The Pathless Path

RECOMMENDED if you're a vaguely disaffected knowledge worker

The Pathless Path

Paul Millerd

Finished 15/08/22

There are books that you feel could've hit you hard if you'd found them at the right time, but they came too early, or too late. This one came just right for me. It's a book about a consultant who's questioning where he's at in his career after some health issues, finding that leaving his full-time job to do freelancing fixes some but not all of his issues, and rethinking what he wants and how it might change the way he approaches not just work but everything else. I've done roughly 2/3rds of that in a slightly different order, so I'm being pretty well laser-targeted to help me get the rest straight here.

The book's not a how-to guide, but rather a brief life-story sketch, and a series of provocations. It proceeds through author Paul Millerd's life, showing how he acquired, wrestled with, and is ultimately discarding the 'default' life script of continuous upward corporate progression and increasing consumption for one of a more curiosity-driven exploration. The default script, here, is one that seeks to trade the removal of some deep fears for a certainty of stability, progress and advancement—but at the cost of something profound within you. Embracing your uncertainty, breaking out of an (ultimately false) stability can, in Millerd's telling, lead to a different, better life.

There's a lot of talk about the way that you might get in your own way—you might be in thrall to the 'arrival fallacy'—that the next thing, the next promotion, the next whatever, that'll be when you'll be fine, you might be pursuing membership of CS Lewis' Inner Ring, you might be acting from fear due to a scarcity mindset around what work may come. It also covers how you might recognise your problem, and beyond the big-picture similarities I mentioned earlier a lot of the specific descriptions here resonated with me: other people perceiving my achievements differently to how I do, the feeling of being a passive participant in my own life, the pebble-in-the-shoe feeling of dissatisfaction.

The bottom line is that only intrinsic motivation lasts—so if you're feeling some kind of dissatisfaction about your job, you want to find work that aligns with you in a more fundamental way. Millerd's prescriptions are cautious and gradual in a way that I appreciated: question the default, think about where you are, do some experiments. That, for me, is the big takeaway—think about what you'd like to change in your life, then see if you can run some experiments on it. Move somewhere for a month and see how you find it, or try (as I'm going to, at some point in the near future) taking more frequent time off. Build a network, see what you can do that people want to give you money for, try doing it for them, try doing it for others. Find someone who's on a similar path you can Talk Real to about this. All of these are, to a greater or lesser extent, things I was already doing or thinking about in a somewhat inchoate way, but reading the book really helped put it all together, so now I'm thinking of it as a process.

I've been reading and listening to people talking on this kind of topic for years—when I was a teenager, years before I actually got the kind of job under discussion I was listening to Merlin Mann and Dan Benjamin on Back To Work, so I've been steeped in the Quit Your Job style of career re-evaluation for years. Consequently, I really liked Millerd's suggestions and his way of approaching things. It's somehow both vague and precise in a way that (stick with me here) almost reminds me of Marx: superb articulation of a problem and somewhat vaguer nods toward solutions because he's not necessarily in a position to provide more detail.

Your mileage may vary—if you're not a vaguely disaffected knowledge worker, I think there's a lot here that will not be entirely For You, but for me I found it a profoundly useful and clarifying read.