When to write? Now How to write? However.
The best way to write is like the best plan for anything, the way you’ll stick with. Journaling or blogging. Public or private. Digital or fountain pen on Moleskin it doesn’t matter. Just write.
When Robert Caro wrote in college he did a lot of his work at the last minute. His work was fine, his feedback was fine, his process was fine - everything was just fine. At the end of the term he met with his instructor, Professor Blackmun. “At that final meeting, however, after first saying something generous about my writing, he added: ‘But you’re never going to achieve what you want to, Mr. Caro, if you don’t stop thinking with your fingers.’”
Caro’s last minute work was fine, not good or someday great. That admonishment stuck with him. That moment was the fork in the road Caro didn’t even notice. That exchange pointed the direction down a path that could lead to books like The Power Broker and Caro’s ongoing series on Lyndon Johnson.
Writing led Caro to a deeper understanding.
So how does someone do this? By starting small. Anne Lamont wrote that writing can seem like a vast undertaking but she tells her students to look at things through a one inch square. Caro does this too. How does someone cover Robert Moses, the man who built roads, parks, and other public works and the people who reaped the benefits and the people who wept the costs? Through one inch frames.
Then, if it’s something good you’ll rewrite it. ‘Writing’ gets all the attention but ‘rewriting’ is where the work happens. Mental juggling is hard. We’re better seeing things, on paper.
Dan Ariely said, "Because I find the logical flow so crucial to my writing, I always spend a lot of time upfront writing an outline. But, the problem is that when the outline is in my head, most of the details are abstract and sketchy, and when I actually sit down and write them out, I almost always have to reshuffle things and rewrite sections."
The best time to plant a tree was thirty years ago, the next best time to plan one is now. The same holds for writing, or any skill you’d like to build.