Getting an entry level technical writing job without connections

Sep 04 2021

Disclaimer: this is a highly personal post and take all advice with a grain of salt.
I am neurotypical so I still have things a lot easier than some.

Introduction #

The job search is luck and connections. If you have less luck, you better have more connections. Otherwise, if you have less connections, pray for a lucky streak.

Despite technical writing being considered far-flung from the literary scene, I got my foot in the door through creative—fucking—writing.

I have a “techy” resume and a “literary” resume with mostly the same content. My “literary” resume soon became my main resume, because I got more fucking responses from it.

I should be mad. Yeah, I sunk my time in a bajillion personal GitHub projects and studied a few Computer Science courses as electives. Four years of desperation-fueled hustling. I’m facepalming at myself. So much for LeArN tO cOdE.

(don’t get me wrong, as a technical writer, you probably want to learn some coding. Enough to be literate, not a master by any stretch)

Classic fallacy of the job seeker: I thought having technical skills would make a technical writer more hireable.

My “literary” resume had more humanity to it. That’s why it caught fire. People want to hire writers who can write. Who woulda thunk?

Most people, including recruiters, don’t know what a technical writer is. First and foremost, they assume it’s some kind of journalist (it’s always a journalist). This means that a technical writing resume needs to be stuffed with keywords from writing industries, not tech (software) industries.

Become a caricature #

Some people give the unhelpful advice of “imagine yourself 5 years in the future.” They say it’ll make you more focused on your goals, and you gotta “fake it 'till you make it,” and to use the Jedi mind trick they call “make a good first impression.”

Yes, but fuck no. They don’t say that to give you permission to exercise creativity. Your next step is to hijack the laziest slobs on the planet: people who don’t want to exercise empathy on you.

Flat out frank, your best bet is to be stereotypically writerly.

Ok, not to the extent of “since I was 4 years old I’ve used my grandmother’s Olympia SM8 Typewriter and I can faintly remember the smell of spooled ink,” because it doesn’t matter if you’ve been writing since highschool or preschool (coincidentally this reeks of “I’ve been programming since I was 8” rhetoric).

A long time ago, I read someone’s blog post about their career as a graphic designer, and he mentioned he didn’t appear like the “typical designer.” He didn’t drink coffee. He dressed as a casual man, instead of the… hipster metro yuppie way. You know, the carries-a-Macbook-and-a-coffee-everywhere image. Whenever he met new clients, he’d get the, “You don’t look like a designer,” sometimes as a joke, but who can really tell? From that point on, he wasn’t sure if they also thought poorly of his qualifications.

Bothered by the frequency of comments, he started adopting beanies, plaid, and kept a coffee mug nearby at all times. Lo and behold, people stopped asking him about his appearance and doubting his qualifications. They just trusted him and his line of work. This is a “halo effect” related to your career.

Unfortunately, I can’t find that blog post, as I never bother to bookmark these things, so this is only a memory of my interpretation.

You need to use the shortcuts. Animators in character design and fashion artists will attest to the power of silhouettes. People latch onto every justification available that confirms they’ve “hired the right person.” If you want a writer’s job, conforming to the writer stereotype is necessary.

Not all places are as ignorant of the field, but most are. Until you’re actually employed and facing a problem, most people don’t know what kind of writer they’re looking for. Part of the process is that you grow into the role and fill the gaps. Remember, they think you’re a journalist, a writer, a living walkie-talkie. Maybe not a crime scene journalist, but just someone who reports on things that are otherwise missed. A vector for insight.

Qualifications of a writer #

What is a “writer?” It might share some aspects with the graphic designer, such as the eternal coffee, a pencil over your ear, and carrying an oversized notebook, but those are the superficial of the superficial. What about being some kind of brilliant teacher-historian who labored during their scant leisure time, until audacity lands them publisher recognition and blockbuster movie deals, becoming a literary giant like J. K. Rowling and G. R. R. Martin? Or on the opposite end of the spectrum, toiling in secret as a tortured, Kafkaesque soul, only to become famous after your grandnephew stumbles upon a trove of brilliance and sends the USB 2.0 for post-mortem publication?

