The Pathless Path: Imagining a New Story For Work and Life

Paul Millerd

I have to admit a little bias here – I started my own journey only a few months ago, and a bunch of things that Paul Millerd has written about in The Pathless Path resonates very well and mimics the thoughts and paths that I have experienced recently. I also share some of his influences in terms of thinkers – Erich Fromm, David Graeber – both of who have had a lot to say about the human condition in the context of work.

The book is divided into two very broad sections. The first, with six chapters, focuses on the default path. The default is what most of the world does – predictable incomes, predictable lives, “life’s existential fears are traded for certainty”. Paul also quotes Keynes – “it is better for reputation to fail conventionally than to succeed unconventionally.” And it provides prestige, which as Paul Graham says, is “a powerful magnet that warps even your beliefs about what you enjoy.” However the story is cracking. “You work hard, but get laid off anyway. You have the perfect life on paper, but no time to enjoy it. You retire with millions in the bank, but no idea what to do with your time.”

He introduces us to his own journey from the default to the pathless across his academic and professional lives, how he figured out the hacks to grow fast, his health crisis, and how he then started thinking about his life and work differently.

At this point, he goes back in history to understand where our current beliefs and structure about work came from, how work took the space religion vacated, and how the larger narrative of defining and judging people by their profession became a part of culture. He then continues to take us through his own struggles in the default path as values clashed and the lure subsided, but the pressure of making a living continued. He stresses how moving to the pathless path is not a simple story of sudden glory, but rather a series of experiments, deliberate changes, and iterative learning towards a journey that fulfils the self.

In the second section – the pathless path, the focus is on how one can reimagine one’s life, and address the many barriers that a part of our self comes up with to discourage us – narratives around (lack of) money, creativity, to name the most common ones. He also notes the importance of finding one’s tribe, and designing work in such a way that you love it. His perspective is that ultimately what we want is to be useful to others. In the final chapter, he writes about a couple of things I have spent a lot of time thinking about – the abundance mindset, and playing the long game. Both have the potential to radically change the way one interacts with the world at large.

From what I understand, Paul went off the default in his 30s, so this is not a midlife crisis-management book. Rather, it’s for anyone who has that little ‘pebble in the shoe’ which tells them that there is a better way of living, and working. The pathless path is exactly that – it is deeply personal, a blueprint doesn’t really exist – you have to arrive at your version yourself. It’s uncomfortable, uncertain, and a movement away from conformity. But you’ll know when the shift happens, and when it does, it’s quite liberating. As per Andrew Taggart, crisis moments lead to “existential openings” which forces us to deal with existential questions. These could be of two kinds – a “way of loss” (loved ones, health job) or a “way of wonderment” (moments of undeniable awe and inspiration). But you don’t necessarily need to wait. It’s never too early, or late.

Notes
1. People who face crises often experience ‘post-traumatic’ growth and this manifests as “an appreciation for life in general, more meaningful interpersonal relationships, an increased sense of personal strength, changed priorities, and a richer existential and spiritual life”
2. “But under the hardness of that armor there is the tenderness of genuine sadness.” ~ Pema Chödrön
3. Uncertain discomfort < certain discomfort + coping mechanism. Given sufficient coping strategies, people will be willing to tolerate consistent levels of misery for long stretches of time.
4. Tim Ferriss “fear setting” reflection – what is the change, what are the worst possible outcomes, how can you mitigate them, possible steps/actions to get back to where you are now, what are the benefits, what are the costs of inaction 3/12/months few years
5. “Misery tax” – the spending an unhappy worker allocates to things that “keep you going and keep you functioning in the job”. e.g. alcohol, expensive food and vacations (Thomas J. Bevan)
6.”Belief clings, but faith lets go” ~ Alan Watts
7. There is a kind of status we get from doing impressive things or having impressive traits or skills. In some domains like sports, this works. In the business world, talent is harder to assess, and we tend to use proxies like credentials to determine quality and prestige.
8. “The problem is that our culture has engaged in a Faustian bargain in which we trade our genius and artistry for apparent stability” ~ Seth Godin
9. “Critical thinking without hope is cynicism. But hope without critical thinking is naïveté” ~ Krista Tippett

The Pathless Path

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