12 Lessons Learned from 12 Years of Writing

Writing is hard.

Writing something worth sharing is even harder.

Writing something worth keeping — hardest.

That’s twelve years of professional writing experience summed up in fifteen words.

Experience that starts with a stint as a junior copywriter writing product descriptions … that morphs into a managing editor with my own staff of writers and proofreaders at an international organization … and ends with a successful business as a freelance web content strategist.

Writing has been my professional life. And naturally, I have a lot to say about it.

Like the twelve particularly important lessons that I learned, which I hope will guide you down a path to becoming a world-class writer.

Lesson 1: Write yourself silly

There is only one path from greenhorn to professional when it comes to writing: production.

And a lot of it.

But that’s a pretty daunting task, especially if you are a perfectionist. You tend to write like someone is hovering over your shoulder, inspecting every word as you type.

That’s no way to work.

In fact, in my time as a writer, editor, and teacher, I’ve seen what that pressure can do to a writer. Clunky and ugly sales letters, emails, or blog posts.

Not something you want the world to see.

That’s why you need to get loose. You need to sit down, forget about the world, and write. And you need to write yourself silly.

No doubt when you are done you’ll have a healthy pile of crap on your screen. But now you’ve got something to work with.

See, I’d rather edit down ten pages into one than torment myself by trying to perfect that thing from the ground up.

Once you have the rough draft then you can switch on Hemingway’s BS detector, edit like a ruthless beast and earn your money.

Lesson 2: Beg a hot-shot writer to mentor you

Writers are an uptight bunch.

Sensitive enough to be able to put something worth reading on paper. Sensitive enough to wilt if somebody rejects it.

But without tasting that rejection — without venturing out for that criticism — you’ll be a diarist at best. Better to step out and look for professional help.

Under the leadership of one of my first bosses I grew immensely. This was also true during the year and a half I spent with a critique group. That objective perspective will help you to see your blind spots and improve.

Not every critique will help you. You need to learn how to sift good advice from bad. And it helps to work with someone who knows what they are talking about.

A long time ago I took advantage of a relationship I had to shoot John Carlton a sales letter I was writing. I wanted his input. He was kind enough to reply. And he was kind enough to eat my lunch.

Yet, that was one of those moments where I finally understood what I’d been reading about all along — but it never sunk in until John said it.

Lesson 3: Cultivate a sick sense of humor

Being a web writer has its perks. For instance, when people ask me what I do for a living I’ll tell them I’m a web writer.

The vacant look on their faces indicates I’ve lost them. So I need to elaborate. So I say something like this: “I’m a priest. And I guard the sanctity of the written words on the web.”

I haven’t finished talking and Coke is coming through their nose.

I get a real kick out of that. Why? Because it’s funny. Funny the same way Zach Galifinakas and a group of clog dancers walking through the woods wearing silk pajamas is funny.

It’s odd. It’s weird.

Writers suffer from the same problems that comedians do: generating new material. If you can’t generate anything original, then you’ll fade into the background.

So the question becomes: who would you rather write for you? Someone with a flat personality? Or someone with a clownish streak running through them?

I’d go for the clown every time. Especially since getting attention and visibility online is crucial. So what are you waiting for? Nurture that sense of humor. And make it sick.

Lesson 4: Steal ideas

The blank page hates you. And wants to see you go away. It wants to put you to sleep with a drink here, a toke of marijuana there.

Anything to keep your filthy paws off of her.

If you manage to make some tracks she’ll tease you that it’s not any good. It’s not the least bit original.

Well, she’s right. Most of what you write is boring and ordinary. It’s been written and shaped at some point in history.

Oh well. Your job as a writer is simply to remind readers of what they’ve forgotten. Of bringing back to remembrance what was long ago. But in a completely new way (see lesson 3).

So don’t be shy when it comes to pillaging other people’s works. Tear out articles in magazines you love. Save blog posts to Readability. Highlight lines of a novel.

