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

by Paul Millerd

channeled this sentiment in a letter to his son, telling him, “If it is right, it happens—The main thing is not to hurry. Nothing good gets away.”

I had few possessions, was releasing my grip on the future, and was opening myself up to the unknown. I spent these days shifting back and forth between the dizziness of feeling lost and the certainty that I was exactly where I was supposed to be.

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

“What is your rich life?” The purpose of this question is to stop you from looking at money as an accountant and looking at it as something that might help you live your ideal life. Over time, I’ve found a clear answer: having ownership of my time enriches my life.

No amount of money can buy the peace of mind that comes with finding a path that you want to stay on.

“money is something we choose to trade our life energy for,” it is nearly impossible to give up your time for money without thinking deeply about the trade-offs.97

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.

In today’s world, he says, the most attention and respect goes to people with money, fame, degrees, and power.

Many people realize they are on the wrong path after achieving impressive milestones.

It was incredibly painful for me to realize that if I truly cared about living in a different way, I might need to leave the business world. The journey towards the pathless path often starts at this moment, with a willingness to investigate your

disappointment and to wonder if there is a better way of defining success.

The better way is what I call the “second chapter of success” in which you shift your mindset from what you lack to what you have to offer, from ambition to aspiration, and from hoping that joy will result from a specific outcome to experiencing it as a byproduct of your journey. People are reluctant to flip the page to the second chapter of success because it requires...

recognition from other people who are passionate about ideas.

then the pathless path is the natural story for a digital‑native world in which nothing can stop us from finding others who share our desires, ideas, and questions.

Even if it was never spoken, when I left the default path I felt as if I had immediately crossed an imaginary boundary where I was some sort of rebel that needed to defend my recklessness.

The pathless path is about ignoring the pull of needing to be a “good egg” and learning what truly enables you to thrive. What this really means is developing an appreciation for discomfort. Howard Gray, a consultant and storyteller, and veteran of the pathless path, sees the uncertainty of his path as a positive thing. When his life “stops moving and it calcifies or solidifies, that’s a bad

But the “bad eggs’’ on the pathless path eventually realize there is wisdom in being lost. This doesn’t mean it will be easy. Like Billups, you will sense that you are doing something wrong, or at minimum, don’t know what you are doing. Simple questions from others like “what do

you do?” will expose your own uncertainty and can feel like a death blow to the soul. 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. The pathless path is about releasing yourself from this way of seeing the world and realizing that the number of career paths worth following is infinite.

Enough is the antithesis of unchecked growth because growth encourages mindless consumption and enough requires constant questioning and awareness. Enough is when we reach the upper bound of what’s required. Enough revenue means our business is profitable and can support however many employees/freelancers we have, even if it’s just one person. Enough income means we can live our lives with a bit of financial ease,

and put something away for later. Enough means our families are fed, have roofs over their heads and their futures are considered. Enough stuff means we have what we need to live our lives without excess.125

The researchers concluded that when we feel we lack something, we tend to obsess over it.

One of the best ways to discover your conversation is to start asking questions driven by your curiosity. For me, some of my favorite questions include: 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?

Being at the frontier of your current reality is disorienting. Deep down you might have a sense that you should keep going in a certain direction, but you never know why.

The work that I want to keep doing is writing, sharing stories, helping people, and doing other experiments online.

Guilt drives many people to work, and this is a normal reaction to this uncomfortable emotion. Most people want to contribute, help, and engage with the world. However, sometimes this impulse gets hacked by our shame and we follow paths that aren’t ours because we feel like the world’s love depends on us doing a certain thing. We are afraid that if we step away or make a change, we might be cast out of our family or community. This is one of life’s most terrifying feelings and keeps many from making changes.

Despite many people thinking that their ideal life would be living out the rest of their life on a beach, when given the option of following that path, few people take it.

Many people struggle to start making a living from their creative endeavors because they are still operating within the logic of the default path. On the default path, you have to get the job before you can do the work. On the pathless path, you simply do the work first and then decide if you want to continue.

This is valid. It’s scary to share with the world, and if you do it over a long enough period, criticism is inevitable. At first, however, most people run into a different challenge: not having an audience at all. This can be a good thing because it enables you to experiment while building up your confidence slowly.

While the article makes a valid point about the challenges of making money, it ignores that someone might create something for the sake of it or as a way to learn, connect and feel alive rather than trying to get ahead or get paid.

Tyler Cowen has argued that one of “the most valuable things you can do with your time and with your life” is to believe in people.144 Being a recipient of this encouragement has inspired me to create a rule for myself: 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.”

Creativity by nature is an act of boldness and rebellion. – Robert Greene

why I want to urge you to consider sharing with the world. You care. You want to do things in good faith. You want to help people, to listen, and connect with others who share your passions.

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?

As I read the comments, I realized many people around the world see courage in creation and sharing, and these are the people I now write for.

But I am not nuts. I am happy. 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

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. In his post-World War II writing, Fromm demonstrated that, surprisingly, the urge to conform in this way was most powerful not in Communist societies, but in the West.

Wallace’s point is that doing what almost everyone else is doing is the natural thing in life. If we are serious about other approaches, it will take work.

In his book The Art of Loving, he argued that the root of a positive version of freedom is a deep sense of connectedness with the world. A path to achieve this state was through “creative activity.”

you might also find a mode of being that opens you up to a deeper relationship with the world and yourself.

I’ve become more capable of proactively embracing change, but I’d be lying if I said I am excited about every new shift in my environment, schedule, and work. Nonetheless, I’ve come to see reinvention as one of the most valuable meta‑skills worth developing, and on the other side of these experiments, I am often much more relaxed and confident than before.

more people invent new paths and enter new environments, communities, and online worlds, many will be forced out of their comfort zone. The sooner this happens the better because the era of

living your entire life in a small, local, and familiar community is over. Whether we want to or not, we’ll have to keep reinventing ourselves.

Find ways to give without expectation of anything in return.

HomeAway, a site where hosts offer free lodging and food in exchange for work, typically no more than 4-5 hours per day, in places like farms, restaurants, and hotels. She had found a place that would host her for a couple of months and she was pretty excited about it.

Coming alive over getting ahead.

traded lots of dreams for a bigger paycheck, and I never even realized I was doing it.”

Tuesdays with Morrie,

And he was eminently upbeat and positive and still looking to his dying day to the – to the positivity of people and the goodness of people. And I thought if he could do that in a chair where he can’t move…then certainly with health and so many blessings, I can certainly be optimistic and try to be inspiring to people, too.

Create your own culture.