The Pathless Path: Imagining a New Story For Work and Life (The Pathless Path Collection Book 1)

by Paul Millerd

The philosopher Andrew Taggart believes that crisis moments lead to “existential openings” that force us to grapple with the deepest questions about life.16 He argues there are two typical ways this happens. One is the “way of loss,” when things that matter are taken from us, such as loved ones, our health, or a job. The other path is the “way of wonderment,” when we are faced with moments of undeniable awe and inspiration.

The researchers boldly concluded that if people could find work they saw as a calling it would improve their “life, health, and job satisfaction.”

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My final list included four items: health, relationships, fun & creativity, and career. Since 2013, this list pops up on my phone at 8:30 a.m. each morning. Staring at those four items, in that order, was scary. Without knowing it, I had embraced a question that would shape my decisions: “How do you design a life that doesn’t put work first?” The answer, my dear reader, is simple. You start underachieving at work. You stop setting an alarm and you cancel morning meetings because the energy gained is worth fighting for. You start working remotely on Fridays without asking because the extra 24 hours with your grandmother is worth it. You start taking naps at the office because there’s a nap room and someone has to use it, right?

Jerry Colonna, an investor turned executive coach, asks his clients this question, “How are you complicit in creating the conditions you say you don’t want?”

The one who wonders not only does not know, he is intimately sure that he does not know, and he understands himself as being in a position of not‑knowing. But this un‑knowing is not the kind that brings resignation. The one who wonders is one who sets out on a journey, and this journey goes along with the wonder: not only that he stops short for a moment, and is silent, but also that he persists in searching. – Joseph Pieper

The more experiments I’ve done, the more comfortable I have become, and this gives me more freedom to try new things without being afraid.

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Uncertain Discomfort < Certain Discomfort + Coping Mechanism

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Uncertain Discomfort + Wonder > Certain Discomfort

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One of the ideas that Seth Godin is known for is his suggestion that people on unconventional paths seek to “find the others.” These are the people who give us inspiration that doing things differently is possible and who might even join us on our journey.

Tim Ferriss’ “fear setting” reflection exercise helped me reframe them and see fear in a completely new way.74 The exercise has six steps. The first four are straightforward: Write down the change you are making. List the worst possible outcomes. Identify actions you could take to mitigate those outcomes. List some steps or actions you might take to get back to where you are today.

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The final two questions of Ferriss’ exercise are the most powerful: What could be some benefits of an attempt or partial success? What is the cost of inaction in three months, 12 months, and in a few years?

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