Thumbnail of I published my book, The Pathless Path, in January 2022. I expected to sell about 200-300 copies, maybe 1k if it was a home run. Somehow I've sold more than 40k 🤯

Here are the 30 most popular ideas people tell me they loved👇🧵

#1 The Default Path
A story that people judge their life against based on cultural and familial norms. Centered around 4-5 positive life events before one turns 40. Even if one's life does not follow this path, people will anchor around it and judge themselves against it.

#2 The Pathless Path
An alternative to the default path. Less of a script and more about learning to trust that uncertainty is not a problem to be solved - and also an "off-ramp" to a dominant default path energy that doesn't have many clear alternatives

#3 "Hoop Jumping"
An idea from @WDeresiewicz from his book Excellent Sheep where young people aim their lives at doing things not for the sake of themselves, but to check things off a list that might enable them to compete for other things - jobs, scholarships, grad schools

#4 The Inner Ring
The idea from CS Lewis that there is an inner ring that at one point in our lives we will inevitably be drawn toward. The problem with the inner ring, in Lewis' telling, is that once you are actually inside the entire pressure is to avoid being kicked out

#5 Accidental Meaning
A lot of the meaning previous generations generated by seemingly orienting around full-time corporate jobs was really a result of other circumstances - strong & growing economies, two-family households & cheaper housing (more: https://t.co/poGdMIcvEh)

#6 Work was not always central
In people's minds, work really wasn't seen as the prime aim of life. Or at least as people who wrote tell us. In ancient Greece, the translation for “work” was “not-at-leisure” placing more importance on leisure & active contemplation

#7 Leisure is active
If we travel back in time again, leisure before the 19th century did not really include passive activity like entertainment, television, etc... It was an active state, one that had more to do with how connected you were to the actions than not-working.

#8 Modern Protestant Ethic
The Protestant Work Ethic and its "calling" still has a strong influence on our current relationship to work. Statements like "work is life" and "use your gifts" are clear derivatives of Calvin & Luther (more: https://t.co/zucSNDYeEV)

#9 Meaningful Work Trap
Meaningful work is promised to potential employees of almost every company these days. Yet reaching this imagined blissful state of meaning by what companies are promising is unrealistic. It doesn't stop companies from trying (see 100+ company examples of culture PR: https://t.co/4I6pzbnOIZ)

#10 Aspiration
I've found  @AgnesCallard definition of "aspiration" a great companion for the pathless path. She argues we can't know which values we will acquire before we embark on an aspirational path. This is in contrast to the default path where money, positions, etc. are defined for us.

#11 Spirit of the Fool
One thing that keeps people back from doing new things is that they feel like a fool and retreat to the safe comfort of competence. George Leonard argues this "spirit of the fool" is unavoidable and I think impossible to fast-track on a creative path

#12 Prototyping life shifts
People falsely look at life as all-or-nothing leaps. This is because people tell the story this way and we seek evidence for it. We listen for what we want to hear. Yet if you dig deeper, most people prototype major changes in subtle, slow ways.

#13 Non-work intentional living experiments
My biggest growth & "ahas" have aligned with periods of extended non-work. Whether it is a week off worker mode or a one-month sabbatical - it is how I reconnect with who I am. They also have near 100% approval. See sabbaticals: https://t.co/CSiJNVJ2MC

#14 Wonder tips the scales
People hate change because of uncertain discomfort and will stay on paths with high levels of certain discomfort for a long time. The thing that reliably breaks this is developing a sense of wonder - or excitement about the future and possibilities

#15 Rethinking retirement
Retirement is a default destination & reward on the default path. It frames life as a financial calculation to be solved but undermines the search for things you actually enjoy doing. Take "mini-retirements now" & find what you like doing now

#16 Money & Life Energy
A way to reframe money is to think about the life energy that you are trading for it. If it is a fair trade, go for it. Also easier to assess when income goes down because you are forced into tradeoffs & you may uncover things you were deluded about.

#17 Having enough
The default path defaults to MORE and unless you've defined your own definition of enough, you accept that more money, more stuff, more everything is the natural way of being. Here's my definition

#18 Having faith
You can't solve uncertainty, you can only learn to live with it. Having faith that things will be okay is vital. Many people think unconventional paths are risky - but often they expose to people that they never had a relationship with uncertainty at all before.

