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MAYBE IT’S NAIVE I’m telling you my best writing advice I’ve ever learned at the age of 28. But unlike my friends that went on to be salesmen, tradesmen, and teachers, I decided early on I wanted to write for a living. Now 10 years in, I feel like I’ve learned a thing or two that can be passed down to those who are starting to write, or want to write but need a little nudge.
A quick refresher: I’ve spent the past decade writing for various clients and publications. Some of my proudest work includes freelancing for The Manual, serving as Style & Gear Editor at BroBible, and later as Senior Commerce Editor at Men’s Health. Today, I’m a Senior Brand Copywriter at my dream company: the men’s retailer Huckberry.
Looking back on my first decade as a writer, I pulled together the biggest lessons I’ve learned along the way. I hesitate to call them rules, because my best writing comes when I have guardrails, not someone telling me what I can and can’t do. I’m also not the cleanest writer, so I’ve elected to avoid hard grammar advice. With that all being said, my writing advice ahead comes from a holistic lens.
How I Approach Writing
If you want to get good at writing, you have to commit to the process. Take it serious and aim to be the best you possibly can.
And take big swings. Aim your goals for the stars. If you fail, you’ll probably land somewhere like the moon—a much more advantageous position than if you only ever took small swings.
Read more: The #1 Lesson That Rewired How I Approach Work
One more key: Practice will give you a steady growth of confidence. The more reps the better. Then, someday far down the road, you might feel like you’ve picked up a few tips you’d like to pass on to others.
Imposter Syndrome Sticks Around
Although I’ve accomplished a ton in life up to this point, sometimes I feel like I’ve hardly done anything. I’ll get into a headspace that people will find out I’m a phony. That I’m not as much of a writer as I lead to believe. It becomes a whole doom loop situation.
Read more: 21 Ways to Live a Little More Each Day
That feeling is called Imposter Syndrome, and I’ve learned it never truly goes away. However, you can quiet those thoughts. Make those thoughts so small that you barely hear them.
In order to combat Imposter Syndrome, I’ve learned you have to just fight through it. Keep stacking work so you have tangible proof you are a writer. Bring it out as a reminder when you are feeling the negative forces trying to get to you. Find ways to change your defense into an offense.
Believe In 3. It’s a Magic Number.
Remember Schoolhouse Rock? That educational show with 70+ years of staying power? I can still recite songs from my elementary school years like “I’m Just a Bill” and “Interplanet Janet.” But the one that always stuck with me was “Three Is a Magic Number.”
Our brain loves the number three. It’s easy to remember, comes in clusters, and creates rhythm.
A shape is formed by three lines. All matter comes in states of solid, liquid, and gas. The Holy Trinity is made up of The Father, Son, and Holy Spirit. I could go on….
If I’m writing an intro to a Field Journal, I try to keep in three paragraphs. If I’m trying to convey an idea, or extract some sort of lesson—like what I attempted in my very first Substack post—I keep it to three points. In sentence lists, I never go beyond three names, brands, or products.
Your First Draft Isn’t Your Best
Sometimes you can get away with one-timers. But let’s be real, the first draft is never the best. The first draft is about getting thoughts to paper. Then, you step away to let it sit. Come back for a second draft. Let it sit. Come back for a third.
The irony of this rule is it’s usually is my third draft that turns out best.
However, I have had a handful of stories—especially during my magazine days—where I turned out quite literally five to eight drafts. This interview I did with Jimmy Chin a few years ago took me about seven drafts.
Read Your Writing Out Loud
This simple trick I learned from a longtime golf writer during my college internship at The Golf Channel. He told me if you want fast feedback, read your work out loud to yourself. Follow all the exact spellings, pauses, and punctuation marks of the writing you just created.
You’ll start to hear sentences that can use tightening, and catch misspelled words and small grammar mistakes.
Fun fact: The Golf Channel internship was in this huge facility outside of Orlando, Florida. They had a sweet TV studio (pictured above) we’d mess around in when the show hosts went home.
Weave Writing Into the Fabric of Your Day
Anywhere and everywhere you can. That means bring a Field Notes book with you. Keep one in your car. Another in your work bag.
Brett McKay, co-founder of Art of Manliness and Dying Breed wrote a great story on the art of microjournaling. It involves writing ideas and sayings into your phone’s Notes app. I’ve done a lot more microjournaling this year thanks to him.
Oh, and always have enough pens. Pilot G-2 pens, to be exact.
Write About What You Like
What do you actually like? What do you spend your free time doing? For most people, it’s a hobby, a sport, a movement. It’s 1,000 times easier to write about something you actually find interesting.
Think about it like this: If you’re interested in something, you’re either an expert or you’re on the path to becoming one. Soon enough, time accumulates and you’ve gathered enough information to start forming expert opinions.
