Insights from the book I read in less than 24 hours

Read time: 5 minutes

Welcome to The Ascend Archives Friday Edition where I share insights from the brightest minds in business and life and how I'm applying them to my life.

3 months ago, I got a message from a friend who read my newsletter on building my life by design…

I chatted with this friend several times in the following months, but totally forgot about the book he mentioned…until last Thursday night when I saw this tweet around 8 PM:

I knew this guy sounded familiar. I went back and confirmed it was the book my friend mentioned.

Two hours later as I got into bed, I downloaded The Pathless Path from my library app (Libby) and began to read.

I finished the 220 page book by 1 PM the following day.

Many of the thoughts, questions, and doubts in my head over the past few months, Paul has experienced firsthand. Our journeys from quitting a major consulting firm to pursuing work we enjoy have many similarities. We both left the stable path and went into the unknown. Lucky for me Paul is 7 years ahead on this path.

Paul didn’t provide me with the answers, but he gave me some better questions to ask. He reminded me that I’m not the only one struggling with these thoughts. He helped me realize that it’s ok not to know, it’s part of the journey.

I don’t typically highlight anything when I read. But this book hit different. I was highlighting sentences in my Kindle on almost every page. I went back and took notes on the stuff that still jumped out a few days later.

I still have a lot to reflect on, but here are some quick hitter insights from The Pathless Path:

Background

• The default path: a series of decisions and accomplishments needed to be seen as a successful adult (i.e., good job, buy a home, have a family)

• The pathless path: an alternative to the default path. An embrace of uncertainty and discomfort

• The pathless path is not about escaping work or living an easier life. It’s using your gifts to pursue work you enjoy and to benefit others

• Post-traumatic growth is a thing. Many people gain an appreciation for life, more meaningful relationships, and changed priorities after a traumatic event

• Dramatic life changes don’t happen suddenly. They are often longer, slower, and more interesting journeys

• We are all creative. You don’t need to use certain tools or be in certain industries. Navigating corporate politics, deciding on an emoji, parenting, hosting a party or planning a trip are all forms of creativity

Our relationship with work

• Work is such a powerful force that almost everyone identifies first and foremost as a worker. I am a teacher, a doctor, a lawyer, an athlete

• What is the first question you ask someone when you meet them? I bet it’s “What do you do for work?”

• Why is this our default? Who are you if you are not a worker?

• 4 common shifts when people take a break from work

  1. People become aware of their own suffering. It’s tough to notice it when you are wrapped up in it and constantly living it. It becomes normal or tolerable

  2. Curiosity emerges. With the space and time, people try new activities, revisit old hobbies, start to volunteer

  3. People desire to continue their "non-work" journey

  4. People write

Embrace uncertainty

• When people asked how Paul was doing, he felt compelled to give them proof he had a plan and knew what he was doing

• But learning to exist with the vagueness is vital, especially at the beginning stages of making a change

• People who value comfort and security often cannot understand why anyone would willingly pursue a path that increases discomfort and uncertainty

Play infinite games

• A finite game is played to win

• An infinite game is played to continue playing forever

• Focus on creating conditions for success and limiting the risk of failure instead of just aiming for success itself

• Longer you stay on the path, the higher odds you can sustain it over long term

• Eventually, people realize paying the bills isn’t the problem. It’s finding the time to continue exploring opportunities

Have faith

• Opting out of work and into other aspects of life can create questions about who you used to be. Feels weird at first, but over time it starts to change what you value

• Many people believe having enough money is the formula to live life on your own terms

• Money helps with paying for therapy, time off, vacations, and reducing the stress of "money problems" but will it help you be sure everything is going to be ok?

• It’s not about making the worries disappear, it’s being able to sit with the anxiety and discomfort, focus on what we can control, and open up to the world

What is enough?

• Knowing you have enough gives you freedom to say no to financial opportunities and yes to something that brings you alive and might pay you more in the long term

• If we don’t define enough, we default to more, which makes it impossible to say no

• Saying no to something requires we know what we stand for

• Shift from a mindset of work sucks to designing a life around liking work

How to start?

• Instead of thinking what I want and how to live. Start with what I don’t want to be doing and what failure looks like. We can avoid obvious traps and create space for things to go right

• Find people to support you and go on the journey with

• Know who the people are that you want to serve

• Only by taking action do we learn. Only by learning do we discover what we want

• Experiment with different ways of showing up in the world and make small deliberate changes. This leads to unexpected opportunities, possibilities, and connections that might tell us what comes next

1 Liners

• The hardest questions often don’t have answers

• Wonder is the state of being open to the world, its beauty, and potential possibilities

• Nothing good gets away as long as you create the space for it to emerge

• Humans don’t mind hardship, they thrive on it; what they mind is not feeling necessary

• Creative work runs on uncertainty; it runs on not knowing what you are doing

Thank you for reading! As always please reply and let me know what resonated, what didn’t, or what you question. I love chatting about this stuff!

Cheers,

Andrew