#19 Positive Freedom
Erich Fromm argued that leaning into "positive freedom" was a new thing 1900s-on. And since it was so overwhelming, most people just wanted an easy out - opting into conformity & political movements instead. Still very hard! (a podcast I did on this with @nateliason and @TheRealNeilS: https://t.co/d3aoKn6sC3)

#20 2nd Chapter of success
Many of the happiest people don't avoid the default path - they graduate with a different set of metrics and aims in life. I call this the second chapter of success and it involves deep commitments to things you want to keep doing over the long term

#21 Find the others
The internet makes it such that you can "find the others" who do things like you and care about things like you. The reason to do this is not to fall into the "5 closest friends" nonsense, it is really just to make your life better by being around people you like

#22 Define your own prestige
Prestige is simply what we pay attention to. This is what we care about. With the internet, we can find new forms of prestige beyond money, status, positions, and fame. For example, we can gain prestige by sharing ideas. The more varieties the better

#23 Generosity as a practice
I've learned accidentally that generosity is extremely uncomfortable but can be learned. Giving to charities is not practicing generosity, it just fits into the norms of society. Gifts are uncomfortable because they create bonds. Give before it feels like you are ready. Giving can open you up to more possibility

#24 Who do you serve?
If you think my ideas are dumb, great! I'm not writing for you. Focus on the people that care about what you have to offer. People that get grumpy at what you are offering suck. Go find the people that give a damn and focus on them.

#25 Overcoming cynicism
It's easy to be cynical in today's world. I still fall into the trap. But the person that pays the tax for this is you. If you are trying to do something that requires creativity, cynicism is kryptonite. Aim at optimism and don't give up.

#26 Hustle traps
Instead of figuring out what you want, you aim at what other people are doing or at a script you think you should follow.

Eg. You still work 5 days a week even though you work for yourself. Why not 6 or 4?

See full essay: https://t.co/KA29sX3Vdt

#27 Real work of your life
We have a narrow definition of work as something that can be paid for and that typically exists in the form of a job. The real work is to find the things worth committing to. Then the only “job” is to design your life to continue to do those things.

#28 Escaping work is (usually) a trap
Most people don't want to escape work, they really just want a break from "worker mode." "financially independent" is a delusion in today's world because it just means relying on other workers. Coast FIRE is probably the best FIRE

#29 We want to be useful
Most people want to contribute. Even in nomad hubs where people could easily stop working forever, I find most people do things to help others, create, etc.. Realizing this can help you realize how important it is to search for the "real work"

#30 You don't have to "buy the culture"
From Tuesday's with Morrie - he says you don't have the buy the culture, you can create your own. Your life is what you make of it. The default path is one path that can work but is also high risk for many - leading to numbness and cynicism.

If you are still curious you should probably check out my book. People say it's awesome and I believe them: https://t.co/b4ARw5pFj9

Please repost if you made it this far. It's a form of digital generosity.Thumbnail of I published my book, The Pathless Path, in January 2022. I expected to sell about 200-300 copies, maybe 1k if it was a home run. Somehow I've sold more than 40k 🤯

Here are the 30 most popular ideas people tell me they loved👇🧵

#1 The Default Path
A story that people judge their life against based on cultural and familial norms. Centered around 4-5 positive life events before one turns 40. Even if one's life does not follow this path, people will anchor around it and judge themselves against it.

#2 The Pathless Path
An alternative to the default path. Less of a script and more about learning to trust that uncertainty is not a problem to be solved - and also an "off-ramp" to a dominant default path energy that doesn't have many clear alternatives

#3 "Hoop Jumping"
An idea from @WDeresiewicz from his book Excellent Sheep where young people aim their lives at doing things not for the sake of themselves, but to check things off a list that might enable them to compete for other things - jobs, scholarships, grad schools

#4 The Inner Ring
The idea from CS Lewis that there is an inner ring that at one point in our lives we will inevitably be drawn toward. The problem with the inner ring, in Lewis' telling, is that once you are actually inside the entire pressure is to avoid being kicked out

#5 Accidental Meaning
A lot of the meaning previous generations generated by seemingly orienting around full-time corporate jobs was really a result of other circumstances - strong & growing economies, two-family households & cheaper housing (more: https://t.co/poGdMIcvEh)

#6 Work was not always central
In people's minds, work really wasn't seen as the prime aim of life. Or at least as people who wrote tell us. In ancient Greece, the translation for “work” was “not-at-leisure” placing more importance on leisure & active contemplation

#7 Leisure is active
If we travel back in time again, leisure before the 19th century did not really include passive activity like entertainment, television, etc... It was an active state, one that had more to do with how connected you were to the actions than not-working.

