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by
Paul Millerd
As the world continues to change and technology reshapes our lives, the stories we use to navigate life become outdated and come up short.
You retire with millions in the bank, but no idea what to do with your time.
I've Read this multiple ti.es on the past but is this trulu a fact
John Maynard Keynes once pointed out, “that it is better for reputation to fail conventionally than to succeed unconventionally.”
The ease of having an ambition is that it can be explained to others; the very disease of ambition is that it can be so easily explained to others. – David Whyte
Paul Graham, the founder of a startup incubator and mentor to thousands of young people, sees this attention as a trap. In his view, prestige is “a powerful magnet that warps even your beliefs about what you enjoy.”
Zen philosopher Alan Watts argued that “the desire for security and the feeling of insecurity are the same thing,” and that “we look for this security by fortifying and enclosing ourselves in innumerable ways. We want the protection of being ‘exclusive’ and ‘special.’”
My unease quickly morphed into a desire to escape.
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.
It was clear to me in those moments that family,
love, and relationships were the most important things in the world.
missed this moment because of some silly emails? I
What was I living for? What did I really want? How did I want to look back on my life when it was my time to go?
In Weber’s view, a “traditionalist” view of work is one where people work as much as they need to maintain their current lifestyle, and once that aim is achieved, they stop working.
Sociologist André Gorz spent the latter half of the 20th century writing about the role of work in society.
He called these places “wage-based societies” where the central ethic was, “never mind what work you do, what counts is having a job.“
The ultimate way you and I get lucky is if you have some success early in life, you get to find out early it doesn’t mean anything. – David Foster Wallace
Changed jobs when I stopped learning.
Could this be the right decision in a career?
The word burnout was coined in the 1970s by Herbert Freudenberger, an American psychologist who studied workers in free health clinics.
“If work dominated your every moment, would life be worth living?” the philosopher Andrew Taggart offered a powerful question that spoke to the underlying tension I lived with for most of my adult life.
The idea of total work was inspired by the German philosopher Josef Pieper, who first wrote about it in his book Leisure, The Basis of Culture. Writing in Germany after World War II, Pieper was shocked at how people were eager to throw themselves into work without pausing to reflect on what kind of world they wanted to build.
To Pieper, leisure was above work. It was “a condition of the soul,” and the “disposition of receptive understanding, of contemplative beholding, and immersion – in the real.”57
Uncertain Discomfort < Certain Discomfort + Coping Mechanism
The professors argue that people rarely regret the things they do in their lives. This is exactly because of the power of our “ought to” selves – even if we fail, we tend to take immediate action to fix those mistakes.
Callard defines aspiration as the slow process of “trying on the values that we hope one day to possess.”69 This is in contrast to an ambitious journey where we already know what we value.
According to Callard, people on aspirational journeys, or what I call the pathless path, are “characteristically needy people.” Because their worldviews are incomplete and evolving, they are dependent on the support of other people.
In today’s world, we are lucky to have an abundance of people sharing their stories with us.
However, this kind of digital inspiration is often only helpful at the beginning of the journey. Ultimately, you need to find people who are open to a deeper friendship and willing to spend meaningful time together.
In a blog post titled, “Five Regrets of The Dying,” one of the most viewed online posts, she shared her reflections. The most common regret? Not staying “true to themselves” in their lives and focusing too much on what others expected of them.
That thing the nature of which is totally unknown to you is usually what you need to find, and finding it is a matter of getting lost.
more we associate experience with cash value, the more we think that money is what we need to live. And the more we associate money with life, the more we convince ourselves that we’re too poor to buy our freedom. – Rolf Potts
is nearly impossible to give up your time for money without thinking deeply about the trade-offs.97
In today’s world, he says, the most attention and respect goes to people with money, fame, degrees, and power.101
As author Ryan Holiday wrote, “You know deep down that accomplishing things won’t make you happy, but I think I always fantasized that it would at least feel really good. I was so wrong. Hitting #1 for the first time as an author felt like…nothing. Being a ‘millionaire’…nothing. It’s a trick of evolution that drives us, and no one is immune from making this mistake.”
This is what Harvard professor Dr. Ben‑Shahar calls the arrival fallacy, the idea that when we reach a certain milestone we will reach a state of lasting happiness.
Economist Adam Smith once wrote that people desire
“not only to be loved, but to be lovely.”107 As soon as I landed the job at McKinsey, I felt lovely, drunk on prestige.
writer Sarah Kendzior argues, places “money over merit, brand over skill.”109
Paul Graham, the investor and startup mentor, argues that far too many young people believe learning how to hack bad tests is a necessary part of success.
He shares a common back-and-forth he has with founders about the factors that lead to success:
The way you get lots of users is to make the product really great.
While the quality of your work was important, other tests like getting senior partners to like me, taking any work given to me, dressing the right way, and learning to speak in a certain way were much more important in getting promoted, getting a raise, and
continuing on an impressive career trajectory.
I agree with Graham when he says, “It used to be true. In the mid-20th century, when the economy
was composed of oligopolies, the only way to the top was by playing their game.”
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.
On the pathless path, knowing you have enough is what gives you the freedom to say “no” to clear financial opportunities and say “yes” to something that might bring you alive and might even pay off much more over the long term.
If we don’t define “enough,” we default to more, which makes it impossible to understand when to say no.
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
I understand people like him and their message. But for someone like me, for a small town, being in the system seems to be the only way. The older I get, maybe my confidence is disappearing. And that scares me.
American anthropologist Ernest Becker was convinced that most of our actions in life are driven by a fear of death.
Do I still worry about money? Yes. But now I’m hyper‑aware of how my financial insecurities might distract me from efforts that will help me stay
