How to Write Like a Hipster (And Be Professional Too!)

by Emma Siemasko

Last updated on April 17th, 2018

Hipster is sort of a dated and overdone term, but we all understand what it means. A hipster is someone who’s super cool, ahead of the times, and has a little bit of an edge.

A hipster is found at an underground club in an indie urban neighborhood, rather than in a suburban shopping mall.

As an internet writer, it’s hard to strike a balance between the professionalism in an office park and the coolness of an electronica club, but doing so can set you apart.

The best content marketing is inspirational, emotional, amusing—and cool.

Face it, the best writing out there is hip.

So in today’s competitive internet space, how do you stand out and be hip? How do you write like a hipster while staying professional?

1. Cast your essays about modern literary theory aside

I came into the field of content marketing after writing literary essays about Hilda Doolittle and Robert Frost. I love my degree in English and creative writing, but I had to cast aside my my high-brow style in order to be casual, cool, and fun on the internet.

Don’t get me wrong—my English degree is a huge asset because it taught me how to articulate ideas, but writing in MLA or Chicago format with long sentences and total verbosity will not work in online marketing. This sort of writing is professional, but not hip.

My English professors are probably cringing, but does it make you feel good when you stumble upon something like this on the web?


I didn’t think so.

2. Don’t be mean

A lot of people think that standing out means you have to do something outrageous and controversial. They think that writing in a youthful style without respect for authority will help them on their way.

The truth?  Being mean/offensive/controversial/sexist/racist is never hip. It’s actually really un-hip—us hipsters are all about peace, love, equality, art and exploration!

It seems obvious and I’m NOT trying to patronize. I’m just saying that you should always think before you type. If it might offend someone, stop. This doesn’t mean you can’t have an opinion, but you must express your opinion gracefully and with respect for those who disagree.

37signal’s blog post on Yahoo’s work from home policy sparked a ton of comments—some from those who agreed with the opinion, while others vehemently disagreed. The post was written tastefully, however. It’s hard to find anything mean or offensive in it. The post wasn’t personal.

And by all means—tell jokes! But only tell jokes you’d be comfortable making in front of your significant other’s family.

3. Be natural

The worst kind of hipster is one who tries too hard. If you’re straying from who you really are in order to uphold a certain image, you’ll turn people off. Your family and friends love you because they think you’re funny, bizarre, and particularly you.

Your individual spirit is what makes you hip, so don’t throw it away just because you have to put on a suit every morning. Be yourself—boldly.

There are tons of beauty and lifestyle sites that do this. Full disclosure: I am obsessed with beauty (both content and products). Many tutorial videos irk me, though.

Instead of making me feel like I’m in a room with my hairdresser or girl friend, I feel as though I’m at a party with the fake and phony. The video content is as canned as cranberry sauce out of a tin can.

I started watching a company video when I was trying to learn to use hot rollers and was so annoyed with the phony voices that I started searching for videos from regular people on YouTube.

But don’t worry- I’m not just going to talk about content that’s anything but natural. charity: water’s videos provide a stark contrast: these FOR REAL videos have awesome artistic cinematography, real human emotions, compelling imagery, and great stories. These videos are hip.

This one inspired me to start my own campaign! Every time I watch it, I cry.

See also: 4 Essential Ingredients for a Video that Converts

4. Use interesting metaphors and comparisons

All of my hipness comes from making weird and unexpected metaphors and comparisons. I just compared tutorial videos to cranberry sauce. Weird, right? But it’s also hip. And it didn’t make you cringe or think I couldn’t be trusted with writing your content.

One of the best ways to stand out and be different is to say things in ways that other people wouldn’t. Don’t rely on conventional phrases when you’re writing. Strive to find odd, compelling examples.

Copyblogger recently compared the old saying about sex being like pizza (when they’re bad, they’re still good) to website hosting. Talk about an unexpected metaphor. It definitely kept readers interested—the post has been tweeted 308 times (and counting!)