#8 Modern Protestant Ethic
The Protestant Work Ethic and its "calling" still has a strong influence on our current relationship to work. Statements like "work is life" and "use your gifts" are clear derivatives of Calvin & Luther (more: https://t.co/zucSNDYeEV)

#9 Meaningful Work Trap
Meaningful work is promised to potential employees of almost every company these days. Yet reaching this imagined blissful state of meaning by what companies are promising is unrealistic. It doesn't stop companies from trying (see 100+ company examples of culture PR: https://t.co/4I6pzbnOIZ)

#10 Aspiration
I've found  @AgnesCallard definition of "aspiration" a great companion for the pathless path. She argues we can't know which values we will acquire before we embark on an aspirational path. This is in contrast to the default path where money, positions, etc. are defined for us.

#11 Spirit of the Fool
One thing that keeps people back from doing new things is that they feel like a fool and retreat to the safe comfort of competence. George Leonard argues this "spirit of the fool" is unavoidable and I think impossible to fast-track on a creative path

#12 Prototyping life shifts
People falsely look at life as all-or-nothing leaps. This is because people tell the story this way and we seek evidence for it. We listen for what we want to hear. Yet if you dig deeper, most people prototype major changes in subtle, slow ways.

#13 Non-work intentional living experiments
My biggest growth & "ahas" have aligned with periods of extended non-work. Whether it is a week off worker mode or a one-month sabbatical - it is how I reconnect with who I am. They also have near 100% approval. See sabbaticals: https://t.co/CSiJNVJ2MC

#14 Wonder tips the scales
People hate change because of uncertain discomfort and will stay on paths with high levels of certain discomfort for a long time. The thing that reliably breaks this is developing a sense of wonder - or excitement about the future and possibilities

#15 Rethinking retirement
Retirement is a default destination & reward on the default path. It frames life as a financial calculation to be solved but undermines the search for things you actually enjoy doing. Take "mini-retirements now" & find what you like doing now

#16 Money & Life Energy
A way to reframe money is to think about the life energy that you are trading for it. If it is a fair trade, go for it. Also easier to assess when income goes down because you are forced into tradeoffs & you may uncover things you were deluded about.

#17 Having enough
The default path defaults to MORE and unless you've defined your own definition of enough, you accept that more money, more stuff, more everything is the natural way of being. Here's my definition

#18 Having faith
You can't solve uncertainty, you can only learn to live with it. Having faith that things will be okay is vital. Many people think unconventional paths are risky - but often they expose to people that they never had a relationship with uncertainty at all before.

#19 Positive Freedom
Erich Fromm argued that leaning into "positive freedom" was a new thing 1900s-on. And since it was so overwhelming, most people just wanted an easy out - opting into conformity & political movements instead. Still very hard! (a podcast I did on this with @nateliason and @TheRealNeilS: https://t.co/d3aoKn6sC3)

#20 2nd Chapter of success
Many of the happiest people don't avoid the default path - they graduate with a different set of metrics and aims in life. I call this the second chapter of success and it involves deep commitments to things you want to keep doing over the long term

#21 Find the others
The internet makes it such that you can "find the others" who do things like you and care about things like you. The reason to do this is not to fall into the "5 closest friends" nonsense, it is really just to make your life better by being around people you like

#22 Define your own prestige
Prestige is simply what we pay attention to. This is what we care about. With the internet, we can find new forms of prestige beyond money, status, positions, and fame. For example, we can gain prestige by sharing ideas. The more varieties the better

#23 Generosity as a practice
I've learned accidentally that generosity is extremely uncomfortable but can be learned. Giving to charities is not practicing generosity, it just fits into the norms of society. Gifts are uncomfortable because they create bonds. Give before it feels like you are ready. Giving can open you up to more possibility

#24 Who do you serve?
If you think my ideas are dumb, great! I'm not writing for you. Focus on the people that care about what you have to offer. People that get grumpy at what you are offering suck. Go find the people that give a damn and focus on them.

#25 Overcoming cynicism
It's easy to be cynical in today's world. I still fall into the trap. But the person that pays the tax for this is you. If you are trying to do something that requires creativity, cynicism is kryptonite. Aim at optimism and don't give up.

#26 Hustle traps
Instead of figuring out what you want, you aim at what other people are doing or at a script you think you should follow.

Eg. You still work 5 days a week even though you work for yourself. Why not 6 or 4?

