Highlights from The Pathless Path by Paul Millerd
Highlights from this book
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If there are clear boundaries to behavior within a given field of endeavor, then there is also great freedom to adapt and imagine within those lines. These boundaries, however, should always be tested to see if they are actually still real. It takes conscious acts by individuals to test these edges. – David Whyte
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I returned to my office and sat at my desk, staring blankly at my screen. If you had told me when I was building that spreadsheet of dream jobs during college that not only would I work for several of those companies, but also directly with some of the most famous CEOs in the world, I would have been shocked. But I also would have thought that was exactly what I wanted. As I sat there, I didn’t know how to want it anymore.
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The offices of the senior partners, still mostly men, were located along the building’s outside walls. Decades after the offices had been built, their positions and sizes were still clear markers of importance. My small office was a step up from the cubicles, but I was still years away from having a real office. I always appreciated the clarity of these distinctions. So many companies seem afraid to make these power dynamics visible, disguising them behind open offices and casual dress codes.
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However, some fear‑related problems cannot be solved. The authors of Designing Your Life offer a helpful reframe, calling these issues “gravity problems” which are part of life “…but, like gravity, it’s not a problem that can be solved.”
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That thing the nature of which is totally unknown to you is usually what you need to find, and finding it is a matter of getting lost.
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In his book, On Liberty, published in 1859, John Stuart Mill was giving similar advice, arguing that societies need people to embrace their individuality and perform “experiments in living.” He argued that such experiments are vital to the pursuit of knowledge and that cultures only learn and evolve when original approaches to living are discovered. Mill wanted people to act on their inspiration because “the worth of different modes of life should be proved practically when anyone thinks fit to try them.”91 By choosing a unique and personal fixed point, in Mill’s view, you are not only raising the odds of finding a path worth staying on, but you are also serving an important role in pushing culture forward.
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The secret to doing good research is always to be a little underemployed. You waste years by not being able to waste hours. — Amos Tversky
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Many people I talk to are convinced that the formula for living on their own terms is saving up enough money. I wish they knew what I know: the longer we spend on a path that isn’t ours, the longer it takes to move towards a path that is. Money might help pay for therapy, time off, and healing retreats, but it won’t help you come to a place where you really trust and know that everything will be okay.
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Yet this is the world we live in. This means embracing the pathless path requires grappling with the feeling of being a “bad egg.” This often drives people who leave the default path to eagerly embrace new identities that are still recognizable as legible to the “traditional” economy. They gravitate to titles like a startup founder, entrepreneur, freelance consultant, or even the newly emerging “creator.”
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Instead of optimizing for a future “exit,” or a sale of the company, he built a company he wanted to keep working at and all his decisions continue to be based on this goal. As his platform grew, corporations started asking the company to do customized installations for them. John decided he didn’t want to deal with these high‑maintenance customers and turned them down. Despite this obvious opportunity, Ghost still does not employ a single employee that works with enterprise customers. John learned the same lesson I had in taking the client that had drained my energy. No money is worth it if it undermines your desire to stay on the journey.
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On the pathless path, the goal is not to find a job, make money, build a business, or achieve any other metric. It’s to actively and consciously search for the work that you want to keep doing.
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Brene Brown’s clarification of shame and guilt helped me understand what’s really going on when we struggle to pay attention to our intuitions and desires. She defines shame as “the intensely painful feeling or experience of believing that we are flawed and therefore unworthy of love and belonging.” She believes that most people give too much power to this emotion when making life choices.”
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Over the last 100 years, the number of ways you can engage with life has exploded beyond imagination. Now, not only political leaders offer narratives for interacting with the world, but also employers, companies, media outlets, and other institutions. Everyone gives you roadmaps for living life and becoming free. You just have to buy their products, embrace their story, or join their company, and instead of having to develop your own agency, the respective institution will make you part of their special group.
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Ultimately, figuring out what to do with freedom once we have it is one of the biggest challenges of the pathless path. Writer Simon Sarris argues that we can only do this by increasing our capacity for agency, or our ability to take deliberate action in the world. He argues, “the secret of the world is that it is a very malleable place, we must be sure that people learn this, and never forget the order: Learning is naturally the consequence of doing.”158 In other words, only by taking action do we learn and only by learning do we discover what we want. Without this, we will struggle to take advantage of the freedom that the pathless path offers.