How to Write Well When You’re Just Getting Started

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A reader writes in asking:

I was challenged and impressed by your piece “How to Get Ahead when You Have Nothing to Offer” today. In it, you write that you thought you could write well as a student, but that writing in the real world is on a different plane. More specifically, what do you mean by this? What are some resources and tools you suggest for becoming a more effective writer outside of a college curriculum?

I love this question.

Writing is one of those few high-leverage skills. Once you learn to do it well, you can apply it in marketing, sales, software development, fundraising, product development, education, or running your own business. It transfers between industries and jobs astonishingly well. A marketer who understands how to market well is valuable — a marketer who can communicate that well in writing is even more valuable. A software developer who knows how to write beautiful code is valuable — a software developer who can communicate what he’s writing and why is even more valuable.

I’ve written before about how to become a better writer and how to use what you’re already consuming to improve your writing and creating abilities. My writing improves non-linearally when I write more often and when I read more often. My writing style is an amalgam of my favorite writers that I read and iterations on my own former writing.

Schools rarely foster this kind of writing, though. Writing seminars in most colleges are laughable attempts at making formulaic and sophomoric writers out of people who, up until that point, had only really been trained to write for the SATs or ACTs or their English teachers. Excellent students know what kind of style and content their teachers and schools want to read. In time, this means excellent students develop a great ability to write for school without developing the separate ability to write for the real world. The only people who enjoy academic writing outside of academia are those intellectuals who should have gone to graduate school (or went and couldn’t cut it) and now sit at home with The New Yorker on Saturday mornings.

That is not what most educated readers look for.

So, how do you foster this writing outside of school? How do you take somebody who enjoys writing but hasn’t had the opportunity to enjoy it since matriculating into school? Even harder, how do you take somebody who only views writing as a set of assignments and develop that sense of enjoyment.

This is what I did to preserve my love of writing and reclaim it from an academic style that started infecting it when I went to college.

How to Get Started

Writing well for the casual reader is constant process of sales and seduction. Unlike your high school English teacher or your university TA, the casual reader doesn’t earn money for reading and critiquing your writing. They can choose to close the tab, close the book, or toss away the letter at any minute. Each sentence builds upon the previous sentence to give them reason to keep reading.

People come for you to tell them something. If you write fiction, they come for you to entertain them with a story. If you write non-fiction (as I do), they come for you to inform them.

The problem is that new writers either get caught up looking for a formula to write — akin to the paragraph styles that you learn in high school English class for the SAT — or they get so caught up in perfectionism of the message that they never start in the first place. Neither of these are important if you don’t actually have an essay to write. Just like sales and seduction, the best way to get over this fear of getting started is to start small. When I work with my one-on-one clients who have never done outreach or sales before, I encourage them to get started with as many small cases as possible.

This isn’t because I believe in spray-and-pray — I don’t, it’s better to send 10 quality emails than 100 shitty emails — but because you see that getting started is always the hardest part, even though it shouldn’t be. Game and dating coaches encourage their clients to approach attractive people on the street and try to get their numbers. Not because you’ll find your future girlfriend or wife on the street — you probably won’t — but because getting over the initial fear of even getting started is more important at first than perfecting the pitch.

So, in improving your writing and writing for real people, focus on opportunities to write first, opportunities to get started, and opportunities to sharpen your skills over time.

The list of excuses that come up to prevent a writer from getting started are myriad. I hear these often:

I don’t know where to write.

I don’t know what to write about.

Nobody is interested in listening to me.

How do I write?

What rewards would I get for writing?

How do I know if my writing is any good?

This is what I recommend you do:

  1. Start a Blog
  2. Start reading outside of class.
  3. Start writing about subjects that interest you.
  4. Start writing for audiences other than your peers.
  5. Trade up to new publications
  6. Get serious editors to look at your work.

Let’s break each of these down.

1. Start a Blog

One of the best pieces of professional advice I ever received was from Josh Blackman: start a blog. He gave me this advice when I was in high school and the blog I started then evolved into today over the last decade.

Starting a blog is the easiest way to build up a portfolio of your thinking & writing, allows you to get the attention of the right people in the space you want to go into, and gives you an excuse to write on topics outside of school.