See full essay: https://t.co/KA29sX3Vdt

#27 Real work of your life
We have a narrow definition of work as something that can be paid for and that typically exists in the form of a job. The real work is to find the things worth committing to. Then the only “job” is to design your life to continue to do those things.

#28 Escaping work is (usually) a trap
Most people don't want to escape work, they really just want a break from "worker mode." "financially independent" is a delusion in today's world because it just means relying on other workers. Coast FIRE is probably the best FIRE

#29 We want to be useful
Most people want to contribute. Even in nomad hubs where people could easily stop working forever, I find most people do things to help others, create, etc.. Realizing this can help you realize how important it is to search for the "real work"

#30 You don't have to "buy the culture"
From Tuesday's with Morrie - he says you don't have the buy the culture, you can create your own. Your life is what you make of it. The default path is one path that can work but is also high risk for many - leading to numbness and cynicism.

If you are still curious you should probably check out my book. People say it's awesome and I believe them: https://t.co/b4ARw5pFj9

Please repost if you made it this far. It's a form of digital generosity.Thumbnail of I published my book, The Pathless Path, in January 2022. I expected to sell about 200-300 copies, maybe 1k if it was a home run. Somehow I've sold more than 40k 🤯

Here are the 30 most popular ideas people tell me they loved👇🧵

#1 The Default Path
A story that people judge their life against based on cultural and familial norms. Centered around 4-5 positive life events before one turns 40. Even if one's life does not follow this path, people will anchor around it and judge themselves against it.

#2 The Pathless Path
An alternative to the default path. Less of a script and more about learning to trust that uncertainty is not a problem to be solved - and also an "off-ramp" to a dominant default path energy that doesn't have many clear alternatives

#3 "Hoop Jumping"
An idea from @WDeresiewicz from his book Excellent Sheep where young people aim their lives at doing things not for the sake of themselves, but to check things off a list that might enable them to compete for other things - jobs, scholarships, grad schools

#4 The Inner Ring
The idea from CS Lewis that there is an inner ring that at one point in our lives we will inevitably be drawn toward. The problem with the inner ring, in Lewis' telling, is that once you are actually inside the entire pressure is to avoid being kicked out

#5 Accidental Meaning
A lot of the meaning previous generations generated by seemingly orienting around full-time corporate jobs was really a result of other circumstances - strong & growing economies, two-family households & cheaper housing (more: https://t.co/poGdMIcvEh)

#6 Work was not always central
In people's minds, work really wasn't seen as the prime aim of life. Or at least as people who wrote tell us. In ancient Greece, the translation for “work” was “not-at-leisure” placing more importance on leisure & active contemplation

#7 Leisure is active
If we travel back in time again, leisure before the 19th century did not really include passive activity like entertainment, television, etc... It was an active state, one that had more to do with how connected you were to the actions than not-working.

#8 Modern Protestant Ethic
The Protestant Work Ethic and its "calling" still has a strong influence on our current relationship to work. Statements like "work is life" and "use your gifts" are clear derivatives of Calvin & Luther (more: https://t.co/zucSNDYeEV)

#9 Meaningful Work Trap
Meaningful work is promised to potential employees of almost every company these days. Yet reaching this imagined blissful state of meaning by what companies are promising is unrealistic. It doesn't stop companies from trying (see 100+ company examples of culture PR: https://t.co/4I6pzbnOIZ)

#10 Aspiration
I've found  @AgnesCallard definition of "aspiration" a great companion for the pathless path. She argues we can't know which values we will acquire before we embark on an aspirational path. This is in contrast to the default path where money, positions, etc. are defined for us.

#11 Spirit of the Fool
One thing that keeps people back from doing new things is that they feel like a fool and retreat to the safe comfort of competence. George Leonard argues this "spirit of the fool" is unavoidable and I think impossible to fast-track on a creative path

#12 Prototyping life shifts
People falsely look at life as all-or-nothing leaps. This is because people tell the story this way and we seek evidence for it. We listen for what we want to hear. Yet if you dig deeper, most people prototype major changes in subtle, slow ways.

#13 Non-work intentional living experiments
My biggest growth & "ahas" have aligned with periods of extended non-work. Whether it is a week off worker mode or a one-month sabbatical - it is how I reconnect with who I am. They also have near 100% approval. See sabbaticals: https://t.co/CSiJNVJ2MC

#14 Wonder tips the scales
People hate change because of uncertain discomfort and will stay on paths with high levels of certain discomfort for a long time. The thing that reliably breaks this is developing a sense of wonder - or excitement about the future and possibilities

#15 Rethinking retirement
Retirement is a default destination & reward on the default path. It frames life as a financial calculation to be solved but undermines the search for things you actually enjoy doing. Take "mini-retirements now" & find what you like doing now

#16 Money & Life Energy
A way to reframe money is to think about the life energy that you are trading for it. If it is a fair trade, go for it. Also easier to assess when income goes down because you are forced into tradeoffs & you may uncover things you were deluded about.

