The Pathless Path - Paul Millerd

In the default path, a person pursues an upward-moving career. In the pathless path, you seek work that you can control. The author does not put a label on what jobs should be pursued. This book is not prescriptive - it does not give instructions for getting on the pathless path. Instead, it provides a philosophy of transitioning to and working on the pathless path. 

The first step in this journey is acknowledging other paths exist.

Here are my 5 takeaways from this book - 

  • On Being a Creative
  • On Choosing Opportunities Wisely
  • Recognizing Bad Tests
  • Mini Retirements
  • Wu Wei

On being a creative

There is creativity in every aspect of life. The default path puts limits on what it means to be creative.

There are no gatekeepers to your creativity in these current times. Everything can be published on the Internet if that is your creative medium. Physical objects, too, can be sold online, unlike in the past.

Detach yourself from conventional notions of what creativity means, and you’ll see it everywhere.

There might be detractors or critics of your creative work - but the author exhorts us to know who our audience is.

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.

Countering online detractors - the author compares a Wells Fargo advisor and an online Yoga instructor on social media. Our preconceived notions of work would lead us to support or respect the financial advisor rather than the Yoga Instructor. However, Yoga Instructor has put their reputation on the line for the world to see. In contrast, financial institutions haven’t necessarily been the most respected institutions if you were to follow all the news.

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


On Choosing Opportunities Wisely

The creator of the Ghost blogging platform set up his company so it could never be sold. Additionally, he never expanded his company beyond himself. An essential part of his story was that he refused to take on enterprise clients because they would drain his time and take him away from his passion.

No money is worth it if it undermines your desire to stay on the journey.

This book is about the philosophy of thinking about the pathless journey. It is about doing what you enjoy and learning when to say NO so that you can continue to do what you love.

Money is essential, but it should not be the driver. Instead, a vital aspect of the pathless path is learning when to say NO to opportunities, which opens up the possibility of better ones. This is a challenging paradigm shift to accept.

While money is important on the pathless path, using it as a filter for finding the work worth doing, especially at first, is a mistake.

On the default path, optionality can be a trap. This is because you are trapped within your own career narrative. On the pathless path, however, optionality can pay consistent dividends because you are not holding out for another job but leaving space for a little more life.

Recognizing Bad Tests

The default path often comprises a series of hacks or “bad tests.”

In the business world, however, talent is harder to assess and we tend to use proxies like credentials to determine quality and prestige.

The author describes how students at college gamed the system and chose coursework that would ensure a high GPA. This extended into corporate life by actions guaranteeing career success - choosing good teams and promising projects, increasing workloads, and switching jobs at every opportunity.

The Bad Test - On the default path, the underlying skill we are often rewarded for is the ability to hack the system.

Mini Retirements

People choose to retire at the end of their careers. Retirement is often accompanied by depression and anxiety brought about by the loss of purpose.

Mini-Retirements were introduced in Timothy Ferriss’ book - Four Day Week. Long breaks or sabbaticals are taken mid-career rather than at the end. Each interval is at least four weeks long - Retirement in stages. The career progression requirements in the Default path make such breaks impossible.

Wu Wei

This book introduced me to the concept of Wu Wei.

For most of my life, I had paired the idea of doing nothing with laziness. Living in another country enabled me to see that this was a very American way of seeing the world. In Taiwan, I was able to embrace a state of doing nothing that was not filled with anxiety and tension but reflective and open.