Yes, you need to pretend that you are all of those. The Twitter mob will kill you if you peddle a “mentally-ill tortured artist” meme, but people love caricatures.

It also depends on the type of writing position you want. Maybe a grant writer or copywriter should resemble an extroverted go-getter. I have no advice for copywriting or UX writing, because I don’t want that type of job.

Technical writers deal with NDAs and plenty of confidential sauce. If you are a secretive, tortured soul, try to emphasize the “not overly talktative” and “very careful” part. Be very careful: don’t show that you are just a tortured soul who will only end up adding to the heap of existing tortured souls. You are going to be the thankless savior dealing with the tortured souls at your company who can’t communicate, and it’s not for lack of trying.

Do you have a track record of making rocks bleed? Can you get a tuff-as-tungsten, tight-lipped German to sing? If so, congrats! You might have enough empathy to be a technical writer!

Résumé #

There’s a lot of debate on how to do resumes, like whether to include your photo or not. Those kinds of things rely on your culture of origin. It’s customary in the United States of America to never include profile pictures, so American resumes should take advantage of that extra space. Some people add charts and bars to gamify their skill progress, but the meaning tends to get lost in front of busy recruiters.

In a nutshell:

  • Indicate that you read a lot.
  • Indicate that you crack people a lot.
  • Also have some cool “technical” skills, like photography or cooking or attending jury duty. Just enough to label you as someone who understands the rut that obsessive geeks drive themselves into.
  • Use keywords from related industries too.

Yes, tailor to the writerly caricature. You’ve gotta pass through the applicant tracking systems.

Portfolio? #

The great thing about college is that the professors want to see you grow as a human being. “Techical communication is about media. You get to dabble in video production, create content for learning & development, or engage with web design. You can do anything!”

They shield you from the real world and forget to tell you, “No one cares. Make a portfolio that only has the best 1-2 projects on it, because the rest are garbage and you’re not proud of them. If you don’t know what’s been vetted and what’s trash about your own work, what makes you think anyone else wants to pick through them?”

It’s why people like to know you’re published, because someone has done the vetting already.

If you have 15 portfolio pieces, that’s 14 pieces of amateur hour.

I get it, professionals flaunt a megalist of their accomplishments, and it’s tempting to copy the crowd and provide a link to a megalist of your own. But from the perspective of most normal people, they just want to hear about the latest and greatest. It’s why we read more news and less textbooks.

Think about it. Do you want the people who have no idea of the industry, who think you’re a journalist, to determine what’s good? Or do you want to be the one who makes that judgement?

Hand one thing over. “This is my best work.”

Will they ask for more? Smile and wait, because they probably won’t.

Example “Literary” resume #

I put “literary” in quotes because I call it my literary resume (relative to my former attempts at breaking into engineering, only to get a mental breakdown). But honestly it’s more technically-oriented than actual academic literary resumes.

Names redacted for obvious reasons.

Compared to my “techy” resume:

  • I dropped the link to my GitHub account and dropped the words “Web Development.”
  • Under Skills, added “Give and take criticism.”
  • I added a Fiction section with my beta reading hobby.
  • Keyword stuffing from editorial jobs and the traditional publishing industry.

Cover letters are the writer’s wheelhouse, so abuse them. #

My job search process started long before I graduated from university. It started with me trying to find internships and failing. I never actually had a real internship, just a volunteer data entry position that I labeled as a grant writing job. Yeah, I got 2 email conversations training me on how to do grant writing, and was given a few examples to look at. Then I went off and wrote LOI drafts, got them checked, and spent the rest of my time emailing as many companies as I could to fish for sponsorships and donations.

Most liberal arts internships are unpaid. My skills weren’t worth being paid for at the time. It’s just how it is.