#17 Having enough
The default path defaults to MORE and unless you've defined your own definition of enough, you accept that more money, more stuff, more everything is the natural way of being. Here's my definition

#18 Having faith
You can't solve uncertainty, you can only learn to live with it. Having faith that things will be okay is vital. Many people think unconventional paths are risky - but often they expose to people that they never had a relationship with uncertainty at all before.

#19 Positive Freedom
Erich Fromm argued that leaning into "positive freedom" was a new thing 1900s-on. And since it was so overwhelming, most people just wanted an easy out - opting into conformity & political movements instead. Still very hard! (a podcast I did on this with @nateliason and @TheRealNeilS: https://t.co/d3aoKn6sC3)

#20 2nd Chapter of success
Many of the happiest people don't avoid the default path - they graduate with a different set of metrics and aims in life. I call this the second chapter of success and it involves deep commitments to things you want to keep doing over the long term

#21 Find the others
The internet makes it such that you can "find the others" who do things like you and care about things like you. The reason to do this is not to fall into the "5 closest friends" nonsense, it is really just to make your life better by being around people you like

#22 Define your own prestige
Prestige is simply what we pay attention to. This is what we care about. With the internet, we can find new forms of prestige beyond money, status, positions, and fame. For example, we can gain prestige by sharing ideas. The more varieties the better

#23 Generosity as a practice
I've learned accidentally that generosity is extremely uncomfortable but can be learned. Giving to charities is not practicing generosity, it just fits into the norms of society. Gifts are uncomfortable because they create bonds. Give before it feels like you are ready. Giving can open you up to more possibility

#24 Who do you serve?
If you think my ideas are dumb, great! I'm not writing for you. Focus on the people that care about what you have to offer. People that get grumpy at what you are offering suck. Go find the people that give a damn and focus on them.

#25 Overcoming cynicism
It's easy to be cynical in today's world. I still fall into the trap. But the person that pays the tax for this is you. If you are trying to do something that requires creativity, cynicism is kryptonite. Aim at optimism and don't give up.

#26 Hustle traps
Instead of figuring out what you want, you aim at what other people are doing or at a script you think you should follow.

Eg. You still work 5 days a week even though you work for yourself. Why not 6 or 4?

See full essay: https://t.co/KA29sX3Vdt

#27 Real work of your life
We have a narrow definition of work as something that can be paid for and that typically exists in the form of a job. The real work is to find the things worth committing to. Then the only “job” is to design your life to continue to do those things.

#28 Escaping work is (usually) a trap
Most people don't want to escape work, they really just want a break from "worker mode." "financially independent" is a delusion in today's world because it just means relying on other workers. Coast FIRE is probably the best FIRE

#29 We want to be useful
Most people want to contribute. Even in nomad hubs where people could easily stop working forever, I find most people do things to help others, create, etc.. Realizing this can help you realize how important it is to search for the "real work"

#30 You don't have to "buy the culture"
From Tuesday's with Morrie - he says you don't have the buy the culture, you can create your own. Your life is what you make of it. The default path is one path that can work but is also high risk for many - leading to numbness and cynicism.

If you are still curious you should probably check out my book. People say it's awesome and I believe them: https://t.co/b4ARw5pFj9

Please repost if you made it this far. It's a form of digital generosity.Thumbnail of I published my book, The Pathless Path, in January 2022. I expected to sell about 200-300 copies, maybe 1k if it was a home run. Somehow I've sold more than 40k 🤯

Here are the 30 most popular ideas people tell me they loved👇🧵

#1 The Default Path
A story that people judge their life against based on cultural and familial norms. Centered around 4-5 positive life events before one turns 40. Even if one's life does not follow this path, people will anchor around it and judge themselves against it.

