Short summary: The Pathless Path
Paul Millerd is an author, consultant and thinker specialising in career, work and life design. With a background in strategy consulting and a passion for exploring alternative career paths, he has compiled his experiences and insights in his book "The Pathless Path".
"The Pathless Path" is more than just a book about work; it is a philosophy and guide for those who have the courage to think beyond the traditional paths. Millerd explores the history and philosophy of work, from Aristotle to modern times, and asks how we can find meaning in our work. He challenges readers to question the "standard path", often seen as the only way to success, and instead explore the "pathless path", a path that welcomes uncertainty and discomfort, yet leads to a fulfilling and meaningful life.
Core concepts, key learnings and notes on "The Pathless Path" by Paul Millerd
The agony of (job) choice - which path is the right one?
Especially people who are still at the beginning of their career and are wondering which job to choose very often feel overwhelmed by the many possibilities. Often there is an inner voice, ideas, longings that give a hint in which direction they want to give - which then immediately collide with external resistance and opinions of others why this is not possible under any circumstances and why they should definitely choose the famous "safe job".
Millerd's work is concerned with the nature, definition and change of "work".  He illustrates his points through his own career, distinguishing between the standard path and the pathless path, which is the core concept of the book: in doing so, he does not provide the one right path, but challenges the notion that the standard path is the only way to achieve the goal.
1. A life of security - the standard path
The standard path, on the one hand, according to Millerd, is characterised by a set of choices and achievements needed to be considered a "successful adult." 
There are also many other labels for this: Researchers Dorthe Berntsen and David Rubin speak of "life scripts", which they refer to as "culturally shared expectations about the sequence and timing of life events in a protoytpic life course" that usually happen before the age of 35 (Ex: getting a job, falling in love, getting married, etc.). 
This is so relevant because these events have a disparate impact on lives, while the rest of our lives remain largely unscripted as a consequence, and people then do not know how to deal with them because no one has prepared them for them.
In this uncertainty, most people then follow these scripts from which they hope for security and guidance.
2. Finding one's own way - the pathless way
The pathless path, on the other hand, is much harder to grasp because there is no one rule, one form, of what this path looks like:
"We are not able to grasp what it means." - David Whyte 
Millerd himself says that it is a great challenge, above all an overcoming, to engage in this process of discovery - especially if one gives up a career that is regarded in the standard way for it (as in his case in strategy consulting at McKinsey). But it is worth it, he says, because truly great and unique things can only be discovered along this seemingly uncertain path:
"That which is completely unknown to you by nature, you usually have to find, and to find it, you have to get lost." - Rebecca Solnit 
He also brings up the Chinese concept of "Wu wei" (无为) from Daoism in this context: Literally translated, this means "non-action" (in the sense of abstaining from action directed against nature) and at the same time refers to a deep connection, a trust with the world. The Chinese philosopher Lao Tzu wrote about this already about 2,500 years ago in the Tao Te Ching:
"One must force things less and less until one finally comes to doing nothing. When nothing is done, nothing remains undone. True mastery is achieved by letting things go their own way. You cannot attain it by interfering." - Lao Tzu 
In order to find one's own "pathless way", he says, it takes patience, courage, letting go of the familiar, the tried and tested, and the habitual, and embarking on a journey that reveals a lot about oneself and then leads to that path through detours, experiments.
The Origin of Work, Accidental Meaning and the Generation Gap
The "Meaningful Work" Trap
Interesting are the remarks on the origin of work, whose development in recent times he regards as corresponding to the times and necessary, but which he criticises in today's context. In particular, he speaks of the "Meaningful Work" trap, according to which many young people, especially the Millenial generation and upwards, realise that the standard path is not right for them per se, but they then use the wrong criteria or would not find it in the standard path; thus, some chase prestige and status in constant status battles, others look for what they consider "fulfilling" and "meaningful work". This is particularly confusing because in a self-examination he collected over 100 slogans from well-known companies that advertise precisely this concept, which people in search of happiness & fulfilment expect.  However, studies on this show that "real meaning" in the context tends to be "associated with mixed, unpleasant or even painful thoughts and feelings, not just a sense of unadulterated joy and happiness".  In this respect, there is a discrepancy between the high expectations and the actual decisive circumstances, which in turn can lead to disappointment.
Another problem is that these attitudes are often shaped by family environment, upbringing, social expectations, as these pressures are passed on from generation to generation, even if the underlying circumstances have long since ceased to exist.
Accidental Meaning here refers to accidental or unintended meaning that people have found in their work in the past, specifically citing the baby boomer generation who grew up in a time of unique economic and historical circumstances:
"Because established careers worked for them [baby boomers], they can't imagine that they won't work for their children." - Peter Thiel. 
