The Pathless Path: Imagining a New Story For Work and Life (The Pathless Path Collection Book 1)
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On the default path, you are automatically a “good egg.” On the pathless path, people default to seeing you as a “bad egg.”
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Embracing a new identity can be a useful way to enter the uncertain world of the pathless path. At a minimum, it gives you an answer when people inevitably start asking about your plans. However, many people quickly realize that they’ve created the same conditions that they sought to escape. Luckily,
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We can weaken the impact of these kinds of questions by knowing that there is no way to avoid being seen as a “bad egg.” The only way forward is to eventually get to a point when you realize that, in fact, there are no good eggs or bad eggs at all.
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Are you helping people? Are they happy? Are you happy? Are you profitable? Isn’t that enough? – Derek Sivers
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She was incredibly productive, but for her, it was not enough.126
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Enough is knowing that no amount in my bank account will ever satisfy my deepest fears. It’s knowing that I have enough friends that would gladly open their door and share a meal if I was ever in need. It’s the feeling that I’ve been able to spend my time over an extended stretch of time working on projects that are meaningful to me, helping people with a spirit of generosity, and having enough space and time in my life to stay energized to keep doing this over the long‑term. Enough is seeing a clear opportunity that will increase my earnings in the short‑term, but knowing that saying “no” ...more
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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
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The researchers concluded that when we feel we lack something, we tend to obsess over it.
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Becker argues that the only way to transcend these existential fears is to live a life that feels heroic. He argues that “if everyone honestly admitted his urge to be a hero it would be a devastating release of truth.”129
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I’ve been inspired by the poet David Whyte’s way of interpreting the world, which he calls the “conversational nature of reality.” He believes all of us have an ongoing “conversation” with the world.
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What matters? Why do we work? What is the “good life”? What holds people back from change? How do we find work that brings us alive?
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but when I learned to be guided by my curiosity and pay attention, I started noticing that answers would spontaneously emerge as a byproduct of living my life.
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Introspection means talking to yourself, and one of the best ways of talking to yourself is by talking to another person. One other person you can trust, one other person to whom you can unfold your soul.
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We are always falling in love or quarreling, looking for jobs or fearing to lose them, getting ill and recovering, following public affairs. If we let ourselves, we shall always be waiting for some distraction or other to end before we can really get down to our work. The only people who achieve much are those who want knowledge so badly that they seek it while the conditions are still unfavorable. Favorable conditions never come. – C.S. Lewis
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He shifted his approach towards building a business that he wanted to be “stuck with” and revisited an idea that he had sidelined:
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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. This is one of the most important secrets of the pathless path. With this approach, it doesn’t make sense to chase any financial opportunity if you can’t be sure that you will like the work. What does make sense is experimenting with different kinds of work, and once you find something worth doing, working backward to build a life around being able to keep doing it.
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Finding work you want to keep doing, says author Stephen Cope, is “the great work of your life.”
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If you bring forth what is within you, what you bring forth will save you. If you do not bring forth what is within you, what you do not bring forth will destroy you.
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He researched the lives of Susan B. Anthony, Robert Frost, John Keats, Harriet Tubman, and Henry David Thoreau and found that the common trait they shared was seriously attempting to bring forth what was inside of them. This didn’t come easy to any of them and they all faced challenges, rejection, and criticism. Yet at every key point in their lives, they either kept looking for what brought them alive or protected their time so that they could work on what mattered.
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Where does the impulse to find a comfortable job, no matter the personal cost, come from? I think it is partly due to our narrow conception of work as only a full‑time job with a salary and benefits. Like Cope, however, I have embraced a broader conception of work and agree with him that the search for work worth doing is the real work and one of the most important pursuits in life.
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While money is important on the pathless path, using it as a filter for finding the work worth doing, especially at first, is a mistake.
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people pay attention to a slightly different emotion, guilt. She defines guilt as “holding something we’ve done or failed to do up against our values and feeling psychological discomfort.”
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“humans don’t mind hardship, in fact, they thrive on it; what they mind is not feeling necessary.”140 Junger argues that “modern society has perfected the art of making people not feel necessary.”
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Here’s the truth you have to wrestle with: the reason that art (writing, engaging, leading, all of it) is valuable is precisely why I can’t tell you how to do it. If there were a map, there’d be no art, because art is the act of navigating without a map. Don’t you hate that? I love that there’s no map. – Seth Godin
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“The world just gave you control over the means of production. Not to master them is a sin.”142
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But eventually, I realized I wasn’t writing for them. I was writing for people like me:
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any time I consume something from an individual that inspires me, I have to send them a note to let them know. Creating and sharing in public takes an incredible amount of courage and I remember how awkward and scared I was at the beginning of my journey. It’s easy to tell people what they got wrong but much harder to say “I love what you are doing. I hope you keep going and let me know if I can help.”
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This doesn’t mean you need to build an audience or a business, but what might emerge if you dare to share your writing, painting, dancing, crafts, or other acts of creativity with others? What friends might you meet? What opportunities could you pursue? What communities could you join?
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You can start small or do something in your local community. Host a dinner party in your city or town, start a book club, share a poem or essay you’ve written with a couple of close friends, or even join a local art class.
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I am successful on my own terms. Because if your success is not on your own terms, if it looks good to the world but does not feel good in your heart, it is not success at all. – Anna Quindlen
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Instead of thinking about what I want to do and how I want to live, I start instead with what I don’t want to be doing and what failure looks like.
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For example, instead of asking what makes up an amazing life, we first define the worst‑case scenario and then work backward. What does a miserable life entail? What actions would make achieving such a life more likely? Then figure out how you can avoid these things from becoming true.
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In the paycheck world, there used to be a saying: dress for the job you want, not the job you have. The analogous idea in the free agent world is: learn to exercise the freedoms you might acquire, not just the freedoms you have. – Venkatesh Rao
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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.
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how to keep from going through your comfortable, prosperous, respectable adult life dead, unconscious, a slave to your head and to your natural default setting of being uniquely, completely, imperially alone day in and day out.156
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you might also find a mode of being that opens you up to a deeper relationship with the world and yourself. In this way, the creative act is one of the most sacred things in the world and should be taken seriously in itself and not with any expected outcome.
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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.
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When we think about the future, we tend to underestimate how much things will change, especially for ourselves. Researchers call this the “end of history illusion.”
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Nothing has helped me improve this skill more than living in other countries. People often ask me how to prepare for living abroad. My response? You can’t, and when you leave the place you know, you will inevitably face challenges. From forgetting my passport on the other side of Italy to a stray dog biting me in Taiwan and a parasite infection in Mexico, I’ve dealt with scary uncertainty head-on.
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Until the 1600s when clocks became ubiquitous, people rarely thought about time. English historian E.P. Thompson noted that instead, people thought in terms of activities. In Madagascar, a half-hour was a “rice cooking,” and a brief moment was “frying a locust.” When they had clocks, people increasingly thought about time as something related to money. Thompson noted that “time is now currency, it is not passed but spent.”
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