Notes on One Year of Writing Coaching (28/30)

I'm writing 30 posts in 30 days. This is number 28.

The other day, Paul Millerd asked me to write down my philosophy of coaching. While this is a lovely request, I don't think I'm ready to do that kind of bloviating just yet. I've only been at it for a year, and I still obviously have much to learn. There’s no ‘philosophy’ as such.

On the other hand, it's been a good year: my income is such that I could survive on coaching alone if I chose to, I've achieved results like these, and I have a waitlist going. So my intuitions are probably not all worthless.

Here are some of those intuitions.

It's Not Therapy, But It's Not Not Therapy

Among other things, a good therapist is a provider of a curated outside view. You've got a skewed perspective on your life by default, and your therapist offers an alternate one. Coaching, as a profession, points out that this is not only useful in the domains of trauma and marital strife. Generally, we have blind spots, and coaches can point them out instantly, which can be massively helpful.

As well, given the interconnectedness of experience, coaching in one area can often improve your overall existence in hard-to-predict ways. For example, performance coaching with this guy improved my emotional life along with my work life. (Freeing up extra time can lead to a life better-lived, more meaningful relationships, and so on.)

Good Coaches Get Obsessed With People

In the beginning of my ‘career’, I tried to have a fixed curriculum and approach. Then, this idea collided with reality and exploded. Tactics that were effective with one person weren't with the next, communication habits that delighted one person annoyed the next, and so on.

Now, I consider rapid befriending part of my job: I want to learn as much as possible about every visible element of every person I work with, to the extent that it's not weird to do so. The job goes a lot better when you learn that person A wants emoji-laden encouragement messages at random times, but person B needs to be left alone except for structured conversations. This requires individual sensitivity and flexibility. And, while I have opinions about writing that are fairly durable, my ways of communicating them vary dramatically from call to call.

This also places a nice neat upper bound on the number of clients I take on: I stop if getting obsessed with another person would rupture my brain.

There Are Important Things About Writing Education That Don't Scale

When I was learning piano, it wasn't really about me, so much. I practiced scales, learned canonical beginners' pieces, and so on. While I put emotion into my playing, I wasn't skilled enough to do anything approximating personal artistry. This is the domain of the experts: people like Gould and Richter can do idiosyncratic things only after being totally in command of their instrument.

Writing is the opposite. It's personal artistry all the way down. Great writers, on the page, are totally themselves—they're just gussied-up versions of themselves. Becoming a better writer is, fundamentally, about tapping into what you are, and learning how best to verbally channel your peculiarities.

This requires focused, discriminating attention to all of your personal mental weirdness, and how it manifests linguistically. That's really hard to get from group learning, or a general curriculum, and only a few geniuses can manage to self-administer. (I needed help, myself.) Writing groups can be fantastic for accountability and feedback, but some amount of one-on-one mentorship is maybe indispensable in the long-run, if you really want results. Some evidence of this: I've had a few clients come to me after getting unsatisfactory results from writing programs, including MFAs from fancy schools.

Two Reasons Good Coaches Charge So Much

I work with my average client for about 10-12 hours in total, between calls, asynchronous communication, note-taking, editing, and other random stuff that happens. I charge a lot of money for 10-12 hours of ‘work’, if you're looking at ‘work’ as a general thing. But it's not a general thing. If you happen to click with my personal style—if I'm the collaborator who will work best with you—I'm not fungible. There's no competing product.

As well, I attempt to deliver categorical change, as good coaches generally do. What I'm after is a permanent improvement of expressive ability. And that's usually what happens. But what you do with categorical change is up to you. If, after coming to me, you write four novels you wouldn't have otherwise, then I should've charged you way more money, $1500 is a stupidly good deal. But, on the other hand, you might choose to work with me and then do nothing with what you've learned, in which case $1500 was a lot to pay for some individual attention. It’s difficult to price something that’s so variable in worth. As a client recently put it, the potential upside of working with me is infinity, but half of infinity is still infinity.