29 Writing tips for my 19-Year-Old-Self

This is what I was put on earth to do, and I have the 1099s to prove it.

My first story was published exactly ten years ago, the summer after my 19th birthday. Two years ago, I started freelance writing full time.

These are notes to my 19-year-old self. These are the things I wish I had known going into the writing game.

Forget about Being a Writer. Write.

Focus on doing the verb (writing) rather than being the noun (a writer.)

Your Only Job is to Communicate

Like every undergraduate wannabe author, I was under the impression that the purpose of writing was to get attention, brag, and impress people.

I would have told you that I don’t write for anyone but myself, but the truth is I was writing for everyone but myself.

I was broadcasting rather than communicating.

Story Over Style

If you tell a good story, you can get away with a clunky style. But no amount of style will save a bad story.

My 19-year-old self would have said, “I’d read a 600-page grocery list if it were well written.” I want to slap that guy.

Just Make Lots of Stuff

The best way to come up with good ideas is to get lots of bad ideas out of your system.

If I’d posted three blog posts or stories or poems or whatever per week from the time I was 19, I’d have 521 posts up. If I’d shared something every day (like Austin Kleon recommends,) I’d have over 3,000 posts.

Perfectionism has been the only thing stopping me. My unhealthy obsession with getting it right kept me from getting it written.

Taking action is what matters. With so much content out there, volume can be the difference between obscurity and finding an audience.

Assume Nobody Cares

Your job is to use your words to make them care. You’re not entitled to an audience. Attention must be earned.

But because nobody cares, you can stop beating yourself up over how your work might be received.

It’s Possible to Make Writing your Day Job (you don’t have to starve)

There is so much well-paid freelancing work out there, and the internet makes it accessible from anywhere.

Everyone approaches the day job issue differently. But for me, there’s immense satisfaction in making a living with creative work alone. This is what I was put on earth to do, and I have the 1099s to prove it.

Have Stuff to Write About

If you focus on living, you’ll have plenty to write about. Writing is not like playing the violin, more hours of practice do not necessarily equal better results.

You’re better off working smarter, not harder.

Never go back to School

The last time someone asked me if I’ve thought about doing an MFA, I told them the same thing I told my parents after my first day of kindergarten:

“I hate school.”

College dropout, and New Yorker art critic, Peter Schjeldahl, argues that good artists tend to be bad students because art isn’t about climbing a ladder of accomplishment and earning approval from teachers.

Have Friends who aren’t Writers

Besides preserving your sanity and helping you keep things in perspective, non-writer friends can offer all kinds of shortcuts when it comes to research and character-building.

Different jobs have unique jargon and rhythms of speech. Listening will make you a better friend and tune your ear for dialogue.

Stop Drinking and Getting High

It’s no coincidence that the year I got my shit together in this regard (at age 25) was also the year I got paid to write for the first time.

It’s like Iggy Pop told Anthony Bourdain:

“If you just flame out, you’re in such voluminous and undistinguished company. And all your work will flame out with you.”

Don’t be an Asshole

The bar is set so low in this department that even basic manners and social awareness will set you apart.

Kindness is indispensable when dealing with the unsung, uncredited people who work behind the scenes to publish and edit your work.

Go on an Information Diet

It’s in your best interest to care about as few things as possible and not to get distracted by idiots on Twitter.

A World War started and ended while Joyce was working on Ulysses. It’s probably safe to ignore the latest hashtag call-to-rage.

You’re being paid for your Ideas and Experience

There’s a story about Picasso that’s been told a few different ways, but the gist is that someone tried to pay him for a quick charcoal sketch (on a napkin as one version has it.) He named what seemed like an absurdly high price for the drawing. The would-be patron protested,

“But that took you thirty seconds to draw.”

“No,” he replied, “It took me forty years to draw.”

When you hire any creative — and they don’t have to be Picasso — you’re paying for their cumulative experience. You’re paying for them not to make the mistakes they’ve already made and learned from.

Freelancers often agonize over how to price themselves. Getting comfortable putting a dollar amount on your work requires a mindset shift. You’re going to end up charging more as the work becomes easier and faster. This is because you’re being paid for your creativity and your experience, not your time or your sweat.

You Can’t do it Alone

Writing is probably the most solitary creative pursuit. Friends and family are the difference between solitude and loneliness. Cherish them.

Not everyone in your life is going to get your commitment to the craft, but having a strong support system means not everybody has to get it.

Money = Freedom

There’s an old saying: “when bankers get together, they talk about art. When Artists get together, they talk about money.”

It makes sense to focus on making and saving money when you think of it as buying you the freedom to do your creative work.

You owe it to your writing to learn how money works and how to get enough of it to secure the time you need to write.

