The Pathless Path: Imagining a New Story For Work and Life (The Pathless Path Collection Book 1)
Rate it:
Open Preview
4%
Flag icon
The pathless path is an alternative to the default path. It is an embrace of uncertainty and discomfort. It’s a call to adventure in a world that tells us to conform. For me, it’s also a gentle reminder to laugh when things feel out of control and trusting that an uncertain future is not a problem to be solved.
Catalina
.work .life
4%
Flag icon
most people, including myself, have a deep desire to work on things that matter to them and bring forth what is inside them. It is only when we cling to the logic of the default path that we fail to see the possibilities for making that happen.
Catalina
.personal-development .work
5%
Flag icon
We are convinced that the only way forward is the path we’ve been on or what we’ve seen people like us do. This is a silent conspiracy that constrains the possibilities of our lives.
Catalina
.personal-development
11%
Flag icon
This is the trap of prestigious career paths. Instead of thinking about what you want to do with your life, you default to the options most admired by your peers.
Catalina
.work
23%
Flag icon
beyond the headlines of dramatic life changes are almost always longer, slower, and more interesting journeys.
25%
Flag icon
“creative work runs on uncertainty; it runs on not knowing what you’re doing.”
30%
Flag icon
success for the company does not always align with what is best for the person, and over time, a disconnect can emerge.
Catalina
.work
33%
Flag icon
living in a world dominated by total work undermines the “playful contemplation concerned with our asking, pondering and answering the most basic questions of existence.”58 As I gained confidence on my new path, I was starting to be able to ask these questions and was open to the possibilities that were about to emerge.
Catalina
.work
36%
Flag icon
Many people dislike some parts of their jobs. But they stay in their jobs because their suffering is familiar. To change would be to trade the known for the unknown and change brings discomfort in hard to predict forms. So people avoid change and develop coping strategies.
Catalina
.work
50%
Flag icon
A person is successful if they have followed their own interests and talents to become the best they can be at what they care about most.
Catalina
.success .personal.development
52%
Flag icon
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.
Catalina
.personal-development .success
54%
Flag icon
I participate in an evolving “creator economy” ecosystem that has developed on Twitter, in private groups and online courses, and through real‑life meetups. One way to earn prestige in this world is to give generously and share everything you know.
Catalina
.creator.economy
55%
Flag icon
On the pathless path, powered by digital communities, we can surround ourselves with people that inspire us and push us to improve in the ways we care about.
Catalina
.digital.communities
56%
Flag icon
developing an appreciation for discomfort.
Catalina
.pathless.path
56%
Flag icon
The comfort we feel when we do what is expected keeps us from developing the skills we need to face uncertainty.
Catalina
.personal.development
60%
Flag icon
prescribed paths of the modern world can trap people into conforming to the expectations of others instead of taking steps to create their own unique path.
Catalina
.work
63%
Flag icon
No money is worth it if it undermines your desire to stay on the journey.
Catalina
.personal.monopoly
63%
Flag icon
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.
65%
Flag icon
Instead of looking to external cues to learn how to live, we need to have a coherent internal narrative about why we are living a certain way.
Catalina
.personal.development
68%
Flag icon
once you figure out who you intend to serve, you can go all‑in and focus on what it takes to become great.143 Thinking we have to serve a mass audience is default path thinking.
73%
Flag icon
“A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play.”
85%
Flag icon
Most of us run on autopilot through life but we can break out of this mode by considering even the simplest reflection exercises. For me creating a daily reminder of four priorities that mattered to me and revisiting the leadership principles I aspired to in grad school helped me see that the gap between what I claimed to care about and how I was living was larger than I wanted.