch´s last blog ..Start from the Middle to Avoid “Top Heavy Content” =-.

  24. Leon the Brave says:

    Blah blah blah. Dudes…, it boils down to this. Most people, especially those applying to work at a BLOG, are going to be ultra douchebags. So who did you expect would be applying – Edgar Allan Poe? Wasn’t all this hiring drama about an unpaid position at your blog? Most blog want ads start out with “hey there’s no money but you’ll get lots of great experience…” YUH. I’m used to making $4/word writing, er ‘creating content’ for four-color glossies… and blogs are paying what… $.03 a word to “create content” and another $.03 to edit ? Thanks but no thanks guys.

  25. @Leon – Thanks for reading this post, which I wrote absolutely free (not even $0.03 a word!)for your personal pleasure. Oh, and by the way… your assumptions (and your ego) seem to be getting in the way of your brains. You might want to do something about that. Hugs and kisses – James.

    @Jack – I know we freelancers are all a little off the wall (take my friend Leon up there, for example), but that ‘be sane’ was a big one for me. Whew.

    @Mongezi – Ah, but I’m sure those five years have taught you many great things and made you a better person because of them. 🙂

    @George – I expected some self-kicking from a few applicants. Writers aren’t really known for their ability to hug themselves, eh? But I *was* taken by surprise on just how much uncertainty, doubt, and self-depreciation there was. I hope that changes, because the applicants were all very fine people who should be proud of themselves. (Yes, even the un-sane ones.)

    @Joshua – Well, I can understand it, really. I expected a lot of applications, in fact, simply because of how many people are out of jobs these days. And that was okay with me – remember, I got my start that way myself 🙂

    @Tammy – Welcome!

    @Ed – Aye, it’s your sort of book that comes in very handy in cases like these!

    @Larry – That switch from “I” to “you” was awesome. Got my whole attention right from the first word.

  26. I so totally agree with you on every point.

    That being said, the part about not “squeeing” can constitute a fine line. If someone has been reading your site for years and years and is totally obsessed with you, I think they should say that. Obviously they need the chops to back all that up along with a kick ass portfolio, but an obvious passion and total understanding of what you do backed by enthusiasm (read: exclamation points) is “authentic”.

    This, however, it totally determined by the one doing the hiring (of course). I once applied for a job at my favorite museum and my cover letter read: “I had a mini-heart attack when I found out you guys were hiring.” They told me later that first line is what got me the job.
    .-= Marian Schembari´s last blog ..Finding “My London” =-.

  27. Great post, James, thanks. I’d like to add another thing: actually submitting an application. I’m not being facetious. I have sometimes had conversations along the following lines:

    Co-worker: I’d love to have landed that promotion.
    Me: Yes, it’s a shame you were passed over.
    Co-worker: Well I wasn’t passed over exactly: I didn’t apply for it.
    Me: Why not?
    Co-worker: I didn’t think I’d be successful.

    This illustrates Woody Allen’s dictum: 80% of success is showing up.

    Two further comments:

    @Matt: in the UK, ‘judgmental’ is spelt ‘judgemental’. I think this illustrates the importance of making sure, in this international age, that when you apply for a post based in another country it’s probably a good idea to use the appropriate spell-checker.

    Regarding formality, here in the UK we would tend towards formality in a job application, ie err on the side of caution. That’s because, generally speaking, informality and frivolity are frowned upon in such situations.

    I suppose that taking these two points together, it would probably be wise for someone in my position to make sure they drew attention to the fact that s/he hailed from the UK as early in the application email as possible 🙂 Would you agree?
    .-= Terry Freedman´s last blog ..10 Obligations of Bloggers =-.

  28. I can tell this blog is going to be a great one to read. This article was very helpful, and I genuinely learned something. Copy is something that I’ve really neglected, and I’m sure that shows in my job applications. My applications are mostly stoic and don’t really show personality, but I just figured that it’s a safer bet. But if I place myself on the other side of the spectrum and imagine myself as the one READING the applications, I can see how some personality would be refreshing.

    Thanks for the post, and I’m definitely subscribed 🙂
    .-= Joseph McCullough´s last blog ..Why I Wish iPhone Apps Were More Expensive =-.

  29. @Marian – As they say, flattery gets you everywhere. But it’s a fine art, and some people lack finesse 😉

    @Terry – Thanks for defending my literary honor in regards to Canadian/UK spelling – I stared at that word for a while thinking, “That doesn’t look wrong… but it doesn’t look right…” I’ve trained myself out of spelling properly ( 😉 )but every now and then I slip and get it right. Always throws me for a bit!

    @Joseph – Thanks for the kind words, and welcome! Good point, too, of trying to put yourself in the other person’s shoes. That’s often a handy way of reaching into their mind – and nailing it 🙂

  30. Can’t wait for the update on the successful candidates and reading their blogs!
    .-= Matthew´s last blog ..The ICON1 Paging Microphone is Arriving Soon. =-.


  1. […] advertisement for new writers. As is typical, the site got a ton of responses. Even more typically, most of those responses were terrible. I’ve had my fair share of really bad queries sent to me and I’ve posted do and […]

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