Talent, Motivation, and Serendipity: How to Make It as a Writer

Rob joins me on the podcast to talk about what it takes to become a writer, “public intellectual,” or however one wants to describe what we do. This conversation can serve as a guide for those who might try to follow a similar path. But even if you’re not going to be writing for a living, I think there’s still a lot you can get out of our talk, as it served as an opportunity for us to take a step back and reflect on our previous work — and really our lives — up to this point.

When we got to the topic of each of our writing processes, I came to realize that we have deep differences regarding how we get motivated, and our approach to life more generally. Rob says don’t romanticize the process, while my philosophy is that romanticizing everything is the key to joy and meaning. Writing is something he occasionally has to force himself to do, while I hate taking breaks and vacations, and wish family life didn’t pull me away from working even more. Rob of course is the psychologically normal one here, and which of us you decide to take advice from is going to depend on how exactly your mind works. Ironically, in the midst of our discussion about how we get ideas, I realized that I needed to at some point write an article on my romanticize everything philosophy. This is something I have thought about before but it’s been a while since I’ve reflected on it.

Other topics we cover include:

• How we describe our jobs to other people

• What it was like having one foot out the door of academia

• How we both sort of stumbled into our current positions

• The odds of actually making money at this

• How to build an audience

• The ways in which we use X

• Internet fame as a way for single young men to find girlfriends

• Avoiding audience capture

• Why we were both lucky to start our newsletters around the time that we did, rather than a few years later

• Dealing with book publishers and the prestige media

• Why journalists, academics, and independent writers all tend to share similar characteristics

• The ways in which various writers like Razib Khan, Scott Alexander, Freddie deBoer, and others have been able to make it on their own, and how their different backgrounds have contributed to their success

This ended up being one of the most inspiring conversations I’ve had in a while. It was fascinating to hear Rob’s story and invigorating to reflect on my own, and I felt a sense of overwhelming gratitude when considering just how much serendipity was needed for both of us to end up where we are.

Below, you can watch the video of our discussion or read the transcript, lightly edited for clarity.