When I feel gloomy, my childhood anxieties come to haunt me. When I was fed up, I typed all my thoughts into a rant. Then I forgot about it.

Several months later while sifting through Google Drive, I found the rant again. Was I the only person in the world who felt this way? Yes, because it’s a unique experience, but also no, because emotions of inadequacy are universal. Wouldn’t it be great if I could share this, but without getting looked at like some freak?

Who am I kidding? I’m an angry, socially awkward freak who talks funny. I’ve been like this my whole life. My social skills are enough to pass off in the first 5 minutes of an interview, but I can’t fool people for long. I’m not normal.

So I’m going to put this on my cover letter. I’m going to skip the hype, the trying-to-be-macho talk, the bullshit that gets farted onto cover letters. I’m going to tell a story. I’m going to surprise you and hopefully make you laugh, amuse you, and relieve you from the boredom of your sad office job.

If a recruiter sees my cover letter, I want them to think, “This is so interesting that I’m dumping the rest of the applications.” Make them laud you. Short circuit the recruitment process by letting them know more about your personality in 5 minutes than most candidates reveal in a 60 minute interview. Entertain them a bit. You’re a writer, right?

Cover letters are the writer’s wheelhouse, so write.

Case 1 - A story instead of a cover letter #

This took up one page of 11x8.5 inch paper. Got a positive response in less than 24 hours.

Every time I visit the IDE, I get anxiety. A programmer who gets anxiety from entering the IDE? How the hell does that work?

I always thought that maybe one day, exposure therapy will cure me.

A sleek building looms overhead, and I’m at the front gate. I press the button and a portal materializes, like a blanket falling from the sky. The ghosts of the projects greet me with whispers. I whisper back, Hello, otherworldly environment. When was the last time I was here?

The lights flicker and the clocks stop turning. It’s really late at night, so I pull up my earbuds and some music to calm me before I step inside.

The baby ghosts need to be fed, so I make the rounds into their pens. Their crying is faint, like a low hum vibrating across my arms. I call out their names, like “Test2” and “HeapExperiment6,” and I try to channel good memories into their cribs. That makes them calm down.

So far, so good. There’s many broken pieces of equipment, and red tape outlines their location. What I’m really worried about is the—

“You’re not supposed to be here.”

My heels dig into the linoleum, and I crank my head around slowly. I can’t see anything in this damn darkness, and I know the warden has come.

“Oh, why not?” I answer, but it sounds weak and shaky.

“The more you stay here, the more you shorten your lifespan.”

“Thanks for the concern.” I’ve told my friends I’d probably end up dying from eating too many fried Oreos.

As I take another step, the wraith hisses at me. “I’ll show you the way out. Come.”

It seems like I couldn’t make it past the front desk. I really wanted to know what was beyond those halls, where few people reach.

How many times had I played this game? I walk into the wraith’s arms, who exposes his murky mass to me. His hand, one that looks quite human, extends onto my shoulders.

As long as I go back, my friends and family will stay safe. There’s no telling what the warden will do if I don’t.

A funny realization starts to creep into me, like a fish trying to swim into my skull. Why do I always end up here, time and time again? It’s like wondering why a drunkard ends up at the hospital time and time again.

I look for the wraith’s face, and a pair of blood-red eyes stare back at me. My heart skips two beats, but I try to keep my own face straight. “You know, I really like fried Oreos. I’d eat a million of them if I could.”

The wraith, unerring in it’s tone, says, “Aren’t those bad for you?”

“How can they be bad when they taste so good?”

Original Rant #

Where does this feeling come from? Why do I deal with something so irrational? I envision a future of myself as a programmer, and it’s very bleak. I imagine myself scaring off people and not having friends if I mention what I do as a living. I imagine my coworkers blaming me for everything that goes wrong. I imagine my mom berating me because I played too many videogames, and if I went into game dev I’d be causing videogame addiction to the next generation. I imagine feeling trapped and alone. I imagine I’ll never make any friends and a whole lot of enemies. I imagine digging myself an early grave every time I open the damn IDE.