#2 The Pathless Path
An alternative to the default path. Less of a script and more about learning to trust that uncertainty is not a problem to be solved - and also an "off-ramp" to a dominant default path energy that doesn't have many clear alternatives

#3 "Hoop Jumping"
An idea from @WDeresiewicz from his book Excellent Sheep where young people aim their lives at doing things not for the sake of themselves, but to check things off a list that might enable them to compete for other things - jobs, scholarships, grad schools

#4 The Inner Ring
The idea from CS Lewis that there is an inner ring that at one point in our lives we will inevitably be drawn toward. The problem with the inner ring, in Lewis' telling, is that once you are actually inside the entire pressure is to avoid being kicked out

#5 Accidental Meaning
A lot of the meaning previous generations generated by seemingly orienting around full-time corporate jobs was really a result of other circumstances - strong & growing economies, two-family households & cheaper housing (more: https://t.co/poGdMIcvEh)

#6 Work was not always central
In people's minds, work really wasn't seen as the prime aim of life. Or at least as people who wrote tell us. In ancient Greece, the translation for “work” was “not-at-leisure” placing more importance on leisure & active contemplation

#7 Leisure is active
If we travel back in time again, leisure before the 19th century did not really include passive activity like entertainment, television, etc... It was an active state, one that had more to do with how connected you were to the actions than not-working.

#8 Modern Protestant Ethic
The Protestant Work Ethic and its "calling" still has a strong influence on our current relationship to work. Statements like "work is life" and "use your gifts" are clear derivatives of Calvin & Luther (more: https://t.co/zucSNDYeEV)

#9 Meaningful Work Trap
Meaningful work is promised to potential employees of almost every company these days. Yet reaching this imagined blissful state of meaning by what companies are promising is unrealistic. It doesn't stop companies from trying (see 100+ company examples of culture PR: https://t.co/4I6pzbnOIZ)

#10 Aspiration
I've found  @AgnesCallard definition of "aspiration" a great companion for the pathless path. She argues we can't know which values we will acquire before we embark on an aspirational path. This is in contrast to the default path where money, positions, etc. are defined for us.

#11 Spirit of the Fool
One thing that keeps people back from doing new things is that they feel like a fool and retreat to the safe comfort of competence. George Leonard argues this "spirit of the fool" is unavoidable and I think impossible to fast-track on a creative path

#12 Prototyping life shifts
People falsely look at life as all-or-nothing leaps. This is because people tell the story this way and we seek evidence for it. We listen for what we want to hear. Yet if you dig deeper, most people prototype major changes in subtle, slow ways.

#13 Non-work intentional living experiments
My biggest growth & "ahas" have aligned with periods of extended non-work. Whether it is a week off worker mode or a one-month sabbatical - it is how I reconnect with who I am. They also have near 100% approval. See sabbaticals: https://t.co/CSiJNVJ2MC

#14 Wonder tips the scales
People hate change because of uncertain discomfort and will stay on paths with high levels of certain discomfort for a long time. The thing that reliably breaks this is developing a sense of wonder - or excitement about the future and possibilities

#15 Rethinking retirement
Retirement is a default destination & reward on the default path. It frames life as a financial calculation to be solved but undermines the search for things you actually enjoy doing. Take "mini-retirements now" & find what you like doing now

#16 Money & Life Energy
A way to reframe money is to think about the life energy that you are trading for it. If it is a fair trade, go for it. Also easier to assess when income goes down because you are forced into tradeoffs & you may uncover things you were deluded about.

#17 Having enough
The default path defaults to MORE and unless you've defined your own definition of enough, you accept that more money, more stuff, more everything is the natural way of being. Here's my definition

#18 Having faith
You can't solve uncertainty, you can only learn to live with it. Having faith that things will be okay is vital. Many people think unconventional paths are risky - but often they expose to people that they never had a relationship with uncertainty at all before.

#19 Positive Freedom
Erich Fromm argued that leaning into "positive freedom" was a new thing 1900s-on. And since it was so overwhelming, most people just wanted an easy out - opting into conformity & political movements instead. Still very hard! (a podcast I did on this with @nateliason and @TheRealNeilS: https://t.co/d3aoKn6sC3)

#20 2nd Chapter of success
Many of the happiest people don't avoid the default path - they graduate with a different set of metrics and aims in life. I call this the second chapter of success and it involves deep commitments to things you want to keep doing over the long term

#21 Find the others
The internet makes it such that you can "find the others" who do things like you and care about things like you. The reason to do this is not to fall into the "5 closest friends" nonsense, it is really just to make your life better by being around people you like

#22 Define your own prestige
Prestige is simply what we pay attention to. This is what we care about. With the internet, we can find new forms of prestige beyond money, status, positions, and fame. For example, we can gain prestige by sharing ideas. The more varieties the better

#23 Generosity as a practice
I've learned accidentally that generosity is extremely uncomfortable but can be learned. Giving to charities is not practicing generosity, it just fits into the norms of society. Gifts are uncomfortable because they create bonds. Give before it feels like you are ready. Giving can open you up to more possibility

#24 Who do you serve?
If you think my ideas are dumb, great! I'm not writing for you. Focus on the people that care about what you have to offer. People that get grumpy at what you are offering suck. Go find the people that give a damn and focus on them.