When I first started writing in college, I created a music blog on WordPress called DropThree. I wanted to cover music similar to Pitchfork and Lyrical Lemonade. After college, I fell into writing about men’s style, which put me on the track of where I am today.
ABC—Always Be Cutting
When I was at Men’s Health, my editors would cut my drafts by about 50% on the first pass. Followed by more violent cutting on the second. Then third.
Why cut? I’m convinced our brains love to fill in the blanks. It likes to put together pieces around a story. Not get overloaded with every little detail. In fact, some of the best novels intentionally leave out details. That way our imagination can take over and we can fill in all the open parts with our own creative interpretations.
I’m in the camp of thought one should always be cutting. Strip it down. Distill it. Writing in it’s most condensed and tightest form is awesome. Can you tell I like Hemingway?
To Find Your Voice, Writing How You Talk
If you want to have an authentic voice to your writing, the best way to find it is to start by writing how you actually talk. It’s ok if there’s weird phrases or pauses, just as long as your words make sense.
From there, you can start playing with sentence-level formats like short, short, long. You can also try copywork if you want to take on an element of a writer’s voice you admire.
Read more: The Style Code of Cormac McCarthy
Copywork is the practice of handwriting passages from who you want to sound like. I’ve done copywork on writings from Bourdain and Hemingway in the past. The idea is that by writing down their words verbatim and by hand, you absorb their rhythm, sentence structure, and pacing.
Be Specific. Not General.
One year at a holiday part in West Village, my EIC at Men’s Health told me an awesome writing tip. He said you should write specific to what you actually experienced. Not write in general speak to try and capture a broad audience.
For example, if you write you hate late-night movies. Mention the time you went to see Megalopolis at 11pm and didn’t get out until 130am. If you say you love a good steakhouse, talk about how you love the strip steak at The Majestic in downtown Kansas City.
Another way for me to try to explain this point is: Specificity will help you, not hurt you.
Experiences Are a Fun Way to Write
The idea of feeling something in the real world and then bringing it to life on paper is a damn fun way to write. It also makes writing easy, because you’ve got the sights, sounds, and touch of what it was like visiting a new country or trying a new food.
LIVE A LITTLE is really driven by a whole lot of going out and experiencing the world.
However, the qualifier to this point is you don’t always have to rely on experience. For example, true crime writers don’t have to know what it’s like to k*ll someone to write a thrilling crime piece.
Robert Greene has mentioned how after he had a stroke, he learned how to write by transporting his mind to other places. He no longer was physically capably to travel on a whim like before. His writing is still really good.
Read Old Books, Magazines, and Advertisements
Make a hobby out of it too. That’s what I’ve done in collecting vintage men’s style magazines from GQ and Esquire.
Old school writing is pure gold. It gives inspiration. Gives real examples of great writing before the era of social media. All these old materials are the OG references creative directors and artists will refer to when drumming up new ideas.
One Exclamation Is Enough
I learned this tip from a senior editor early in my time at Men’s Health. Back then, I used to write with a lot of exclamation marks. When I handed him an important piece to edit, he came back to me stone-cold and said, “Enough with the exclamation marks.”
A lot of writers rely on exclamation marks to try and sound exciting and capture attention. But if you’re a believer in writing how you talk, do you really ever need to use more than one exclamation per story? Is adding an exclamation mark to multiple sentences in a paragraph that exciting?
You might be one of the few where exclamations are natural in your writing voice. I’ve met writers with that trait. But I’m not one of those writers, which is why this tip was a huge unlock in focusing on the content of my sentences to stoke interest—as opposed to slapping a “!” to drum up fake excitement.
Write Sooner in Life…and Earlier in the Day
Early bird gets the worm. Make hay while the sun shines. Time waits for no one. It’s all the same idea.
Kinda like how people regret investing at an earlier age, I regret not writing earlier in life. Both will compound exponentially.
Many days during the week, I regret not waking up earlier to give myself more time to write. The morning is core writing hours for me.
Once You Decide You’re a Writer, You’re a Writer
This idea comes from Stephen King’s half memoir and half masterclass, On Writing.
King explains there’s nobody out there that grants you the official title of “writer.” Instead, writing is an identity you can claim through action. By showing up. By getting the reps in.
Read more: The LIVE A LITTLE Origin Story
So if you want to be a writer, congratulations. You can become one today. Now the only way to get better is by reading and writing. A lot.
Just to Say It Again—Don’t Quit
Writing has given me a lot of opportunities in life, and my best explanation for why I’ve got to enjoy those fruits is based on the fact I haven’t quit.
Just know whatever goal or vision you have for your own writing is attainable. In fact, it’s oftentimes a lot closer than you realize.
LIVE A LITTLE
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This is good. Definitely worth a second look.
This article and a cup of coffee was just what I needed.