And, by the way, if you happen to have money — from a spouse or inheritance or whatever — quit apologizing for it.

Live at Home (at least at first)

The Brontës, Jack Kerouac, and more recently, Mark Manson and Tim Burton are just a few of the greats who credit moving back in with their families — or never leaving — as key to their success.

Martin Scorsese‘s mom catered the release party for Mean Streets. Justin Halpern wrote Shit my Dad Says after moving back in with his father at 28.

I want to tell 19 year-old-Charlie to get over the idea that it’s a loser move to live at home. And if this Forbes article encouraging entrepreneurs to do just that didn’t convince him, I’d point out that Kerouac put more than a hundred names on his infamous list of sex partners while living with his mother.

Don’t be Afraid to Abort Projects

Part of writing the novel I’m working on now was throwing away four or five others that no amount of rewriting could have salvaged.

I call these “abortions.” The first novel I finish and do something with will be my first novel. I was talking about this the other day with my cousin — who’s also a writer — she said,

“But you’ve written novels before.”

“Yeah,” I said, “ but if you had three abortions, you wouldn’t go around saying ‘this is my fourth child’ when you finally carry one to term.”

And while you’re at it, don’t Worry About Offending People…

Seriously though, it’s good to be polarizing.

If my abortion analogy upsets you, you really aren’t going to like the trashy pulp novel I’m working on…

This isn’t a matter of shock-value or attention seeking. Simply put, trying to appease over-serious people makes me feel alone. Sharing a sick joke with strangers online reminds me I’m not alone.

Read Outside your Genre

Getting into pulp and hard boiled detective novels was the best thing that ever happened to me as a reader. It started when I was deep into literary fiction. I picked up The Big Sleep and told myself, “might do me some good to read something with a plot…”

Now that hard-boiled crime fiction has become my genre, it’s time to keep exploring and read outside that genre. (Leave a comment with SciFi recommendations)

Shun Complainers

Don’t read them. Don’t listen to them. Don’t take their complaints seriously. Jettison them from your life when possible. Above all, don’t be one of them. Never complain.

…and Explainers

19 year-old Charlie was a prodigious explainer who would talk to you about Raymond Carver and Chekov as if you couldn’t possibly have heard of them. If I could, I’d give my 19 year-old self a rule:

If people need something explained or elaborated on, they’ll let you know.

Nothing Matters Besides the Work

Nothing. Fuck being well-rounded.

Write Sloppier First Drafts

In Bird by Bird, Anne Lamott talks about “shitty first drafts.” Just getting everything out on the page and fix it later.

When I was younger, I paid lip service to this idea but my perfectionism wouldn’t let me make a mess. I’d tell myself I was just sketching, but I’d secretly hold out hope of getting it right the first time. This made rewrites a nightmare.

Outlines are Your Friend

Some people can make it up as they go along. I’m not one of those people.

As an undergrad, every story I wrote turned out to be five pages long. I’d write a twenty-page short story and end up with five usable pages. Looking back, I think five pages was about the maximum amount of time I could keep an entire scene in my head.

Studying screenwriting changed everything. I learned that plot is the product of deliberate and meticulous choices, not a happy accident of improvisation.

Work the Whole Canvas

This is a painting term that means to start with broad shapes and shades rather than starting with a ton of detail in one spot.

The first draft of the novel I’m working on is turning out more like a treatment or an outline than a manuscript. I’m leaving a lot of loose ends to work on later rather than perfecting scenes I might end up cutting.

Don’t Take Any of it too Seriously

Hey, Whipple, Squeeze This, the definitive textbook for the ad business in the 21st century cautioned against buying into the myth of the tortured artist.

“…All that crap about how writers need to ‘work from pain.’ Oh puh-lease, it’s a coupon ad for Jell-O.”

How you Write Doesn’t Matter, as Long as it Works

I’ve had plenty of rituals and writing fetishes in the past 10 years, from filling my fountain pen with green ink to sharpening a half dozen pencils before I start to writing with a typewriter.

Now I use a laptop and legal pads. When I get stuck, I switch between the two. There’s no ritual, it’s just a matter of getting it done. I use index cards to collect research notes and outline.

I still like a good fountain pen, but not in a totemic way that I ought to see a therapist about.

“Fuck Yes! or No”

Derek Sivers has a simple rule for emotional decluttering: HELL YES or no. If a project, a place, a person doesn’t get an enthusiastic “hell yeah” out of you, then you should say “no.” He writes,

“When you say ‘no’ to most things, you leave room in your life to throw yourself completely into that rare thing that makes you say ‘hell yeah!’”

Mark Manson expanded on how this rule applies to relationships and renamed it “Fuck Yes or No

Get some Sleep

The ultimate productivity hack: getting enough rest to actually be productive.