See Also: 10 Tips to Energize Boring Copy

5. A Professional Attitude in Creative Mediums

Ebooks and guides are useful, but they’re not exactly cool. Challenge yourself to think of new and unexpected ways to create professional web content.

I know we’ve been talking about writing like a hipster, but you also need to think like a hipster. A hipster would think beyond writing into the next greatest content channels.

Some good examples of professional attitudes in creative mediums?

Portent’s Content Idea Generator is useful and professional, but creative and spunky. It makes you chuckle, provides you with real, usable headlines, and gets you wondering about what else Portent has created.


Grasshopper’s Startup Magic 8 Ball does something similar. In order to reach an audience of founders and entrepreneurs, Grasshopper made a web-friendly magic 8 ball to answer all of the toughest business questions.


 6. Talk to people like they’re your dentist.

You wouldn’t tell your dentist about your sex life but, since you’ve gotten to know him or her over the years, you might ask him how his kids are, or how long he’s been a dentist, or engage in some chit chat about your city or town.

You aren’t acting like an instruction manual, but you’re (hopefully) not making racist comments.

If you’re like me, you’ll joke with the dentist about the mayor’s latest blunder or mention that the farmer’s market has an excellent selection of strawberries.

Talking to people like they’re human—like they’re people you meet at the street—is the golden rule of balancing hip with professional. It’s all about combining your natural spirit with your professional savvy.

Be hip, professional, and honest to convert customers and fans

If you want to convert the world into customers and screaming fans, then you’ve got to let a bit of your natural hipster-spirit fly free.

It’s a challenging balancing act, but I always default to honesty. If I’m being myself when I’m writing—no matter the topic—I’m being a heck of a lot hipper than a lot of writers out there, even if I’m wearing a polo shirt and bermuda shorts.

To write like a hipster, you should unbuckle your seatbelt, but always stay seated in the professional car.

What does it take to be hip? A nice, natural, tasteful, and genuine attitude about both business and pleasure. Let that attitude ooze into your writing.



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Emma Siemasko

Emma Siemasko is a freelancer writer and content marketing specialist at Grasshopper, the entrepreneur’s phone system. Emma recently completed JUMP: The Ultimate Guide to Starting and Growing a Business to help startup founders and employees get companies off the ground.


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  1. Dawn says:
    February 14, 2014 at 5:33 am

    Loved this – can I hire you?

    • February 14, 2014 at 10:01 am

      Hi Dawn. Glad you liked this & love your site (looks like you’re already very hip). I do take on freelance work, so if you’re interested why don’t you send me an email at emmafaye at

  2. October 4, 2013 at 9:34 am

    Fab post! I love the hipster analogy, and agree 100% that you should write as if you were talking to someone on the street. I’m an English degree-holder too, so I know how it is to drop pretty much every grammar rule to write in a more fun style.

    • October 4, 2013 at 9:40 am

      Susan, thanks for the comment. Grammar is important, but breaking the rules can definitely make us more relatable 🙂

  3. September 29, 2013 at 7:25 pm

    Hipsters need to actually write really compelling stuff too, yeah?

    • September 30, 2013 at 7:44 am

      Ha– anyone who is writing online needs to be writing compelling stuff, not just hipsters!

  4. Anne says:
    September 28, 2013 at 9:18 am

    #2 is so important. I’m really glad you pointed that out.

    • September 30, 2013 at 7:43 am

      People take “being nice” for granted but it’s one of the best (and easiest!) ways to inspire trust in your brand. There’s never a reason to be mean or snarky when representing a company- doesn’t make you look good. Thanks for commenting.

  5. Klauster says:
    September 27, 2013 at 5:10 pm

    Hi Emma, you hit my soul. I havn’t an English degree, I not even learned English at school, just I had to cope with it when working as IT professional – but life taught me how to articulate ideas and writing is a part of it. Good starting points for me to review my content. Well presented. Thank you.

    • September 30, 2013 at 7:41 am

      Hi Klauster- glad you enjoyed the article. Hope you can continue to find ways to be compelling with your writing 🙂

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