Josh Blackman used his blog as a way to become a leading voice on issues of constitutional law.

Go to and buy a domain (it’s worth the $10). If you can buy your, do that. If not, .co doesn’t look as cheap as it did a decade ago.

Then spin up a WordPress site on a service like Tap.

Your site does not have to be fancy. My site for years was a simple theme with some minor tweaks. It wasn’t until 2017 that I seriously looked at incorporating new components onto my site.

The site won’t make the writing happen for you but it removes the excuse of “I don’t know where to write” for you. It also doubles as a professional homepage for you.

If you absolutely do not want to start a WordPress site, Medium makes it easy to start writing now. It’s well-designed for writing and does already have an audience built-in.

2. Read Outside of Class

If you don’t already read outside of school assignments, start. It doesn’t matter what you want to read about — underwater Japanese cinema of the 1960s, baseball, economic theory from the 1800s, mystical stories of warlocks — just start reading more.

What you enjoy reading about determines two important factors about your writing: your style and your subject matters. Nobody is birthed into this world with a distinct writing style. Your writing style is an amalgam of all the authors you enjoy reading and the people they enjoyed reading and the people they enjoyed reading. Don’t stress about not having a style. Your style will evolve over time. My writing today in 2018 is considerably crisper than it was in 2015 or 2013 or 2011.

Just get started.

What you read determines the fodder you have to write about, as well. My collection of essays, The End of School, came out of a desire to learn more about education and schooling. I dove into the best books I could find on the subject and ended up writing about my experience with school informed by these books.

If you absolutely cannot read more outside of school, write about what you’re reading in school. If you go back and look at this site circa 2013, you’ll see blog posts and essays on philosophy, bioethics, and political economy. That’s what I was reading at the time.

3. Write About Subjects that Interest You

What subjects interest you?

What do you currently spend time reading?

Do you read fiction? Do you read about productivity? Careers? Economics? Art? Horses? Education?

Do your friends ask you about specific topics? The gym? Coding? Jogging? Art?

Start writing about those topics. Your posts don’t have to be long — I’ve written haikus during writing marathons inspired by Isaac Morehouse — they just have to be.

Here are some blog post ideas for early blogging:

  • Book reviews/book notes
  • Comparing and contrasting two authors on a single subject
  • How you applied a concept from a blogger or author you follow
  • What you’re currently reading and why
  • Answers to questions your friends ask you about often
  • What got you interested in the subjects you enjoy
  • Where popular advice is wrong
    • E.g., Anything on this site related to college and higher ed

Set a schedule and set a time of day that you have time to sit down and actually write. You’re more likely to engage in writing if you develop a habit around it instead of just waiting for inspiration to strike you. When I got serious about writing, I wrote every day for 30 days. Most days, I wrote around 7:30 AM – 9:00 AM. Some days I wrote late in the evening. You don’t have to write every day to get started, but you do want to try to develop the habit as much as possible. Like going to the gym, it’s easier once you have a habit loop developed.

fantastic resource for getting started with writing is Quora. Quora is a question-and-answer site where anybody can answer questions posed by other users. It literally feeds you prompts based on what you already know. This overcomes the “how do I know what to write about?” objection and helps you get the gears moving when you want to write but can’t get started. I still use Quora when I want to write about something unrelated to my laundry list of topics I have saved in Evernote.

4. Write for Audiences Other Than Your Peers

Your peers are a great source of inspiration for writing. Ask them how they would describe you. Think about what questions they ask you. You’re an authority on something to them.

They are not the best judges of writing, though.

If you want quality feedback on your writing, get it in front of real people who have no reason to read it besides that it interests them. Your friends have an incentive to tell you that your writing is good or coming along since they are your friends and they don’t want to offend you. Your writing seminar instructors have are paid to critique your writing in a specific way that the college’s writing program dictates.

Writing on your own blog won’t get you an audience outside of the people who already follow you. Send in writing for other blogs. Publications on Medium are a good place to start. Find bloggers you enjoy following and see if they’d be willing to publish a post of yours as a guest post. Even if they say no, you can get feedback on your writing style and overcome that fear of pitching that many people have while starting out.