Then take those ideas, put them on the blank screen and shape them into something new. It’s one of the quickest ways to conquer that blank page.

Lesson 5: Writer’s block is a myth

Colson Whitehead said that writer’s block is a tool. It’s a tool that you use when you don’t feel like working.

If your spouse asks why you are lying underneath the river birch with a stout and not punching the keyboard, all you have to say is, “Muse. She’s left me. But she told me to meet her here.”

Whitehead is being sarcastic. In reality writer’s block isn’t a disease. It’s a romantic way of saying I’m lazy.

As a professional for the last twelve years I have to tell you: I’ve felt like writing for only about half of those years.

Maybe even less.

But if you want production and progress, then you need to sit down and write. Even if you stare at the wall and just type, which was what Orson Scott Card would do when he fought the blank page.

In truth, writer’s block is also a symptom that your idea tank is low. And what a better way to fill it by reading a thousand books? See the next lesson.

Lesson 6: Read like mad

Teddy Roosevelt wrote 150,000 letters in his lifetime. He wrote a handful of books on subjects from natural history to naval warfare.

It’s probably no surprise to learn that he also read about one book a day. If he had more time, he’d read two or three.

Most writers I know read like mad. But they also read smart. They know when to abandon a book, pace through the chapters or absorb it into their bloodstream.

Yet, don’t stop with just reading. Memorize stretches of texts, speeches, and poems. Think of it like programming your mind and filling up your idea tank.

Lesson 7: Experiment

I hate people who wake up at the age of four and say, “I want to be a veterinarian. Or a lawyer. Or a novelist.”

And then grow up and do just that.

It’s like their life were scripted and they nailed it on their first rehearsal. My life (and résumé) looks a lot less polished.

But I wouldn’t trade it for the world. That experiment with experiences informs what I write.

That’s why I can speak from the perspective of a rock climber, monk, and bonehead in the same breath. That’s why I can consult international non-profit organizations about their social media and content marketing strategies.

Of course, it’s also why I have a string of failed social media platforms in my wake. The thing is I find what works — and stick with it. That’s what experimenting is all about.

If you aren’t learning and improving, then you are doing it wrong. Step out of your comfort box and toy with the world.

You’ll love the treasure you find.

Lesson 8: Fall in love with the human condition

Pull out my Myers-Briggs score and you’ll see I’m a Scientist. INTJ. I value knowledge, ideas. And I’m quick to apply those ideas in practical ways.

The running joke in our house is that I love ideas more than I love people. Fair enough. I am more comfortable in a university library than at a cocktail party.

The thing is — I like people … just not so close. At a distance. A clinical distance.

I devour books on the criminal mind. Scoop up articles on negotiating and persuasion. I tinker with the way I say or write something to see what kind of response I can get out of a person.

Can I make him cry? Laugh? Yell?

I do like to meet strangers. Partly because I like to force myself to do things that make me uncomfortable (see Lesson 7). I try to network, even if this means volunteering at the local food pantry, harassing people on Google+ or crossing the country like a vagabond.

Remember: you are writing to people. You will always be writing to people. So it’s essential that you understand them inside and out.

Lesson 9: Catch hell

Let me confess something: I’m a coward. I spook easy. But I also like to stir the pot.

Like … a lot.

Fortunately, catching hell is a quick and dirty way to develop your copy chops. How? Rocking the boat forces you to defend your ideas, stretch your thinking, and evaluate what you can stomach.

So how do you catch hell? For starters, you can write a marginally scandalous post, book or article. For example:

1. Challenge a popular person or position.
2. Expose a dirty secret.
3. Challenge the status quo.
4. Toe the line of racy.
5. Question authority.

There is a dark side to catching hell. Just look at people like Lindsay Lohan or Julian Assange. These people age fast.

That means your catch-hell strategy needs to be carefully planned.