But in the end, I can’t help but follow the spiral of doom, like a moth to a flame. Regardless of my path and decisions, I will be subject to emotional torture every day, for as long as we are human. That is simply our fate.

If I don’t act as a mascot for the men in my life, I am a useless woman. If I don’t act as a mascot for the women in my life, I am a useless woman. If I don’t act as a mascot for myself, I am… guess what? A useless woman.

The demons mock me, telling me I’m good-for-nothing, that if I try to break into a male-dominated field I will be eaten alive, and I will grow grey and shrivel into dust from fighting endless power struggles.

But you know what? Even as I marinate in my own personal hell, I still program.

The original rant is…well, it’s raw. Nobody likes angst-driven memoirs, ok? Use fiction to abstract away the misery into something relatable.

The short story approach used industry jargon, although it’s intended to be understandable to anyone. Try it and see what reactions you get.

Example 2: Formatted Cover Letter #

If you’re not feeling ballsy, a more normal letter:

  • Use serif font for a conservative look
  • “Handwritten” signature
  • If I had time to redo this, I’d consider using a font size of 14-16pt. Make it easier for old people. I’m starting to feel it.
  • Talk about books you’ve read that are related to the organization. For some reason, people think highly of book readers.

To XXX Specific Department Name, I am an aspiring editor who recently graduated with a B.S. in Technical Communication. I have found editing to be more suited to my skillset than writing, because I have a strong background in linguistics and rhetoric. My all-time favorite non-fiction book is Last Chance in Texas: The Redemption of Criminal Youth by John Hubner. I was a teenager when I read it, just browsing the library, and since then, I've given in to a soft spot for true-crime, mystery thrillers and morally grey stories. I am applying to XXX because I believe that public research is a gift that relies on the hard work of our community. I continually work on my writing skills, studying the art of creative writing on the side to improve my narrative chops. Thus, I can contribute a balanced viewpoint that is both logically sound and supported with high quality, accessible communication. Thank you for considering me, N. S. Reiss

While writing this whole thing, I imagined myself swamped by stacks of yellowed papers, nit-picking on Oxford commas. Pretty funny, to be honest. There’s merit to “channeling the fantasy self.”

Got an interview from the head editor in 2 weeks. Not too bad, if I say so.

Loving cover letters. #

I decided to make the cover letter an opportunity to practice my craft. Why does job searching have to be miserable? It doesn’t. At least in the face of a soul-crushing experience, I can reclaim my pride.

Criticisms #

Talking about this experience has gotten me downvoted on Reddit. “Terrible advice. Is this a joke?”

What a shame. This is what happens when you don’t parrot the same platitudes from LinkedIn career counselors.

I’ve tried much worse. I’ve made my resume explode with stickers and neon colors. When I got sick of going to career fairs and being ignored? I went into a career fair wearing a silkscreen t-shirt and gave stickers to recruiters.

To be fair, company reps don’t have the inclination to deal with divas. Recruiters politely tolerated me or just grumpily dismissed me. I spent my last career fair strutting around and collecting free junk because I didn’t expect to make a connection with anybody.

My friend said that passing out stickers was a nice thing to do, and I probably made someone’s day. That’s nice of her to offer a positive viewpoint. I would’ve been considered a creep if I was born male.

When you spend your whole life with people telling you how cringey you are, you just accept the fact that you’re cringe. Yeah, I’m fucking cringe. If you’re desperate and you look like you need help, people will turn away from you like you’re a diseased hobo. Of course I’m fucking cringe, that’s the least of my worries.

I’m not upset at being cringe. I’m upset at being lost.

Rejection is Creativity #

Beauty is morality. Someone who is ugly must earn respect in some other facet: humor, gumption, intelligence, or skills. If you are socially ugly, then the only way to endure the throes of rejection is to be brilliantly creative.

Being alone is easy. It’s rejection that hurts.