#25 Overcoming cynicism
It's easy to be cynical in today's world. I still fall into the trap. But the person that pays the tax for this is you. If you are trying to do something that requires creativity, cynicism is kryptonite. Aim at optimism and don't give up.

#26 Hustle traps
Instead of figuring out what you want, you aim at what other people are doing or at a script you think you should follow.

Eg. You still work 5 days a week even though you work for yourself. Why not 6 or 4?

See full essay: https://t.co/KA29sX3Vdt

#27 Real work of your life
We have a narrow definition of work as something that can be paid for and that typically exists in the form of a job. The real work is to find the things worth committing to. Then the only “job” is to design your life to continue to do those things.

#28 Escaping work is (usually) a trap
Most people don't want to escape work, they really just want a break from "worker mode." "financially independent" is a delusion in today's world because it just means relying on other workers. Coast FIRE is probably the best FIRE

#29 We want to be useful
Most people want to contribute. Even in nomad hubs where people could easily stop working forever, I find most people do things to help others, create, etc.. Realizing this can help you realize how important it is to search for the "real work"

#30 You don't have to "buy the culture"
From Tuesday's with Morrie - he says you don't have the buy the culture, you can create your own. Your life is what you make of it. The default path is one path that can work but is also high risk for many - leading to numbness and cynicism.

If you are still curious you should probably check out my book. People say it's awesome and I believe them: https://t.co/b4ARw5pFj9