Catching hell is a great way to gain critical mass if you have a new blog. But eventually you’ll need to ease your foot off the pedal before your readers expect nothing but controversy.

Position a spicy post about two to four weeks (or more) apart to keep from burning the conflict candle at both ends.

Lesson 10: Offer majestic amounts of customer service

Before the printing press, do you know how much an average book cost? About $10,000. That’s because it took someone half a year to copy the book.

These days we treat books like chewing gum. Easy to get. Easy to consume. Books have become a commodity. And the only thing that a commodity competes on is price.

As a writer, teacher and consultant, I vowed never to compete on price. In the end, a hack writer will work for $10 blog posts. Like an assembly line worker who gets paid per widget, he’ll grind out 5 of those an hour.

That’s no way to live. He’ll burnout in a year. He’ll be obsolete in ten.

I don’t want to burn out in three months NOR be obsolete. I want my work to live for twelve months at minimum. One thousand at maximum. But more importantly I want my relationship with my client to last a lifetime.

And that can only happen when you deliver majestic amounts of customer service. When you bend over backwards and pour yourself out for your client.

Think you’ll lose money on this platform? You won’t because you’ll get to charge premium rates. Rates that make people flinch.

But if they want the best service, they’ll cowboy up. If not, move on. Look for people with the deep pockets. They are out there. I promise.

Lesson 11: Step into the ring

I like Jeff Goins. I’m so happy about the success of his blog. Thrilled to hear about his book. But when he makes statements like “You are a writer when you call yourself one,” I have to scratch my head. (Actually, he was quoting Steven Pressfield.)

See, if that logic were true, then I’d be an iron worker the moment I called myself an “iron worker.” I’d be a Marine the moment I called myself a “Marine.” A boxer the moment I called myself a “boxer.”

The truth is you are not a boxer until you step into the ring. And even then, you don’t have the right to call yourself a boxer. At least not until you fought a few matches.

Another piece of advice you’ll hear is that you should write 1,000 words a day — and you’re a writer. Ray Bradbury gave that advice, too. But he said you didn’t become a writer until you did that for 3 years straight.

Three years.

True, the definition of a writer is all over the map. It is subjective. But here’s my point: at minimum you have to write, publish, and get readers. And live with the consequences.

You won’t gather steam calling simply calling yourself a writer. You’ll gather steam when you start producing — and then creating something worthwhile. And you can’t do that if you aren’t even in the ring.

Lesson 12: Stay in for the long haul

There is a secret to becoming a world-famous writer. You have to stay in the ring. For a long time. It’s all about the 10,000 hours devoted to deliberate, purposeful practice.

Geoff Colvin popularized this concept in his book Talent Is Overrated.

His premise is simple: adopt the habits of people with high ability in sports, arts, and business — people like Michael Phelps, Chris Rock, and Benjamin Franklin — and you can excel at anything.

But it takes years to develop this ability. And sadly too many people bail before the tipping point.

My own writing has been in development for the past twelve years. You’d laugh at my first attempts at an article or a sales letter. And it took about five years where I could command the written word without embarrassment.

This may seem totally obvious, but I would not be the writer I am today if I had given up ten years ago. So, it boils down to this: practice, adjust, experiment, and repeat.

Ad nauseum.

My conclusion …

Listen, writing for a living is not easy.

The fact is, there are much better careers to pursue. But if you simply can’t NOT write — if you simply can’t imagine a life WITHOUT writing — then you will probably make a pretty good writer.

And even if you never taste success (fame, wealth, or power) this side of death, don’t worry. There are dozens of “failed” writers who got the attention they deserved after they were dead.

Franz Kafka. Phillip K. Dick. John Kennedy Toole. Anne Frank.

Sure, it would be nice to have the perks of an E. L. James or Stephanie Meyer, but who remembers superficial 50 years from now?

Nobody.

Write for the long haul. The legacy. The forever after. Either way you’ll win.