Tim Ferriss and the Titans (2): On Planning, Journaling, and Note-Taking

This is the second part of a four-part series on Titans, by Tim Ferriss. Other parts are listed below:

3. Planning

You can’t build anything without a plan. Even simple projects require a sequence. First … Second … Third …

Every plan begins with the category. Every writer needs to ask: What’s the genre? The audience? The style? The level of intellect? The attitude? Real success come from owning a particular category.

Consider Bill Simmons (one of my former students, at Holy Cross College), who broke all the rules of inside-dopester sportswriting when he started a blog called The Sports Guy. Rather than hanging out in press boxes and locker rooms, Simmons covered sports from the viewpoint of a passionate and knowledgeable fan. He blended all kinds of pop culture — movies, music, politics, fashion, TV, you name it — into his long posts about the Celtics or the DH rule. If Simmons had taken the usual sports scribe track, he would have been invisible. Instead, he stood out. He owned the category of crazy fan commentator.

There are lots of other examples. Who owns the category of theory-fueled stories with a theme? Malcolm Gladwell. Who owns the world of wizardry? J.K. Rowling. How about economics turned on its head? Stephen Dubner and Steven Levitt. Histories involving murders or attempted murders? Bill O’Reilly. Love and romance amid luxury? Danielle Steel. One more. Who owns legal thrillers? John Grisham. Other authors make a nice living as No. 2 or 3 or 4 or more. But to own a category is to be set for life. More important, it’s to have a real purpose.

Kaskade, one of the founders of Progressive House music, uses the metaphor of putting stones in the bucket. If you put sand before stones, you might not get everything into the bucket. Make sure to put in the big stones first, then smaller stones that can fill the gaps between those bigger stones, and then finally the sand, which fills in the open spaces between the stones.

The legendary chess wizard Josh Waitzkin, the subject of the movie Searching for Bobby Fisher, adapts advice from the ancient Greeks: Start with the end in mind. To master any challenge, don’t start with the simple fundamentals. Instead, jump to the end game. The challenge is to understand the dynamics of the game. Waitzkin’s chess teacher taught him by showing the endgames—say, a king and a pawn against a king. What do you do with that?

At every level of your writing—sentence, paragraph, section, and whole piece—know how you are starting and finishing. It’s like taking a journey. You’re most likely to know the journey’s route and steps if you know the starting and ending point. If you don’t, you’re likely to wander all over the place.

You need to start somewhere, right? So Cheryl Strayed, the author of Wild, offers a set of prompts. She suggests using them to write two pages, without interruption by your inner perfectionist, to draw the creativity out of your repressed self. Here are a few of them:

  • Write about a time that you realized you were mistaken.
  • Write about a lesson you learned the hard way.
  • Write about something you lost that you’ll never get back.
  • Write about a memory of a physical injury.
  • Write about why you could not do it.

That should get you going. Now you’re about to encounter the greatest challenge of all creative—keeping your eye on the ball.

4. Journaling and note-taking

Lots of titans keep journals—first to pause and focus their thoughts, second to capture the countless thoughts that occur throughout the day.

Mike Bibiglia, a comedian, says: “Write everything down because it’s all very fleeting.” Capturing ideas during the day is the difference between good and great. “What I find, the older I get, is that a lot of people are good, and a lot of people are smart, and a lot of people are clever. But not a lot of people give you their soul when they perform.” Your soul emerges all day, in your thought and feelings; you give it form when you take the pieces and sort the wheat from the chaff.

Brian Koppelman, a screenwriter, novelist, and creator of the hit show Billions, follows the routine that Julie Cameron suggests in The Artist’s Way. “It’s three longhand pages where you just keep the pen moving for three pages, no matter what. No censoring, no rereading. It’s the closest thing to magic I’ve come across. If you really do it every day and a real disciplined practice, something happens to your subconscious that allows you to get to your most creative place.”

He says he’s given the book to 200 people. Of those, maybe 10 of them have done the exercises. “Of those 10, seven have had books, movies, TV shows, and made out successful. It’s incredible. That book changed my life, even though it’s very spiritual and I’m an atheist.”

Tim Ferriss keeps a five-minute journal to center his mind. The journal is really just filling in the blanks:

  • I am grateful for 1. –––––––––. 2. –––––––––. 3. –––––––––.
  • What would make today great? 1. –––––––––. 2. –––––––––. 3. –––––––––.
  • Daily affirmations. I am 1. –––––––––. 2. –––––––––. 3. –––––––––.

He concludes at night with:

  • Three amazing things that happened today: 1. –––––––––. 2. –––––––––. 3. –––––––––.
  • How could I have made today better? 1. –––––––––. 2. –––––––––. 3. –––––––––.

B.J. Novak uses a Moleskine Cahier notebook for jotting notes during the day. Because it’s thinner than the standard Moleskine, it’s easy to carry.

What to do once you’ve filled a notebook?

Every midnight, Robert Rodriguez types notes about the day into a Word document. Any time he wants to recover a forgotten insight—or just review his thoughts over time—he can search his Word files. (I do something similar: I outline books that I consider challenging. Surprisingly, it doesn’t take long. I can take notes on a 300-page book in about an hour. The process helps me understand the book for the first time—to make it my own—and then leaves a trail of great ideas to use later.)

James Altucher, a serial entrepreneur and bestselling author, creates lists for everything that might spawn a creative project. A few examples:

  • 10 old ideas I can make new
  • 10 books I can write
  • 10 business ideas for Google/Amazon/Twitter/etc.
  • 10 industries where I can remove the middleman
  • 10 things I disagree with that everyone else assumes is religion

What if you can’t meet these goals? I mean, 10 ideas? Really?

“Here’s the magic trick,” Altucher says. “If you can’t come up with 10 ideas, come up with 20 ideas. … You’re putting too much pressure on yourself. Perfectionism is the enemy of the idea muscle. … It’s your brain trying to protect you from harm, from coming up with an idea that is embarrassing and stupid and could cause you to suffer pain. The way you shut this off is by forcing the brain to come up with bad ideas.

“Suppose you have written down five ideas for books and they are all pretty good. And now you’re stuck… Well, let’s come up with some bad ideas. Here’s one: Dorothy and the Wizard of Wall Street. Dorothy is in a hurricane in Kansas and she lands right at the corner of Broadway and Wall Street and she has to find the Wizard of Wall Street. To get home to Kansas, he offers her a job to be a high-frequency trader.”

That’s bad, all right.

Once he comes up with his 10 (or 20) good and bad ideas, Altucher lists the first steps he would take to realize each one. “Remember,” he says, “only the first step. Because you have no idea where that first step will take you.”

Reid Hoffman of LinkedIn writes things down to prime his subconscious.

“What are the kinds of key things that might be constraints on the solution, or might be the attributes of the solution, and what are the tools or assets I might have?” he says. “I actually think that most of our thinking is subconscious. Part of what I’m trying to do is allow the fact that we have this kind of relaxation, rejuvenation period in sleeping, to essentially possibly bubble up the thoughts and solutions to it.”

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