7 Lessons from a Six-Figure Writer
The best one is “know how to be stupid”

It’s already tomorrow in Australia. Maybe that’s why Tim Denning can see the future.
When Tim came on the scene, I thought he was a hack. I never read his work, much less attempted to talk to the guy. That was a mistake. Tim is a good thinker, a good writer, and a good person. He also happens to have made $300,000 writing.
He and I have been chatting a lot these days. Thanks to the time difference, Tim comes into the call fresh off a workout and full of energy. I’m often blinking away the afternoon lull and wondering if my wine is chilled yet. Still, I’m learning.
Here’s what I’m picking up.
When You Make a Lot, People Want Your Money
Sales guys, marketing guys, lawyers, accountants, web designers, regular designers, course creators, and personal brands all come to Tim regularly to strike up a revenue-sharing deal. Guess whose revenue they want to share? Hint: It isn’t theirs.
When you are successful, everyone wants a piece of you. With every new relationship, Tim has to wonder if a person wants to work with him or wants his money. It’s a little sad. Be aware of this if you want wealth.
The More You Write, the More You Make
Quantity is not the only way to make money as a writer. It is a very good way, though. Quality is subjective. You have to guess at what people write. Tim taught me that typically the best way to grow your audience is to write as well as you can as often as you can.
Tim writes like a freak of nature: Two whole days per week, he locks himself away and creates five to eight blog posts. He often writes 20,000 words in a single day. This is longer than some books. This process has led to a new blog post every day for five years. So around 2,000 blog posts.
Do you have to write this way? No. I can’t. I am too romantic about the process. My routine is a little less rigid, but I’m writing a lot every day.
The more you write, the better you get. The better you get, the more you make. Don’t get precious about this. If volume writing is good enough for Lousia May Alcott, it’s good enough for you.
You Don’t Have to Be Artistic to Be a Writer
Writing can be an art form, but it is also a means of expressing yourself.
Writing is as basic a human function as speaking. Better, you can take the time to arrange your thoughts and words to form an argument. An argument is not a fight. It’s simply an analysis of something you believe.
Tim recently wrote a piece about Warren Buffet’s comments on how the definition of money is changing. This is not something an artist would ever write about (or care about).
Don’t think you have to know a billion vocabulary words or be schooled in literature to write something interesting. Write about what you care about. Learn to do it in a way that makes other people care.
Know How to Be Stupid
Tim has a superpower. Whenever you tell him something he doesn’t know, he says: “I don’t know anything about that.”
This enables him to get answers without even trying. Because people are always trying to impress him (remember, they want his money), they will tell Tim all they know. Soaking in all this information allows Tim to reach a superhuman level of knowledge and insight. He could never reach this level if he pretended to know everything.
Put down your ego and ask questions. That’s the whole point of meeting new people in the first place.
The Further You Spread, the More Chance You Will Be Misunderstood
Although Tim isn’t an A-list celebrity, he’s starting to experience some of the same effects.
It’s easy to feel like you “know” celebrities. In reality, your impressions come from a headshot, a quick bio, and whatever you infer from that person’s choice of work projects or interviews.
This is a consequence of becoming a public figure of any level. The wider you spread, the more tempting it is for people to poke holes in the person they think you are. You can never make everyone understand you, but you do your best work despite the hate.
A Creative Partnership Is Always Fluid
“The smallest indivisible human unit is two people, not one.”
— Tony Kushner
Your identity changes depending on who you are with. You probably don’t slam Red Bulls and curse around your grandparents, and you probably don’t chat about the stock market with your five-year-old nephew.
When Tim and I started working together, we both had a vague idea of what tasks each of us would take. That went out the window when we started building. He writes. I edit. He’s serious. I make jokes. He cares, and I help him express that care. He has a ton of knowledge. I ask questions to bring that information to mind.
Don’t be stiff about the person you assume you are. Learn, grow, talk, and most importantly — figure out how you can serve the people you work with.
Empathy Is a Good Business Strategy
Tim makes well above the average writer on Medium because each time he sits down to write, he asks this question: “What is good for Medium’s business model?”
The rest of us are getting hung up on what we want to write. Tim knows that the best strategy for getting a cut of any business is to grow that business.
Selfishness can only get you so far. With any venture, set your own desires aside. They should take a backseat to the broader goals of whomever you are working with or for.
A final thought. When in doubt, give.
During my very first conversation with Tim, I told him the exact amount of money I had in the bank, down to the dime. (Trust me, he wasn’t impressed.) But he was generous and transparent in his advice.
There are plenty of ways to make money, and as a banker, Tim knows them all. Still, he chooses to wake up and write. He takes notes on what he sees and shares them with the world.
Writing with an open heart is the best strategy there is.






