How I got started writing

May 12, 2022 · living

Given how important books and writing have become to my career, I was surprised to remember that I didn’t begin writing (at all) until ~12 years ago, when I was 26 years old and 3 years into startups. 

My first book (which has done well enough) was started when I was only 2 years into writing.

Here’s how I got started in that first year or two:

1 // Each morning, I’d write a messy, stream-of-consciousness braindump of whatever was top of mind, just for myself. This took 5-10 minutes and was hugely helpful with overcoming the fear of the blank page, as well as getting into the habit of closing the distractions and sitting down to write. (Sitting down to do it is the hardest part.)

2 // I committed to publishing 3 blog posts per week for 3 months (~36 posts, although I ended up continuing till 200 since I was having fun and learning plenty). To avoid discouraging myself, I refused to check the analytics for those early months. This helped build the sharing muscle, and  perhaps more crucially, it taught me the lesson that writing effort != writing impact. (The important bit is what the reader gets out of it, not what you put into it.)

3 // Meanwhile, I also began teaching/mentoring the topics about which I was writing (first unofficially, and eventually with a price tag as I got better at it), which taught me that most lessons don’t stick, that most ideas aren’t actionable, that most advice is infotainment, and that good education requires testing and iteration.

With those foundations in place, the idea of writing a useful book didn’t seem like such a crazy leap. 

4 // For the books in particular, I also needed to clear my calendar for a week or two to get the manuscript started. That felt easiest while on vacation, where I was away from my normal daily rhythms, obligations, and distractions. After that first pile of words was down on paper, it was just a matter of shaping them into something I could start giving to readers for feedback. And if you just keep doing that, you eventually end up with a book that people (mostly) like.

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