Please repost if you made it this far. It's a form of digital generosity.
I published my book, The Pathless Path, in January 2022. I expected to sell about 200-300 copies, maybe 1k if it was a home run. Somehow I've sold more than 40k 🤯 Here are the 30 most popular ideas people tell me they loved👇🧵 #1 The Default Path A story that people judge their life against based on cultural and familial norms. Centered around 4-5 positive life events before one turns 40. Even if one's life does not follow this path, people will anchor around it and judge themselves against it. #2 The Pathless Path An alternative to the default path. Less of a script and more about learning to trust that uncertainty is not a problem to be solved - and also an "off-ramp" to a dominant default path energy that doesn't have many clear alternatives #3 "Hoop Jumping" An idea from @WDeresiewicz from his book Excellent Sheep where young people aim their lives at doing things not for the sake of themselves, but to check things off a list that might enable them to compete for other things - jobs, scholarships, grad schools #4 The Inner Ring The idea from CS Lewis that there is an inner ring that at one point in our lives we will inevitably be drawn toward. The problem with the inner ring, in Lewis' telling, is that once you are actually inside the entire pressure is to avoid being kicked out #5 Accidental Meaning A lot of the meaning previous generations generated by seemingly orienting around full-time corporate jobs was really a result of other circumstances - strong & growing economies, two-family households & cheaper housing (more: https://t.co/poGdMIcvEh) #6 Work was not always central In people's minds, work really wasn't seen as the prime aim of life. Or at least as people who wrote tell us. In ancient Greece, the translation for “work” was “not-at-leisure” placing more importance on leisure & active contemplation #7 Leisure is active If we travel back in time again, leisure before the 19th century did not really include passive activity like entertainment, television, etc... It was an active state, one that had more to do with how connected you were to the actions than not-working. #8 Modern Protestant Ethic The Protestant Work Ethic and its "calling" still has a strong influence on our current relationship to work. Statements like "work is life" and "use your gifts" are clear derivatives of Calvin & Luther (more: https://t.co/zucSNDYeEV) #9 Meaningful Work Trap Meaningful work is promised to potential employees of almost every company these days. Yet reaching this imagined blissful state of meaning by what companies are promising is unrealistic. It doesn't stop companies from trying (see 100+ company examples of culture PR: https://t.co/4I6pzbnOIZ) #10 Aspiration I've found @AgnesCallard definition of "aspiration" a great companion for the pathless path. She argues we can't know which values we will acquire before we embark on an aspirational path. This is in contrast to the default path where money, positions, etc. are defined for us. #11 Spirit of the Fool One thing that keeps people back from doing new things is that they feel like a fool and retreat to the safe comfort of competence. George Leonard argues this "spirit of the fool" is unavoidable and I think impossible to fast-track on a creative path #12 Prototyping life shifts People falsely look at life as all-or-nothing leaps. This is because people tell the story this way and we seek evidence for it. We listen for what we want to hear. Yet if you dig deeper, most people prototype major changes in subtle, slow ways. #13 Non-work intentional living experiments My biggest growth & "ahas" have aligned with periods of extended non-work. Whether it is a week off worker mode or a one-month sabbatical - it is how I reconnect with who I am. They also have near 100% approval. See sabbaticals: https://t.co/CSiJNVJ2MC #14 Wonder tips the scales People hate change because of uncertain discomfort and will stay on paths with high levels of certain discomfort for a long time. The thing that reliably breaks this is developing a sense of wonder - or excitement about the future and possibilities #15 Rethinking retirement Retirement is a default destination & reward on the default path. It frames life as a financial calculation to be solved but undermines the search for things you actually enjoy doing. Take "mini-retirements now" & find what you like doing now #16 Money & Life Energy A way to reframe money is to think about the life energy that you are trading for it. If it is a fair trade, go for it. Also easier to assess when income goes down because you are forced into tradeoffs & you may uncover things you were deluded about. #17 Having enough The default path defaults to MORE and unless you've defined your own definition of enough, you accept that more money, more stuff, more everything is the natural way of being. Here's my definition #18 Having faith You can't solve uncertainty, you can only learn to live with it. Having faith that things will be okay is vital. Many people think unconventional paths are risky - but often they expose to people that they never had a relationship with uncertainty at all before. #19 Positive Freedom Erich Fromm argued that leaning into "positive freedom" was a new thing 1900s-on. And since it was so overwhelming, most people just wanted an easy out - opting into conformity & political movements instead. Still very hard! (a podcast I did on this with @nateliason and @TheRealNeilS: https://t.co/d3aoKn6sC3) #20 2nd Chapter of success Many of the happiest people don't avoid the default path - they graduate with a different set of metrics and aims in life. I call this the second chapter of success and it involves deep commitments to things you want to keep doing over the long term #21 Find the others The internet makes it such that you can "find the others" who do things like you and care about things like you. The reason to do this is not to fall into the "5 closest friends" nonsense, it is really just to make your life better by being around people you like #22 Define your own prestige Prestige is simply what we pay attention to. This is what we care about. With the internet, we can find new forms of prestige beyond money, status, positions, and fame. For example, we can gain prestige by sharing ideas. The more varieties the better #23 Generosity as a practice I've learned accidentally that generosity is extremely uncomfortable but can be learned. Giving to charities is not practicing generosity, it just fits into the norms of society. Gifts are uncomfortable because they create bonds. Give before it feels like you are ready. Giving can open you up to more possibility #24 Who do you serve? If you think my ideas are dumb, great! I'm not writing for you. Focus on the people that care about what you have to offer. People that get grumpy at what you are offering suck. Go find the people that give a damn and focus on them. #25 Overcoming cynicism It's easy to be cynical in today's world. I still fall into the trap. But the person that pays the tax for this is you. If you are trying to do something that requires creativity, cynicism is kryptonite. Aim at optimism and don't give up. #26 Hustle traps Instead of figuring out what you want, you aim at what other people are doing or at a script you think you should follow. Eg. You still work 5 days a week even though you work for yourself. Why not 6 or 4? See full essay: https://t.co/KA29sX3Vdt #27 Real work of your life We have a narrow definition of work as something that can be paid for and that typically exists in the form of a job. The real work is to find the things worth committing to. Then the only “job” is to design your life to continue to do those things. #28 Escaping work is (usually) a trap Most people don't want to escape work, they really just want a break from "worker mode." "financially independent" is a delusion in today's world because it just means relying on other workers. Coast FIRE is probably the best FIRE #29 We want to be useful Most people want to contribute. Even in nomad hubs where people could easily stop working forever, I find most people do things to help others, create, etc.. Realizing this can help you realize how important it is to search for the "real work" #30 You don't have to "buy the culture" From Tuesday's with Morrie - he says you don't have the buy the culture, you can create your own. Your life is what you make of it. The default path is one path that can work but is also high risk for many - leading to numbness and cynicism. If you are still curious you should probably check out my book. People say it's awesome and I believe them: https://t.co/b4ARw5pFj9 Please repost if you made it this far. It's a form of digital generosity.

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