5. Trade Up to New Publications

As you get on new websites with your writing and get feedback from editors, site owners, and readers, you can trade up to new and larger publications.

The advantage here is to get your writing in front of more people who have no reason to read it. You want to see what sticks and what doesn’t. Sometimes your writing will hit a nerve and allow you to pursue that subject matter relentlessly for a few months or years. In my own experience, writing on education and schooling and, more recently, on communication techniques to improve your career have been the result of trading up to new publications and seeing what sticks well.

Most publications have an editor email address or a submission page. If you have to send an email, a quick pitch like this works well:

Hi [Editor’s name],

My name is [Name] and I’ve been reading [publication] since [time]. I love the content you put out [for sincere reason].

I’m a young writer looking to expand his/her portfolio and, based on what I’ve read on [publication] and what I know about your audience, I have a few post ideas I’d like to pitch you.

  1. [Pitch idea 1]
  2. [Pitch idea 2]
  3. [Pitch idea 3]

I’ve been published already at [smaller, other publications]. Based on the reception to my writing there, I thought it’d make sense to send you these pitches.

Do any of these interest you? If so, I can put together a post and send it your way.

This lets you get an idea of what you need to write before you write it. In the case of sites that do republish work from elsewhere, you can send them articles or posts you’ve already written on your personal site and see if they’d like to republish them. What you don’t want to do is write a long post for a specific publication before the editor of that publication has expressed interest in your idea.

6. Get Serious Editors to Look at Your Work

If you wanted to get better at running, you’d hire a running coach in addition to your regular practice. If you wanted to get better at art, you’d pay an art instructor in addition to your regular practice. If you wanted to get better at cooking, you’d hire a cooking instructor in addition to your regular practice.

Why is writing any different?

“Wait, but I thought you said you want to write for people who aren’t paid to review your writing?”

Yes, those are the people you write for but that does not mean that you cannot benefit from quality and experienced editors.

Famous writers love to shit on editors. HL Mencken wrote that he was thoroughly convinced an editor never helped writers. Nassim Nicholas Taleb lumps most copyeditors into the same category as DC bureaucrats.

But you are not Nassim Taleb or HL Mencken — not yet. A quality editor helps you make sense of your structure, iron out stylistic quirks before they become endemic, and makes your blind spots clear to you.

You don’t have to hire serious editors regularly, especially if you just want to improve your writing on the side. You should approach the people you know who are quality writers in the real world and ask them to take a pen to your writing. They’ll remove academic jargon that infected your writing during school and will clean up your long, run-on sentences that are acceptable in academia.

Getting somebody with a serious eye to look at my writing has been the most painful and helpful addition to my writing experience. I started writing what I thought would become the manuscript to a new self-published book a little more than a year ago. It made sense to me and read well. This manuscript became the sample chapters for my new book, How to Get Ahead When You Have Nothing to Offer. When I sent it to my literary agent, I expected minor changes and feedback.

She eviscerated it.

I rewrote much of the manuscript and several chapters entirely. The process was painful and a hit to my ego.

The finished proposal was some of the cleanest, crispest writing I have ever produced.

Get somebody to look at your writing.

A Few Recommended Books

I’m generally not a fan of referring people to books about writing. Like I said above, it’s better to read what you enjoy reading and start writing than to take a thousand writing seminars.

That being said, there are a few books that I’ve enjoyed on the subject of writing.

The Elements of Style 

This is essentially the Bible of modern writing. Some of the conventions recommended in the book can feel outdated (I recall the authors disparaging contractions, for example), but you should own it and leaf through it at least once.

On Writing Well 

This was recommended by my agent and sat on my shelf for a month before I cracked it open because I thought it was going to be a textbook more than a guide to clear, crisp writing.

“Writing is not a special language owned by the English teacher. Writing is thinking on paper. Anyone who thinks clearly can write clearly, about anything at all.” – p 147

The Curmudgeon’s Guide to Getting Ahead

This book is actually a little guide on early career etiquette that I recommend if you work around Baby Boomers or any older, stodgier people of influence. Murray has a section on writing in the workplace that’s worth digging into for professional writing.

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