However, this "accidental meaning" no longer applies to later generations, such as Millennials, to the same extent, as economic conditions, social expectations and the working landscape have changed and the old paths no longer offer the same fulfilment or meaning. Millerd therefore urges readers to explore the "Pathless Path" and develop a more conscious, individual relationship with work and life, rather than relying on the random meanings of the past.
He refers here to history, where for the longest time, including by Aristotle, work was seen only as a necessary evil, but not as the goal of life, which would be eudamonia (happiness / flourishing) on the pathless path.
Optimisation for the CV and bullshit jobs
Another concept he mentions is the term "hoop jumper", which goes back to the author and former Yale professor William Deresiewicz, expressing his concern that his students were increasingly more concerned about getting good grades and adding more points to their CVs, rather than spending their time at the best universities following their curiosity.  Students therefore decided their next internship, their next courses based on the likelihood of success, improving their career and thereby finding fulfilment in life, rather than focusing on curiosity, interests and talents. Cal Newport also warns against this trap in his book "So good they can't ignore you":
"The passion hypothesis is not only wrong, it is dangerous." - Cal Newport. 
Paul Graham also sees status as a false motivator:
"Prestige is a powerful magnet that twists even your beliefs about what you enjoy." - Paul Graham 
David Graeber even goes a step further and calls the jobs that students "optimise" for "bullshit jobs", certain types of jobs that even those who do them find pointless or redundant and that are neither necessary in modern economies nor have any real meaning or value to society.  Yet they are in demand because they often bring prestige or are simply expected by the environment. In this tone also Seth Godin:
"The educated, hard-working masses still do what they are told, but they no longer get what they deserve." - Seth Godin 
The only way out of this nonsense, according to Millerd, is to embrace the pathless way - whatever the outcome.
Finding your own path - in 10 steps
After Millerd has extensively discussed the reasons and challenges that one can expect when changing from the standard path to the pathless path, he summarises ten recommendations on how one can find one's own path or more meaning in one's work:
- Question the status quo
- Find out what you have to offer
- Stop and switch off
- Find a friend
- Create something
- Give generously
- Commit yourself
- Be patient
He speaks of the "experiments in living" that one has to dare - in other words, a proactive approach. Overall, however, proactivity pays off and leads to a fulfilling and meaningful life.
In my perception, the book has a great core concept, which is the recommendation to embark on the pathless journey despite uncertainties, hardships, headwinds and challenges.
This is also the advice given by other successful people - whether you read up on Paul Graham, Seth Godin, Steve Jobs, Cal Newport, Naval Ravikant or other greats, the pattern is often the same ("be useful, be proactive, try things out, follow your gifts" etc.).
So if you have already studied the subject intensively, you will find many parallels here, or possibly not too much new input, but many examples and elaborations of how the concept is expressed in practice.
Millerd describes this very vividly and extensively using his own development process and career. This makes it very appealing, authentic and comprehensible, especially for people who feel in a similar situation. If this is the reason that someone gets hope or a feeling that they can make it and perhaps see the next step more clearly, then reading the book or its sources is definitely recommended.
What could the "pathless way" mean to you?
- Paul Millerds Blog, Think Boundless (2018).
- Millerd, The Pathless Path – Imagining a New Story for Work and Life* (2022), 7.
- Berntsen/Rubin, Cultural Life Scripts Structure Recall from Autobiographical Memory, Memory & Cognition 32 (2004), 427.
- Whyte, The Three Marriages: Reimagining Work, Self and Relationship* (2010).
- Solnit, A Field Guide to Getting Lost* (2006).
- Tzu/Mitchell, Tao Te Ching: An Illustrated Journey* (1999).
- Millerd, 100+ Examples of Culture PR, Twitter Posting vom 28.01.2021.
- Bailey/Madden, What make Work meaningful – or meaningless?, MIT Sloan Management Review 57 (2016), 53 (61).
- Thiel, Zero To One: Wie Innovation unsere Gesellschaft rettet* (2014).
- Deresiewicz, Excellent Sheep: The Miseducation of the American Elite and the Way to a Meaningful Life* (2015).
- Newport, So Good They Can't Ignore You* (2016), 24.
- Graham, How To Do What You Love (2006).
- Graeber, Bullshit Jobs: Vom wahren Sinn der Arbeit* (2018).
- Godin, Linchpin: Are You Indispensable?* (2018).
Note: The books marked with * contain affiliate links. This means that I receive a small contribution if you buy the book via my link. You will not incur any additional costs, but you will help me to finance the blog so that I can continue to write such extensive articles. Thank you! - Niko