There are studies that argue loneliness will decrease your cognitive capabilities as seen during the Coronavirus mandates for isolation.

There are studies that say rejection makes you creative, maybe because you have to try harder.

Nobody really knows. When it comes to feral children who’ve been raised by dogs, are they ever going to speak and react like a normal person? No. Are they braindead? No. Do they deserve to learn and survive? Do they deserve to thrive in human society, or are they too doomed to be saved? (don’t answer those questions; definitive answers lead to death).

When you write batshit crazy, you get attention. There’s “no such thing as negative attention.” I got a rejection in less than 24 hours, and a response to move forward in less than 24 hours. Call me crazy, but it’s better than getting ghosted for indefinite stretches of time.

Yeah, I’m starved for positive attention. It elates me like a helium balloon.

What the fuck is GitHub or JavaMarkdownScriptFlaremakerCapDITA insert properitary software of the month? Stories trump the truth every time.

An interviewer straight up said, “I respect people who can write creatively.”

If I have to job search again in the future, I will absolutely continue to write unconventional cover letters. For one, it’s fun. And two, I cannot forgot how painful rejection feels, because I will feel it again. Hopefully, I’ll have better coping mechanisms by then.

I’m not gonna pretend that this post is a map to launching a technical writing career. Most people I know go through a quasi-spiritual ego death while job seeking. When they finally land a job, they conveniently forget about the pain. Then they go to career panels and share the positives to the next generation, not wanting to focus on the crying and the shame.

Black Boxes #

Creative writing saved me. Instead of languishing in an irrelevant field after graduation, I was able to get responses in magnitudes shorter than I was used to.

Again, luck. The biggest factors are probably:

  • Don’t be an illegal immigrant in the US of A
  • Filed my own tax returns
  • Mooched off COVID-19 unemployment benefits so I could think about what I wanted to do

Mental health and reality:

  • Ignore the people who keep telling you to achieve higher. The world is upside down. Sometimes you need to dig.

  • It’s easier to get an entry-level job than an internship. You don’t need internships, although apply for them like you would a contracting job.

    • Companies prefer to hire graudates who aren’t beholden to classes. Still, interns are exploitable and training newbs is a necessary evil.
    • Some companies have policies which mandate that interns must be enrolled in college (to combat the tendency that companies would rather exploit a cheap FT contractor)

Make it braindead for the reader.

  • Keyword stuff your resume from adjacent communications industries: publishing, journalism, marketing, etc.
  • Conform to a writer stereotype. Give off that “vibe”
  • To not come off as pretentious, make it clear that you participate and contribute to your industry.
  • Leave out words like intern
Engineering is one kind of black box.
It's treated like magic, the domain of an intellectual elite.
Nobody likes to admit that often the case
turns out to be, "When I was young, my daddy bought me
functional robots to play with
and now I'm an engineer! But all I do is
punch paper and fix other people's mistakes."
Geniuses are expensive.
Creative writing is another black box.
It's not nearly as profitable, but the arts are valued implicitly.
Many people also treat creative writing as
a freedom that they can't afford.
Creative writing is easier to get into than engineering,
but it's harder to be recognized.
Hence, the black box becomes admiration
(or morphs into the evil cousin, jealousy).

I don’t know what it is with these black boxes. Maybe I’m lucky that I can stick a hand into both and come out intact.

Let me offer you closing advice: just be more empathetic with a high 📈 EQ! Generating empathy is the only thing a writer is good for 👏 If you keep 🤔 going at it, your work might be the next Mein Kampf 🧠!


Tyler has identified talent either earlier than or missed by top undergraduate programs, the best biotech startups, and the best biotech investors, all without any insider knowledge of biotech.

Tyler has compounded his skills in selecting talent over decades of deliberate practice in “cracking cultural codes.”

Tyler’s nose for talent, even in technical fields like biotech, comes from his study of the humanities: art, music, complex novels, religion, anthropology, et cetera.

—Tony Kulesa, Tyler Cowen is the best curator of talent in the world